Phenyl / pyridyl-n-phenyl / pyridyl derivatives for treating a RNA virus infection

Abstract

The invention in question relates to a compound of the formula (Ie), where Y1 represents an aryl group, X2 represents an -O- group, an -NH- group, an -S- group, an -CO-NH- group, an -NH-CO-NH- group, an -NH-CO- group, an -CH(OH)- group, an -CH(COOH)NH- group, an -CH(COOCH3)NH- group, an -C(OH)(CH2OH)-, an (AA) group, a divalent 5-membered heteroaromatic ring containing 1, 2, 3 or heteroatoms, an -SO2- group or an -SO2-NH- group, Y2 represents a hydrogen atom, a hydroxyl group, a (C1-C4)alkoxy group, an -CHC(OH)2, a COORf, where Rf represents a hydrogen atom or a (C1-C4)alkyl group, a morpholinyl group, a The dihydropyranyl group represents a (BB) group, a (CC) group, a -PO(ORf)(OR'f) group, where Rf and R'f are independently a hydrogen atom or a (C1-C4)alkyl group, an oxetanil group, a -S?(CH3)3 group,It represents an -NHCOO-(C1-C4)alkyl group or an -CR1R2R3 group or any of its pharmaceutically acceptable salts. The invention in question also relates to pharmaceutical compositions containing these and the synthesis process for their production.

Description

PHENYL / PYRIDYL-N- FOR THE TREATMENT OF AN RNA VIRUS INFECTION PHENYL / PYRIDYL DERIVATIVES The invention in question concerns an RNA virus infection, most commonly known as a Baltimore viral infection. an RNA virus caused by RNA viruses belonging to group IV or V of its classification It relates to compounds that are useful for the prevention and / or treatment of infection. The invention in question also specifically addresses an RNA virus infection, and is the most preferred method. as stated, an RNA virus belonging to group IV or V of the Baltimore classification to prevent and / or treat an RNA virus infection caused by It is related to some new compounds that are useful. In addition, pharmaceutical compositions containing these new compounds and their derivations It is related to chemical synthesis processes aimed at production. BACKGROUND Viruses are one of the leading causes of disease worldwide. Viruses generally Because they do not possess a fully autonomous replication mechanism, they are only suitable for living organisms. They are defined as small, non-living, infectious agents that multiply inside cells. Shape and size Although they differ in some ways, they typically contain at least one nucleic acid molecule and optionally depending on the type of virus, it contains one or more proteins or nucleoproteins. It consists of a virus particle (known as a "virion") made of a protein coating. Because viruses do not have a completely autonomous replication mechanism, They are necessarily infected in order to replicate and produce multiple copies of themselves. It must rely on the mechanism and metabolism of the cell or host. Although replication cycles vary greatly between species, the life cycles of viruses... It is generally accepted that the cycle includes six basic steps: attachment, Penetration, peeling, replication, fusion, and release. 35 2 Depending on the nature of the targeted virus, one or more of these mechanisms may be used. Therapeutic molecules capable of addressing the excess have been designed. Among these, the replication step involves not only the multiplication of the viral genome, but also the same At the same time, viral messenger RNA, viral protein synthesis, and host transcription or It also includes modulation of the translation mechanism. However, the genome type (single (stranded, double stranded, RNA, DNA...) significantly characterizes this replication step. It is also clear that, for example, most DNA viruses assemble at the core, while most RNA viruses... It develops only in the cytoplasm. Also, single-stranded RNA viruses like Influenza have a host. There is increasing evidence that it utilizes an RNA splicing and maturation mechanism. Accordingly, and taking into account the effects of a particular genome type during the replication step. By taking these factors into account, the Baltimore classification of viruses was developed. This classification, It classifies viruses into families (or “groups”) based on their genome type. The subject matter... The virus classification, as in 2018, includes seven different groups: - Group I: double-stranded DNA viruses (dsDNA); - Group II: single-stranded DNA viruses (ssDNA); - Group III: double-stranded RNA viruses (dsRNA); - Group IV: (+)stranded or sense RNA viruses ((+)ssRNA); - Group V: (-)stranded or antisense RNA viruses ((-)ssRNA); - Group VI: Single-stranded RNA viruses with DNA intermediates (ssRNA-RT); - Group VII: Double-stranded DNA viruses with RNA intermediates (dsDNA-RT). According to this classification, viruses belonging to Group VI are strictosensu RNA viruses. They are not. For the same reasons, viruses belonging to Group VII are stricto sensu DNA viruses. It is not. A well-studied example of a virus family belonging to Group VI is HIV. Retroviridae (retroviruses) is a family of viruses belonging to Group VII and is a well-studied group of viruses. An example is the Hepadnaviridae family, which includes the Hepatitis B virus (HBV). Picornaviruses (Hepatitis A virus, as a representative of Group IV viruses) including well-known viruses such as enteroviruses, rhinoviruses, polio virus and foot-and-mouth disease virus. (a family of viruses), SARS virus, Hepatitis C virus, yellow fever virus, and rubella virus This can be shown. The Togaviridae family also belongs to group IV, and one known genus of it is Chikungunya. It is an alphavirus that includes the Flaviridae family, a well-known virus transmitted by mosquitoes. It is a family of viruses, including the dengue virus, belonging to group IV. 35 3 As a representative of Group V viruses, the Filoviridae family includes the Ebola virus. The Paramyxoviridae family includes the Respiratory Syncytial Virus (RSV). The Rhabdoviridae family includes Influenza virus A, Influenza virus B, and Influenza virus C. The Orthomyxoviridae family, which includes these, can be shown. Specifically, the groups within the virus families that are the focus of this discovery are RNA. viruses, especially single-stranded RNA viruses, and more specifically Baltimore viruses. These include RNA viruses belonging to groups IV and V of the classification. RNA virus infections, especially single-stranded RNA viruses, and more specifically RNA originating from viruses belonging to groups IV and V of the Baltimore classification. There are very few treatments for diseases caused by viral infections. Treatment It focuses on relieving symptoms. Therefore, it specifically targets small chemical molecules. including RNA virus infections such as group IV and V RNA virus infections There is still a need to identify new antiviral drugs to treat these conditions. The previous technical document WO2006 / 037117, mediated by TNF-α, IL-1β, IL-6 and / or IL-8. useful compounds in the treatment of diseases and pain and other conditions such as diabetes They explain. In particular, the compounds described are related to diseases or conditions involving inflammation. It is useful for the prophylaxis and treatment of these conditions. The compounds with the following registration numbers are found in the REGISTRATION database: (“REGISTRY COPYRIGHT 2023 ACS on STN”): RN: 512834-81-0; RN: 1985111-93-0; RN: 1985111-90-7; RN: 1990430-84-6; RN: 1988220-74-1 and RN: 1923315-23-4, supplement This is explained in addition to the following compound: Bianchi et al, “compounds with antiulcer and antisecretory activity”, 1981, 19, n°4, pp. This is explained in the document 321-326, Eur. J. Med. Chem - Chimica Therapeutica. 35 4 DEFINITIONS As used here, the term "sick" refers to animals intended for breeding, companionship, or protection purposes. in relation to an animal such as a valuable animal or preferably one as described herein or suffering from, or potentially suffering from, more diseases and conditions. It refers to a person or a human child. Specifically, as used in the application in question, the term "patient" includes rodents, cats, dogs, It refers to a mammal, such as a primate or human, preferably the subject in question is a It includes humans and also birds. Patients who need treatment for the diseases and conditions described here Defining it is within the ability and knowledge of a person skilled in the field. A person skilled in the field a veterinarian or physician, clinical tests, physical examination, medical / family history or biological and By using diagnostic tests, we can easily identify patients who need this type of treatment. In the context of the invention, the term “treat” or “cure” as used herein refers to RNA virus. from infection, and more specifically from RNA virus infection of group IV or V as opposed to the disease resulting from or one or more symptoms of such a disease It means to be diverted, mitigated, hindered, or prevented from progressing. As used herein, “an effective amount” refers to the number of diseases and conditions described herein. situations, in other words, RNA virus infection, and especially group IV or prevention, reduction of symptoms of RNA virus infection from V. the issue that is effective in eliminating, treating or controlling It refers to a quantity of a compound belonging to the invention. The term "controlling" here refers to... slowing down or interrupting the progression of the described diseases and conditions refers to all processes that may be interrupted, paused or stopped The goal is, however, to completely eliminate all symptoms of the disease or condition. This does not mean it has been cured, and the aim is to include prophylactic treatment. The term “effective dose” includes both “prophylaxis-effective dose” and “therapeutic-effective dose”. As used here, the term "prevention" refers to the prevention of a specific phenomenon, in other words, the issue at hand. The invention describes an infection with an RNA virus, and more specifically from group IV or V. 35 5 Reducing the risk of developing a disease caused by RNA virus infection. or means slowing down its occurrence. As used here, "prevention" also means "reducing the likelihood of occurrence". This also includes "reducing the likelihood of recurrence". The term "prophylaxis-effective dose" refers to RNA viruses, and more specifically to Baltimore viruses. the probability of disease caused by an RNA virus from classification group IV or V inhibition, prevention, reduction or inhibition of RNA virus infection and especially in the prevention of RNA virus infection from group IV or V, or before infection, in other words, to RNA virus, and specifically from group IV or V. before, during and / or slightly after the period of exposure to the RNA virus When applied, it is an RNA virus, and more specifically an RNA virus from group IV or V. this invention is effective in preventing delayed onset of the disease It refers to a concentration of the compound. Similarly, the term “therapeutic-effective dose” refers to the amount of medication needed after an infection has occurred. when applied following an examination, for example in the treatment of RNA virus infection. an effective compound, for example, one that leads to a reduction in RNA viral infection It refers to concentration. As used here, the term “pharmaceutically acceptable” refers to reasonable medical judgment. Within this context, excessive toxicity, irritation, allergic reaction are considered in proportion to a reasonable benefit / risk ratio. suitable for contact with human and animal tissues without other problematic complications. It refers to compounds, materials, excipients, compositions, or dosage forms. As used here, “viral infection or related condition” refers to a virus, more commonly specifically an RNA genome and, in particular, group IV according to the Baltimore classification or The virus in question, which has an RNA virus belonging to the V genus, refers to a status infection. Viruses can also be classified into different families, orders, and genera. For reference, the content of the “Baltimore classification” reported here is from March 12. Published online in 2018 at http: / / ictvonline.org / virusTaxonomy.asp published in 2017 in the International Committee on Virus Taxonomy (ICTV) database As mentioned, it includes further references to virus taxonomy. 35 6 Alphaviruses are particularly noteworthy in this invention, and positive-sense single-stranded RNA Group IV RNA viruses, which can be identified as viruses or (+)ssRNA viruses, and It may belong to the Togaviridae family. According to the 2017 Virus Taxonomy, this order is... "Not assigned." The Togaviridae family includes the genera Alphavirus and Rubivirus. Examples of Alphaviruses considered by the invention include: Barmah Forest virus, Chikungunya virus, Mayoro virus, O'nyong'nyong virus, Ross River virus, Semliki Forest virus, Una virus, Eastern equine encephalitis virus, Tonate virus, Venezuela Equine encephalitis virus and Western equine encephalitis virus. As most commonly preferred, according to the invention, an alphavirus infection or alphavirus-related The condition is a Chikungunya virus infection or a condition related to the Chikungunya virus. More specifically, the Chikungunya virus (CHIKV) belongs to the Togaviridae family, in other words It is an RNA virus belonging to the alphavirus genus, Group IV in the Baltimore classification. Chikungunya was first identified during an outbreak in southern Tanzania in 1952. It is a mosquito-borne viral disease. CHIKV is a virus approximately 12 kb nucleotide long. CHIKV is an enveloped, positive-sense, single-stranded RNA virus with a genome. The genome of CHIKV... It is arranged as follows: 5'-header-nsPl-nsP2-nsP3-nsP4-(merge region)-C- E3-E2-6k-El-poly(A)-3', where the first four proteins (nsPl-4) are non-structural proteins and The structural proteins are capsid (C) and envelope proteins (E). Africa, Asia and Indian Ocean There is no significant serotypic difference between the CHIKV isolated from the islands. El gene Phylogenetic analyses based on sequences can divide CHIKV into three genotypes (lineages): Asian, East / Central / Southern Africa (ECSA) and West Africa. Asian genotype, ECSA and West Africa. differences in genotypes based on nucleotide levels of -5% and -15%, respectively. This has been shown. African genotypes (West African vs. ECSA) were -15% different. Three Amino acid identities in the genotype varied from 95.2% to 99.8%. Chikungunya virus can cause outbreaks associated with serious morbidity. Chikungunya is a viral disease transmitted to humans by infected mosquitoes. Both Ae. aegypti and Ae. albopictus play a role in major Chikungunya outbreaks. It has played a role. Ae. aegypti is limited to tropical and subtropical regions, while Ae. 35 7 Ae. albopictus is also found in temperate and even cold temperate regions. In recent years, Ae. albopictus has been observed. Albopictus spread from Asia and became established in Africa, Europe, and the Americas. After infection with the chikungunya virus, there is an incubation period that lasts an average of 2-4 days. And then there are disease symptoms. Such symptoms include fever and severe joint pain. Pain may be present. Other symptoms include muscle pain, headache, nausea, and back pain. Serious clinical signs of chikungunya infection include fatigue, myalgia, and rash. For example, it can manifest as hemorrhagic fever, conjunctivitis, photophobia, hepatitis, stomatitis, encephalitis, and febrile illness. Neurological symptoms such as seizures, meningeal syndrome, and acute encephalopathy have also been reported. Joint pain is often debilitating and its duration can vary. The proximity of mosquito breeding grounds to human settlements is an important factor for Chikungunya. It is a risk factor. The distribution of Chikungunya virus is mainly in Africa, India and Southeast Asia. It is observed that in recent years, mosquito vectors of Chikungunya have spread to Europe and America. In 2007, the first localized outbreak of disease transmission was reported in northeastern Italy. It was done. Since then, outbreaks have been recorded in France and Croatia. Dengue viruses exhibiting various serotypes can also be evaluated under the invention and classified as Group IV. RNA viruses can be defined as positive-sense single-stranded RNA or (+)ss RNA viruses. It may belong to the Flaviviridae family. More specifically, the Dengue virus, according to the Baltimore classification. It is a group IV (+)ssRNA virus. It belongs to the Flavivirus genus of the Flaviviridae family. It is part of the Flaviviridae family. Other viruses belonging to the Flaviviridae family are hepatitis C virus and yellow fever virus. Viruses belonging to the order Mononegavirales are also given particular consideration by the invention. The Mononegavirales order includes viruses belonging to Group V of the Baltimore classification. 2018 Accordingly, this group primarily includes the following virus families: Bornaviridae, Mymonaviridae, Filoviridae, Nyamiviridae, Paramyxoviridae, Pneumoviridae, Rhabdoviridae and Sunviridae. Human respiratory syncytial virus (HRSV) causes respiratory tract infections. It is a syncytial virus. It causes lower respiratory tract infections in infancy and childhood. and is a major reason for hospital visits. The HRSV virus, in particular, was discovered by the expert. It can be evaluated and may belong to Group V of RNA viruses. More specifically, RSV. 35 8 The virus is a (-)ssRNA virus belonging to group V of the Baltimore classification. A member of the Paramyxoviridae family, which belongs to the Mononegavirales order. It is a pneumovirus. Among the other viruses of the order Mononegavirales, it is identified by invention. Those that are particularly considered include: measles virus, mumps virus, Nipah virus, rabies virus and human parainfluenza virus (HPIV-1, HPIV-2, HPIV-3 and HPIV-4) (includes). The Paramyxovirinae subfamily is part of the Mononegavirales order, updated in 2016. It is traditionally grouped with the Paramyxoviridae family by reference to its taxonomy. Specifically, the virus genera considered within the Paramyxoviridae family are as follows: Includes: Aquaparamyxovirus, Avulavirus, Ferlavirus, Henipavirus, Morbillivirus, Respirovirus and Rubulavirus genera. Viruses belonging to the family Orthomyxoviridae are also given particular consideration by this invention. The family Orthomyxoviridae belongs to an "Unassigned" order according to the 2017 Virus Taxonomy. Specifically, the virus genera considered within the Orthomyxoviridae family are as follows: Includes: Alphainfluenzavirus, Betainfluenzavirus, Deltainfluenzavirus, Gammainfluenzavirus, Isavirus, Quaranjavirus and Thogotovirus. Influenza A virus, Influenza B virus, Influenza C virus, especially by invention can be evaluated and Group V RNA viruses and negative-sense single-stranded RNA or (-)ss It may belong to the Orthomyxoviridae family, which can be defined as RNA viruses. Isavirus and Thogotovirus also belongs to the order Orthomyxoviridae. DETAILED DESCRIPTION OF THE INVENTION Surprisingly, the inventors found that aryl-N-aryl compounds can be applied to RNA viruses and more. especially single-stranded RNA viruses belonging to Group IV or V of the Baltimore classification They found that it has a broad-spectrum activity. Groups IV and V, respectively. This includes (+)ssRNA viruses and (-)ssRNA viruses; these are also known as positive-sense single viruses. It refers to both stranded RNA viruses and negative-sense single-stranded RNA viruses. For reference, the content of the "Baltimore classification" is from the 10th Virus classification dated 2017. Classification and Naming of Viruses as stated in the Taxonomy report. It is evaluated in light of this. 35 9 The document in question is a formula (I) which is not within the scope of the expression of the claims. explains the compound Here: ring and The ring independently refers to a phenylene or a pyridylene group, here group , On the ring, it is in a meta or money position according to the -NH- group, especially meta. is in position, 1 X is an alkenylene group, specifically an ethenylene group, an -NH-CO- group, an -CO-NH- group. The group represents a -CR R O- group, ab 1 Y represents an aryl group selected from either a 2-pyridyl group or a pyrimidinyl group. 35 1 Here, one of the nitrogen atoms in the pyrimidinyl group is in the ortho position relative to X, 10 1 1 Alternatively, X -Y represents a group (A) belonging to the following formula. 2 X is a -CO-NH- group, a -NH-CO-NH- group, an -OCH- group, and a -NH-CO- group. 2 or represents an -SO -NH- group, 2 n is 0, 1, 2, or 3. m and m' are independently 0, 1, or 2. 2 1 2 3 Y represents a hydrogen atom, a hydroxyl group, or an -CR RR group. 1 2 3 Here R, R, and R can independently represent a hydrogen atom, a fluorine atom, or a (C 1- 1 2 3 C) represents an alkyl group, where at most one of R, R, and R is a hydrogen atom. 4 1 2 or R and R with a (C-C)cycloalkyl group along with the carbon atom carrying them. 3 8 It is understood that the (C-C)cycloalkyl group in question is formed as one or two optional groups. 3 8 The (C-C)alkyl group is substituted with a halogen atom or a (C-C)alkoxy group, and the word 1 4 1 4 1 2 The subject is the (C-C)cycloalkyl group, optionally on the R and / or R in question. 3 8 It is interrupted by an oxygen atom. R and R' are independently a halogen atom, a (C -C )alkyl group, and a (C -C )cycloalkyl group. 1 4 3 6 group, an (CC) alkoxy group, an -SO -NR R group, an -SO H group, an -OH group, 1- 5 2 ab 3 It represents an -O-SO-OR group or a -OP(=O)-(OR)(OR) group, R, R, R 2 ccdabc and R independently represents either a hydrogen atom or an (C-C)alkyl group, d 1 4 1 1 The condition for this is that X is a -CR R O- group, and Y is also a halogen atom, a (C ab 1- (C)alkyl group, a cyano group, a (CC)alkoxy group, a trifluoromethyl group, a 4 1- 5 trifluoromethoxy group, a -SO-NR R group, a -SO-H group, an -OH group, a -O-SO- 2 ab 3 2 with one or two substituents selected from an OR group or a -OP(=O)-(OR )(OR ) group CCD The optional substitution can be a 3-pyridyl, a 4-pyridyl, or a phenyl group. 35 or any of its pharmaceutically acceptable salts, 11 Caused by an RNA virus belonging to Group IV or V of the Baltimore classification. an RNA virus infection, and specifically a Chikungunya viral infection, a Dengue fever a viral infection, an influenza viral infection or an RSV viral infection or It is intended for use in the treatment and / or prevention of viral conditions. According to a first aspect which is not included in the scope of the expression of the claims, a formula (Ie) The compound is explained, Here 1 Y, R, R', R, R, m, m', ab ring, 2 2 The ring, X, n and Y are defined as above with respect to formula (I), or any pharmaceutically acceptable salt of it. According to the first aspect mentioned, the invention in question also includes compounds belonging to the formula (Ie) is related, here the group , 35 12 on the ring, according to the -NH- group, in a meta or money position and preferably meta is in position, m is 0, n is 0, 1, 2 or 3, 1 Y is a halogen atom, a (C-C)alkyl group and a cyano group, a (C-C)alkoxy group, a 1 4 1 5 trifluoromethyl group, a trifluoromethoxy group, an -SO₄ -NR R group, an -SO₄ H group, an -OH group 2 ab 3 one or two groups selected from an -O-SO -OR group or an -OP(=O)-(OR )(OR ) group 2 CCD It represents a pyridyl or phenyl group that is optionally substituted with a substituent. 2 1 2 3 gr Y represents a hydrogen atom, a hydroxyl group, or an -CR RR group. 1 2 3 Here, R, R, and R represent either a hydrogen atom or an (C-C)alkyl group independently. 1 2 1 2 3 1 2 It represents that at most one of R, R and R is a hydrogen atom, or that R and R are It is understood that these atoms form a (C-C)cycloalkyl group together with the carbon atom they carry. 3 6 The (C-C)cycloalkyl group in question can be optionally paired with one or two halogen atoms. 3 6 1 is substituted and the (C3-C6)cycloalkyl group in question is optionally used in the R group. 2 and / or interrupted by an oxygen atom on R, or any pharmaceutically acceptable salt of it. In an application, a compound belonging to the formula (Ie) according to Claim 1 or its pharmaceutical equivalent Any of the acceptable salts are provided. In another application, a compound or its considered pharmaceutical under Claim 10. Any of the available salts are provided. According to a second perspective, the description in question is Group IV or of the Baltimore classification. An RNA virus infection caused by an RNA virus belonging to the genus V, and specifically a Chikungunya viral infection, Dengue viral infection, Influenza viral infection in the treatment of infection or an RSV viral infection or a virus-related condition formulated as described above for use in and / or prevention It is related to compounds belonging to (Ie). 35 13 In an application, a compound or formula (Ie) intended for use according to Claim 12. Any of its pharmaceutically acceptable salts is provided. In an application, a compound or formula (Ie) intended for use according to Claim 13. Any of its pharmaceutically acceptable salts is provided. According to a third aspect which is not included in the scope of the expression of the claims, a part of the formula (Ie) compound explained Here ring and The ring independently refers to a phenylene or a pyridylene group, 1 Y represents a phenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl group, or a pyrimidinyl group. It represents an aryl group selected from the group, that aryl group being optional a halogen atom, a (C-C)alkyl group, a cyano group, a (C-C)alkoxy group, a 1 4 1 5 trifluoromethyl group, a trifluoromethoxy group, an -SO₄ -NR R group, an -SO₄ H group, a 2 ab 3 -OH group, an -O-SO-OR group or an -OP(=O)-(OR )(OR ) group is selected. 2 CCD or substituted with two substituent(s), 2 X represents the following: 35 a -O- group, 14 a -NH- group, an -S- group, a -CO-NH- group, a -NH-CO-NH- group, a -NH-CO- group, a -CH(OH)- group, a -CH(COOH)NH- group, a -CH(COOCH )NH- group, 3 a -C(OH)(CH OH)-, 2 One group, two heteroatoms containing 1, 2, 3 or 4 heteroatoms, such as a triazole, a tetrazole or an oxadiazole a 5-membered heteroaromatic ring with multiple valence, a -SO- group, 2 or a -SO -NH- group, 2 n is 0, 1, 2, or 3. m and m' are independently 0, 1, or 2. 2 Y represents the following: a hydrogen atom, a hydroxyl group, a (C-C) alkoxy group, 1 4 a -CHC(OH) , 2 a COOR, where R represents a hydrogen atom or a (C -C )alkyl group, ff 1 4 a morpholinyl group, a dihydropyranyl group, a group, 35 15 One group, a -PO(OR )(OR' ) group, where R and R' are independently either a hydrogen atom or a ffff (C -C) represents the alkyl group. 1 4 an oxetanil group, a -Si(CH ) group, 3 3 a -NHCOO-(C -C )alkyl group, 1 4 or 1 2 3 1 2 3 a -CR RR group, where R, R and R are independent hydrogen atoms, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 1 2 is a hydrogen atom or R and R together with the carbon atom that carries them (C - 3 It is understood that (C-C)cycloalkyl group is formed, and the said (C-C)cycloalkyl group is optional. 8 3 8 as one or two (C-C)alkyl groups, halogen atoms, or (C-C)alkoxy groups 1 4 1 4 is substituted and the (C-C)cycloalkyl group in question is optionally replaced. 3 8 1 2 R and / or R is interrupted by an oxygen atom on R, 2 2 Alternatively, X -Y represents a -CONR R group, where R and R, cdcd Along with a nitrogen atom, optionally a hydroxyl group or a (C-C)alkyl group. 1 4 It forms a heterocyclic group that is substituted with another group. R and R' independently represent the following: a (C-C)alkyl group, 1 4 a -S-(C -C )alkyl group, 1 4 a (C-C)cycloalkyl group, 3 6 a halogen atom, like a fluorine atom, a trifluoromethyl group, a -SO (C -C )alkyl group, 2 1 4 a (C-C)cycloalkenyl group, 3 6 a (C-C) alkoxy group, 1 5 a -SO -NR R group, 2 ab a -SO H or SO -CH group, 3 2 3 an -OH group, 35 a -CONHR, where R represents a hydrogen atom or a (C -C )alkyl group, gg 1 416 a -O-SO -OR group, 2 c an azetidinyl group, a morpholinyl group or a cyano group, "R" is a hydrogen atom, optionally substituted with a -COOH group (C - 1 C) represents the alkyl group. 4 or any of its pharmaceutically acceptable salts. According to a fourth perspective, the statement in question is intended for use as a medicine. It relates to a compound with the formula (Ie) as defined above. In an application, a compound or formula (Ie) intended for use according to Claim 11. Any of its pharmaceutically acceptable salts is provided. According to a fifth perspective, the description in question is Group IV or of the Baltimore classification. An RNA virus infection caused by an RNA virus belonging to the genus V, and specifically a Chikungunya viral infection, Dengue viral infection, Influenza viral infection in the treatment of infection or an RSV viral infection or a virus-related condition formulated as described above for use in and / or prevention It is related to a compound belonging to (Ie). According to another interpretation, the statement in question is as defined in Claim 16. a compound in the formulation (Ie) intended for use or its pharmaceutical acceptance It relates to any of its available salts. In an application, a compound or formula (Ie) intended for use according to Claim 17. Any of its pharmaceutically acceptable salts is provided. The compounds (I) and (Ie) mentioned above indicate a viral infection or related condition, specifically caused by an RNA virus belonging to group IV or V of the Baltimore classification is an RNA virus infection or related condition and is most often preferred a Chikungunya viral infection, a Dengue viral infection, an Influenza viral infection treatment of infection or an RSV viral infection or a condition related to the virus It is particularly suitable for the purpose of preventing or mitigating such actions. 35 17 The compounds mentioned above can cause a Chikungunya viral infection, a Dengue viral infection. an infection or an RSV viral infection or a virus-related condition, especially a More on the treatment or prevention of RSV viral infection It is particularly suitable. Other aspects of the invention in question, for example, the new compounds belonging to the formula (Ie) may be used as a drug, later on, such as its use in pharmaceutical composition and as a synthetic process. It will be explained. The subject of the document in question is as defined above and the expression of the claims. Describes a compound of formula (I) not covered by, where the alkenyle group is a It is an (E)-alkenylene group. m and m' are independently either 0 or 1. 2 1 2 3 1 2 3 Y represents a -CR RR group, where R, R, and R are independent hydrogens. 1 2 3 an atom represents a fluorine atom or an (C-C)alkyl group, R, R and R at most. 1 2 1 2 one of them is a hydrogen atom, or R and R are carbon atoms carrying them. It is understood that together they form a (C-C)cycloalkyl group, the (C-C)cycloalkyl in question 3 6 3 6 The group is optionally substituted with one or two halogen atoms, and the group in question 1 2 The (C-C)cycloalkyl group is optionally placed on the R and / or R in question. 3 6 It is interrupted by an oxygen atom. R and R' are independently a halogen atom, a (C -C )alkyl group, and a (C -C )cycloalkyl group. 1 2 3 6 It represents a group or an (C-C) alkoxy group, 1 2 or any of its pharmaceutically acceptable salts, Caused by an RNA virus belonging to Group IV or V of the Baltimore classification. an RNA virus infection, and specifically a Chikungunya viral infection, a Dengue fever a viral infection, an influenza viral infection or an RSV viral infection or It is intended for use in the treatment and / or prevention of viral conditions. The document in question is a formula (I) which is not within the scope of the expression of the claims. explains the compound 35 18 Here: ring and The ring independently refers to a phenylene or a pyridylene group, here group , On its ring, according to the -NH- group, it is in a meta or currency position. 1 X is an alkenylene group, a -NH-CO- group, a -CO-NH- group, and a -CR R O- group. ab represents, 1 Y represents an aryl group selected from either a 2-pyridyl group or a pyrimidinyl group. 1 Here, one of the nitrogen atoms in the pyrimidinyl group is in the ortho position relative to X. 1 1 Alternatively, X -Y represents a group (A) belonging to the following formula. 35 19 2 X is a -CO-NH- group, a -NH-CO-NH- group, an -OCH- group, and a -NH-CO- group. 2 or represents an -SO -NH- group, 2 n is 0, 1, 2, or 3. m and m' are independently 0, 1, or 2. 2 1 2 3 Y represents a hydrogen atom, a hydroxyl group, or an -CR RR group. 1 2 3 Here R, R, and R can independently represent a hydrogen atom, a fluorine atom, or a (C 1- 1 2 3 C) represents an alkyl group, where at most one of R, R, and R is a hydrogen atom. 4 1 2 or R and R with a (C-C)cycloalkyl group along with the carbon atom carrying them. 3 8 It is understood that the (C-C)cycloalkyl group in question is formed as one or two optional groups. 3 8 The (C-C)alkyl group is substituted with a halogen atom or a (C-C)alkoxy group, and the word 1 4 1 4 1 2 The subject is the (C-C)cycloalkyl group, optionally on the R and / or R in question. 3 8 It is interrupted by an oxygen atom. R and R' are independently a halogen atom, a (C -C )alkyl group, and a (C -C )cycloalkyl group. 1 4 3 6 group, an (CC) alkoxy group, an -SO -NR R group, an -SO H group, an -OH group, 1- 5 2 ab 3 It represents an -O-SO-OR group or a -OP(=O)-(OR)(OR) group. 2 CCD R, R, R, and R each independently represent a hydrogen atom or a (C-C)alkyl group. abcd 1 4 1 1 The condition for this is that X is a -CR R O- group, and Y is also a halogen atom, a (C ab 1- (C)alkyl group, a cyano group, a (CC)alkoxy group, a trifluoromethyl group, a 4 1- 5 trifluoromethoxy group, a -SO-NR R group, a -SO-H group, an -OH group, a -O-SO- 2 ab 3 2 with one or two substituents selected from an OR group or a -OP(=O)-(OR )(OR ) group CCD The optional substitution can be a 3-pyridyl, a 4-pyridyl, or a phenyl group. 1- 1 2 and the condition is that when YX represents a 2-pyridylethene group, X is a -CO-NH- 2 1 2 3 1 2 Y represents the group -CR RR, where R is R 3 and R independently represents either a hydrogen atom or a (C-C)alkyl group and 1 4 m' is different from 0, or any of its pharmaceutically acceptable salts, a viral infection caused by an RNA virus belonging to group IV or V of the Baltimore classification It is intended for use in the treatment and / or prevention of RNA virus infection. 35 20 The document in question, notwithstanding the scope of the wording of the claims above, It relates to a compound with the formula (Ie) as defined, ring and either ring represents a phenylene group or The ring represents a pyridylene group and The ring represents a phenylene group, or any of its pharmaceutically acceptable salts. In another application, the invention in question is a part of the formula (Ie) as defined above. It is related to the compound, here m and m' are independently either 0 or 1. 2 1 2 3 1 2 3 Y represents a -CR RR group, where R, R, and R are independent hydrogens. 1 2 3 an atom represents a fluorine atom or an (C-C)alkyl group, R, R and R at most. 1 2 1 2 one of them is a hydrogen atom, or R and R are carbon atoms carrying them. It is understood that together they form a (C-C)cycloalkyl group, the (C-C)cycloalkyl in question 3 6 3 6 The group is optionally substituted with one or two halogen atoms, and the word 1 2 The subject (C -C )cycloalkyl group is optionally located on the R and / or R in question. 3 6 It is interrupted by an oxygen atom. 35 21 R and R' are independently a halogen atom, a (C -C )alkyl group, and a (C -C )cycloalkyl group. 1 2 3 6 It represents a group or an (C-C) alkoxy group, 1 2 or any of its pharmaceutically acceptable salts. In another application, the invention in question relates to the compound of the formula (Ie), where R" is a a hydrogen atom or any of its pharmaceutically acceptable salts. In another application, the invention in question relates to the compound of the formula (Ie), where 1 Y represents a phenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl group, or a pyrimidinyl group. It represents an aryl group selected from the group, that aryl group being optionally a a halogen atom, a (C-C)alkyl group, a cyano group, a (C-C)alkoxy group, a 1 4 1 5 a trifluoromethyl group with one or two substituent(s) selected from a trifluoromethoxy group is substituted, or any of its pharmaceutically acceptable salts. 2 In another application, the invention in question relates to the compound of the formula (Ie), where X represents the following an -O- group, a -NH- group, an -S- group, a -CO-NH- group, a -NH-CO-NH- group, a -NH-CO- group, two heteroatoms containing 1, 2, 3 or 4 heteroatoms, such as a triazole, a tetrazole or an oxadiazole a 5-membered heteroaromatic ring with multiple valence, a -SO- group, 2 or a -SO -NH- group, 2 or any of its pharmaceutically acceptable salts. The document in question, notwithstanding the expression of the claims, pertains to the formula (Ie). 2 It relates to the compound, where Y represents the following: a hydrogen atom, a hydroxyl group, 35 22 a -PO(OR )(R' ) group, where R and R' are independently either a hydrogen atom or a ffff (C -C) represents the alkyl group. 1 4 or 1 2 3 1 2 3 a -CR RR group, where R, R and R are independent hydrogen atoms, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 1 2 is a hydrogen atom or R and R together with the carbon atom that carries them (C - 3 It is understood that (C-C)cycloalkyl group is formed, and the said (C-C)cycloalkyl group is optional. 8 3 8 as one or two (C-C)alkyl groups, halogen atoms, or (C-C)alkoxy groups 1 4 1 4 is substituted and the (C-C)cycloalkyl group in question is optionally replaced. 3 8 1 2 R and / or R is interrupted by an oxygen atom on R, or any of its pharmaceutically acceptable salts. In an application, a compound belonging to the formula (Ie) or its pharmaceutical equivalent according to Claim 5 Any of the acceptable salts are provided. In another application, the invention in question relates to a compound of the formula (Ie), where R and R' independently represents the following: a (C-C)alkyl group, 1 4 a (C-C)cycloalkyl group, 3 6 a halogen atom, like a fluorine atom, a trifluoromethyl group or a -SO3H or SO2-CH3 group, or any of its pharmaceutically acceptable salts. In another application, the invention in question is not covered by the wording of the claims. It relates to the compound with the formula (Ie), where ring and 35 23 Both rings represent a phenylene group, "R" is a hydrogen atom, 1 Y represents a phenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl group, or a pyrimidinyl group. It represents an aryl group selected from the group, that aryl group being optionally a a halogen atom, a (C-C)alkyl group, a cyano group, a (C-C)alkoxy group, a 1 4 1 5 a trifluoromethyl group with one or two substituent(s) selected from a trifluoromethoxy group is substituted, 2 X represents the following: an -O- group, a -CO-NH- group, a -NH-CO-NH- group, a -NH-CO- group, two heteroatoms containing 1, 2, 3 or 4 heteroatoms, such as a triazole, a tetrazole or an oxadiazole a 5-membered heteroaromatic ring with multiple valence, or a -SO -NH- group, 2 2 Y represents the following: a hydrogen atom, a hydroxyl group, a -PO(OR )(R' ) group, where R and R' are independently either a hydrogen atom or a ffff It represents the (C1-C4)alkyl group. or 1 2 3 1 2 3 a -CR RR group, where R, R and R are independent hydrogen atoms, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 1 2 is a hydrogen atom or R and R together with the carbon atom that carries them (C - 3 It is understood that (C-C)cycloalkyl group is formed, and the said (C-C)cycloalkyl group is optional. 8 3 8 as one or two (C-C)alkyl groups, halogen atoms, or (C-C)alkoxy groups 1 4 1 4 is substituted and the (C-C)cycloalkyl group in question is optionally replaced. 3 8 1 2 R and / or R is interrupted by an oxygen atom on R, And R and R' independently represent the following: a (C-C)alkyl group, 1 4 a (C-C)cycloalkyl group, 3 6 a halogen atom, like a fluorine atom, 35 24 a trifluoromethyl group, a -SO H or SO -CH group or 3 2 3 a morpholinyl group, or any of its pharmaceutically acceptable salts. In an application, a compound belonging to the formula (Ie) or its pharmaceutical equivalent according to Claim 7 Any of the acceptable salts are provided. In another application, the invention in question relates to the compound of the formula (Ie), where ring and Both rings represent a phenylene group, "R" is a hydrogen atom, 1 Y represents either a phenyl group or a pyridyl group. 2 X represents the following: an -O- group, a -CO-NH- group, a -NH-CO- group, or a divalent compound containing 1, 2, 3, or 4 heteroatoms, such as a triazole, tetrazole, or an oxadiazole a 5-member heteroaromatic ring, 2 Y represents the following: a -PO(OR )(R' ) group, where R and R' are independently either a hydrogen atom or a ffff (C -C) represents the alkyl group. 1 4 or 1 2 3 gr 1 2 3 a -CR RR ubu, where R, R and R are independently a hydrogen atom, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 35 25 1 2 is a hydrogen atom or R and R together with the carbon atom that carries them. It is understood that it forms a (C -C )cycloalkyl group, 3 8 And R and R' independently represent the following: a (C-C)alkyl group, 1 4 a (C-C)cycloalkyl group or 3 6 a morpholinyl group, or any of its pharmaceutically acceptable salts. Any combination of the applications defined above for R, R', R", m, m', ring, 1 2 1 2 The ring, X, X, n, Y, Y, R and R, forms part of the invention that is related to each other. ab Depending on the preferred application of the invention in question, the following compounds are obtained: - (36) N-(2-cyclopentylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (37) N-isopentyl-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (38) N-(2-cyclohexylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (39) N-(2-cyclopentylethyl)-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (40) N-(2-cyclopentylethyl)-3-((3-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide  (41) N-(2-cyclopentylethyl)-3-((6-(pyridin-2-ylmethoxy)pyridin-3-yl)amino)benzamide - (42) N-(2-cyclopentylethyl)-6-((4-(pyridin-2-ylmethoxy)phenyl)amino)picolinamide - (43) N-(2-cyclopentylethyl)-3-((3-methoxy-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (44) N-(2-cyclopentylethyl)-3-((5-(pyridin-2-ylmethoxy)pyridin-2-yl)amino)benzamide - (45) N-(2-cyclopropylethyl)-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (46) N-(2-cyclobutylethyl)-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (47) N-(2-cyclohexylethyl)-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide 35 - (48) N-(2-cyclobutylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide 26 - (49) N-(2-cyclopropylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (50) N-(2-cyclopentylethyl)-3-((4-((2-fluorobenzyl)oxy)phenyl)amino)benzamide - (51) 3-((4-((2-cyanobenzyl)oxy)phenyl)amino)-N-(2-cyclopentylethyl)benzamide - (52) 3-((4-(benzyloxy)phenyl)amino)-N-(2-cyclopentylethyl)benzamide - (53) N-(2-cyclopentylethyl)-3-((3-hydroxy-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (54) N-isopentyl-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (55) N-(2-cyclopentylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzenesulfonamide - (56) N-(2-cyclohexylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzenesulfonamide - (57) 3-((2-ethyl-4-(pyridin-2-ylmethoxy)phenyl)amino)-N-isopentylbenzamide - (58) N-(2-cyclopentylethyl)-3-((2-ethyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (59) N-(2-cyclopropylethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzenesulfonamide - (60) N-(2-cyclopentylethyl)-3-((2-cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (61) 3-((2-cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl)amino)-N-isopentylbenzamide - (62) N-(cyclopentylmethyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (63) N-((3-methyloxetane-3-yl)methyl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (64) N-(pentane-2-yl)-3-((4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (65) 3-((4-(pyridin-2-ylmethoxy)phenyl)amino)-N-(3,3,3-trifloropropyl)benzamide - (66) N-(2-cyclopentylethyl)-3-((2-methyl-4-(1-(pyridin-2-yl)ethoxy)phenyl)amino)benzamide - (67) N-isopentyl-3-((2-methyl-4-(1-(pyridin-2-yl)ethoxy)phenyl)amino)benzamide - (68) 1-isopentyl-3-(3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)phenyl)urea - (69) 3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)-N-(oxetane-3-yl)benzamide - (70) N-(2-(3,3-difluorocyclobutyl)ethyl)-3-((2-methyl-4-(pyridine-2- ylmethoxy)phenyl)amino)benzamide - (71) N-cyclopentyl-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (72) 3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)-N-(4-methylpentyl)benzamide - (73) 3-(3-cyclopentylpropoxy)-N-(4-(pyridin-2-ylmethoxy)phenyl)aniline - (74) 3-((2-methylpentyl)oxy)-N-(4-(pyridin-2-ylmethoxy)phenyl)aniline - (75) N-(2-(cyclohexyl)ethyl)-3-((2-ethyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (76) N-(2-(cyclohexyl)ethyl)-3-((2-cyclopropyl-4-(pyridine-2- ylmethoxy)phenyl)amino)benzamide - (77) N-(1-methylbutyl)-3-((2-methyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (78) N-(1-methylbutyl)-3-((2-ethyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (79) N-(2-(cyclohexyl)ethyl)-3-((2-cyclopropyl-4-(pyridine-2- ylmethoxy)phenyl)amino)benzenesulfonamide 35 27 - (80) (3-(cyclohexyl)propanamide), N-[3-([2-cyclopropyl-4-(pyridine-2-) [ylmethoxy]phenyl]amino)phenyl] - (81) N-(3-methylbutyl)-4-((2-cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (82) N-(2-(cyclopentyl)ethyl)-3-((2-cyclopropyl-4-(phenylmethoxy)phenyl)amino)benzamide - (83) 3-(3-cyclohexylpropoxy)-N-(2-cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl)aniline - (84) 3-((2-cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzamide - (85) N-(2-cyclohexylethyl)-3-((2-cyclopropyl-4-(pyridin-3-ylmethoxy)phenyl)amino)benzamide - (86) N-(2-cyclohexylethyl)-6-((2-cyclopropyl-4-(pyridine-2- ylmethoxy)phenyl)amino)picolinamide - (87) 3-((2-cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl)amino)benzenesulfonamide - (88) N-(2-cyclohexylethyl)-5-((2-cyclopropyl-4-(pyridine-2- ylmethoxy)phenyl)amino)nicotinamide - (89) N-(2-cyclopentylethyl)-3-((2-cyclopropyl-4-(pyridin-4-ylmethoxy)phenyl)amino)benzamide - (90) N-(2-cyclohexylethyl)-2-((2-cyclopropyl-4-(pyridine-2- ylmethoxy)phenyl)amino)isonicotinamide - (91) N-(3-{[4-(benzyloxy)-2-tert-butylphenyl]amino}phenyl)-3-cyclohexylpropamide - (92) N-(3-{[4-(benzyloxy)-2-(cyclopent-1-en-1-yl)phenyl]amino}phenyl)-3- cyclohexylpropanalamide - (93) N-(3-{[4-(benzyloxy)-2-cyclopentylphenyl]amino}phenyl)-3-cyclohexylpropanalamide - (94) N-(3-{[4-(benzyloxy)-2-(methylsulfanyl)phenyl]amino}phenyl)-3- cyclohexylpropanalamide - (95) N1-[4-(benzyloxy)-2-cyclopropylphenyl]-N3-(3-cyclohexylpropyl)benzene-1,3-diamine - (96) 1-(2-cyclohexyl)-3-[3-({2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}amino)phenyl]urea - (97) 1-(3-{ [4-(benzyloxy)-2-cyclopropylphenyl] amino}phenyl)-4-cyclohexylbutan-1-ol - (98) N-(3-{[4-(benzyloxy)-2-(trifluoromethyl)phenyl]amino}phenyl)-3-cyclohexylpropanalamide - (99) 3-cyclohexyl-N-[3-({4-[(4-fluorophenyl)methoxy]-2- (trifluoromethyl)phenyl}amino)phenyl]propanamide - (100) N-{3-[4-(cyclohexylmethyl)-1H-1,2,3-triazol-1-yl]phenyl}-2-cyclopropyl-4- [(pyridin-2-yl)methoxy]aniline - (101) 2-{[4-(benzyloxy)-2-tert-butylphenyl]amino} -N-(2-cyclohexylethyl)benzamide - (102) 1-cyano-N-[3-({ 2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)-2- methylphenyl]cyclopropane-1-carboxamide - (103) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-N-(3-cyclohexylpropyl)benzamide - (104) 3-{[4-(benzyloxy)-2-(trifluoromethyl)phenyl]amino}-N-(2-cyclopentylethyl)benzamide 35 28 - (105) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)-2-methylphenyl]-2-cyclopropylaniline - (106) 2-cyclopropyl-N-{3-[(4-methylpentyl)oxy]phenyl}-4-[(pyridin-2-yl)methoxy] aniline - (107) N-(3-{[4-(benzyloxy)-2-methanesulfonylphenyl]amino}phenyl)-3-cyclohexylpropamide - (108) N'1-[3-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)-2- methylphenyl]cyclopropane-1,1-dicarboxamide - (109) [3-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)-2- methylphenoxy]phosphonic acid - (110) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-N-(cyclohexylmethyl)benzamide - (111) N-(2-cyclohexylethyl)-3-({2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}(methyl)amino)benzamide - (112) 2-cyclopropyl-N-{3-[4-(3-methylbutyl)-1X-1,2,3-triazol-1-yl]phenyl}-4-[(pyridin-2- yl)methoxy]aniline - (113) N-(cyclopentylmethyl)-2-({2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}amino)benzamide - (114) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]-2-(morpholin-4-yl)aniline - (115) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-N-(2-cyclohexylethyl)benzamide - (116) N-(5-{[4-(benzyloxy)-2-(trifluoromethyl)phenyl]amino}-2-fluorophenyl)-3- cyclohexylpropamide - (117) N-(2-cyclohexylethyl)-4-({2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}amino)pyridine-2-carboxamide - (118) N-{3-[1-(3-cyclohexylpropyl)-1H-1,2,3,4-tetrazol-5-yl]phenyl}-2-cyclopropyl-4- [(pyridin-2-yl)methoxy]aniline - (119) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]-2-(propan-2-yl)aniline - (120) 2-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)-N-(3,3,3- trifluoropropyl)benzamide - (121) 3-cyclohexyl-N-[2-fluoro-5-({4-[(4-fluorophenyl)methoxy]-2- methylphenyl}amino)phenyl]propanamide - (122) 4-(benzyloxy)-N-[2-(3-cyclohexylpropansulfonyl)phenyl]-2-cyclopropylaniline - (123) 2-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)-N-(3-methylbutyl)benzamide - (124) 3-{[4-(benzyloxy)-2-(trifluoromethyl)phenyl]amino}-N-(2-cyclohexylethyl)benzene- 1-sulfonamide - (125) 3-cyclohexyl-N-[2-fluoro-5-({4-[(4-fluorophenyl)methoxy]-2- (trifluoromethyl)phenyl}amino)phenyl]propanamide - (126) 2-cyclopropyl-N-{3-[1-(4-methylpentyl)-1H-1,2,3,4-tetrazol-5-yl]phenyl}-4- [(pyridin-2-yl)methoxy]aniline 35 29 - (127) 2-cyclopropyl-N-{3-[5-(3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}-4-[(pyridin- 2-yl)methoxy]aniline - (128) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-6-cyano-N-(propan-2-yl)benzamide - (129) N-{3-[5-(2-cyclohexylethyl)-1,2,4-oxadiazol-3-yl]phenyl}-2-cyclopropyl-4- [(pyridin-2-yl)methoxy]aniline - (130) N-{3-[5-(2-cyclohexylethyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-cyclopropyl-4- [(pyridin-2-yl)methoxy]aniline - (131) 2-(azetidin-1-yl)-4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]aniline - (132) N-(3-{ [4-(benzyloxy)-2-methylphenyl]amino}phenyl)-3-cyclohexylpropanalamide - (133) [3-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)phenoxy]phosphonic acid - (134) tert-butyl 4-[3-({2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}amino)benzoyl]piperazine-1-carboxylate - (135) 2-(3-{ [4-(benzyloxy)-2-cyclopropylphenyl] amino}phenyl)-2-[(2- cyclohexylethyl)amino]acetic acid - (136) N-(1-cyanocyclopropyl)-2-({2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}amino)benzamide - (137) N-(3-cyclobutoxyphenyl)-2-cyclopropyl-4-[(pyridin-2-yl)methoxy] aniline - (138) methyl 2-(3-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}phenyl)-2-[(2- cyclohexylethyl)amino]acetate - (139) 2-{ [4-(benzyloxy)-2-methylphenyl]amino}-N-(2-cyclohexylethyl)benzamide - (140) 3-cyclohexyl-N-[3-({4-[(4-fluorophenyl)methoxy]-2- methylphenyl}amino)phenyl]propanamide - (141) 2-cyclopropyl-4-[(pyridin-2-yl)methoxy]-N-{3-[(trimethylsilyl)oxy]phenyl}aniline - (142) 4-(benzyloxy)-N-[3-(3-cyclohexylpropansulfonyl)phenyl]-2-cyclopropylaniline - (143) N-(2-cyclohexylethyl)-2-[(2-cyclopropyl-4-{ [4- (trifluoromethoxy)phenyl]methoxy}phenyl)amino]pyridine-4-carboxamide - (144) tert-butyl N-[2-(3-{ [4-(benzyloxy)-2-methylphenyl] amino}phenoxy)ethyl] carbamate - (145) 2-cyclopropyl-N-{3-[4-(2-methylpropyl)-1H-1,2,3-triazol-1-yl]phenyl}-4-[(pyridine- 2-yl)methoxy]aniline - (146) N-(5-{[4-(benzyloxy)-2-methylphenyl]amino}-2-fluorophenyl)-3-cyclohexylpropanamide - (147) 2-cyclopropyl-N-{3-[2-(2-methylpropyl)-2H-1,2,3,4-tetrazol-5-yl]phenyl}-4- [(pyridin-2-yl)methoxy]aniline - (148) N-[3-(3-cyclohexylpropoxy)phenyl]-2-methyl-4-[(pyridazin-3-yl)methoxy] aniline - (149) 4-(benzyloxy)-N-{3-[(3-cyclohexylpropyl)sulfanyl]phenyl}-2-cyclopropylaniline - (150) N-(3-{[4-(benzyloxy)-2-fluorophenyl]amino}phenyl)-3-cyclohexylpropanamide 35 30 - (151) 2-cyclopropyl-N-[3-(oxetan-3-yloxy)phenyl]-4-[(pyridin-2-yl)methoxy] aniline - (152) N-[3-(3-cyclohexylpropoxy)phenyl]-2-methyl-4-[(pyrimidin-2-yl)methoxy] aniline - (153) 3-cyclohexyl-N-{3-[(2-methyl-4-{[4-) (trifluoromethoxy)phenyl]methoxy}phenyl)amino]phenyl}propanamide - (154) 4-(benzyloxy)-N-[2-(3-cyclohexylpropoxy)phenyl]-2-cyclopropylaniline - (155) 2-(3-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}phenyl)-4-cyclohexylbutan-1,2-diol - (156) N-[3-(3-cyclohexylpropoxy)phenyl]-2-cyclopropyl-N-methyl-4-[(pyridine-2- yl)methoxy]aniline - (157) 3-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)phenyl diethyl phosphate - (158) N-(2-cyclohexylethyl)-3-[(2-cyclopropyl-4-{[4- (trifluoromethoxy)phenyl]methoxy}phenyl)amino]benzene-1-sulfonamide - (159) N-[3-(3-cyclohexylpropoxy)phenyl]-2-methyl-4-[(pyrimidin-4-yl)methoxy] aniline - (161) 2-cyclopropyl-N-{3-[2-(3-methylbut-2-en-1-yl)-2H-1,2,3,4-tetrazol-5-yl]phenyl}- 4-[(pyridin-2-yl)methoxy]aniline - (160) 3-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)-2-methylphenyl diethyl phosphate - (162) 2-cyclopropyl-N-{3-[2-(2-methoxyethyl)-2H-1,2,3,4-tetrazol-5-yl]phenyl}-4- [(pyridin-2-yl)methoxy]aniline - (163) 2-cyclopropyl-N-{3-[1-(cyclopropylmethyl)-1H-1,2,3,4-tetrazol-5-yl]phenyl}-4- [(pyridin-2-yl)methoxy]aniline - (164) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]-2-(oxan-4-yl)aniline - (165) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]-2-(3,6-dihydro-2H-pyran- 4-yl)aniline - (166) 5-(3-cyclohexylpropoxy)-N-{2-cyclopropyl-4-[(pyridine-2- yl)methoxy]phenyl}pyridine-3-amine - (167) 4-(benzyloxy)-N-{2-[(3-cyclohexylpropyl)sulfanyl]phenyl}-2-cyclopropylaniline - (168) 5-{ [4-(benzyloxy)-2-(trifluoromethyl)phenyl] amino}-2-fluorobenzamide - (169) 3-cyclohexyl-N-{3-[(2-cyclopropyl-4-{[4-(trifluoromethyl)phenyl, methoxy}phenyl}amino]phenyl}propanamide - (170) 3-cyclohexyl-N-[3-({2-cyclopropyl-4-[(4- methoxyphenyl)methoxy]phenyl}amino)phenyl]propanamide - (171) 2-(3-{[4-(benzyloxy)-2-methylphenyl]amino}phenoxy)ethane-1-ol - (172) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]aniline - (173) ethyl 5-(3-{[4-(benzyloxy)-2-methylphenyl]amino}phenoxy)pentanoate - (174) 4-(benzyloxy)-N-[3-(2-methoxyethoxy)phenyl]-2-methylaniline - (175) 4-(benzyloxy)-N-[3-(cyclopentylmethoxy)phenyl]-2-methylaniline 35 31 - (176) N-[3-(3-cyclohexylpropoxy)phenyl]-2-methyl-4-[(pyrimidin-5-yl)methoxy]aniline - (177) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)phenyl]-2-methylaniline - (178) 3-{1-[3-({2-cyclopropyl-4-[(pyridin-2-yl)methoxy]phenyl}amino)phenyl]-1H-1,2,3- triazole-4-yl}propan-1-ol - (179) 2-cyclopropyl-N-[3-(1,3-oxazol-5-yl)phenyl]-4-[(pyridin-2-yl)methoxy]aniline - (180) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-6-methyl-N-(propan-2-yl)benzamide - (181) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-N-(propan-2-yl)-6- (trifluoromethyl)benzamide - (182) [3-({2-cyclopropyl-4-[(pyridine-2- 1)methoxy]phenyl}amino)phenoxy](methoxy)phosphonic acid - (183) 5-(benzyloxy)-2-{ [3-(3-cyclohexylpropoxy)phenyl] amino}benzonitrile - (184) 2-{[4-(benzyloxy)phenyl]amino}-N-(2-cyclohexylethyl)benzamide - (185) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)-4-methylphenyl]-2-cyclopropylaniline - (186) 4-(benzyloxy)-N-[3-(3-cyclohexylpropoxy)-5-methylphenyl]-2-cyclopropylaniline - (187) 4-(benzyloxy)-N-[5-(3-cyclohexylpropoxy)-2-methylphenyl]-2-cyclopropylaniline - (188) 4-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-2-(3-cyclohexylpropoxy)benzamide - (189) 3-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-5-(3-cyclohexylpropoxy)benzamide - (190) N-(2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}phenyl)-3-cyclohexylpropanamide - (191) 3-{[4-(benzyloxy)-2-methylphenyl][3-(3- cyclohexylpropoxy)phenyl]amino}propanoic acid - (192) 2-(3-{[4-(benzyloxy)-2-methylphenyl]amino}phenoxy)acetic acid - (193) 5-(3-{[4-(benzyloxy)-2-methylphenyl]amino}phenoxy)pentanoic acid - (194) methyl 2-(3-{[4-(benzyloxy)-2-methylphenyl]amino} phenoxy)acetate - (195) 4-(benzyloxy)-2-methyl-N-[3-(trifluoromethoxy)phenyl]aniline - (196) 4-(benzyloxy)-2-methyl-N-{3-[(oxan-4-yl)methoxy]phenyl}aniline - (197) 4-(3-cyclohexylpropoxy)-N-{2-methyl-4-[(pyridin-3-yl)methoxy]phenyl}pyridin-2-amine - (198) 6-(3-cyclohexylpropoxy)-N-{2-methyl-4-[(pyridin-3-yl)methoxy]phenyl}pyridin-2-amine - (199) N-[4-(benzyloxy)-2-methylphenyl]-4-(3-cyclohexylpropoxy)pyridine-2-amine - (200) N-[4-(benzyloxy)-2-methylphenyl]-6-(3-cyclohexylpropoxy)pyridine-2-amine - (201) N-[3-(3-cyclohexylpropoxy)phenyl]-2-methyl-4-[(pyrazine-2-yl)methoxy] aniline - (202) N-(5-{[4-(benzyloxy)-2-fluorophenyl]amino}-2-fluorophenyl)-3-cyclohexylpropamide - (203) N-[3-(morpholin-4-yl)propyl]-3-({4-[(pyridin-2-yl)methoxy]phenyl}amino)benzamide - (204) 2-cyclopropyl-4-[(pyridin-2-yl)methoxy]-N-[3-(1H-1,2,3,4-tetrazol-5-yl)phenyl]aniline - (205) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-6-cyclopropyl-N-(propane-2- il)benzamide 35 32 - (206) 2-{[4-(benzyloxy)-2-cyclopropylphenyl]amino}-6-chloro-N-(propan-2-yl)benzamide and their pharmaceutically acceptable salts. The invention in question is the compounds (36) to (206) and their hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, tosylate, triflate, maleate, mesylate, formate, acetate and It includes pharmaceutically acceptable salts such as fumarate. From another perspective, the subject of the invention in question is intended for use as a medicine. compounds (36) to (206) or pharmaceutically acceptable salts thereof It relates to someone. From another perspective, the subject matter of the invention in question falls under Group IV of the Baltimore classification. or an RNA virus infection caused by an RNA virus belonging to the V gene to be used as an agent for the prevention, inhibition or treatment of a compound belonging to the formula (Ie) as defined above or its pharmaceutical any of the salts that can be accepted as and any of the compounds (36) to (206) It relates to one or any of its pharmaceutically acceptable salts. Compounds (38), (40), (43), (45), (46), (48), (49), (61), (62), (64), (35), (68), (82), (98), (119), (121), (132), (140), (150), (151), (156), (169), (175), (176) and (192) or these Any of the pharmaceutically acceptable salts of dengue fever can be used to treat dengue fever. It can be particularly useful for prevention, inhibition, or treatment. Compounds (36), (38), (39), (45), (46), (47), (54), (57), (60), (61), (64), (68), (70), (71), (72), (75)-(80), (82)-(86), (88)-(142), (147)-(156), (164)-(166) and (179) or these Any of the pharmaceutically acceptable salts of RSV can be used to treat RSV infection. It can be particularly useful for prevention, inhibition, or treatment. Compounds (36)-(41), (43), (45)-(52), (53), (54), (57), (58), (60)-(62), (64), (68), (70), (71) and (73) or any of their pharmaceutically acceptable salts, Prevention, inhibition, or treatment of chikungunya infection It can be particularly useful for this purpose. The invention's compounds may be combined with free bases or pharmaceutically acceptable acids. It may be present in the form of added salts. 35 33 "The pharmaceutically acceptable salt of this" is inorganic acids (e.g., hydrochloric acid). formed with acids, hydrobromic acid, sulfuric acid, phosphoric acid, nitric acid and the like) Besides acid additives and salts, acetic acid, oxalic acid, tartaric acid, succinic acid, and malic acid are also available. fumaric acid, maleic acid, ascorbic acid, benzoic acid, tannic acid, palmoic acid, alginic acid, polyglutamic acid, naphthalene sulfonic acid, naphthalene disulfonic acid, and polygalacturonic acid It refers to salts formed from organic acids, such as those mentioned above. Suitable, physiologically acceptable acid additive salts of the compounds belonging to formula (Ie). hydrobromide, tartrate, citrate, trifluoroacetate, ascorbate, hydrochloride, tosylate, triflate, maleate, It contains mesylate, formate, acetate, and fumarate. Compounds belonging to formula (Ie) and any of the compounds (36) to (206) or thereof any of the pharmaceutically acceptable salts are solvates or hydrates. It can be formed, and the invention includes all these solvates and hydrates. Compounds belonging to the formula (Ie) can also exist under tautomer forms and are part of the invention. The terms “hydrates” and “solvates” simply refer, according to the invention, to compounds (Ie) that are either a hydrate or a solvate. It can be in the form of one or more water or solvent molecules. This means that they can be combined or linked. This refers to such compounds. It is purely a chemical property and can be applied to all organic compounds of this type. In the context of the invention in question, the following term is used: - "halogen" means chlorine, fluorine, bromine, or iodine, and specifically chlorine, fluorine, or It is understood that it refers to bromine. - as used herein, “(C -C )alkyl”, C -C normal, secondary or 1 x 1 x It refers to a tertiary saturated hydrocarbon, for example, a (C -C )alkyl. Examples include these. 1 6 including but not limited to methyl, ethyl, 1-propyl, 2-propyl, butyl, pentyl, - an “alkenylene”, a divalent (C-C)alkyl group containing a double bond and more 1 x Specifically, it refers to an ethenylene group, also known as vinylene or 1,2-ethendiyl, • As used here, “(C -C )cycloalkyl” refers to a cyclic saturated hydrocarbon. 3 6 Examples include, but are not limited to, cyclopropyl, cyclobutyl, and cyclopentyl. It is cyclohexyl. 35 34 - as used herein, “(C-C)cycloalkenyl” means containing at least one unsaturated bond. 3 6 It refers to a cyclic non-aromatic hydrocarbon. Examples are not limited to these. These are cyclopentenil and cyclohexenil, but not exclusively. - As used here, “(C -C )alkoxy” refers to an O-(C -Cx)alkyl moiety, 1 x 1 Here, the alkyl group is the alkoxy as defined above, for example (C-C)alkoxy. Examples are limited to these. 1 6 not limited to, methoxy, ethoxy, 1-propoxy, 2-propoxy, butoxy, pentoxy, - as used here, "aryl" refers to a molecule containing 6 carbon atoms and nitrogen, oxygen, or a monocyclic aromatic group containing 0 to 2 heteroatoms such as sulfur and especially nitrogen It refers to examples of aryl groups, including but not limited to phenyl. Pyridine, pyrimidine, pyridazine, pyrazine, and similar compounds can be mentioned. The invention in question... In this context, aryl is advantageous compared to phenyl, pyridazine, pyrazine, pyridine, for example 2-pyridine or 3-pyridine and pyrimidine. Aryl, and more advantageously phenyl and pyridine, - as used here, “divalent 5-membered cell containing 1, 2, 3 or 4 heteroatoms” "Heteroaromatic ring", consisting of 5 chains and 1, 2, 3 or selected nitrogen and oxygen atoms. It refers to a divalent ring consisting of an aromatic ring containing 4 heteroatoms. In practice, it contains at least one heteroatom and preferably at least one nitrogen atom. Another In practice, for example, it contains at least one nitrogen atom and at least two heteroatoms. Another Depending on the application, it contains 2, 3 or 4 nitrogen atoms, preferably 3 nitrogen atoms. Even one according to other applications, one nitrogen atom and one oxygen atom or two nitrogen atoms and contains one oxygen atom. Examples include, but are not limited to, 1,2,3- or 1,2,4- Divalent triazoles such as triazoles, 1,2,4-oxadiazole or 1,2,3-oxadiazole These include oxdiazoles and divalent diazoles such as diazole and imidazole. Compounds with formula (I) may contain one or more asymmetric carbon atoms. Therefore, these exist in the form of enantiomers or diastereoisomers. These include enantiomers, diastereoisomers, and racemic mixtures. Mixtures of these are within the scope of the invention in question. The components of the invention in question are manufactured using traditional methods applied by experts in the field. It can be prepared using organic synthesis methods. The general reactions are outlined below. The series provide a useful general guide for preparing the components of the invention in question. It represents a procedure and is not intended to be restrictive in terms of scope or benefit. Compounds with the general formula (Ie) can be prepared according to Scheme 1 below. 35 35 The synthesis begins with a coupling from a halo-aromatic compound belonging to formula (III). It depends on the reaction, where R, R', m, m', ring, 1 2 1 2 The ring is X, X, n, Y, Y as defined above, and X is a chlorine atom, n is an iodine atom. or a bromine atom. According to an application, procedure (A1) , on the ring, according to the -NH- group, when in a commodity or currency position It can be used advantageously. According to route (A1), the compound with formula (III) is placed in a protic solvent such as tert-butanol. It can be placed. The compound belonging to formula (II) is an inorganic compound such as Cs CO or K CO. 2 3 2 3 35 36 in the presence of a base, in a molar ratio varying from 1 to 1.5 depending on the compound in the formula (III), For example, Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene), X-Fos (2- in the presence of a diphosphine such as dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) or rac-BINAP in a molar ratio ranging from 1 to 5 depending on the compound in formula (III), especially in the formula (III) according to the total amount of the compound and Pd(OAc), Pd dba or BrettPhos Pd G3 2 2 3 in the presence of an organometallic catalyst such as this, a concentration ranging from 2 molar to 15 molar. in an amount ranging from 2 moles to 25 moles of the total amount of the compound belonging to formula (III). It can be added in varying amounts. The reaction mixture is then heated from 80 to 130 °C. It can be heated to a temperature that varies, for example 90 °C, and for 15 to 25 hours. for a varying period of time, for example 20 hours, under an inert gas, for example argon. They can be mixed. The reaction mixture can be concentrated under low pressure and the residue, It can be diluted with an organic solvent such as ethyl acetate. The organic phase can be washed away with water. It can be drained, dried on magnesium sulfate, filtered, and then... It can be concentrated under low pressure to give a compound belonging to formulas (I) and (Ie). According to an application, procedure (A2) , On the ring, it is advantageous when it is in the ortho position relative to the -NH- group. It can be used in this way. According to procedure (A2), the compound with formula (II) is mixed with a polar aprotic solvent such as dimethyl sulfoxide. can be inserted. The compound belonging to formula (III) can then be placed in a container such as Cs CO or K CO, for example. 2 3 2 3 a molar value varying from 1 to 1.5 depending on the compound with formula (II) in the presence of an inorganic base in the ratio, for example in the presence of a ligand such as L-proline, from 1 to 5 depending on the compound in the formula (II). in a varying molar ratio, especially depending on the total amount of the compound belonging to formula (II) and such as CuI In the presence of an organometallic catalyst, in an amount ranging from 2 molar to 25 molar, Depending on the total amount of the compound in formula (II), it varies from 2 mol% to 25 mol%. 35 can be added in sufficient quantity. The reaction mixture is then heated at a temperature ranging from 80 to 130 °C. It can be heated to a temperature, for example 90 °C, and for a period ranging from 15 to 25 hours. For example, the reaction can be stirred for 20 hours under an inert gas, such as argon. The mixture can be diluted with an organic solvent such as ethyl acetate. The organic phase can be washed away with water. can be drained, dried on magnesium sulfate, filtered and then formulated (I) and can be concentrated under low pressure to give a compound of (Ie). The starting compounds for the formula (II) and (III) are available or can be determined by a person with expertise in the field. It can be prepared according to known methods. Accordingly, the document in question also includes matters not covered by the wording of the claims. for the production of new compounds belonging to the formula (I) and (Ie) as defined above. It describes the synthesis process, which is the most effective way to obtain a compound with the formula (I) or (Ie). at least one of the compounds belonging to formula (II) This involves the step of binding with a compound belonging to formula (III). 1 1 Here X, Y, R, R', m, m', ring, 35 38 2 2 The ring, X, Y is as defined above, where X is an inorganic base and Y is a diphosphine. in the presence of and in the presence of an organometallic catalyst a chlorine atom, an iodine atom or It is a bromine atom. According to the invention, compounds with the general formula (Ie) can be prepared according to Scheme 1 below. The synthesis starts from a halo aromatic compound with formula (IIIe) and ends with a compound with formula (IIe). It depends on a coupling reaction with the compound, where R, R', R", m, m', n, ring, 1 2 1 2 The ring, X, X, n, Y, Y, R and R are as defined above, and X is a chlorine atom, a ab It is either an iodine atom or a bromine atom. More specifically, the invention in question belongs to the formula (Ie) as defined above. 35 It relates to the synthesis process for producing compounds, which is a 39 of the formula (Ie). to obtain the compound in the presence of an inorganic base and a ligand and an organometallic In the presence of a catalyst, a compound with the formula (IIe) It includes at least one coupling step with a compound belonging to the formula (IIIe). 1 1 Here X, Y, R, R', m, m', n, ring, 2 2 The ring, X, Y, R, and R are as defined above, X being a chlorine atom and Y being an iodine atom. ab 1 or a bromine atom and Y is a phenyl group, a pyridine group, a pyrazine group, a It is a pyridazine group or a pyrimidine group. To satisfy (Ie), when R" ≠ H, an additional step (K) can be applied, where the compound, In the presence of NaH in a molar ratio ranging from 2 to 5, for example 3, anhydrous N,N- It can be placed in an anhydrous polar solvent such as dimethylformamide and the reaction the mixture for a period varying from 10 minutes to 50 minutes, for example, 30 minutes. It can be mixed at room temperature throughout. The halide derivative (R"-X) is then... Additions can be made, and the resulting mixture can last from 2 hours to 10 hours, for example, 5 hours. 35 a 40°C that varies over a period of time, for example from 70 to 110°C, such as 90°C. It can be stirred at a certain temperature. After cooling to room temperature, the reaction mixture can be stirred at a lower temperature. It can be concentrated under pressure, and the resulting residue is an organic compound such as ethyl acetate. It can be diluted with solvent. The organic phase is then dissolved in a saturated aqueous solution of brine. It can be washed with the solution, dried over MgSO, filtered and formulated (Ie). 4 It can be concentrated under low pressure to give a compound where R" ≠ H. More specifically, compounds with the formula (IIe) where R = R = H and the formula (Ie) ab When used to prepare related compounds, they can be prepared according to Scheme 6 below. If R or R ≠ H, then from the 4-nitrophenol derivative and the appropriate alcohol. ab A route starting from the derive and using classic Mitsunobu conditions, of this type It can produce compounds such as those defined in Table I herein (66 and 67). Preparation of (IIe) for (Ie). Intermediate compounds belonging to formulas (IIe) and (IVe) are, according to the invention, compounds belonging to formula (Ie). It is useful for preparation. According to route (I), the 4-nitrophenol derivative is poured into a polar solvent such as N,N-dimethylformamide. can be substituted. The 2-(bromomethyl)aryl derivative can then be used, for example, as CsCO or KCO. 2 3 2 3 in the presence of an inorganic base, for example, compared to the 4-nitrophenol derivative, still from 1 to 5 , in a varying molar ratio, for example, from 1 to 2 depending on the 4-nitrophenol derivative. It can be added in varying molar ratios. The reaction mixture is then heated from 50 to 150 °C. It can be heated to a temperature varying up to, for example, 90 °C and kept for 15 to 30 hours. for a period of time, for example 24 hours, under an inert gas, for example argon. They can be mixed. The reaction mixture can be concentrated under low pressure and the residue, It can be separated between an organic solvent such as dichloromethane and water. The organic phase separates into water. It can be washed, drained, dried on magnesium sulfate, filtered, and 35 It can be concentrated under low pressure to give a compound of the formula (IVe). 41 According to route (C), the compound with formula (IVe) and tin (II) chloride dihydrate, from 3 to 8 equivalents. It is placed in a protic solvent such as ethanol in varying proportions. The reaction mixture is then Then it can be heated to a temperature varying from 40 to 80 °C, for example, 60 °C and from 15 It can be mixed for a period of time varying up to an hour, for example, for 20 hours. The mixture can be poured into a 1N NaOH aqueous solution and treated with an organic solvent such as ethyl acetate. It can be extracted. The organic phase is then mixed with a saturated aqueous solution of water and saline. can be washed with, dried on magnesium sulfate, filtered and formulated (IIe) It can be concentrated under low pressure to give a compound. More specifically, compounds with the formula (IIe) where R = R, = H and an R' group ab (In other words, R') compounds belonging to the formula (Ie) are different from H and Me. c When used for preparation, it can be prepared according to Diagram 7 below. The preparation of (IIe) for (Ie) when R' ≠ Me and R' ≠ H cc Intermediate compounds belonging to formulas (IIe), (IVe) and (Ve) are, according to the invention, compounds belonging to formula (Ie). It is useful for preparation. According to route (I), the 4-nitrophenol derivative is poured into a polar solvent such as N,N-dimethylformamide. can be substituted. The 2-(bromomethyl)aryl derivative can then be used, for example, as CsCO or KCO. 2 3 2 3 in the presence of an inorganic base, for example, compared to the 4-nitrophenol derivative, still from 1 to 5 , in a varying molar ratio, for example, from 1 to 2 depending on the 4-nitrophenol derivative. It can be added in varying molar ratios. The reaction mixture is then heated from 50 to 150 °C. 35 42 It can be heated to a temperature varying up to, for example, 90 °C and kept for 15 to 30 hours. for a period of time, for example 24 hours, under an inert gas, for example argon. They can be mixed. The reaction mixture can be concentrated under low pressure and the residue, It can be separated between an organic solvent such as dichloromethane and water. The organic phase separates into water. It can be washed, drained, dried on magnesium sulfate, filtered, and It can be concentrated under low pressure to give a compound belonging to the formula (Ve). According to route (J), the compound belonging to formula (Ve) and the amount of the compound belonging to formula (Ve) are 2%. Pd(dppf)Cl .CH Cl in an amount varying from 20 moles to 20 moles. 2 2 2 An organometallic catalyst can be placed in a nonpolar solvent such as 1,4-dioxane. A boronic acid (R'-B(OH)₂) is then, for example, from 1 to 5 depending on the compound to which the formula (Ve) belongs. c 2 in a varying molar ratio, in the presence of an inorganic base such as K₂PO₄ or K₂CO₃, for example 3 4 2 3 Depending on the compound in the formula (Ve), it is still added in a molar ratio ranging from 2 to 5. The reaction mixture is then heated at a temperature ranging from 50 to 150 °C, for example. It can be heated to 100 °C and for a period ranging from 10 to 70 hours, for example 20 For hours, the reaction mixture can be stirred under an inert gas, such as argon. It can be concentrated under low pressure to give a compound with the formula (IVe). According to route (C), the compound with formula (IVe) and tin (II) chloride dihydrate, from 3 to 8 equivalents. It can be placed in a protic solvent such as ethanol in varying proportions. The reaction mixture is then Then it can be heated to a temperature varying from 40 to 80 °C, for example, 60 °C and from 15 It can be mixed for a period of time varying up to an hour, for example, for 20 hours. The mixture can be poured into a 1N NaOH aqueous solution and treated with an organic solvent such as ethyl acetate. It can be extracted. The organic phase is then mixed with a saturated aqueous solution of water and saline. can be washed with, dried on magnesium sulfate, filtered and formulated (IIe) It can be concentrated under low pressure to give a compound. Chemical structures and spectroscopic data of some compounds belonging to the formula (Ie) of the invention, These are shown in Table I and Table II below, respectively. Table I 35 43 (Ie) 36 37 38 39 40 41 42 43 44 45 35 44 (Yes) 46 47 48 49 50 51 52 53 54 55 35 45 (Yes) 56 57 58 59 60 61 62 63 64 65 35 46 (Yes) 66 67 68 69 70 71 72 73 74 75 35 47 (Yes) 76 77 78 79 80 81 82 83 84 85 35 48 (Yes) 86 87 88 89 90 91 92 93 94 35 49 (Yes) 95 96 97 98 99 100 101 102 103 35 50 (Yes) 104 105 106 107 108 109 110 111 35 51 (Yes) 112 113 114 115 116 117 118 119 35 52 (Yes) 120 121 122 123 124 125 126 127 35 53 (Yes) 128 129 130 131 132 133 134 135 35 54 (Yes) 136 137 138 139 140 141 142 143 144 35 55 (Yes) 145 146 147 148 149 150 151 152 153 35 56 (Yes) 154 155 156 157 158 159 160 161 162 35 57 (Yes) 163 164 165 166 167 168 169 170 35 58 (Yes) 171 172 173 174 175 176 177 178 179 35 59 (Yes) 180 181 182 183 184 185 186 187 35 60 (Yes) 188 189 190 191 192 193 194 195 196 35 61 (Yes) 197 198 199 200 201 202 203 204 205 35 62 (Ie) 206 Table II Örnek Karakterizasyonlar 1 36 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4.2 Hz, 1H), 8.30 (t, J = 5.4 Hz, 6 1H), 8.03 (s, 1H), 7.84 (td, J = 7.7, 1.7 Hz, 1H), 7.53 (d, J = 7.8 Hz, 1H), 7.39 - 7.32 (m, 2H), 7.20 (d, J = 7.8 Hz, 1H), 7.14 (d, J = 7.7 Hz, 1H), 7.06 (d, J = 9.0 Hz, 3H), 6.97 (d, J = 9.0 Hz, 2H), 5.14 (s, 2H), 3.22 (dd, J = 13.3, 6.8 Hz, 2H), 1.86 - 1.70 (m, 3H), 1.62 - 1.42 (m, 7H), 1.10 - 1.07 (m, 2H). + [M+H] = 416.0 1 37 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,1 Hz, 1H), 8.28 (t, J = 5,2 Hz, 6 1H), 8.03 (s, 1H), 7.84 (td, J = 7,7, 1,6 Hz, 1H), 7.52 (d, J = 7,8 Hz, 1H), 7.39 - 7.31 (m, 2H), 7.20 (d, J = 7,7 Hz, 1H), 7.14 (d, J = 7,6 Hz, 1H), 7.05 (d, J = 9,0 Hz, 2H), 6.97 (d, J = 9,0 Hz, 2H), 5.13 (s, 2H), 3.23 (dd, J = 13,2, 6,6 Hz, 2H), 1.59 (d, J = 6,6 Hz, 1H), 1.39 (dd, J = 13,2, 6,6 Hz, 2H), 0.89 (d, J = 6,6 Hz, 6H). + [M+H] = 390.0 1 38 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,2 Hz, 1H), 8.26 (t, J = 5,4 Hz, 6 1H), 8.03 (s, 1H), 7.84 (td, J = 7,7, 1,7 Hz, 1H), 7.52 (d, J = 7,9 Hz, 1H), 7.39 - 7.31 (m, 2H), 7.20 (d, J = 7,8 Hz, 1H), 7.13 (d, J = 7,7 Hz, 1H), 7.06 (d, J = 9,0 Hz, 2H), 7.03 (s, 1H), 6.97 (d, J = 9,0 Hz, 2H), 5.13 (s, 2H), 3.23 (dd, J = 13,2, 6,8 Hz, 2H), 1.77 - 1.55 (m, 5H), 1.39 (dd, J = 14,1, 6,8 Hz, 2H), 1.31 - 1.12 (m, 4H), 0.97 - 0.79 (m, 2H). + [M+H] = 430.3 35 63 Örnek Karakterizasyonlar 1 39 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,3 Hz, 1H), 8.26 (t, J = 5,5 Hz, 6 1H), 7.85 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,7 Hz, 1H), 7.47 (s, 1H), 7.35 (dd, J = 6,9, 5,5 Hz, 1H), 7.20 - 7.05 (m, 4H), 6.97 (d, J = 2,7 Hz, 1H), 6.85 (dd, J = 8,6, 2,7 Hz, 1H), 6.75 (d, J = 7,7 Hz, 1H), 5.16 (s, 2H), 3.21 (dd, J = 13,4, 6,5 Hz, 2H), 2.14 (s, 3H), 1.82 - 1.70 (m, 2H), 1.64 - 1.39 (m, 6H), 1.12 - 1.07 (m, 3H). 13 C NMR (75 MHz, d -DMSO) δ 165.1, 155.5, 153.2, 147.6, 145.4, 135.5, 6 134.4, 132.7, 132.3, 127.3, 123.6, 121.5, 120.1, 117.8, 115.6, 114.6, 114.2, 111.3, 111.2, 35.9, 34.0, 30.7, 23.2, 16.6 + [M+H] = 430.3 1 40 H NMR (300 MHz, CDCl ) δ 8.59 (d, J = 4,8 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.56 (d, J = 7,8 Hz, 1H), 7.36 - 7.31 (m, 1H), 7.24 - 7.17 (m, 2H), 7.10 (d, J = 7,7 Hz, 1H), 7.03 - 6.98 (m, 1H), 6.95 (d, J = 2,4 Hz, 1H), 6.90 (dd, J = 8,6, 2,6 Hz, 1H), 6.78 (d, J = 8,6 Hz, 1H), 6.25 (t, J= 5,3 Hz, 1H), 5.78 (s, 2H), 5.18 (s, 1H), 3.42 (dd, J = 14,5, 6,0 Hz, 2H), 2.30 (s, 3H), 1.88 - 1.73 (m, 3H), 1.63 - 1.47 (m, 6H), 1.15 - 1.10 (m, 2H). 1 41 H NMR (300 MHz, d -DMSO) δ 8.56 (d, J = 4,1 Hz, 1H), 8.32 (t, J = 5,7 Hz, 6 1H), 8.13 (s, 1H), 7.97 (d, J= 2,7 Hz, 1H), 7.81 (td, J = 7,7, 1,7 Hz, 1H), 7.57 (dd, J = 8,8, 2,8 Hz, 1H), 7.46 (d, J = 7,9 Hz, 1H), 7.34 (s, 1H), 7.33 - 7.29 (m, 1H), 7.23 (d, J = 7,7 Hz, 1H), 7.18 (d, J = 7,6 Hz, 1H), 7.01 (d, J = 8,6 Hz, 1H), 6.93 (d, J = 8,8 Hz, 1H), 5.38 (s, 1H), 3.22 (dd, J = 13,8, 6,3 Hz, 1H), 1.83 - 1.70 (m, 1H), 1.62 - 1.40 (m, 1H). 1 42 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,8 Hz, 1H), 7.85 (t, J = 5,5 Hz, 1H), 3 7.73 (td, J = 7,7, 1,7 Hz, 1H), 7.61 - 7.51 (m, 3H), 7.24 (d, J = 9,0 Hz, 3H), 6.99 (d, J = 8,9 Hz, 2H), 6.77 (dd, J = 6,5, 2,7 Hz, 1H), 6.43 (s, 1H), 5.21 (s, 2H), 3.44 (dd, J = 14,1, 6,4 Hz, 2H), 1.89 - 1.79 (m, 3H), 1.66 - 1.53 (m, 6H), 1.18 - 1.12 (m, 2H). 1 43 H NMR (300 MHz, CDCl ) δ 8.58 (d, J = 4,2 Hz, 1H), 7.71 (td, J = 7,7, 1,7 Hz, 3 1H), 7.58 (d,J = 7,7 Hz, 1H), 7.36 (s, 1H), 7.25 - 7.17 (m, 2H), 7.11 (d, J = 7,7 Hz, 1H), 7.04 (dd, J = 8,0, 1,5 Hz, 1H), 6.82 (d, J = 8,5 Hz, 1H), 6.73 (d, J = 2,4 Hz, 1H), 6.61 (dd, J = 8,5, 2,5 Hz, 1H), 6.03 (s, 1H), 5.65 (s, 1H), 5.26 (s, 2H), 3.87 (s, 3H), 3.44 (dd, J = 14,5, 6,0 Hz, 2H), 1.86 - 1.76 (m, 3H), 1.57 - 1.52 (m, 5H), 1.18 - 1.08 (m, 2H). + [M+H] = 446.4 1 44 H NMR (300 MHz, d -DMSO) δ 8.99 (s, 1H), 8.58 (d, J = 4,1 Hz, 1H), 8.31 (t, J 6 = 5,6 Hz, 1H), 7.97 (d, J = 3,1 Hz, 1H), 7.94 (s, 1H), 7.84 (tt, J = 4,7, 2,4 Hz, 2H), 7.54 (d, J = 7,8 Hz, 1H), 7.41 (dd, J = 9,0, 3,1 Hz, 1H), 7.35 (dd, J = 7,0, 5,3 Hz, 1H), 7.30 - 7.21 (m, 2H), 6.84 (d, J = 9,0 Hz, 1H), 5.17 (s, 2H), 3.24 (dd, J = 13,9, 6,3 Hz, 2H), 1.84 - 1.72 (m, 3H), 1.64 - 1.43 (m, 6H), 1.18 - 1.02 (m, 2H). + [M+H] = 417.4 35 64 Örnek Karakterizasyonlar 1 45 H NMR (300 MHz, CDCl ) δ 8.59 (d, J = 4,8 Hz, 1H), 7.72 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.27 - 7.22 (m, 1H), 7.19 (d, J = 7,8 Hz, 1H), 7.15 - 7.12 (m, 1H), 7.11 (d, J = 8,6 Hz, 1H), 7.06 (d, J = 7,7 Hz, 1H), 6.89 (d, J = 2,8 Hz, 1H), 6.81 - 6.76 (m, 1H), 6.36 (t, J = 5,3 Hz, 1H), 5.45 (s, 1H), 5.17 (s, 1H), 3.49 (dd, J = 12,9, 6,8 Hz, 2H), 2.18 (s, 3H), 1.48 (dd, J = 12,9, 6,8 Hz, 2H), 0.76 - 0.62 (m, 1H), 0.45 (dt, J = 8,0, 5,0 Hz, 1H), 0.07 (dt, J = 8,0, 5,0 Hz, 1H). + [M+H] = 402.3 1 46 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.26 - 7.23 (m, 1H), 7.19 (t, J = 7,8 Hz, 1H), 7.14 - 7.11 (m, 2H), 7.04 (d, J = 7,7 Hz, 1H), 6.90 (d, J = 2,9 Hz, 1H), 6.80 (dd, J = 9,3, 3,0 Hz, 2H), 5.98 (s, 1H), 5.32 (s, 1H), 5.20 (s, 2H), 3.35 (dd, J = 13,4, 6,7 Hz, 1H), 2.35 (dt, J = 15,5, 7,8 Hz, 1H), 2.20 (s, 3H), 2.15 - 2.02 (m, 2H), 1.94 - 1.79 (m, 2H), 1.68 - 1.63 (m, 4H). + [M+H] = 416.3 1 47 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,3 Hz, 1H), 8.22 (t, J = 5,6 Hz, 6 1H), 7.85 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.45 (s, 1H), 7.35 (dd, J = 6,9, 5,2 Hz, 1H), 7.14 (d, J = 7,8 Hz, 1H), 7.11 - 7.04 (m, 3H), 6.97 (d, J = 2,7 Hz, 1H), 6.85 (dd, J = 8,6, 2,8 Hz, 1H), 6.75 (d, J = 7,7 Hz, 1H), 5.16 (s, 2H), 3.22 (dd, J = 13,2, 6,6 Hz, 2H), 2.14 (s, 3H), 1.73 - 1.63 (m, 5H), 1.42 - 1.35 (m, 2H), 1.32 - 1.11 (m, 4H), 0.94 - 0.83 (m, 2H). + [M+H] = 444.4 1 48 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.35 - 7.28 (m, 1H), 7.25 - 7.19 (m, 2H), 7.08 (d, J = 8,9 Hz, 2H), 7.00 (dd, J = 8,4, 1,9 Hz, 1H), 6.95 (d, J = 8,9 Hz, 2H), 5.98 (s, 1H), 5.61 (s, 1H), 5.20 (s, 2H), 3.35 (dd, J = 13,5, 6,5 Hz, 2H), 2.36 (dt, J = 15,6, 7,9 Hz, 1H), 2.16 - 2.00 (m, 2H), 1.97 - 1.79 (m, 2H), 1.72 - 1.65 (m, 4H). + [M+H] = 402.3 1 49 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,1 Hz, 1H), 8.31 (t, J = 5,6 Hz, 6 1H), 8.02 (s, 1H), 7.84 (td, J = 7,7, 1,8 Hz, 1H), 7.52 (d, J = 7,8 Hz, 1H), 7.37 (d, J = 1,9 Hz, 1H), 7.36 - 7.31 (m, 1H), 7.20 (d, J = 7,7 Hz, 1H), 7.14 (d, J = 7,7 Hz, 1H), 7.06 (d, J = 9,0 Hz, 1H), 6.97 (d, J = 9,0 Hz, 2H), 5.13 (s, 2H), 3.27 (dd, J = 14,3, 7,1 Hz, 2H), 1.40 (dd, J = 14,3, 7,1 Hz, 2H), 0.70 (m, 1H), 0.39 (dd, J = 12,0, 3,9 Hz, 2H), 0.04 (dd, J = 12,0, 3,9 Hz, 2H). + [M+H] = 388.3 1 50 H NMR (300 MHz, d -DMSO) δ 8.31 (t, J = 5.6 Hz, 1H), 8.05 (s, 1H), 7.57 6 (td, J = 7.4, 1.5 Hz, 1H), 7.47 - 7.36 (m, 2H), 7.30 - 7.19 (m, 3H), 7.15 (d, J = 7.7 Hz, 1H), 7.07 (d, J = 9.0 Hz, 2H), 7.05 -7.0 (m, 1H), 6.98 (d, J = 9.0 Hz, (2H), 5.10 (s, 2H), 3.23 (dd, J = 13.8, 6.3 Hz, 2H), 1.86 - 1.72 (m, 3H), 1.62 - 1.45 (m, 6H), 1.11 - 1.04 (m, 2H). 13 C NMR (75 MHz, d -DMSO) δ 164.6, 160.2, 156.9, 151.1, 143.3, 134.4, 6 134.2, 128.9, 128.8, 128.4, 127.1, 122.7, 122.7, 122.4, 122.2, 118.7, 117.4 115.3, 114.9, 113.8, 113.4, 111.8, 62.0, 35.6, 33.7, 30.4, 22.9 35 65 Örnek Karakterizasyonlar 1 51 H NMR (300 MHz, d -DMSO) δ 8.30 (t, J = 5.5 Hz, 1H), 8.07 (s, 1H), 7.92 (d, J 6 = 7,6 Hz, 1H), 7.81 - 7.72 (m, 2H), 7.62 - 7.55 (m, 1H), 7.40 (s, 1H), 7.22 (d, J = 7,7 Hz, 1H), 7.16 (d, J = 7,7 Hz, 1H), 7.08 (d, J = 9,0 Hz, 2H), 7.01 (d, J = 9,1 Hz, 2H), 5.21 (s, 2H), 3.23 (dd, J = 13,9, 6,2 Hz, 2H), 1.79 - 1.70 (m, 3H), 1.60 - 1.49 (m, 7H). 1 52 H NMR (300 MHz, d -DMSO) δ 8.29 (t, J = 5,6 Hz, 1H), 8.01 (s, 1H), 7.44 6 (dd, J = 9,5, 4,1 Hz, 3H), 7.41 - 7.30 (m, 4H), 7.20 (d, J = 7,7 Hz, 1H), 7.14 (d, J = 7,7 Hz, 1H), 7.06 (d, J = 9,0 Hz, 2H), 7.00 (s, 1H), 6.97 (d, J = 9,0 Hz, 2H), 5.07 (s, 2H), 3.23 (dd, J = 13,7, 6,2 Hz, 2H), 1.79 - 1.70 (m, 3H), 1.63 - 1.46 (m, 6H). 1 53 H NMR (300 MHz, d -DMSO) δ 8.76 (d, J = 5,0 Hz, 1H), 8.32 (t, J = 5,3 Hz, 6 1H), 8.25 (t, J = 6,7 Hz, 1H), 7.90 (d, J = 7,8 Hz, 1H), 7.70 (s, 1H), 7.44 (s, 1H), 7.31 - 7.14 (m, 2H), 7.07 (d, J = 7,1 Hz, 1H), 6.93 (d, J = 8,6 Hz, 1H), 6.67 (d, J = 2,4 Hz, 1H), 6.49 (dd, J = 8,6, 2,3 Hz, 1H), 5.27 (s, 2H), 3.23 (dd, J = 13,4, 6,4 Hz, 2H), 1.82 - 1.73 (m, 3H), 1.62 - 1.43 (m, 6H), 1.12 - 1.04 (m, 2H). + [M+H] = 432.3 1 54 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,0 Hz, 1H), 8.23 (t, J = 5,6 Hz, 6 1H), 7.85 (td, J = 7,7, 1,8 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.45 (s, 1H), 7.36 (dd, J = 6,9, 5,3 Hz, 1H), 7.16 (t, J = 7,8 Hz, 1H), 7.12 - 7.04 (m, 3H), 6.97 (d, J = 2,8 Hz, 1H), 6.85 (dd, J = 8,6, 2,9 Hz, 1H), 6.74 (dd, J = 7,9, 1,5 Hz, 1H), 5.16 (s, 2H), 3.22 (dd, J = 13,8, 6,3 Hz, 2H), 2.14 (s, 3H), 1.68 - 1.51 (m, 1H), 1.38 (dd, J = 14,4, 6,9 Hz, 2H), 0.89 (d, J = 6,6 Hz, 6H). + [M+H] = 404.3 1 55 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,2 Hz, 1H), 7,73 (td, J = 7,7, 1,7 Hz, 3 1H), 7,54 (d, J = 7,8 Hz, 1H), 7.34 (d, J = 1,7 Hz, 1H), 7.29 - 7.21 (m, 3H), 7.07 (d, J = 8,9 Hz, 2H), 7.05 - 7.01 (m, 1H), 6.95 (d, J = 8,9 Hz, 2H), 5.89 (s, 1H), 5.19 (s, 2H), 4.67 (t, J = 6,1 Hz, 1H), 2.95 (dd, J = 14,3, 6,6 Hz, 2H), 1.78 - 1.62 (m, 3H), 1.60 - 1.42 (m, 6H), 1.05 - 0.94 (m, 2H). + [M+H] = 452.3 1 56 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,2 Hz, 1H), 8.29 (s, 1H), 7.85 6 (td, J = 7,7, 1,8 Hz, 1H), 7.53 (d, J = 7,7 Hz, 1H), 7.42 (t, J = 5,6 Hz, 1H), 7.38 - 7.27 (m, 3H), 7.10 - 7.06 (m, 4H), 7.01 (d, J = 9,0 Hz, 2H), 5.16 (s, 2H), 2.81 - 2.69 (m, 2H), 1.64 - 1.53 (m, 5H), 1.26 - 1.10 (m, 6H), 0.83 - 0.69 (m, 2H). + [M+H] = 466.3 1 57 H NMR (300 MHz, CDCl) δ 8.59 (d, J = 4.5 Hz, 1H), 7.72 (td, J = 7.7, 1.7 Hz, 3 1H), 7.55 (d, J = 7.8 Hz, 1H), 7.28 - 7.16 (m, 2H), 7.16 - 7.09 (m, 2H), 7.04 (d, J = 7.7 Hz, 1H), 6.92 (d, J = 2.8 Hz, 1H), 6.81 - 6.72 (m, 2H), 6.23 (t, J = 5.3 Hz, 1H), 5.44 (s, 1H), 5.18 (s, 2H), 3.41 (dd, J = 14.6, 6.0 Hz, 2H), 2.54 (q, J = 7.5 Hz, 2H), 1.72 - 1.57 (m, 1H), 1.46 (dd, J = 14.7, 7.1 Hz, 2H), 1.14 (t, J = 7.5 Hz, 3H), 0.92 (d, J = 6.6 Hz, 6H). + [M+H] = 418.3 35 66 Örnek Karakterizasyonlar 1 58 H NMR (300 MHz, CDCl) δ 8.60 (d, J = 4.8 Hz, 1H), 7.73 (td, J = 7.7, 1.7 Hz, 3 1H), 7.55 (d, J = 7,8 Hz, 1H), 7.27 - 7.19 (m, 1H), 7.17 - 7.11 (m, 3H), 7.04 (d, J = 7,8 Hz, 1H), 6.93 (d, J = 2,9 Hz, 1H), 6.83 - 6.73 (m, 2H), 6.13 (t, J = 5,2 Hz, 1H), 5.38 (s, 1H), 5.20 (s, 2H), 3.42 (dd, J = 14,4, 6,1 Hz, 2H), 2.56 (q, J = 7,5 Hz, 2H), 1.86 - 1.75 (m, 3H), 1.66 - 1.49 (m, 6H), 1.15 (t, J = 7,5 Hz, 3H), 1.11 - 1.07 (m, 2H). + [M+H] = 444.2 1 59 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,1 Hz, 1H), 8.29 (s, 1H), 7.84 6 (td, J = 7,7, 1,8 Hz, 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.47 (t, J = 5,8 Hz, 1H), 7.39 - 7.28 (m, 3H), 7.12 - 7.06 (m, 4H), 7.00 (d, J = 9,0 Hz, 2H), 5.15 (s, 2H), 2.78 (dd, J = 13,4, 7,0 Hz, 2H), 1.28 - 1.20 (m, 2H), 0.71 - 0.57 (m, 1H), 0.37 - 0.29 (m, 2H), -0.02 - -0.08 (m, 2H). + [M+H] = 424.2 1 60 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,2 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,7 Hz, 1H), 7.26 - 7.19 (m, 3H), 7.16 (d, J = 8,6 Hz, 1H), 7.08 (d, J = 7,7 Hz, 1H), 6.95 (dd, J = 7,7, 1,7 Hz, 1H), 6.78 (dd, J = 8,6, 2,9 Hz, 1H), 6.68 (d, J = 2,9 Hz, 1H), 6.03 (s, 1H), 5.71 (s, 1H), 5.18 (s, 2H), 3.43 (dd, J = 9,8, 4,7 Hz, 2H), 1.90 - 1.78 (m, 5H), 1.66 - 1.51 (m, 4H), 1.17 - 1.09 (m, 3H), 0.94 - 0.87 (m, 2H), 0.67 - 0.59 (m, 2H). 13 C NMR (75 MHz, CDCl3) δ 165.4, 155.1, 152.7, 146.9, 143.9, 135.4, 134.5, 133.8, 132.2, 127.0, 120.9, 120.3, 119.0, 115.3, 114.4, 111.8, 111.2, 110.0, 68.6, 37.2, 35.6, 33.6, 30.4, 22.8, 9.3, 4.9 + [M+H] = 456.4 1 61 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,5 Hz, 1H), 7.72 (td, J = 7,7, 1,6 Hz, 3 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.28 - 7.18 m, 3H), 7.15 (d, J = 8,7 Hz, 1H), 7.08 (d, J = 7,7 Hz, 1H), 6.93 (dd, J = 7,9, 1,7 Hz, 1H), 6.77 (dd, J = 8,6, 2,9 Hz, 1H), 6.67 (d, J = 2,8 Hz, 1H), 6.11 (s, 1H), 5.74 (s, 1H), 5.17 (s, 2H), 3.44 (dd, J = 14,5, 6,0 Hz, 2H), 1.91 - 1.82 (m, 1H), 1.71 - 1.60 (m, 1H), 1.48 (dd, J = 14,7, 7,1 Hz, 2H), 0.94 (d, J = 6,6 Hz, 6H), 0.92 - 0.85 (m, 2H), 0.66 - 0.56 (m, 2H). + [M+H] = 430.3 1 62 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,2 Hz, 1H), 8.34 (t, J = 5,6 Hz, 6 1H), 8.04 (s, 1H), 7.85 (td, J = 7,7, 1,7 Hz, 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.37 - 1.33 (m, 2H), 7.21 (d, J = 7,7 Hz, 1H), 7.15 (d, J = 7,6 Hz, 1H), 7.07 (d, J = 9,0 Hz, 2H), 7.10 - 7.01 (m, 1H), 6.98 (d, J = 9,0 Hz, 2H), 5.14 (s, 2H), 3.15 (t, J = 6,3 Hz, 2H), 2.19 - 2.07 (m, 1H), 1.72 - 1.44 (m, 6H), 1.30 - 1.18 (m, 2H). + [M+H] = 402.3 1 63 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,1 Hz, 1H), 8.52 (t, J = 6,0 Hz, 6 1H), 8.07 (s, 1H), 7.85 (td, J = 7,7, 1,7 Hz, 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.39 (s, 1H), 7.35 (dd, J = 7,3, 5,7 Hz, 1H), 7.23 (d, J = 7,7 Hz, 1H), 7.18 (d, J = 7,7 Hz, 1H), 7.07 (d, J = 8,9 Hz, 2H), 7.09 - 7.03 (m, 1H), 6.98 (d, J = 9,0 Hz, 2H), 5.14 (s, 2H), 4.47 (d, J = 5,7 Hz, 2H), 4.19 (d, J = 5,7 Hz, 2H), 3.42 (d, J = 6,1 Hz, 2H), 1.24 (s, 3H). + [M+H] = 404.2 35 67 Örnek Karakterizasyonlar 1 64 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,1 Hz, 1H), 8.04 - 8.01 (m, 2H), 6 7.85 (td, J = 7,7, 1,8 Hz, 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.37 - 7.33 (m, 2H), 7.21 (d, J = 7,7 Hz, 1H), 7.16 (d, J = 7,6 Hz, 1H), 7.06 (d, J = 9,0 Hz, 2H), 7.02 - 7.00 (m, 1H), 6.98 (d, J = 9,0 Hz, 2H), 5.14 (s, 2H), 4.05 - 3.92 (m, 1H), 1.57 - 1.25 (m, 4H), 1.11 (d, J = 6,6 Hz, 3H), 0.87 (t, J = 7,2 Hz, 3H). + [M+H] = 390.1 1 65 H NMR (300 MHz, d -DMSO) δ 8.58 (d, J = 4,1 Hz, 1H), 8.54 (d, J = 5,7 Hz, 6 1H), 8.08 (s, 1H), 7.85 (td, J = 7,7, 1,8 Hz, 1H), 7.53 (d, J = 7,9 Hz, 1H), 7.38 (d, J = 2,0 Hz, 1H), 7.37 - 7.32 (m, 1H), 7.23 (d, J = 7,8 Hz, 1H), 7.14 (d, J = 7,7 Hz, 1H), 7.07 (d, J = 9,0 Hz, 2H), 7.03 - 7.01 (m, 1H), 6.98 (d, J = 9,0 Hz, 2H), 5.14 (s, 2H), 3.46 (dd, J = 12,6, 6,8 Hz, 2H), 2.50 (dd, J = 12,6, 6,8 Hz, 2H). + [M+H] = 416.1 1 66 H NMR (300 MHz, d -DMSO) δ 8.56 (d, J = 4,2 Hz, 1H), 8.25 (t, J = 5,7 Hz, 6 1H), 7.80 (td, J = 7,7, 1,7 Hz, 1H), 7.46 (d, J = 7,9 Hz, 1H), 7.40 (s, 1H), 7.30 (dd, J = 6,9, 5,4 Hz, 1H), 7.12 (d, J= 7,7 Hz, 1H), 7.09 - 7.05 (m, 2H), 7.02 (d, J = 10,0 Hz, 1H), 6.95 (d, J = 11,7 Hz, 1H), 6.84 (d, J = 2,8 Hz, 1H), 6.69 (dd, J = 8,6, 2,9 Hz, 2H), 5.41 (q, J = 6,5 Hz, 1H), 3.20 (dd, J = 13,6, 6,4 Hz, 1H), 2.08 (s, 3H), 1.82 - 1.70 (m, 4H), 1.58 (d, J = 6,5 Hz, 3H), 1.54 - 1.42 (m, 5H), 1.09 (t, J = 7,0 Hz, 3H). + [M+H] = 444.2 1 67 H NMR (300 MHz, d -DMSO) δ 8.56 (d, J = 4,2 Hz, 1H), 8.23 (t, J = 5,6 Hz, 6 1H), 7.80 (td, J = 7,7, 1,7 Hz, 1H), 7.46 (d, J = 7,9 Hz, 1H), 7.40 (s, 1H), 7.30 (ddd, J = 7.5, 4.8, 1,0 Hz, 1H), 7.12 (d, J = 7,8 Hz, 1H), 7.09 - 7.05 (m, 2H), 7.02 (d, J = 9,5 Hz, 1H), 6.95 (d, J = 11,8 Hz, 1H), 6.85 (d, J = 2,8 Hz, 1H), 6.73 - 6.65 (m, 2H), 5.42 (q, J = 6,4 Hz, 1H), 3.21 (dd, J = 13,7, 6,4 Hz, 2H), 2.08 (s, 3H), 1.58 (d, J = 6,5 Hz, 4H), 1.37 (dd, J = 14,4, 6,9 Hz, 2H), 0.88 (d, J = 6,6 Hz, 6H). + [M+H] = 418.3 1 68 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,5 Hz, 1H), 8.15 (s, 1H), 7.85 6 (td, J = 7,9, 1,5 Hz, 1H), 7.54 (d, J = 7,9 Hz, 1H), 7.39 - 7.31 (m, 1H), 7.18 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.96 - 6.90 (m, 2H), 6.82 (dd, J = 8,6, 2,8 Hz, 1H), 6.73 (s, 1H), 6.67 (d, J = 7,9 Hz, 1H), 6.21 (d, J = 7,9 Hz, 1H), 5.92 (t, J = 5,4 Hz, 1H), 5.14 (s, 2H), 3.06 (dd, J = 13.3, 6,7 Hz, 2H), 2.14 (s, 3H), 1.57 (td, J = 13,3, 6,7 Hz, 1H), 1.33 - 1.25 (m, 2H), 0.88 (d, J = 6,7 Hz, 6H). + [M+H] = 419.4 1 69 H NMR (300 MHz, d -DMSO) δ 8.93 (d, J = 6,4 Hz, 1H), 8.59 (d, J = 4,8 Hz, 6 1H), 7.85 (td, J = 7,8, 1,8 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.49 (s, 1H), 7.36 (dd, J = 6,7, 5,0 Hz, 1H), 7.23 - 7.12 (m, 3H), 7.08 (d, J = 8,6 Hz, 1H), 6.97 (d, J = 2,8 Hz, 1H), 6.85 (dd, J = 8,6, 2,9 Hz, 1H), 6.77 (d, J = 7,5 Hz, 1H), 5.16 (s, 2H), 4.96 (dd, J = 14,0, 7,1 Hz, 1H), 4.74 (t, J = 6,9 Hz, 2H), 4.57 (t, J = 6,4 Hz, 2H), 2.14 (s, 3H). + [M+H] = 490.3 35 68 Örnek Karakterizasyonlar 1 70 H NMR (300 MHz, d -DMSO) δ 8,59 (d, J = 4,5 Hz, 1H), 8.29 (t, J = 5,7 Hz, 6 1H), 7.85 (dd, J = 7,7, 6,1 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.47 (s, 1H), 7.40 - 7.32 (m, 1H), 7.17 (s, 1H), 7.12 - 7.04 (m, 3H), 6.97 (d, J = 2,7 Hz, 1H), 6.85 (dd, J = 8,6, 2,7 Hz, 1H), 6.75 (d, J = 7,8 Hz, 1H), 5.16 (s, 2H), 3.19 (dd, J = 12,5, 6,4 Hz, 2H), 2.76 - 2.57 (m, 3H), 2.33 - 2.15 (m, 2H), 2.14 (s, 3H), 1.68 (q, J = 6,8 Hz, 2H). + [M+H] = 452.3 1 71 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,6 Hz, 1H), 8.11 (d, J = 7,3 Hz, 6 1H), 7.85 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.44 (s, 1H), 7.36 (dd, J = 7,3, 4,8 Hz, 1H), 7.14 (dd, J = 14,1, 6,3 Hz, 2H), 7.07 (d, J = 8,8 Hz, 2H), 6.97 (d, J = 2,7 Hz, 1H), 6.85 (dd, J = 8,6, 2,8 Hz, 1H), 6.73 (d, J = 7,5 Hz, 1H), 5.16 (s, 2H), 4.17 (dd, J = 14,0, 7,1 Hz, 1H), 2.14 (s, 3H), 1.93 - 1.79 (m, 2H), 1.71 - 1.62 (m, 2H), 1.58 - 1.46 (m, 4H). + [M+H] = 402.3 1 72 [ H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,8 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.27 - 7.21 (m, 1H), 7.20 (d, J = 7,6 Hz, 1H), 7.16 (s, 1H), 7.12 (d, J = 8,6 Hz, 1H), 7.05 (d, J = 7,6 Hz, 1H), 6.90 (d, J = 2,7 Hz, 1H), 6.83 - 6.73 (m, 2H), 6.14 (s, 1H), 5.39 (s, 1H), 5.18 (s, 2H), 3.39 (dd, J = 13,2, 7,1 Hz, 2H), 2.19 (s, 3H), 1.63 - 1.50 (m, 3H), 1.27 - 1.20 (m, 2H), 0.88 (d, J = 6,6 Hz, 6H). + [M+H] = 418.3 1 73 H NMR (300 MHz, CDCl ) δ 8.59 (d, J = 5,2 Hz, 1H), 7.71 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d,J = 7,7 Hz, 1H), 7.21 (dd, J = 7,0, 5,2 Hz, 1H), 7.12 -7.03 (m, 3H), 6.96 - 6.89 (m, 2H), 6.50 - 6.44 (m, 2H), 6.38 (dd, J = 7,7, 1,7 Hz, 1H), 5.55 (br s, 1H), 5.18 (s, 2H), 3.88 (t, J = 6,6 Hz, 2H), 1.82 - 1.68 (m, 7H), 1.66 - 1.46 (m, 5H), 1.17 - 1.04 (m, 3H). + [M+H] = 403.4 1 74 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,8 Hz, 1H), 7.73 (td, J = 7,7, 1,6 Hz, 3 1H), 7.54 (d, J = 7,9 Hz, 1H), 7.22 (d, J = 7,0 Hz, 1H), 7.14 - 7.04 (m, 3H), 6.98 - 6.93 (m, 2H), 6.51 - 6.45 (m, 2H), 6.42 - 6.35 (m, 1H), 5.49 (s, 1H), 5.19 (s, 2H), 3.76 (dd, J = 9,0, 5,8 Hz, 1H), 3.66 (dd, J = 9,0, 5,8 Hz, 1H), 1.94 - 1.83 (m, 1H), 1.51 - 1.32 (m, 4H), 1.21 - 1.13 (m, 2H), 0.99 (d, J = 6,7 Hz, 3H), 0.91 (t, J = 7,1 Hz, 3H). + [M+H] = 377.3 1 75 H NMR (300 MHz, CDCl3) δ 8.61 (d, J = 4,8 Hz, 1H), 7.74 (td, J = 7,7, 1,7 Hz, 1H), 7.56 (d, J = 7,8 Hz, 1H), 7.22 (dd, J = 7,5, 1,6 Hz, 1H), 7.19 - 7.12 (m, 3H), 7.03 (d, J = 7,7 Hz, 1H), 6.94 (d, J = 2,9 Hz, 1H), 6.81 (dd, J = 8,6, 2,9 Hz, 1H), 6.77 (dd, J = 8,0, 1,8 Hz, 1H), 5.99 (s, 1H), 5.33 (s, 1H), 5.21 (s, 2H), 3.44 (dd, J = 14,4, 6,1 Hz, 2H), 2.56 (q, J = 7,5 Hz, 2H), 1.81 - 1.65 (m, 6H), 1.48 (dd, J = 14,6, 7,0 Hz, 2H), 1.37 - 1.27 (m, 2H), 1.16 (t, J = 7,5 Hz, 4H), 0.99 - 0.91 (m, 2H). + [M+H] = 458.1 35 69 Örnek Karakterizasyonlar 1 76 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,1 Hz, 1H), 7.73 (t, J = 7,8 Hz, 1H), 3 7.54 (d, J = 7,6 Hz, 1H), 7.25 - 7.20 (m, 2H), 7.16 (d, J = 8,6 Hz, 1H), 7.08 (d, J = 7,6 Hz, 1H), 6.96 (t, J = 7,8 Hz, 1H), 6.78 (dd, J = 8,7, 2,9 Hz, 1H), 6.68 (d, J = 2,8 Hz, 1H), 5.99 (s, 1H), 5.71 (s, 1H), 5.18 (s, 2H), 3.45 (dd, J = 14,6, 7,0 Hz, 2H), 1.91 - 1.82 (m, 1H), 1.77 - 1.72 (m, 5H), 1.49 (dd, J = 14,6, 7,0 Hz, 2H), 1.30 - 1.17 (m, 3H), 1.02 - 0.83 (m, 5H), 0.63 (q, J = 5,8 Hz, 2H). + [M+H] = 470.4 1 77 H NMR (300 MHz, CDCl ) δ 8,61 (d, J = 4,2 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.25 - 7.16 (m, 3H), 7.13 (d, J = 8,6 Hz, 1H), 7.03 (d, J = 7,7 Hz, 1H), 6.90 (d, J = 2,7 Hz, 1H), 6.83 - 6.75 (m, 2H), 5.81 (d, J = 8,1 Hz, 1H), 5.33 (s, 1H), 5.20 (s, 2H), 4.23 - 4.08 (m, 1H), 2.20 (s, 3H), 1.55 - 1.45 (m, 2H), 1.44 - 1.32 (m, 2H), 1.21 (d, J = 6,6 Hz, 3H), 0.93 (t, J = 7,1 Hz, 3H). + [M+H] = 404.4 1 78 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,8 Hz, 1H), 7.74 (td, J = 7,7, 1,7 Hz, 3 1H), 7.56 (d,J = 7,7 Hz, 1H), 7.22 (dd, J = 8,1, 2,5 Hz, 1H), 7.18 - 7.12 (m, 3H), 7.01 (d, J = 7,9 Hz, 1H), 6.94 (d, J = 2,9 Hz, 1H), 6.81 (dd, J = 8,7, 3,0 Hz, 1H), 6.76 (dd, J = 8,1, 1,7 Hz, 1H), 5.80 (d, J = 8,7 Hz, 1H), 5.32 (s, 1H), 5.21 (s, 2H), 4.23 - 4.14 (m, 1H), 2.57 (q, J = 7,5 Hz, 2H), 1.55 - 1.34 (m, 4H), 1.21 + (d, J = 6,6 Hz, 3H), 1.17 (t, J = 7,6 Hz, 3H), 0.93 (t, J = 7,1 Hz, 3H). [M+H] = 418.4 1 79 H NMR (300 MHz, CDCl ) δ 8.62 (d, J = 4,8 Hz, 1H), 7.74 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,7 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.27 - 7.21 (m, 3H), 7.16 (d, J = 8,7 Hz, 1H), 7.00 - 6.94 (m, 1H), 6.80 (dd, J = 8,7, 2,8 Hz, 1H), 6.68 (d, J = 2,8 Hz, 1H), 5.77 (s, 1H), 5.19 (s, 2H), 4.23 (t,J = 6,0 Hz, 1H), 2.99 (dd, J = 14,0, 7,0 Hz, 2H), 1.93 - 1.87 (m, 1H), 1.70 - 1.56 (m, 5H), 1.35 (dd, J = 14,0, 7,0 Hz, 2H), 1.22 - 1.10 (m, 4H), 0.94 - 0.88 (m, 2H), 0.87 - 0.80 (m, 2H), 0.67 - 0.59 (m, 2H). + [M+H] = 506.4 1 80 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,4 Hz, 1H), 7.72 (td, J = 7,7, 1,6 Hz, 3 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.26 - 7.08 (m, 5H), 6.83 (d, J = 7,9 Hz, 1H), 6.78 (dd, J = 8,7, 2,9 Hz, 1H), 6.68 (d, J = 2,8 Hz, 1H), 6.60 (d, J = 7,2 Hz, 1H), 5.64 (s, 1H), 5.17 (s, 2H), 2.37 - 2.28 (m, 2H), 1.87 (dq, J = 8,3, 5,2 Hz, 1H), 1.73 - 1.56 (m, 10H), 1.31 - 1.14 (m, 8H), 0.99 - 0.83 (m, 5H), 0.61 (q, J = 5,2 Hz, 2H). + [M+H] = 470.4 1 81 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,8 Hz, 1H), 7.74 (td, J = 7,7, 1,8 Hz, 3 1H), 7.62 (d, J = 8,4 Hz, 2H), 7.54 (d, J = 7,7 Hz, 1H), 7.24 (d, J = 6,6 Hz, 1H), 7.18 (d, J = 8,7 Hz, 1H), 6.85 - 6.74 (m, 3H), 6.67 (d, J = 2,9 Hz, 1H), 5.93 (t, J = 5.2 Hz, 1H), 5.80 (s, 1H), 5.19 (s, 2H), 3.51 - 3.40 (m, 2H), 1.93 - 1.82 (m, 1H), 1.76 - 1.66 (m, 1H), 1.50 (dd, J = 14,7, 7,1 Hz, 2H), 0.95 (d, J = 6,6 Hz, (6H), 0.93 - 0.87 (m, 2H), 0.67 - 0.57 (m, 2H). + [M+H] = 430.3 35 70 Örnek Karakterizasyonlar 1 82H NMR (300 MHz, CDCl₂) δ 7.45 - 7.33 (m, 5H), 7.21 (d, J = 7.8 Hz, 1H), 7.16 3 (d, J = 8.6 Hz, 1H), 7.08 (d, J = 7.6 Hz, 1H), 6.94 (d, J = 6.5 Hz, 1H), 6.78 (dd, J = 8.7, 2.9 Hz, 1H), 6.66 (d, J = 2.7 Hz, 1H), 6.02 (s, 1H), 5.70 (s, 1H), 5.03 (s, 2H), 3.48 (dd, J = 14.0, 7.0 Hz, 2H), 1.92 - 1.76 (m, 5H), 1.61 (dd, J = 14.2, 7.1 Hz, 5H), 1.17 - 1.10 (m, 2H), 0.94 - 0.87 (m, 2H), 0.67 - 0.59 (m, 2H). + [M+H] = 455.3 1 83 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,2 Hz, 1H), 7.72 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d,J = 7,8 Hz, 1H), 7.25 - 7.20 (m, 1H), 7.18 (d, J = 8,7 Hz, 1H), 7.09 (t, J = 8,0 Hz, 1H), 6.77 (dd, J = 8,7, 2,9 Hz, 1H), 6.68 (d, J = 2,9 Hz, 1H), 6.45 (d, J = 8,0 Hz, 1H), 6.42 (t, J = 2,1 Hz, 1H), 6.37 (d, J = 8,1 Hz, 1H), 5.60 (s, 1H), 5.17 (s, 2H), 3.88 (t, J = 6,6 Hz, 2H), 1.88 (tt, J = 8,4, 5,4 Hz, 1H), 1.80 - 1.62 (m, 8H), 1.26 (ddt, J = 24,7, 14,6, 6,6 Hz, 7H), 0.91 (dd, J = 12,6, 6,2 Hz, 4H), 0.62 (q, J = 5,9 Hz, 2H). + [M+H] = 457.4 1 84 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,6 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d,J = 7,8 Hz, 1H), 7.34 -7.30 (m, 1H), 7.28 - 7.21 (m, 2H), 7.17 -7.14 (m, 2H), 6.98 (dd, J = 7,9, 1,8 Hz, 1H), 6.79 (dd, J = 8,6, 2,9 Hz, 1H), 6.68 (d, J = 2,9 Hz, 1H), 6.07 (s, 1H), 5.73 (s, 2H), 5.17 (s, 2H), 1.91 - 1.82 (m, 1H), 0.95 - 0.86 (m, 2H), 0.66 - 0.58 (m, 2H). + [M+H] = 360.0 1 85 H NMR (300 MHz, CDCl ) δ 8.69 (d, J = 1,6 Hz, 1H), 8.59 (dd, J = 4,8, 1,4 Hz, 3 1H), 7.79 (d, J = 7,9 Hz, 1H), 7.34 (dd, J = 7,8, 4,9 Hz, 1H), 7.30 - 7.29 (m, 1H), 7.22 (d, J = 7,8 Hz, 1H), 7.18 (d, J = 8,7 Hz, 1H), 7.08 (d, J = 7,7 Hz, 1H), 6.96 (dd, J = 8,0, 1,7 Hz, 1H), 6.78 (dd, J = 8,7, 2,9 Hz, 1H), 6.66 (d, J = 2,8 Hz, 1H), 6.01 (s, 1H), 5.74 (s, 1H), 5.05 (s, 2H), 3.45 (dd, J = 14,6, 7,0 Hz, 2H), 1.92 - 1.82 (m, 1H), 1.79 - 1.59 (m, 6H), 1.49 (dd, J = 14,6, 7,0 Hz, 2H), 1.41 - 1.29 (m, 1H), 1.19 - 1.13 (m, 2H), 1.01 - 0.87 (m, 4H), 0.67 - 0.60 (m, 2H). + [M+H] = 470.4 1 86 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,3 Hz, 1H), 7.86 - 7.82 (m, 1H), 7.74 3 (t, J = 7,7 Hz, 1H), 7.60 - 7.51 (m, 3H), 7.33 (d, J = 8,7 Hz, 1H), 7.25 - 7.22 (m, 1H), 6.82 (dd, J = 8,7, 2,9 Hz, 1H), 6.68 (d, J = 2,8 Hz, 1H), 6.65 (dd, J = 6,6, 2,6 Hz, 1H), 6.39 (s, 1H), 5.19 (s, 2H), 3.46 (dd, J = 14,6, 7,0 Hz, 2H), 1.97 - 1.87 (m, 1H), 1.81 - 1.61 (m, 7H), 1.52 (dd, J = 14,6, 7,0 Hz, 2H), 1.43 - 1.29 (m, 1H), 1.29 - 1.12 (m, 3H), 1.02 - 0.90 (m, 4H), 0.68 - 0.61 (m, 2H). + [M+H] = 471.3 1 87 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,2 Hz, 1H), 7.74 (td, J = 7,7, 1,8 Hz, 3 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.32 - 7.29 (m, 3H), 7.24 - 7.22 (m, 1H), 7.15 (d, J = 8,6 Hz, 1H), 7.00 - 6.94 (m, 1H), 6.80 (dd, J = 8,6, 2,9 Hz, 1H), 6.67 (d, J = 2,9 Hz, 1H), 5.76 (s, 1H), 5.18 (s, 2H), 4.74 (s, 2H), 1.90 - 1.81 (m, 1H), 0.95 - 0.87 (m, 2H), 0.66 - 0.60 (m, 2H). + [M+H] = 396.2 35 71 Örnek Karakterizasyonlar 1 88 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,8 Hz, 1H), 8.29 (d, J = 1,7 Hz, 1H), 3 8.27 (d, J = 2,8 Hz, 1H), 7.74 (td, J = 7,7, 1,7 Hz, 1H), 7.53 (d, J = 7,9 Hz, 1H), 7.51 - 7.48 (m, 1H), 7.23 (d, J = 7,0 Hz, 1H), 7.14 (d, J = 8,6 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.68 (d, J = 2,8 Hz, 1H), 6.08 (s, 1H), 5.74 (s, 1H), 5.18 (s, 2H), 3.47 (dd, J = 14,7, 7,0 Hz, 2H), 1.90 - 1.80 (m, 1H), 1.78 - 1.61 (m, 6H), 1.50 (dd, J = 14,7, 7,0 Hz, 2H), 1.38 - 1.30 (m, 2H), 1.01 - 0.86 (m, 4H), 0.67 - 0.60 (m, 2H). + [M+H] = 471.3 1 89 H NMR (300 MHz, CDCl ) δ 8.62 (d, J = 6,0 Hz, 2H), 7.36 (d, J = 6,0 Hz, 2H), 3 7.32 - 7.29 (m, 1H), 7.23 (t, J = 7,9 Hz, 1H), 7.17 (d, J = 8,6 Hz, 1H), 7.08 (d, J = 7,8 Hz, 1H), 6.96 (dd, J = 8,0, 1,6 Hz, 1H), 6.74 (dd, J = 8,6, 2,9 Hz, 1H), 6.66 (d, J = 2,8 Hz, 1H), 6.07 (s, 1H), 5.74 (s, 1H), 5.05 (s, 2H), 3.44 (dd, J = 14,5, 6,0 Hz, 2H), 1.92 - 1.77 (m, 4H), 1.71 - 1.50 (m, 7H), 1.18 - 1.10 (m, 2H), 0.96 - 0.86 (m, 2H), 0.68 - 0.59 (m, 2H). + [M+H] = 456.4 1 90 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 5,5 Hz, 1H), 8.22 (d, J = 5,5 Hz, 1H), 3 7.73 (td, J = 7,7, 1,6 Hz, 1H), 7.53 (d, J = 7,9 Hz, 1H), 7.38 (d, J = 8,7 Hz, 1H), 7.23 (d, J = 7,9 Hz, 1H), 6.90 - 6.79 (m, 3H), 6.68 (d, J = 2,8 Hz, 1H), 6.56 (s, 1H), 5.96 (s, 1H), 5.19 (s, 2H), 3.43 (dd, J = 14,8, 7,0 Hz, 2H), 1.94 - 1.84 (m, 1H), 1.78 - 1.61 (m, 6H), 1.48 (dd, J = 14,8, 7,0 Hz, 2H), 1.38 - 1.14 (m, 4H), 1.01 - 0.88 (m, 3H), 0.66 - 0.61 (m, 2H). + [M+H] = 471.3 1 91 H NMR (400 MHz, DMSO-d6) δ 9.52 (s, 1H), 7.48 (d, J = 7,1 Hz, 2H), 7.41 (t, J = 7,4 Hz, 2H), 7.37 - 7.32 (m, 1H), 7.01 - 6.96 (m, 2H), 6.96 - 6.85 (m, 4H), 6.71 (s, 1H), 6.21 (d, J = 8,2 Hz, 1H), 5.08 (s, 2H), 2.26 - 2.17 (m, 2H), 1.64 (dt, J = 17,6, 10,7 Hz, 5H), 1.43 (q, J = 7,0 Hz, 2H), 1.32 (s, 9H), 1.17 (qd, J = 19,9, 17,7, 8,0 Hz, 4H), 0.86 (q, J = 10,4, 9,1 Hz, 2H) + [M+H] = 485.3 1 92 H NMR (400 MHz, DMSO-d6) δ 7.52 - 7.22 (m, 5H), 6.76 - 6.53 (m, 3H), 6.01 (s, 1H), 4.97 (s, 2H), 4.50 (s, 2H), 2.62 (t, J = 6,6 Hz, 2H), 1.89 (p, J = 7,5 Hz, 2H) + [M+H] = 495.3 1 93 H NMR (400 MHz, DMSO-d6) δ 9.55 (s, 1H), 7.55 - 7.27 (m, 5H), 7.17 (s, 1H), 7.08 - 6.73 (m, 6H), 6.27 (d, J = 8,9 Hz, 1H), 5.08 (s, 2H), 3.26- 3.13 (m, 1H), 2.28 - 2.15 (m, 2H), 1.89 (d, J = 6,1 Hz, 2H), 1.79 - 1.36 (m, 14H), 1.28 - 1.04 (m, 4H), 0.87 (q, J = 10.4, 8,9 Hz, 2H) 13 C NMR (151 MHz, DMSO) δ 171.6, 156.2, 149.1, 144.4, 140.5, 137.8, 133.5, 129.3, 128.8, 128.2, 128.2, 127.9, 113.5, 112.9, 109.1, 108.5, 104.4, 69.8, 37.2, 34.4, 34.2, 33.1, 33.0, 26.6, 26.2, 25.6 + [M+H] = 497.3 35 72 Sample Characterizations 1 94 H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 7.49 (d, J = 7.1 Hz, 2H), 7.42 (t, J = 7.3 Hz, 2H), 7.38 – 7.32 (m, 1H), 7.16 (s, 1H), 7.07 (d, J = 8.6 Hz, 1H), 6.97 (t, J = 7.9 Hz, 1H), 6.92 (d, J = 8.1 Hz, 1H), 6.89 – 6.85 (m, 2H), 6.81 (dd, J = 8.5, 2.8 Hz, 1H), 6.30 (d, J = 7.6 Hz, 1H), 5.13 (s, 2H), 2.35 (s, 3H), 2.27 – 2.21 (m, 2H), 1.72 – 1.59 (m, 5H), 1.45 (q, J = 7.1 Hz, 2H), 1.25 – 1.11 (m, 4H), 0.93 − 0.81 (m, 2H) + [M+H] = 475.2 1 95 H NMR (400 MHz, DMSO-d6) δ 7.44 (d, J = 6,9 Hz, 2H), 7.39 (t, J = 7,3 Hz, 2H), 7.35 - 7.29 (m, 1H), 7.01 (d, J = 8,6 Hz, 2H), 6.82 (t, J = 7,5 Hz, 1H), 6.76 (dd, J = 8,6, 2,9 Hz, 1H), 6.46 (d, J = 2,9 Hz, 1H), 5.97 (s, 3H), 5.03 (s, 2H), 2.88 (t, J = 7,1 Hz, 2H), 1.97 (s, 1H), 1.65 (d, J = 10,9 Hz, 5H), 1.48 (q, J = 7,4 Hz, 2H), 1.23 - 1.07 (m, 6H), 0.90 - 0.79 (m, 4H), 0.64 - 0.55 (m, 2H) + [M+H] = 455.3 1 96 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,4 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d, J = 7,9 Hz, 1H), 7.28 - 7.20 (m, 1H), 7.15 (d, J = 8,6 Hz, 1H), 7.11 (t, J = 8,1 Hz, 1H), 6.81 (t, J = 2,0 Hz, 1H), 6.76 (dd, J = 8,7, 2,9 Hz, 1H),6.67 - 6.63 (m, 2H), 6.57 (dd, J = 8,0, 1,6 Hz, 1H), 6.33 (s, 1H), 5.16 (s, 2H), 4.81 (t, J = 5,5 Hz, 1H), 3.24 (dd, J = 13,9, 6,4 Hz, 2H), 1.92 - 1.79 (m, 1H), 1.72 - 1.57 (m, 5H), 1.38 (dd, J = 13,9, 6,9 Hz, 2H), 1.29 - 1.12 (m, 4H), 0.97 - 0.81 (m, 4H), 0.66 - 0.55 (m, 2H) + [M+H] = 485.5 1 97 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.36 - 7.30 (m, 1H), 7.28 (s, 1H), 7.01 (t, J = 8,7 Hz, 2H), 6.77 (dd, J = 8.6, 2,9 Hz, 1H), 6.67 (s, 1H), 6.56 (d, J = 7,5 Hz, 1H), 6.52 (dd, J = 8,0, 1,7 Hz, 1H), 6.48 (d, J = 2,8 Hz, 1H), 5.05 (s, 2H), 4.91 (d, J = 4,1 Hz, 1H), 4.33 (q, J = 5,2 Hz, 1H), 1.95 (ddd, J = 13,7, 8,4, 5,3 Hz, 1H), 1.68 - 1.57 (m, 5H), 1.54 - 1.40 (m, 2H), 1.38 - 1.26 (m, 1H), 1.26 - 1.06 (m, 7H), 0.88 - 0.75 (m, 4H), 0.66 - 0.57 (m, 2H) + [M+H] = 470.3 1 98 H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 7.48 (d, J = 7,2 Hz, 2H), 7.42 (t, J = 7,4 Hz, 2H), 7.36 (d, J = 7,1 Hz, 1H), 7.30 (dd, J = 6,8, 3,7 Hz, 4H), 7.03 (d, J = 2,6 Hz, 1H), 7.01 (d, J = 8,0 Hz, 1H), 6.95 (d, J = 8,1 Hz, 1H), 6.42 (d, J = 7,8 Hz, 1H), 5.17 (s, 2H), 2.28 - 2.20 (m, 2H), 1.72 - 1.56 (m, 5H), 1.44 (q, J = 7,1 Hz, 2H), 1.25 - 1.09 (m, 4H), 0.93 - 0.81 (m, 2H) + [M+H] = 497.1 1 99 H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 7.53 (dd, J = 8,5, 5,7 Hz, 2H), 7.34 - 7.27 (m, 4H), 7.24 (t, J = 8,9 Hz, 2H), 7.06 - 6.99 (m, 2H), 6.94 (d, J = 8,1 Hz, 1H), 6.42 (d, J = 8,8 Hz, 1H), 5.15 (s, 2H), 2.28 - 2.20 (m, 2H), 1.72 - 1.56 (m, 5H), 1.44 (q, J = 7,1 Hz, 2H), 1.25 - 1.07 (m, 4H), 0.87 (s, 2H) + [M+H] = 515.1 35 73 Örnek Karakterizasyonlar 1 100 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,2 Hz, 1H), 7.73 (td, J= 7,7, 1,7 Hz, 3 1H), 7.63 (s, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.32 - 7.26 (m, 1H), 7.26 - 7.22 (m, 2H), 7.20 (d, J = 8,7 Hz, 1H), 7.04 (dd, J = 7,9, 1,2 Hz, 1H), 6.86 - 6.77 (m, 2H), 6.69 (d, J = 2,9 Hz, 1H), 5.18 (s, 2H), 2.65 (d, J = 6,8 Hz, 2H), 1.96 - 1.85 (m, 1H), 1.79 - 1.64 (m, 6H), 1.29 - 1.17 (m, 3H), 1.04 - 0.97 (m, 2H), 0.95 - 0.89 (m, 2H), 0.66 - 0.61 (m, 2H) + [M+H] = 480.6 101 1H NMR (400 MHz, DMSO-d6) δ 9.47 (s, 1H), 8.40 (s, 1H), 7.61 (d, J = 6,9 Hz, 1H), 7.48 (d, J = 7,1 Hz, 2H), 7.41 (t, J = 7,4 Hz, 2H), 7.34 (t, J = 7,2 Hz, 1H), 7.16 (t, J = 7.7 Hz, 1H), 7.06 (d, J = 8.6 Hz, 1H), 7.00 (d, J = 2.8 Hz, 1H), 6.90 (dd, J = 8.6, 2.8 Hz, 1H), 6.61 (t, J = 7.4 Hz, 1H), 6.49 (d, J = 8.4 Hz, 1H), 5.09 (s, 2H), 3.27 (d, J = 6.8 Hz, 2H), 1.74 (d, J = 12.2 Hz, 2H), 1.64 (dd, J = 20.5, 11.1 Hz, 3H), 1.44 (q, J = 6.9 Hz, 2H), 1.31 (s, 9H), 1.26 - 1.13 (m, 4H), 0.90 (q, J = 13.3, 12.5 Hz, 2H) 13 C NMR (151 MHz, DMSO) δ 169.5, 156.0, 148.9, 147.5, 137.7, 132.5, 132.3, 130.2, 128.9, 128.8, 128.3, 128.2, 116.1, 115.7, 114.6, 113.4, 112.7, 69.8, 37.2, 37.0, 35.2, 35.1, 33.2, 30.5, 26.6, 26.2 + [M+H] = 485.3 1 102 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4.4 Hz, 1H), 7.99 (s, 1H), 7.73 (td, J 3 = 7,7, 1,8 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.22 (d, J = 6,8 Hz, 1H), 7.13 (dd, J = 7,9, 1,4 Hz, 1H), 7.08 (t, J = 7,9 Hz, 1H), 6.93 (d, J = 8,5 Hz, 1H), 6.82 (dd, J = 7,7, 1,4 Hz, 1H), 6.77 - 6.73 (m, 2H), 5.51 (bs, 1H), 5.17 (s, 2H), 2.20 (s, 3H), 1.81 (dd, J = 8,2, 4,5 Hz, 2H), 1.62 (dd, J = 8,1, 4,5 Hz, 2H), 0.90 (dt, J = 6,1, 4,2 Hz, 2H), 0.64 (td, J = 5,9, 4,2 Hz, 2H) 1 103 H NMR (400 MHz, DMSO-d6) δ 9.52 (s, 1H), 8.43 (t, J = 5,6 Hz, 1H), 7.64 - 7.56 (m, 1H), 7.45 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (dd, J = 8,3, 6,0 Hz, 1H), 7.20 (t, J = 7,2 Hz, 1H), 7.12 (d, J = 8,6 Hz, 1H), 6.83 (dd, J = 8,7, 2,9 Hz, 1H), 6.75 (d, J = 8,3 Hz, 1H), 6.67 (t, J = 7,4 Hz, 1H), 6.60 (d, J = 2,9 Hz, 1H), 5.07 (s, 2H), 3.22 (q, J = 6,8 Hz, 2H), 1.90 - 1.78 (m, 1H), 1.67 (t, J = 13,7 Hz, 4H), 1.58 (d, J = 7,0 Hz, 1H), 1.53 (q, J = 7,3 Hz, 2H), 1.27 - 1.08 (m, 6H), 0.87 (ddd, J = 8,4, 6,2, 4,3 Hz, 4H), 0.65 - 0.59 (m, 2H) + [M+H] = 483.2 1 104 H NMR (400 MHz, DMSO-d6) δ 8.25 (t, J = 5,6 Hz, 1H), 7.48 (d, J = 5,9 Hz, 3H), 7.45 - 7.28 (m, 6H), 7.23 - 7.11 (m, 3H), 6.87 - 6.80 (m, 1H), 5.18 (s, 2H), 3.21 (q, J = 6,3 Hz, 2H), 1.76 (s, 3H), 1.52 (ddq, J = 27.4, 13.0, 7,2 Hz, 6H), 1.08 (d, J = 3,5 Hz, 2H) + [M+H] = 483.1 1 105 H NMR (400 MHz, DMSO-d6) δ 7.44 (d, J = 7,1 Hz, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.35 - 7.30 (m, 1H), 6.90 - 6.84 (m, 2H), 6.76 (dd, J = 8,6, 2,8 Hz, 1H), 6.53 - 6.48 (m, 2H), 6.38 (d, J = 8,1 Hz, 1H), 6.11 (d, J = 8,1 Hz, 1H), 5.04 (s, 2H), 3.90 (t, J = 6,3 Hz, 2H), 2.07 (s, 3H), 1.89 (ddd, J = 13,7, 8,4, 5,3 Hz, 1H), 1.75 - 1.60 (m, 7H), 1.36 - 1.12 (m, 6H), 0.89 (q, J = 10,6, 9,6 Hz, 2H), 0.83 - 0.77 (m, 2H), 0.62 - 0.56 (m, 2H) + [M+H] = 470.4 35 74 Örnek Karakterizasyonlar 1 106 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,3 Hz, 1H), 7.72 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,9 Hz, 1H), 7.25-7.20 (m, 1H), 7.18 (d, J = 8,7 Hz, 1H), 7.10 (t, J = 8.0 Hz, 1H), 6.77 (dd, J = 8.7, 2.9 Hz, 1H), 6.68 (d, J = 2.9 Hz, 1H), 6.48 - 6.44 (m, 1H), 6.42 (t, J = 2.1 Hz, 1H), 6.37 (dd, J = 8.0, 1.8 Hz, 1H), 5.17 (s, 2H), 3.89 (t, J = 6.7 Hz, 2H), 1.94 - 1.82 (m, 1H), 1.80-1.70 (m, 2H), 1.65 - 1.52 (m,1H), 1.35 - 1.26 (m, 2H), 0.95 - 0.87 (m, 8H), 0.66 - 0.58 (m, 2H) + [M+H] = 417.4 1 107 H NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 7.48 (d, J = 7,1 Hz, 2H), 7.45 - 7.39 (m, 4H), 7.38 - 7.34 (m, 3H), 7.32 (dd, J = 8.9, 2,7 Hz, 1H), 7.15 (t, J = 8,0 Hz, 1H), 7.10 (d, J = 8,4 Hz, 1H), 6.69 (d, J = 7,4 Hz, 1H), 5.15 (s, 2H), 3.19 (s, 3H), 2.31 - 2.23 (m, 2H), 1.73 - 1.58 (m, 5H), 1.47 (q, J = 7,1 Hz, 2H), 1.23 - 1.08 (m, 4H), 0.95 - 0.82 (m, 2H) + [M+H] = 507.2 1 108 H NMR (300 MHz, CDCl ) δ 10.11 (s, 1H), 8.52 (d, J = 4,2 Hz, 1H), 7.65 3 (td, J = 7,7, 1,7 Hz, 1H), 7.46 (d, J = 7,9 Hz, 1H), 7.25 (d, J = 8,0 Hz, 1H), 7.15 (dd, J = 7,1, 5,2 Hz, 1H), 7.00 (t, J = 8,0 Hz, 1H), 6.83 (dd, J = 7,2, 2,1 Hz, 1H), 6.71 (d, J = 8,8 Hz, 1H), 6.68-6.66 (m, 2H), 5.09 (s, 2H), 2.14 (s, 3H), 1.80 - 1.69 (m, 3H), 1.37 (dd, J = 7,8, 4,6 Hz, 2H), 0.86-0.76 (m, 2H), 0.60 - 0.53 (m, 2H) + [M+H] = 457.3 1 109 H NMR (300 MHz, DMSO) δ 8.59 (d, J = 4,8 Hz, 1H), 7.85 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d,J = 7,8 Hz, 1H), 7.36 (dd, J = 7,0, 5,3 Hz, 1H), 6.94-6.85 (m, 1H), 6.80 (dd, J = 8,6, 2,8 Hz, 1H), 6.72 - 6.65 (m, 1H), 6.55 (d, J = 2,7 Hz, 1H), 6.20 (d, J = 8,1 Hz, 1H), 5.14 (s, 2H), 2.14 (s, 3H), 1.94-1.85 (m, 1H), 0.87 - 0.77 (m, 2H), 0.64 - 0.57 (m, 2H) 13 C NMR (151 MHz, DMSO) δ 157.4, 155.5, 150.7, 149.5, 147.0, 140.0, 137.4, 135.5, 126.2, 126.0, 123.3, 122.2, 116.1, 116.0, 112.6, 111.5, 110.8, 110.3, 70.9, 11.5, 11.0, 8.9 + [M+H] = 427.2 110 1H NMR (400 MHz, DMSO-d6) δ 9.49 (s, 1H), 8.43 (s, 1H), 7.61 (d, J = 7,7 Hz, 1H), 7.45 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.20 (t, J = 7,8 Hz, 1H), 7.13 (d, J = 8,6 Hz, 1H), 6.83 (dd, J = 8,6, 2,8 Hz, 1H), 6.75 (d, J = 8,4 Hz, 1H), 6.68 (t, J = 7,4 Hz, 1H), 6.60 (d, J = 2,8 Hz, 1H), 5.07 (s, 2H), 3.11 (t, J = 6,3 Hz, 2H), 1.84 (s, 1H), 1.71 (t, J = 13,5 Hz, 4H), 1.60 (d, J = 26,4 Hz, 2H), 1.20 (dd, J = 23,1, 8,6 Hz, 3H), 1.00 - 0.91 (m, 2H), 0.91 - 0.84 (m, 2H), 0.62 (d, J = 5,1 Hz, 2H) + [M+H] = 455.2 35 75 Örnek Karakterizasyonlar 1 111 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,2 Hz, 1H), 7.74 (td, J = 7,7, 1,8 Hz, 3 1H), 7.55 (d,J = 7,8 Hz, 1H), 7.27 - 7.22 (m, 1H), 7.15 (t, J = 7,9 Hz, 1H), 7.09 - 7.06 (m, 1H), 7.02 (d, J = 8,6 Hz, 1H), 6.94 (d, J = 7,8 Hz, 1H), 6.80 (dd, J = 8,6, 2,9 Hz, 1H), 6.59 (dd, J = 8,3, 2,1 Hz, 1H), 6.54 (d, J = 2,9 Hz, 1H), 5.98 (t, J = 6,0 Hz, 1H), 5.18 (s, 2H), 3.44 (dd, J = 14,6, 7,0 Hz, 2H), 3.28 (s, 3H), 1.88 - 1.79 (m, 1H), 1.77 - 1.61 (m, 7H), 1.48 (dd, J = 14,6, 7,0 Hz, 2H), 1.23 - 1.14 (m, 2H), 1.00 - 0.91 (m, 2H), 0.86 - 0.78 (m, 2H), 0.65 - 0.58 (m, 2H) + [M+H] = 484.4 1 112 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,2 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.64 (s, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.29 (d, J = 8,0 Hz, 1H), 7.25 - 7.21 (m, 2H), 7.19 (d, J = 6,4 Hz, 1H), 7.03 (dd, J = 7,9, 1,2 Hz, 1H), 6.85 - 6.78 (m, 2H), 6.69 (d, J = 2,9 Hz, 1H), 5.18 (s, 2H), 2.85 - 2.74 (m, 2H), 1.95 - 1.86 (m, 1H), 1.67 - 1.58 (m, 3H), 0.96 (d, J = 6,2 Hz, 6H), 0.94 - 0.88 (m, 2H), 0.67 - 0.61 (m, 2H) + [M+H] = 454.5 1 113 H NMR (300 MHz, CDCl ) δ 9.14 (s, 1H), 8.60 (d, J = 4,8 Hz, 1H), 7.72 (td, J 3 = 7,7, 1,7 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.37 (dd, J = 7,8, 1,4 Hz, 1H), 7.23 (d, J = 7,5 Hz, 1H), 7.18 (d, J = 8,6 Hz, 2H), 6.89 (d, J = 7,8 Hz, 1H), 6.77 (dd, J = 8,7, 2,9 Hz, 1H), 6.69 - 6.63 (m, 2H), 6.13 (bs, 1H), 5.18 (s, 2H), 3.38 (dd, J = 7,2, 5,8 Hz, 2H), 2.16 (dt, J = 15,0, 7,5 Hz, 1H), 2.02 - 1.91 (m, 1H), 1.88 - 1.77 (m, 2H), 1.72 - 1.58 (m, 4H), 1.35 - 1.22 (m, 2H), 0.97 - 0.89 (m, 2H), 0.65 - 0.58 (m, 2H) + [M+H] = 442.4 114 1H NMR (500 MHz, DMSO-d6) δ 7.46 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.36 - 7.30 (m, 1H), 7.12 - 7.06 (m, 1H), 7.00 (t, J = 8,1 Hz, 1H), 6.93 (s, 1H), 6.66 (dd, J = 6,5, 2,8 Hz, 2H), 6.46 (dd, J = 7,9, 1,8 Hz, 1H), 6.41 (t, J = 2,2 Hz, 1H), 6.25 (dd, J = 8,1, 2,3 Hz, 1H), 5.06 (s, 2H), 3.84 (t, J = 6,5 Hz, 2H), 3.67 - 3.59 (m, 4H), 2.87 - 2.80 (m, 4H), 1.72 - 1.58 (m, 7H), 1.30 - 1.09 (m, 6H), 0.87 (q, J = 10,0, 9,5 Hz, 2H) 13 C NMR (151 MHz, DMSO) δ 160.0, 154.9, 147.0, 146.0, 137.8, 130.0, 129.2, 128.8, 128.2, 128.2, 123.4, 108.8, 107.7, 107.2, 104.5, 101.4, 69.9, 67.8, 66.7, 51.1, 37.3, 33.7, 33.3, 26.6, 26.6, 26.3 + [M+H] = 501.2 1 115 H NMR (400 MHz, DMSO-d6) δ 9.52 (s, 1H), 8.40 (t, J = 5,6 Hz, 1H), 7.59 (dd, J = 7,9, 1,4 Hz, 1H), 7.49 - 7.43 (m, 2H), 7.42 - 7.37 (m, 2H), 7.36 - 7.30 (m, 1H), 7.20 (s, 1H), 7.12 (d, J = 8,7 Hz, 1H), 6.83 (dd, J = 8,7, 2,9 Hz, 1H), 6.78 - 6.71 (m, 1H), 6.70 - 6.64 (m, 1H), 6.59 (d, J = 2,9 Hz, 1H), 5.07 (s, 2H), 3.30 - 3.23 (m, 2H), 1.84 (ddd, J = 13,8, 8,4, 5,3 Hz, 1H), 1.73 (d, J = 13,0 Hz, 2H), 1.69 - 1.57 (m, 3H), 1.44 (q, J = 6,9 Hz, 2H), 1.31 (ddt, J = 10,8, 7,3, 3,6 Hz, 1H), 1.26 - 1.09 (m, 3H), 0.97 - 0.84 (m, 4H), 0.66 - 0.58 (m, 2H) + [M+H] = 469.2 35 76 Örnek Karakterizasyonlar 1 116 H NMR (400 MHz, DMSO-d6) δ 9.45 (s, 1H), 7.47 (d, J = 7,2 Hz, 2H), 7.41 (t, J = 7,4 Hz, 2H), 7.36 (d, J = 7,1 Hz, 2H), 7.27 (d, J = 3,2 Hz, 4H), 7.00 (dd, J = 10,4, 9,0 Hz, 1H), 6.46 (dt, J = 8,6, 3,4 Hz, 1H), 5.16 (s, 2H), 2.34 (t, J = 7,6 Hz, 2H), 1.73 - 1.55 (m, 5H), 1.45 (q, J = 7,1 Hz, 2H), 1.24 - 1.09 (m, 4H), 0.94 - 0.80 (m, 2H) + [M+H] = 515.1 1 117 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,9 Hz, 1H), 8.12 (d, J = 5,6 Hz, 1H), 3 7.99 (t, J = 5,7 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 1H), 7.55-7.51 (m, 2H), 7.28 - 7.21 (m, 1H), 7.16 (d, J = 8,6 Hz, 1H), 6.81 (dd, J = 8,6, 2,9 Hz, 1H), 6.67 - 6.61 (m, 2H), 5.19 (s, 2H), 3.45 (dd, J = 14,5, 6,2 Hz, 2H), 1.84 (td, J = 8,4, 4,2 Hz, 1H), 1.77-1.65 (m, 6H), 1.51 (dd, J = 14,6, 6,2 Hz, 2H), 1.21-1.16 (m, 2H), 1.00 - 0.94 (m, 1H), 0.93 - 0.86 (m, 4H), 0.64-0.59 (m, 2H) + [M+H] = 471.4 1 118 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.65 (t, J = 1,5 Hz, 1H), 7.56 (t, J = 8,9 Hz, 2H), 7.31 (t, J = 7,9 Hz, 1H), 7.26 - 7.20 (m, 2H), 6.95 (dd, J = 8,1, 1,7 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.71 (d, J = 2,9 Hz, 1H), 5.19 (s, 2H), 4.60 (t, J = 7,2 Hz, 2H), 2.10 - 2.00 (m, 2H), 1.95 - 1.85 (m, 1H), 1.73 - 1.67 (m, 6H), 1.31 - 1.13 (m, 5H), 0.96 - 0.89 (m, 4H), 0.67 - 0.61 (m, 2H) + [M+H] = 509.6 1 119 H NMR (400 MHz, DMSO-d6) δ 7.47 (d, J = 7,2 Hz, 2H), 7.41 (t, J = 7,4 Hz, 2H), 7.36 - 7.31 (m, 1H), 7.19 (s, 1H), 7.03 (d, J = 8,6 Hz, 1H), 6.97 - 6.91 (m, 2H), 6.84 (dd, J = 8,6, 2,9 Hz, 1H), 6.15 (d, J = 8,0 Hz, 2H), 6.06 (t, J = 2,1 Hz, 1H), 5.08 (s, 2H), 3.80 (t, J = 6,5 Hz, 2H), 3.15 (p, J = 6,8 Hz, 1H), 1.73 - 1.55 (m, 7H), 1.28 - 1.12 (m, 6H), 1.10 (d, J = 6,9 Hz, 6H), 0.92 - 0.80 (m, 2H) + [M+H] = 458.3 1 120 H NMR (300 MHz, CDCl ) δ 9.12 (s, 1H), 8.60 (d, J = 4,1 Hz, 1H), 7.73 (td, J 3 = 7,7, 1,7 Hz, 1H), 7.54 (d, J= 7,9 Hz, 1H), 7.36 (dd, J = 7,9, 1,3 Hz, 1H), 7.26 - 7.21 (m, 2H), 7.17 (d, J = 8,5 Hz, 1H), 6.88 (d, J = 7,8 Hz, 1H), 6.78 (dd, J = 8,6, 2,9 Hz, 1H), 6.70 - 6.63 (m, 2H), 6.36 (t, J = 5,5 Hz, 1H), 5.18 (s, 2H), 3.71 (dd, J = 12,7, 6,3 Hz, 2H), 2.56 - 2.39 (m, 2H), 2.01 - 1.89 (m, 1H), 0.96 - 0.88 (m, 2H), 0.66 - 0.57 (m, 2H) + [M+H] = 456.3 1 121 H NMR (400 MHz, DMSO-d6) δ 9.41 (s, 1H), 7.50 (dd, J = 8.5, 5.7 Hz, 2H), 7.26 - 7.18 (m, 4H), 7.02 (d, J = 8,6 Hz, 1H), 6.96 (dd, J = 10,4, 9,0 Hz, 1H), 6.91 (d, J = 2.8 Hz, 1H), 6.80 (dd, J = 8.6, 2.9 Hz, 1H), 6.39 - 6.31 (m, 1H), 5.04 (s, 2H), 2.33 (t, J = 7,6 Hz, 2H), 2.13 (s, 3H), 1.65 (dt, J = 18,2, 10,5 Hz, 5H), 1.45 (q, J = 7.1 Hz, 2H), 1.16 (td, J = 20.4, 19.2, 11.1 Hz, 4H), 0.87 (q, J = 10.6, 9.5 Hz, 2H) + [M+H] = 479.2 35 77 Örnek Karakterizasyonlar 1 122 H NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H), 7.67 (dd, J = 7.9, 1.4 Hz, 1H), 7.43 (dt, J = 19,3, 7,3 Hz, 5H), 7.37 - 7.30 (m, 1H), 7.15 (d, J = 8,6 Hz, 1H), 6.92 - 6.86 (m, 2H), 6.73 (d, J = 8,4 Hz, 1H), 6.67 (d, J = 2,8 Hz, 1H), 5.10 (s, 2H), 3.36 - 3.32 (m, 2H), 1.78 (ddd, J = 13,7, 8,4, 5,3 Hz, 1H), 1.66 - 1.48 (m, 7H), 1.22 - 1.03 (m, 6H), 0.87 - 0.70 (m, 4H), 0.68 - 0.59 (m, 2H) + [M+H] = 504.3 1 123 H NMR (300 MHz, CDCl ) δ 9.16 (s, 1H), 8.60 (d, J = 4,8 Hz, 1H), 7.72 (td, J 3 = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.36 (d, J = 6,7 Hz, 1H), 7.26 - 7.21 (m, 1H), 7.18 (d, J = 8,6 Hz, 2H), 6.88 (d, J = 8,3 Hz, 1H), 6.77 (dd, J = 8,6, 2,9 Hz, 1H), 6.68 - 6.63 (m, 2H), 6.05 (t, J = 5,6 Hz, 1H), 5.18 (s, 2H), 3.46 (dd, J = 14,6, 7,1 Hz, 2H), 2.03 - 1.92 (m, 1H), 1.78 - 1.63 (m, 1H), 1.52 (dd, J = 14,7, 7,1 Hz, 2H), 0.99 - 0.90 (m, 8H), 0.64 - 0.58 (m, 2H) + [M+H] = 430.4 1 124 H NMR (400 MHz, DMSO-d6) δ 7.82 (s, 1H), 7.48 (d, J = 7,1 Hz, 2H), 7.42 (s, 2H), 7.39 - 7.26 (m, 6H), 7.08 - 7.03 (m, 2H), 6.90 - 6.84 (m, 1H), 5.20 (s, 2H), 2.73 (d, J = 6,3 Hz, 2H), 1.65 - 1.49 (m, 5H), 1.22 (t, J = 5,7 Hz, 3H), 1.19 - 1.05 (m, 3H), 0.76 (d, J = 10,6 Hz, 2H) + [M+H] = 533.2 1 125 H NMR (400 MHz, DMSO-d6) δ 9.45 (s, 1H), 7.53 (dd, J = 8,5, 5,7 Hz, 2H), 7.37 (d, J = 4,5 Hz, 1H), 7.27 (s, 4H), 7.24 (t, J = 8,9 Hz, 2H), 7.00 (dd, J = 10,5, 9,0 Hz, 1H), 6.46 (dt, J = 8,7, 3,3 Hz, 1H), 5.14 (s, 2H), 2.34 (t, J = 7,6 Hz, 2H), 1.73 - 1.58 (m, 5H), 1.45 (q, J = 7,1 Hz, 2H), 1.24 - 1.09 (m, 4H), 0.94 - 0.80 (m, 2H) + [M+H] = 533.1 1 126 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,8 Hz, 1H), 7.73 (td, J = 7,7, 1,8 Hz, 3 1H), 7.68 - 7.64 (m, 1H), 7.58 (d, J = 7,8 Hz, 1H), 7.54 (d, J = 7,9 Hz, 1H), 7.31 (t, J = 7,9 Hz, 1H), 7.22 (d, J = 8,6 Hz, 2H), 6.95 (dd, J = 8,1, 1,6 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.71 (d, J = 2,9 Hz, 1H), 5.19 (s, 2H), 4.61 (t, J = 7,2 Hz, 2H), 2.11 - 1.99 (m, 2H), 1.96 - 1.85 (m, 1H), 1.68 - 1.55 (m, 2H), 1.28 - 1.21 (m, 2H), 0.96 - 0.85 (m, 8H), 0.68 - 0.60 (m, 2H) + [M+H] = 469.5 1 127 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J= 8,1 Hz, 2H), 7.50 (d, J = 7,7 Hz, 1H), 7.32 - 7.26 (m, 1H), 7.26 - 7.22 (m, 1H), 7.20 (d, J = 8,6 Hz, 1H), 6.97 (dd, J = 7,8, 2,0 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.70 (d, J = 2,9 Hz, 1H), 5.18 (s, 2H), 2.99 - 2.89 (m, 2H), 1.89 (tt, J = 8,4, 5,4 Hz, 1H), 1.80 - 1.67 (m, 3H), 0.97 (d, J = 6,4 Hz, 6H), 0.95 - 0.87 (m, 2H), 0.67 - 0.60 (m, 2H) + [M+H] = 455.5 35 78 Örnek Karakterizasyonlar 1 128 H NMR (500 MHz, DMSO-d6) δ ppm 0.57 - 0.64 (m, 2 H), 0.81 - 0.90 (m, 2 H), 1.18 (d, J = 6,6 Hz, 6 H), 1.76 - 1.83 (m, 1 H), 4.12 (dq, J = 13,8, 6,7 Hz, 1 H), 5.07 (s, 2 H), 6.62 (d, J = 2,7 Hz, 1 H), 6.84 (dd, J = 8,6, 2,9 Hz, 1 H), 6.90 (d, J = 8,5 Hz, 1 H), 7.08 (d, J = 8,5 Hz, 1 H), 7.11 - 7.16 (m, 1 H), 7.29 (d, J = 8,0 Hz, 1 H), 7.32 - 7.36 (m, 1 H), 7.37 - 7.42 (m, 2 H), 7.42 - 7.47 (m, 2 H), 7.52 (s, 1 H), 8.79 (d, J = 7,7 Hz, 1 H) + [M+H] = 426.2 1 129 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,2 Hz, 1H), 7.73 (td, J= 7,7, 1,7 Hz, 3 1H), 7.55 - 7.52 (m, 2H), 7.52 - 7.48 (m, 1H), 7.32 - 7.26 (m, 1H), 7.26 - 7.22 (m, 1H), 7.20 (d, J = 8,6 Hz, 1H), 6.97 (dd, J = 7,6, 2,1 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.70 (d, J = 2,9 Hz, 1H), 5.18 (s, 2H), 2.99 - 2.90 (m, 2H), 1.93 - 1.84 (m, 1H), 1.80 - 1.64 (m, 8H), 1.32 - 1.11 (m, 3H), 1.02 - 0.87 (m, 4H), 0.67 - 0.59 (m, 2H) + [M+H] = 495.5 1 130 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.51 - 7.49 (m, 1H), 7.43 (d, J = 7,8 Hz, 1H), 7.30 (t, J = 7,9 Hz, 1H), 7.27 - 7.21 (m, 2H), 7.19 (d, J = 8,7 Hz, 1H), 6.97 (dd, J = 8,1, 1,6 Hz, 1H), 6.81 (dd, J = 8,6, 2,9 Hz, 1H), 6.70 (d, J = 2,8 Hz, 1H), 5.19 (s, 2H), 2.94 - 2.88 (m, 2H), 1.95 - 1.84 (m, 1H), 1.72 (dt, J = 16,7, 9,3 Hz, 8H), 1.30 - 1.16 (m, 3H), 1.00 - 0.95 (t, J = 8,7 Hz, 2H), 0.93 - 0.88 (m, 2H), 0.67 - 0.61 (m, 2H) + [M+H] = 495.4 1 131 H NMR (500 MHz, DMSO-d6) δ 7.48 - 7.43 (m, 2H), 7.40 (dd, J = 8,1, 6,7 Hz, 2H), 7.33 (t, J = 7,3 Hz, 1H), 6.96 - 6.88 (m, 2H), 6.85 (d, J = 8,5 Hz, 1H), 6.37 (dd, J = 8,5, 2,8 Hz, 1H), 6.11 (dq, J = 5,1, 2,7, 2,3 Hz, 3H), 6.00 (t, J = 2,2 Hz, 1H), 5.05 (s, 2H), 3.80 (t, J = 6,5 Hz, 2H), 3.73 (d, J = 7,3 Hz, 4H), 2.07 (p, J = 7,2 Hz, 2H) + [M+H] = 471.2 1 132 H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 7.46 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,2 Hz, 1H), 7.24 (s, 1H), 7.04 (d, J = 8,6 Hz, 1H), 6.98 (t, J = 8,0 Hz, 1H), 6.92 (d, J = 2,2 Hz, 2H), 6.88 (d, J = 8,1 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.32 (d, J = 9,3 Hz, 1H), 5.06 (s, 2H), 2.27 - 2.18 (m, 2H), 2.14 (s, 3H), 1.73 - 1.55 (m, 5H), 1.45 (q, J = 7,0 Hz, 2H), 1.27 - 1.07 (m, 4H), 0.93 - 0.81 (m, 2H) + [M+H] = 443.2 1 133 H NMR (300 MHz, DMSO) δ 8.60 (d, J = 4,5 Hz, 1H), 7.87 (t, J = 6,9 Hz, 1H), 7.55 (d, J = 7,8 Hz, 2H), 7.40 - 7.33 (m, 1H), 7.05 (d, J = 8,6 Hz, 1H), 7.02 (t, J = 8,0 Hz, 1H), 6.81 (dd, J = 8,7, 2,8 Hz, 1H), 6.51 (d, J = 2,8 Hz, 1H), 6.49 (s, 1H), 6.42 (t, J = 8,5 Hz, 2H), 5.15 (s, 2H), 1.96 (ddd, J = 14,4, 8,6, 5,4 Hz, 1H), 0.86 (q, J = 5,7 Hz, 2H), 0.62 (q, J = 5,7 Hz, 2H) + [M+H] = 413.4 35 79 Örnek Karakterizasyonlar 1 134 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,2 Hz, 1H), 7.72 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d, J= 7,8 Hz, 1H), 7.25-7.21 (m, 2H), 7.15 (d, J = 8,7 Hz, 1H), 6.87 (dd, J = 8,1, 1,6 Hz, 1H), 6.83 (s, 1H), 6.80 - 6.74 (m, 2H), 6.67 (d, J = 2,9 Hz, 1H), 5.17 (s, 2H), 3.69 (bs, 2H), 3.42 (bs, 6H) 1.93 - 1.82 (m, 1H), 1.47 (s, 9H), 0.94 - 0.87 (m, 2H), 0.65 - 0.58 (m, 2H) + [M+H] = 529.5 1 135 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,0 Hz, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.36 - 7.30 (m, 1H), 7.09 (d, J = 20,6 Hz, 2H), 7.02 (d, J = 8,7 Hz, 1H), 6.93 (t, J = 7,8 Hz, 1H), 6.84 (d, J = 7,3 Hz, 1H), 6.74 (dd, J = 8,6, 2,9 Hz, 1H), 6.47 (d, J = 2,8 Hz, 1H), 6.42 (d, J = 7,6 Hz, 1H), 5.04 (s, 2H), 1.97 (td, J = 8,4, 4,2 Hz, 1H), 1.90 - 1.80 (m, 2H), 1.67 - 1.53 (m, 5H), 1.19 - 1.02 (m, 6H), 0.88 - 0.72 (m, 5H), 0.65 - 0.56 (m, 2H) + [M+H] = 499.3 1 136 H NMR (300 MHz, CDCl ) δ 9.23 (s, 1H), 8.60 (d, J = 4,2 Hz, 1H), 7.73 (t, J 3 = 7,6 Hz, 1H), 7.54 (d, J = 8,0 Hz, 1H), 7.33 - 7.21 (m, 3H), 7.15 (d, J = 8,5 Hz, 1H), 6.83 (d, J = 8,0 Hz, 1H), 6.78 (dd, J = 8,7, 2,8 Hz, 1H), 6.67 - 6.59 (m, 3H), 5.18 (s, 2H), 2.00 - 1.90 (m, 1H), 1.65 (dd, J = 8,2, 5,7 Hz, 2H), 1.35 (dd, J = 8,2, 5,9 Hz, 2H), 0.93 (dd, J = 13,7, 5,2 Hz, 2H), 0.62 (dd, J = 13,7, 5,2 Hz, 2H) + [M+H] = 425.3 1 137 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,2 Hz, 1H), 7.72 (td, J= 7.7, 1,7 Hz, 3 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.26-7.20 (m, 1H), 7.17 (d, J = 8,7 Hz, 1H), 7.08 (t, J = 8,1 Hz, 1H), 6.77 (dd, J = 8,7, 2,9 Hz, 1H), 6.68 (d, J = 2,9 Hz, 1H), 6.44 (dd, J = 8,0, 1,5 Hz, 1H), 6.34 (t, J = 2,2 Hz, 1H), 6.28 (dd, J= 7,9, 2,0 Hz, 1H), 5.17 (s, 2H), 4.57 (p, J = 7,1 Hz, 1H), 2.44 - 2.33 (m, 2H), 2.22 - 2.06 (m, 2H), 1.91-1.85 (m, 1H), 1.70 - 1.57 (m, 2H), 0.95 - 0.86 (m, 2H), 0.65 - 0.55 (m, 2H) + [M+H] = 387.2 1 138 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,0 Hz, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.34 (d, J = 10,0 Hz, 2H), 7.06 - 6.99 (m, 2H), 6.83 (s, 1H), 6.77 (dd, J = 8,6, 2,8 Hz, 1H), 6.70 (d, J = 7,8 Hz, 1H), 6.53 (d, J = 7,9 Hz, 1H), 6.48 (d, J = 2,8 Hz, 1H), 5.05 (s, 2H), 3.56 (s, 3H), 2.25 - 2.00 (m, 2H), 1.98 - 1.87 (m, 2H), 1.84 - 1.74 (m, 1H), 1.67 - 1.54 (m, 5H), 1.22 - 1.01 (m, 6H), 0.87 - 0.75 (m, 4H), 0.61 (q, J = 5,8 Hz, 2H) + [M+H] = 513.4 1 139 H NMR (400 MHz, DMSO-d6) δ 9.36 (s, 1H), 8.42 (t, J = 5,6 Hz, 1H), 7.60 (dd, J = 7,9, 1,4 Hz, 1H), 7.46 (d, J = 7,0 Hz, 2H), 7.43 - 7.38 (m, 2H), 7.36 - 7.31 (m, 1H), 7.23 - 7.16 (m, 1H), 7.12 (d, J = 8,6 Hz, 1H), 6.98 (d, J = 2,9 Hz, 1H), 6.85 (dd, J = 8.6, 2.9 Hz, 1H), 6.66 (dd, J = 12.9, 7.8 Hz, 2H), 5.08 (s, 2H), 3.30 - 3.24 (m, 2H), 2.14 (s, 3H), 1.73 (d, J = 13.0 Hz, 2H), 1.64 (dd, J = 21.4 11.2 Hz, 3H), 1.44 (q, J = 6.9 Hz, 2H), 1.31 (ddt, J = 10.7, 7.1, 3.5 Hz, 1H), 1.19 (dt, J = 17.8, 8.5 Hz, 3H), 0.90 (q, J = 11.7 Hz, 2H) + [M+Hl = 443.2 35 80 Örnek Karakterizasyonlar 1 140 H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 7.51 (dd, J = 8.5, 5.7 Hz, 2H), 7.26 - 7.19 (m, 3H), 7.05 (d, J = 8.6 Hz, 1H), 6.98 (t, J = 8.0 Hz, 1H), 6.95 - 6.90 (m, 2H), 6.87 (d, J = 8.1 Hz, 1H), 6.81 (dd, J = 8.6, 2.9 Hz, 1H), 6.32 (d, J = 9,4 Hz, 1H), 5.05 (s, 2H), 2.27 - 2.19 (m, 2H), 2.14 (s, 3H), 1.64 (dt, J = 18,1, 10.2 Hz, 5H), 1.45 (q, J = 7.1 Hz, 2H), 1.16 (h, J = 11.8, 11.3 Hz, 4H), 0.87 (q, J = 10,5, 9,3 Hz, 2H) + [M+H] = 461.2 1 141 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,2 Hz, 1H), 7.72 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d, J = 7,9 Hz, 1H), 7.22 (dd, J = 6,9, 5,2 Hz, 1H), 7.17 (d, J = 8,7 Hz, 1H), 7.05 (t, J = 8,0 Hz, 1H), 6.77 (dd, J = 8,7, 2,9 Hz, 1H), 6.69 (d, J = 2,9 Hz, 1H), 6.49 (dd, J = 8,0, 1,5 Hz, 1H), 6.36 (t, J = 2,2 Hz, 1H), 6.31 (dd, J = 8,0, 1,5 Hz, 1H), 5.57 (s, 1H), 5.17 (s, 2H), 1.95 - 1.82 (m, 1H), 0.95 - 0.87 (m, 2H), 0.65 - 0.57 (m, 2H), 0.24 (s, 9H) + [M+H] = 405.4 1 142 H NMR (400 MHz, DMSO-d6) δ 7.98 (s, 1H), 7.46 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,3 Hz, 2H), 7.37 - 7.31 (m, 2H), 7.09 - 7.01 (m, 3H), 6.92 (dd, J = 8,1, 2,2 Hz, 1H), 6.83 (dd, J = 8,6, 2,8 Hz, 1H), 6.53 (d, J = 2,8 Hz, 1H), 5.08 (s, 2H), 3.17 - 3.09 (m, 2H), 1.90 (ddd, J = 13,5, 8,4, 5,3 Hz, 1H), 1.65 - 1.47 (m, 7H), 1.21 - 1.08 (m, 6H), 0.85 - 0.75 (m, 4H), 0.67 - 0.62 (m, 2H) + [M+H] = 504.3 1 143 H NMR (400 MHz, DMSO-d6) δ 8.43 (t, J = 5,6 Hz, 1H), 8.29 (s, 1H), 8.07 (d, J = 5,2 Hz, 1H), 7.59 (d, J = 8,5 Hz, 2H), 7.40 (d, J = 8,2 Hz, 2H), 7.27 (d, J = 8,7 Hz, 1H), 6.92 (d, J = 5,3 Hz, 1H), 6.87 (s, 1H), 6.81 (dd, J = 8,7, 2,8 Hz, 1H), 6.53 (d, J = 2,8 Hz, 1H), 5.12 (s, 2H), 3.23 (q, J = 6,6 Hz, 2H), 1.97 - 1.90 (m, 1H), 1.74 - 1.57 (m, 5H), 1.39 (d, J = 7,3 Hz, 2H), 1.26 (s, 1H), 1.16 (d, J = 8,8 Hz, 3H), 0.93 - 0.84 (m, 2H), 0.84 - 0.79 (m, 2H), 0.60 (d, J = 4,1 Hz, 2H) + [M+H] = 554.2 1 144 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.25 (s, 1H), 7.05 (d, J = 8,6 Hz, 1H), 6.98 (t, J = 8,1 Hz, 1H), 6.96 - 6.91 (m, 2H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.24 (dd, J = 8,1, 1,6 Hz, 1H), 6.20 (dd, J = 8,1, 2,1 Hz, 1H), 6.13 (t, J = 2,0 Hz, 1H), 5.07 (s, 2H), 3.82 (t, J = 5,8 Hz, 2H), 3.23 (q, J = 5,7 Hz, 2H), 2.13 (s, 3H), 1.37 (s, 9H) + [M+H] = 449.3 1 145 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,4 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.64 (s, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.32 - 7.22 (m, 3H), 7.20 (d, J = 8,8 Hz, 1H), 7.04 (dd, J = 7,9, 1,3 Hz, 1H), 6.86 - 6.78 (m, 2H), 6.68 (d, J = 2,8 Hz, 1H), 5.79 (s, 1H), 5.18 (s, 1H), 2.65 (d, J = 7,0 Hz, 2H), 2.03 (dq, J = 13,4, 6,7 Hz, 1H), 1.91 (tt, J = 8,4, 5,6 Hz, 1H), 0.97 (d, J = 6,6 Hz, 6H), 0.95 - 0.88 (m, 2H), 0.68 - 0.61 (m, 2H) + [M+H] = 440.5 35 81 Örnek Karakterizasyonlar 1 146 H NMR (400 MHz, DMSO-d6) δ 9.41 (s, 1H), 7.45 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.25 - 7.18 (m, 2H), 7.02 (d, J = 8,6 Hz, 1H), 6.95 (dd, J = 10,4, 9,0 Hz, 1H), 6.91 (d, J = 2,8 Hz, 1H), 6.80 (dd, J = 8,6, 2,9 Hz, 1H), 6.35 (dt, J = 8,5, 3,3 Hz, 1H), 5.06 (s, 2H), 2.33 (t, J = 7,6 Hz, 2H), 2.13 (s, 3H), 1.65 (dt, J = 18,1, 11,1 Hz, 5H), 1.45 (q, J = 7,1 Hz, 2H), 1.17 (dq, J = 16,0, 8,5, 7,1 Hz, 4H), 0.87 (q, J = 10,6, 9,5 Hz, 2H) + [M+H] = 461.2 1 147 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,6, 1,7 Hz, 3 1H), 7.66 (t, J = 1,5 Hz, 1H), 7.58 (d, J = 7,7 Hz, 1H), 7.54 (d, J = 7,9 Hz, 1H), 7.31 (t, J = 7,8 Hz, 1H), 7.22 (d, J = 8,6 Hz, 2H), 6.95 (dd, J = 7,6, 2,2 Hz, 1H), 6.80 (dd, J = 8,6, 2,9 Hz, 1H), 6.71 (d, J = 2,9 Hz, 1H), 5.19 (s, 2H), 4.45 (d, J = 7,2 Hz, 2H), 1.95 - 1.85 (m, 1H), 1.95 - 1.85 (m, 1H), 0.99 (d, J = 6,7 Hz, 6H), 0.92 (dt, J = 6,0, 4,3 Hz, 2H), 0.67 - 0.60 (m, 2H) + [M+H] = 441.4 1 148 H NMR (400 MHz, DMSO-d6) δ 9.22 (dd, J = 4,9, 1,7 Hz, 1H), 7.83 (dd, J = 8,5, 1,7 Hz, 1H), 7.76 (dd, J = 8,5, 4,9 Hz, 1H), 7.24 (s, 1H), 7.08 (d, J = 8,6 Hz, 1H), 7.02 - 6.93 (m, 2H), 6.87 (dd, J = 8,6, 3,0 Hz, 1H), 6.22 (ddd, J = 10,8, 8,1, 1,9 Hz, 2H), 6.16 (t, J = 2,2 Hz, 1H), 5.37 (s, 2H), 3.82 (t, J = 6,5 Hz, 2H), 2.14 (s, 3H), 1.65 (td, J = 17,0, 14,4, 7,0 Hz, 7H), 1.30 - 1.08 (m, 6H), 0.86 (q, J = 10,4, 9,1 Hz, 2H) + [M+H] = 432.3 1 149 H NMR (400 MHz, DMSO-d6) δ 7.47 - 7.43 (m, 3H), 7.40 (t, J = 7,4 Hz, 2H), 7.36 - 7.30 (m, 1H), 7.02 (t, J = 8,5 Hz, 2H), 6.79 (dd, J = 8,6, 2,9 Hz, 1H), 6.54 (dd, J = 4,0, 2,1 Hz, 2H), 6.50 - 6.44 (m, 2H), 5.06 (s, 2H), 2.80 (t, J = 7,3 Hz, 2H), 1.94 (ddd, J = 13,7, 8,5, 5,3 Hz, 1H), 1.68 - 1.58 (m, 5H), 1.54 (dt, J = 15,1, 7,5 Hz, 2H), 1.27 - 1.06 (m, 6H), 0.88 - 0.76 (m, 4H), 0.67 - 0.58 (m, 2H) + [M+H] = 472.4 1 150 H NMR (400 MHz, DMSO-d6) δ 9.63 (s, 1H), 7.57 (s, 1H), 7.46 (d, J = 7,2 Hz, 2H), 7.41 (t, J = 7,3 Hz, 2H), 7.38 - 7.31 (m, 1H), 7.19 (t, J = 9,2 Hz, 1H), 7.07 (s, 1H), 7.04 - 6.92 (m, 3H), 6.83 (dd, J = 8,8, 2,5 Hz, 1H), 6.42 (d, J = 8,0 Hz, 1H), 5.09 (s, 2H), 2.28 - 2.21 (m, 2H), 1.65 (dt, J = 18,4, 10,9 Hz, 5H), 1.45 (q, J = 7,1 Hz, 2H), 1.26 - 1.09 (m, 4H), 0.87 (q, J = 10,6, 9,5 Hz, 2H) + [M+H] = 447.2 1 151 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,3 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.53 (d,J = 7,8 Hz, 1H), 7.27 - 7.21 (m, 1H), 7.15 (d, J = 8,6 Hz, 1H), 7.08 (t, J = 8,1 Hz, 1H), 6.78 (dd, J = 8,7, 2,9 Hz, 1H), 6.67 (d, J = 2,9 Hz, 1H), 6.47 (dd, J = 8,0, 1,7 Hz, 1H), 6.21 (t, J = 2,2 Hz, 1H), 6.09 (dd, J = 8,0, 2,1 Hz, 1H), 5.18 (s, 2H), 5.16-5.10 (m, 1H), 4.90 (t, J = 6,8 Hz, 2H), 4.76 (t, J = 6,8 Hz, 2H), 1.94 - 1.83 (m, 1H), 0.95 - 0.87 (m, 2H), 0.66 - 0.59 (m, 2H) + [M+H] = 389.3 35 82 Örnek Karakterizasyonlar 1 152 H NMR (400 MHz, DMSO-d6) δ 8.85 (d, J = 4,9 Hz, 2H), 7.47 (t, J = 4,9 Hz, 1H), 7.21 (s, 1H), 7.03 (d, J = 8,6 Hz, 1H), 6.97 (t, J = 8,1 Hz, 1H), 6.89 (d, J = 2,9 Hz, 1H), 6.77 (dd, J = 8,6, 3,0 Hz, 1H), 6.20 (td, J = 8,1, 2,0 Hz, 2H), 6.14 (t, J = 2,2 Hz, 1H), 5.22 (s, 2H), 3.81 (t, J = 6,5 Hz, 2H), 2.12 (s, 3H), 1.66 (td, J = 14,8, 13,2, 5,2 Hz, 7H), 1.29 - 1.06 (m, 6H), 0.93 - 0.79 (m, 2H) + [M+H] = 432.3 1 153 H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 7.59 (d, J = 8,6 Hz, 2H), 7.40 (d, J = 8,2 Hz, 2H), 7.25 (s, 1H), 7.05 (d, J = 8,6 Hz, 1H), 6.98 (t, J = 8,0 Hz, 1H), 6.95 - 6.92 (m, 2H), 6.87 (d, J = 8,0 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.33 (d, J = 7,9 Hz, 1H), 5.10 (s, 2H), 2.28 - 2.20 (m, 2H), 2.14 (s, 3H), 1.65 (dt, J = 18,0, 10,7 Hz, 5H), 1.44 (q, J = 7,1 Hz, 2H), 1.17 (dt, J = 17,1, 9,3 Hz, 4H), 0.87 (q, J = 10,5, 9,4 Hz, 2H) + [M+H] = 527.1 1 154 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 6,9 Hz, 2H), 7.42 - 7.36 (m, 2H), 7.36 - 7.30 (m, 1H), 7.11 (d, J = 8,7 Hz, 1H), 6.92 (d, J = 7,5 Hz, 1H), 6.81 (dd, J = 8,7, 2,9 Hz, 1H), 6.74 (d, J = 3,0 Hz, 2H), 6.70 - 6.65 (m, 1H), 6.63 (d, J = 2,9 Hz, 1H), 6.49 (s, 1H), 5.05 (s, 2H), 4.01 (t, J = 6,4 Hz, 2H), 1.89 - 1.82 (m, 1H), 1.82 - 1.74 (m, 2H), 1.66 (q, J = 17,2, 15,6 Hz, 5H), 1.38 - 1.30 (m, 2H), 1.26 - 1.10 (m, 4H), 0.86 (ddd, J = 8,4, 6,2, 4,1 Hz, 4H), 0.65 - 0.59 (m, 2H) + [M+H] = 456.3 1 155 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,0 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.34 (d, J = 7,1 Hz, 1H), 7.21 (s, 1H), 7.06 - 6.97 (m, 2H), 6.84 (s, 1H), 6.76 (dd, J = 8,7, 2,9 Hz, 1H), 6.67 (d, J = 7,6 Hz, 1H), 6.51 (d, J = 7,9 Hz, 1H), 6.48 (d, J = 2,7 Hz, 1H), 5.05 (s, 2H), 4.52 (t, J = 5,7 Hz, 1H), 4.32 (s, 1H), 3.38 (d, J = 5,7 Hz, 2H), 1.97 (s, 1H), 1.63 (d, J = 27,6 Hz, 7H), 1.19 - 1.01 (m, 5H), 0.84 (d, J = 8,0 Hz, 3H), 0.78 (d, J = 11,1 Hz, 2H), 0.61 (d, J = 3,7 Hz, 2H) + [M+H] = 486.2 1 156 H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J = 4,7 Hz, 1H), 7.85 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.35 (dd, J = 7,4, 4,9 Hz, 1H), 7.07 - 6.94 (m, 2H), 6.90 - 6.81 (m, 1H), 6.55 (d, J = 2,8 Hz, 1H), 6.20 (dd, J = 8,0, 1,9 Hz, 1H), 6.05 (dd, J = 8,2, 1,9 Hz, 1H), 5.97 (s, 1H), 5.16 (s, 2H), 3.81 (t, J = 6,5 Hz, 2H), 3.15 (s, 3H), 1.77 (ddd, J = 13,7, 8,5, 5,3 Hz, 1H), 1.65 (q, J = 9,3, 5,8 Hz, 6H), 1.29 - 1.09 (m, 7H), 0.91 - 0.77 (m, 4H), 0.63 (d, J = 3,6 Hz, 2H) + [M+H] = 471.1 1 157 H NMR (300 MHz, CDCl3) δ 8.60 (d, J = 4,5 Hz, 1H), 7.72 (td, J = 7,7, 1,7 Hz, 1H), 7.53 (d, J = 7,8 Hz, 1H), 7.23 (dd, J = 7,1, 5,2 Hz, 1H), 7.18 - 7.09 (m, 2H), 6.78 (dd, J = 8,7, 2,9 Hz, 1H), 6.71 - 6.59 (m, 4H), 5.17 (s, 2H), 4.25 - 4.14 (m, 4H), 1.94 - 1.81 (m, 1H), 1.33 (td, J = 7.1, 0.6 Hz, 6H), 0.95 - 0.87 (m, 2H), 0.65 - 0.57 (m, 2H) + [M+H] = 469.5 35 83 Örnek Karakterizasyonlar 1 158 H NMR (400 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.59 (d, J = 8.6 Hz, 2H), 7.40 (d, J = 8.2 Hz, 2H), 7.34 (t, J = 5.8 Hz, 1H), 7.27 (t, J = 7.9 Hz, 1H), 7.07 (d, J = 8.6 Hz, 1H), 7.00 (d, J = 2.4 Hz, 2H), 6.85 - 6.80 (m, 2H), 6.52 (d, J = 2.8 Hz, 1H), 5.11 (s, 2H), 2.73 (q, J = 6,7 Hz, 2H), 1.96 - 1.88 (m, 1H), 1.63 - 1.50 (m, (5H), 1.22 (t, J = 5.7 Hz, 3H), 1.17 - 1.03 (m, 3H), 0.87 - 0.81 (m, 2H), 0.80 - 0.69 (m, 2H), 0.67 - 0.61 (m, 2H) + [M+H] = 589.2 1 159 H NMR (400 MHz, DMSO-d6) δ 9.18 (d, J = 1,3 Hz, 1H), 8.84 (d, J = 5,2 Hz, 1H), 7.63 (dd, J = 5,2, 1,1 Hz, 1H), 7.24 (s, 1H), 7.08 (d, J = 8,7 Hz, 1H), 7.02 - 6.93 (m, 2H), 6.84 (dd, J = 8,6, 3,0 Hz, 1H), 6.22 (ddd, J = 12,1, 8,1, 1,9 Hz, 2H), 6.16 (t, J = 2,2 Hz, 1H), 5.19 (s, 2H), 3.82 (t, J = 6,5 Hz, 2H), 2.14 (s, 3H), 1.65 (td, J = 16,9, 14,3, 6,9 Hz, 7H), 1.29 - 1.06 (m, 6H), 0.86 (q, J = 10,5, 9,2 Hz, 2H) + [M+H] = 432.3 1 160 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,8 Hz, 1H), 7.73 (td, J = 7,7, 1,6 Hz, 3 1H), 7.55 (d, J = 7,8 Hz, 1H), 7.23 (d, J = 6,7 Hz, 1H), 7.03 - 6.97 (m, 2H), 6.85 (d, J = 8,2 Hz, 1H), 6.77 (dd, J = 8,6, 2,8 Hz, 1H), 6.71 (s, 1H), 6.70 (d, J = 8,6 Hz, 1H), 5.51 (s, 1H), 5.18 (s, 2H), 4.30 - 4.18 (m, 4H), 2.23 (s, 3H), 1.88 - 1.79 (m, 1H), 1.37 (t, J = 7,1 Hz, 6H), 0.90 (dt, J = 10,0, 5,1 Hz, 2H), 0.64 (dt, J = 10,0, 5,1 Hz, 2H) 1 161 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4,5 Hz, 1H), 7.73 (td, J = 7,7, 1,7 Hz, 3 1H), 7.65 (t, J = 1,9 Hz, 1H), 7.56 (t, J = 8,6 Hz, 2H), 7.30 (t, J = 7,9 Hz, 1H), 7.21 (d, J = 8,6 Hz, 2H), 6.95 (dd, J = 8,1, 1,6 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.71 (d, J = 2,8 Hz, 1H), 5.54 (t, J = 7,2 Hz, 1H), 5.22 (d, J = 7,3 Hz, 2H), 5.18 (s, 2H), 1.95 - 1.87 (m, 1H), 1.85 (s, 3H), 1.80 (s, 3H), 0.95 - 0.88 (m, 2H), 0.67 - 0.61 (m, 2H) + [M+H] = 453.3 1 162 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,7 Hz, 1H), 7.73 (td, J = 7,7, 1,6 Hz, 3 1H), 7.66 (t, J = 1,6 Hz, 1H), 7.59 (d, J = 7,6 Hz, 1H), 7.55 (d, J = 7,8 Hz, 1H), 7.31 (t, J = 7,9 Hz, 1H), 7.22 (d, J= 8,6 Hz, 2H), 6.96 (dd, J = 7,8, 1,8 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.71 (d, J = 2,8 Hz, 1H), 5.19 (s, 2H), 4.81 (t, J = 5,5 Hz, 2H), 3.97 (t, J = 5,5 Hz, 2H), 3.36 (s, 3H), 1.96 - 1.84 (m, 1H), 0.96 - 0.88 (m, 2H), 0.64 (q, J = 5,9 Hz, 2H) + [M+H] = 443.3 1 163 H NMR (300 MHz, CDCl3) δ 8.61 (d, J = 4,2 Hz, 1H), 7.73 (td, J = 7,7, 1,8 Hz, 1H), 7.68 - 7.65 (m, 1H), 7.59 (d, J = 7,7 Hz, 1H), 7.55 (d, J = 7,8 Hz, 1H), 7.31 (t, J = 7,9 Hz, 1H), 7.26 - 7.21 (m, 2H), 6.95 (dd, J = 8,2, 1,5 Hz, 1H), 6.81 (dd, J = 8,7, 2,9 Hz, 1H), 6.71 (d, J = 2,9 Hz, 1H), 5.19 (s, 2H), 4.48 (d, J = 7,4 Hz, 2H), 1.96 - 1.85 (m, 1H), 1.53 - 1.45 (m, 1H), 0.97 - 0.86 (m, 2H), 0.71 - 0.68 (m, 2H), 0.65 - 0.63 (m, 2H), 0.55 - 0.49 (m, 2H) + [M+H] = 439.4 35 84 Örnek Karakterizasyonlar 1 164 H NMR (400 MHz, DMSO-d6) δ 7.48 (d, J = 7,1 Hz, 2H), 7.41 (t, J = 7,3 Hz, 2H), 7.35 (d, J = 7,2 Hz, 1H), 7.21 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 7.00 - 6.91 (m, 2H), 6.86 (dd, J = 8,6, 2,9 Hz, 1H), 6.22 - 6.14 (m, 2H), 6.10 (t, J = 2,1 Hz, 1H), 5.10 (s, 2H), 3.90 (dd, J = 10,8, 3,6 Hz, 2H), 3.81 (t, J = 6,5 Hz, 2H), 3.12 - 3.01 (m, 1H), 1.62 (ddd, J = 28,5, 24,4, 11,6 Hz, 12H), 1.30 - 1.08 (m, 7H), 0.93 - 0.82 (m, 2H) + [M+H] = 500.2 1 165 H NMR (400 MHz, DMSO-d6) δ 7.49 - 7.31 (m, 5H), 7.16 (s, 1H), 7.10 (d, J = 8,6 Hz, 1H), 6.99 - 6.89 (m, 2H), 6.87 (d, J = 3,0 Hz, 1H), 6.26 (d, J = 7,4 Hz, 1H), 6.19 (dd, J = 4,6, 2,3 Hz, 2H), 5.78 (s, 1H), 5.09 (s, 2H), 4.11 (d, J = 2,5 Hz, 2H), 3.81 (t, J = 6,5 Hz, 2H), 3.64 (t, J = 5,3 Hz, 2H), 2.27 (s, 2H), 1.72 - 1.58 (m, 7H), 1.29 - 1.09 (m, 6H), 0.93 - 0.82 (m, 2H) + [M+H] = 498.2 1 166 H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J = 4,8 Hz, 1H), 7.84 (td, J = 7,7, 1,5 Hz, 1H), 7.65 (d, J = 2,4 Hz, 2H), 7.56 (d, J = 2,3 Hz, 1H), 7.52 (d, J = 7,8 Hz, 1H), 7.35 (dd, J = 7,4, 4,9 Hz, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.82 (dd, J = 8,6, 2,8 Hz, 1H), 6.52 (d, J = 2,8 Hz, 1H), 6.41 (t, J = 2,1 Hz, 1H), 5.14 (s, 2H), 3.88 (t, J = 6,5 Hz, 2H), 1.92 (ddd, J = 13,7, 8,5, 5,3 Hz, 1H), 1.64 (dt, J = 21,1, 11,5 Hz, 7H), 1.29 - 1.11 (m, 6H), 0.87 (td, J = 9,3, 8,4, 3,8 Hz, 4H), 0.63 (q, J = 5,8 Hz, 2H) + [M+H] = 458.2 1 167 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,4 Hz, 3H), 7.36 - 7.30 (m, 1H), 7.12 - 7.06 (m, 2H), 6.98 (s, 1H), 6.83 (dd, J = 8,6, 2,9 Hz, 1H), 6.73 - 6.64 (m, 1H), 6.62 (d, J = 2,9 Hz, 1H), 6.60 (d, J = 8,2 Hz, 1H), 5.07 (s, 2H), 2.79 (t, J = 7,2 Hz, 2H), 1.84 (ddd, J = 13,7, 8,4, 5,3 Hz, 1H), 1.63 - 1.55 (m, 5H), 1.54 - 1.47 (m, 2H), 1.28 - 1.21 (m, 2H), 1.19 - 1.05 (m, 4H), 0.85 - 0.73 (m, 4H), 0.67 - 0.61 (m, 2H) + [M+H] = 472.4 1 168 H NMR (400 MHz, DMSO-d6) δ 7.53 (d, J = 11,4 Hz, 2H), 7.50 - 7.45 (m, 2H), 7.45 - 7.38 (m, 3H), 7.38 - 7.32 (m, 1H), 7.31 (s, 3H), 7.05 (dd, J = 10,2, 9,0 Hz, 1H), 7.00 (dd, J = 6,1, 3,0 Hz, 1H), 6.83 (dt, J = 8,8, 4,0 Hz, 1H), 5.18 (s, 2H) + [M+H] = 405.0 1 169 H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 7.77 (d, J = 8,2 Hz, 2H), 7.68 (d, J = 8,0 Hz, 2H), 7.34 (s, 1H), 7.04 (d, J = 8,6 Hz, 1H), 7.01 - 6.94 (m, 2H), 6.88 (d, J = 8,1 Hz, 1H), 6.80 (dd, J = 8,6, 2,9 Hz, 1H), 6.51 (d, J = 2,8 Hz, 1H), 6.34 (d, J = 9,6 Hz, 1H), 5.18 (s, 2H), 2.28 - 2.20 (m, 2H), 1.97 (tt, J = 8,5, 5,2 Hz, 1H), 1.73 - 1.57 (m, 5H), 1.45 (q, J = 7,0 Hz, 2H), 1.21 - 1.10 (m, 4H), 0.90 - 0.80 (m, 4H), 0.66 - 0.57 (m, 2H) + [M+H] = 537.2 35 85 Örnek Karakterizasyonlar 1 170 H NMR (400 MHz, DMSO-d6) δ 9.56 (s, 1H), 7.37 (d, J = 8,6 Hz, 2H), 7.32 (s, 1H), 7.02 (d, J = 8,6 Hz, 1H), 6.96 (dd, J = 11,4, 8,3 Hz, 4H), 6.89 (d, J = 8,3 Hz, 1H), 6.77 (dd, J = 8,6, 2,8 Hz, 1H), 6.47 (d, J = 2,8 Hz, 1H), 6.33 (d, J = 9,1 Hz, 1H), 4.96 (s, 2H), 3.76 (s, 3H), 2.27 - 2.20 (m, 2H), 1.96 (ddd, J = 13,8, 8,5, 5,4 Hz, 1H), 1.72 - 1.57 (m, 5H), 1.45 (q, J = 7,1 Hz, 2H), 1.23 - 1.09 (m, 4H), 0.92 - 0.80 (m, 4H), 0.66 - 0.57 (m, 2H) + [M+H] = 499.2 1 171 H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J = 7,3 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.24 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.98 (t, J = 8,1 Hz, 1H), 6.93 (d, J = 2,7 Hz, 1H), 6.82 (dd, J = 8,6, 2,8 Hz, 1H), 6.27 - 6.17 (m, 2H), 6.15 (s, 1H), 5.07 (s, 2H), 4.78 (t, J = 5,6 Hz, 1H), 3.85 (t, J = 5,0 Hz, 2H), 3.65 (q, J = 5,2 Hz, 2H), 2.14 (s, 3H) + [M+H] = 350.3 1 172 H NMR (400 MHz, DMSO-d6) δ 7.81 (s, 1H), 7.45 (d, J = 7,2 Hz, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.06 - 7.00 (m, 3H), 6.94 (d, J = 8,9 Hz, 2H), 6.47 (d, J = 8,1 Hz, 1H), 6.42 (s, 1H), 6.27 (dd, J = 8,1, 1,8 Hz, 1H), 5.05 (s, 2H), 3.85 (t, J = 6,5 Hz, 2H), 1.74 - 1.57 (m, 7H), 1.30 - 1.10 (m, 6H), 0.87 (q, J = 10,3, 9,5 Hz, 2H) + [M+H] = 416.4 1 173 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.23 (s, 1H), 7.06 (d, J = 8,7 Hz, 1H), 6.97 (t, J = 8,1 Hz, 1H), 6.92 (d, J = 2,8 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.26 - 6.16 (m, 2H), 6.16 - 6.12 (m, 1H), 5.07 (s, 2H), 4.04 (q, J = 7,1 Hz, 2H), 3.85 (t, J = 5,8 Hz, 2H), 2.34 (t, J = 6,9 Hz, 2H), 2.13 (s, 3H), 1.72 - 1.59 (m, 4H), 1.17 (t, J = 7,1 Hz, 3H) + [M+H] = 434.2 1 174 H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.25 (s, 1H), 7.06 (d, J = 8,7 Hz, 1H), 6.98 (t, J = 8,1 Hz, 1H), 6.93 (d, J = 2,8 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.26 - 6.19 (m, 2H), 6.14 (t, J = 2,1 Hz, 1H), 5.07 (s, 2H), 3.99 - 3.92 (m, 2H), 3.64 - 3.57 (m, 2H), 3.28 (s, 3H), 2.14 (s, 3H) + [M+H] = 364.2 1 175 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,2 Hz, 1H), 7.22 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.97 (t, J = 8,1 Hz, 1H), 6.92 (d, J = 2,8 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.23 - 6.18 (m, 2H), 6.18 - 6.14 (m, 1H), 5.07 (s, 2H), 3.72 (d, J = 6,9 Hz, 2H), 2.24 (dt, J = 14,8, 7,4 Hz, 1H), 2.13 (s, 3H), 1.73 (dq, J = 11,8, 6,4 Hz, 2H), 1.64 - 1.47 (m, 4H), 1.28 (dq, J = 14,1, 7,4, 7,0 Hz, 2H) + [M+H] = 388.2 35 86 Örnek Karakterizasyonlar 1 176 H NMR (400 MHz, DMSO-d6) δ 9.18 (s, 1H), 8.91 (s, 2H), 7.25 (s, 1H), 7.08 (d, J = 8,6 Hz, 1H), 7.02 - 6.93 (m, 2H), 6.86 (dd, J = 8,6, 3,0 Hz, 1H), 6.22 (ddd, J = 10.5, 8.1, 2.0 Hz, 2H), 6.15 (t, J = 2.2 Hz, 1H), 5.16 (s, 2H), 3.82 (t, J = 6.5 Hz, 2H), 2.15 (s, 3H), 1.73 - 1.57 (m, 7H), 1.30 - 1.08 (m, 6H), 0.86 (q, J = 10.3, 9.0 Hz, 2H) + [M+H] = 432.3 1 177 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7.1 Hz, 2H), 7.40 (t, J = 7.4 Hz, 2H), 7.33 (t, J = 7.2 Hz, 1H), 7.22 (s, 1H), 7.05 (d, J = 8.6 Hz, 1H), 6.97 (t, J = 8.1 Hz, 1H), 6.92 (d, J = 2.8 Hz, 1H), 6.82 (dd, J = 8.6, 2.9 Hz, 1H), 6.24 – 6.17 (m, 2H), 6.13 (t, J = 2.1 Hz, 1H), 5.06 (s, 2H), 3.82 (t, J = 6.5 Hz, 2H), 2.13 (s, 3H), 1.73 – 1.56 (m, 7H), 1.28 – 1.10 (m, 6H), 0.86 (q, J = 10.3, 9.0 Hz, 2H) + [M+H] = 430.2 1 178 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4.8 Hz, 1H), 7.73 (td, J = 7.7, 1.7 Hz, 3 1H), 7.68 (s, 1H), 7.54 (d, J = 7,9 Hz, 1H), 7.32 - 7.26 (m, 2H), 7.26 - 7.17 (m, 3H), 7.03 (dd, J = 7,9, 1,2 Hz, 1H), 6.87 - 6.77 (m, 2H), 6.68 (d, J = 2,8 Hz, 1H), 5.18 (s, 2H), 3.72 (t, J = 7,3 Hz, 2H), 2.90 (t, J = 7,3 Hz, 2H), 1.99 (beşli, J = 7,3 Hz, 2H), 1.95 - 1.86 (m, 1H), 0.96 - 0.88 (m, 2H), 0.67 - 0.60 (m, 2H) + [M+H] = 442.6 1 179 H NMR (300 MHz, CDCl ) δ 8.61 (d, J = 4,2 Hz, 1H), 7.88 (s, 1H), 7.73 (td, J = 3 7,7, 1,8 Hz, 1H), 7.54 (d, J = 7,7 Hz, 1H), 7.29 (s, 1H), 7.28 - 7.22 (m, 2H), 7.19 (d, J = 8,7 Hz, 1H), 7.13 - 7.09 (m, 2H), 6.84 - 6.78 (m, 2H), 6.70 (d, J = 2,9 Hz, 1H), 5.19 (s, 2H), 1.96 - 1.85 (m, 1H), 0.96 - 0.88 (m, 2H), 0.68 - 0.61 (m, 2H) + [M+H] = 384.4 1 180 H NMR (500 MHz, DMSO-d6) δ ppm 0.52 - 0.66 (m, 2 H), 0.81 - 0.97 (m, 2 H), 1.14 (d, J = 6,6 Hz, 6 H), 1.78 (tt, J = 8,3, 5,4 Hz, 1 H), 2.25 (s, 3 H), 4.11 (dt, J = 7,6, 6,6 Hz, 1 H), 5.05 (s, 2 H), 6.59 - 6.66 (m, 3 H), 6.78 - 6.84 (m, 2 H), 7.02 - 7.08 (m, 2 H), 7.31 (br d, J = 1,4 Hz, 1 H), 7.37 - 7.41 (m, 2 H), 7.42 - 7.48 (m, 2 H), 8.36 (d, J = 7,7 Hz, 1 H) + [M+H] = 415.2 1 181 H NMR (400 MHz, DMSO-d6) δ 8.49 (d, J = 7,9 Hz, 1H), 7.47 - 7.27 (m, 6H), 7.10 - 7.02 (m, 2H), 6.88 - 6.82 (m, 2H), 6.69 (s, 1H), 6.61 (d, J = 2,9 Hz, 1H), 5.07 (s, 2H), 4.15 - 4.04 (m, 1H), 1.89 - 1.80 (m, 1H), 1.12 (d, J = 6,6 Hz, 6H), 0.88 - 0.81 (m, 2H), 0.64 - 0.57 (m, 2H) + [M+H] = 469.1 1 182 H NMR (400 MHz, Metanol-d4) δ 8.56 (d, J = 4,5 Hz, 1H), 7.90 (t, J = 7,7 Hz, 1H), 7.62 (d, J = 7,8 Hz, 1H), 7.42 - 7.37 (m, 1H), 7.13 (d, J = 8,7 Hz, 1H), 7.02 (t, J = 8,1 Hz, 1H), 6.80 (dd, J = 8,6, 2,9 Hz, 1H), 6.64 (s, 1H), 6.59 (d, J = 3,1 Hz, 2H), 6.46 (d, J = 8,1 Hz, 1H), 5.16 (s, 2H), 3.63 (d, J = 11,1 Hz, 3H), 2.07 - 1.92 (m, 1H), 0.93 - 0.87 (m, 2H), 0.62 - 0.57 (m, 2H) + [M+H] = 427.0 35 87 Örnek Karakterizasyonlar 1 183 H NMR (500 MHz, DMSO-d6) δ 8.12 (s, 1H), 7.45 (d, J = 7,2 Hz, 2H), 7.42 (s, 3H), 7.35 (t, J = 7,2 Hz, 1H), 7.30 - 7.24 (m, 2H), 7.09 (t, J = 8,1 Hz, 1H), 6.48 (d, J = 8,0 Hz, 1H), 6.44 (t, J = 2,1 Hz, 1H), 6.40 (dd, J = 8,1, 2,2 Hz, 1H), 5.12 (s, 2H), 3.87 (t, J = 6.5 Hz, 2H), 1.74 − 1.56 (m, 7H), 1.29 − 1.08 (m, 6H), 0.87 (q, J = 9.8, 9.4 Hz, 2H) + [M+H] = 441.1 1 184 H NMR (400 MHz, DMSO-d6) δ 9.52 (s, 1H), 8.43 (t, J = 5.5 Hz, 1H), 7.63 − 7.57 (m, 1H), 7.45 (s, 2H), 7.40 (s, 2H), 7.33 (t, J = 7.1 Hz, 1H), 7.24 (t, J = 7.8 Hz, 1H), 7.10 (d, J = 8.9 Hz, 2H), 7.00 (t, J = 8.9 Hz, 3H), 6.72 (t, J = 7.4 Hz, 1H), 5.08 (s, 2H), 3.27 (q, J = 6.5 Hz, 2H), 1.72 (d, J = 12.7 Hz, 2H), 1.63 (dd, J = 19.8, 11.2 Hz, 3H), 1.42 (q, J = 6.9 Hz, 2H), 1.30 (ddt, J = 10.6, 7.1, 3.5 Hz, 1H), 1.17 (h, J = 11.9 Hz, 3H), 0.91 (t, J = 11.6 Hz, 2H) + [M+H] = 429.2 1 185 H NMR (400 MHz, DMSO-d6) δ 7.44 (d, J = 7.0 Hz, 2H), 7.39 (t, J = 7.4 Hz, 2H), 7.35 - 7.30 (m, 1H), 7.14 (s, 1H), 7.02 (d, J = 8,6 Hz, 1H), 6.82 (d, J = 8,1 Hz, 1H), 6.76 (dd, J = 8,6, 2,9 Hz, 1H), 6.47 (d, J = 2,8 Hz, 1H), 6.31 (d, J = 1,8 Hz, 1H), 6.16 (dd, J = 8,0, 1,9 Hz, 1H), 5.04 (s, 2H), 3.80 (t, J = 6,4 Hz, 2H), 2.00 (s, 3H), 1.95 (ddd, J = 13,7, 8,5, 5,4 Hz, 1H), 1.72 - 1.59 (m, 7H), 1.32 - 1.10 (m, 6H), 0.92 - 0.82 (m, 4H), 0.63 - 0.58 (m, 2H) + [M+H] = 470.4 1 186 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,0 Hz, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.35 - 7.31 (m, 1H), 7.23 (s, 1H), 7.02 (d, J = 8,6 Hz, 1H), 6.78 (dd, J = 8,6, 2,8 Hz, 1H), 6.47 (d, J = 2,8 Hz, 1H), 6.08 (s, 1H), 6.02 (s, 1H), 5.97 (s, 1H), 5.05 (s, 2H), 3.79 (t, J = 6,5 Hz, 2H), 2.12 (s, 3H), 1.95 (ddd, J = 13,8, 8,5, 5,4 Hz, 1H), 1.72 - 1.59 (m, 7H), 1.28 - 1.09 (m, 6H), 0.91 - 0.82 (m, 4H), 0.63 - 0.59 (m, 2H) + [M+H] = 470.4 1 187 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,1 Hz, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 6.93 (dd, J = 12,8, 8,4 Hz, 2H), 6.80 (dd, J = 8,6, 2,8 Hz, 1H), 6.55 - 6.50 (m, 2H), 6.18 (dd, J = 8,1, 2,5 Hz, 1H), 5.90 (d, J = 2,4 Hz, 1H), 5.06 (s, 2H), 3.73 (t, J = 6,5 Hz, 2H), 2.15 (s, 3H), 1.89 (ddd, J = 13,7, 8,4, 5,3 Hz, 1H), 1.67 - 1.56 (m, 7H), 1.22 - 1.07 (m, 6H), 0.87 - 0.78 (m, 4H), 0.63 - 0.58 (m, 2H) + [M+H] = 470.4 1 188 H NMR (400 MHz, DMSO-d6) δ 7.94 (s, 1H), 7.69 (d, J = 8,6 Hz, 1H), 7.45 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,3 Hz, 2H), 7.36 - 7.29 (m, 2H), 7.17 - 7.13 (m, 1H), 7.07 (d, J = 8,6 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.49 (d, J = 2,8 Hz, 1H), 6.27 (d, J = 1,7 Hz, 1H), 6.23 (dd, J = 8,6, 1,8 Hz, 1H), 5.07 (s, 2H), 3.94 (t, J = 6,5 Hz, 2H), 1.95 - 1.89 (m, 1H), 1.80 - 1.73 (m, 2H), 1.72 - 1.59 (m, 5H), 1.29 - 1.13 (m, 6H), 0.91 - 0.81 (m, 4H), 0.67 - 0.62 (m, 2H) + [M+H] = 499.4 35 88 Örnek Karakterizasyonlar 1 189 H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.49 (s, 1H), 7.45 (d, J = 7,1 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.13 (s, 1H), 7.04 (d, J = 8,6 Hz, 1H), 6.81 (dd, J = 8,7, 2,9 Hz, 1H), 6.78 (s, 1H), 6.69 (s, 1H), 6.49 (d, J = 2,8 Hz, 1H), 6.27 (t, J = 1,9 Hz, 1H), 5.06 (s, 2H), 3.87 (t, J = 6,5 Hz, 2H), 1.97 - 1.90 (m, 1H), 1.73 - 1.58 (m, 7H), 1.29 - 1.12 (m, 6H), 0.92 - 0.81 (m, 4H), 0.66 - 0.57 (m, 2H) + [M+H] = 499.4 1 190 H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), 7.43 (s, 2H), 7.39 (t, J = 7,4 Hz, 2H), 7.33 (d, J = 7,1 Hz, 1H), 7.22 (d, J = 8,0 Hz, 1H), 7.01 (t, J = 7,3 Hz, 1H), 6.91 (d, J = 8,7 Hz, 1H), 6.80 - 6.73 (m, 3H), 6.71 (s, 1H), 6.57 (d, J = 2,8 Hz, 1H), 5.04 (s, 2H), 2.39 - 2.34 (m, 2H), 1.88 - 1.80 (m, 1H), 1.68 (dd, J = 23,1, 12,0 Hz, 4H), 1.61 (s. 1H), 1.51 (d, J = 8,0 Hz, 2H), 1.25 (s, 1H), 1.15 (t, J = 11,4 Hz, 3H), 0.93 - 0.83 (m, 4H), 0.60 (q, J = 5,7 Hz, 2H) + [M+H] = 469.2 1 191 H NMR (400 MHz, Kloroform-d) δ 9.00 (s, 1H), 7.46 (d, J = 7,2 Hz, 2H), 7.41 (t, J = 7,4 Hz, 2H), 7.34 (t, J = 7,1 Hz, 1H), 7.08 - 7.00 (m, 2H), 6.92 (d, J = 2,8 Hz, 1H), 6.86 (s, 1H), 6.27 (dd, J = 8,1, 1,9 Hz, 1H), 6.11 (d, J = 8,2 Hz, 1H), 6.07 (d, J = 2,1 Hz, 1H), 5.06 (s, 2H), 3.87 (dt, J = 13,5, 7,0 Hz, 4H), 2.76 - 2.69 (m, 2H), 2.09 (s, 3H), 1.72 (q, J = 13,3, 10,0 Hz, 7H), 1.30 (dd, J = 9,9, 4,8 Hz, 2H), 1.19 (dq, J = 21,1, 12,1, 10,8 Hz, 4H), 0.93 - 0.84 (m, 2H) + [M+H] = 502.2 1 192 H NMR (400 MHz, DMSO-d6) δ 12.90 (s, 1H), 7.46 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,2 Hz, 1H), 7.30 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.98 (t, J = 8,0 Hz, 1H), 6.92 (d, J = 2,7 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.25 (d, J = 7,6 Hz, 1H), 6.19 - 6.13 (m, 2H), 5.07 (s, 2H), 4.52 (s, 2H), 2.14 (s, 3H) + [M+H] = 364.3 1 193 H NMR (400 MHz, DMSO-d6) δ 12.00 (s, 1H), 7.45 (d, J = 7,3 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.23 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.97 (t, J = 8,1 Hz, 1H), 6.92 (d, J = 2,7 Hz, 1H), 6.82 (dd, J = 8,6, 2,8 Hz, 1H), 6.25 - 6.17 (m, 2H), 6.15 (s, 1H), 5.07 (s, 2H), 3.85 (t, J = 6,0 Hz, 2H), 2.26 (t, J = 7,1 Hz, 2H), 2.14 (s, 3H), 1.72 - 1.54 (m, 4H) + [M+H] = 406.4 1 194 H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J = 7,3 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.34 (d, J = 7,1 Hz, 1H), 7.31 (s, 1H), 7.05 (d, J = 8,6 Hz, 1H), 6.99 (t, J = 8,1 Hz, 1H), 6.93 (d, J = 2,7 Hz, 1H), 6.82 (dd, J = 8,6, 2,8 Hz, 1H), 6.27 (d, J = 8,8 Hz, 1H), 6.18 (dd, J = 8,1, 2,0 Hz, 1H), 6.12 (s, 1H), 5.07 (s, 2H), 4.64 (s, 2H), 3.67 (s, 3H), 2.13 (s, 3H) + [M+H] = 378.3 35 89 Örnek Karakterizasyonlar 1 195 H NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.46 (d, J = 7,3 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.34 (t, J = 7,2 Hz, 1H), 7.18 (t, J = 8,2 Hz, 1H), 7.08 (d, J = 8,6 Hz, 1H), 6.97 (d, J = 2,7 Hz, 1H), 6.86 (dd, J = 8,6, 2,8 Hz, 1H), 6.59 (dd, J = 8,3, 1,3 Hz, 1H), 6.53 (d, J = 8,2 Hz, 1H), 6.45 (s, 1H), 5.08 (s, 2H), 2.13 (s, 3H) + [M+H] = 374.2 1 196 H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.36 - 7.31 (m, 1H), 7.23 (s, 1H), 7.06 (d, J = 8,6 Hz, 1H), 6.97 (t, J = 8,1 Hz, 1H), 6.92 (d, J = 2,8 Hz, 1H), 6.82 (dd, J = 8,6, 2,9 Hz, 1H), 6.25 - 6.18 (m, 2H), 6.18 - 6.14 (m, 1H), 5.07 (s, 2H), 3.86 (dd, J = 11,2, 3,5 Hz, 2H), 3.71 (d, J = 6,4 Hz, 2H), 3.35 - 3.27 (m, 2H), 2.13 (s, 3H), 2.00 - 1.88 (m, 1H), 1.63 (d, J = 12,7 Hz, 2H), 1.29 (qd, J = 11,8, 11,3, 3,8 Hz, 2H) + [M+H] = 404.2 1 197 H NMR (400 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.55 (d, J = 4,5 Hz, 1H), 7.88 (s, 2H), 7.80 (d, J = 5,8 Hz, 1H), 7.43 (dd, J = 7,7, 4,8 Hz, 1H), 7.29 (d, J = 8,7 Hz, 1H), 6.92 (d, J = 2,7 Hz, 1H), 6.83 (dd, J = 8,7, 2,8 Hz, 1H), 6.23 (dd, J = 5,8, 1,9 Hz, 1H), 5.97 (d, J = 1,8 Hz, 1H), 5.13 (s, 2H), 3.89 (t, J = 6,5 Hz, 2H), 2.15 (s, 3H), 1.67 (t, J = 10,8 Hz, 6H), 1.29 - 1.08 (m, 7H), 0.92 - 0.80 (m, 2H) + [M+H] = 432.1 1 198 H NMR (400 MHz, DMSO-d6) δ 8.67 (d, J = 1,6 Hz, 1H), 8.55 (d, J = 4,8 Hz, 1H), 7.89 (s, 1H), 7.87 (d, J = 7,9 Hz, 1H), 7.43 (dd, J = 7,8, 4,8 Hz, 1H), 7.36 - 7.30 (m, 2H), 6.93 (d, J = 2,8 Hz, 1H), 6.83 (dd, J = 8,7, 2,9 Hz, 1H), 6.02 (d, J = 7,9 Hz, 1H), 5.97 (d, J = 7,8 Hz, 1H), 5.12 (s, 2H), 4.06 (t, J = 6,7 Hz, 2H), 2.17 (s, 3H), 1.71 - 1.56 (m, 7H), 1.18 (dt, J = 14,7, 9,0 Hz, 6H), 0.90 - 0.78 (m, 2H) + [M+H] = 432.1 1 199 H NMR (400 MHz, DMSO-d6) δ 7.86 (s, 1H), 7.80 (d, J = 5,8 Hz, 1H), 7.45 (d, J = 7,3 Hz, 2H), 7.40 (t, J = 7,4 Hz, 2H), 7.33 (t, J = 7,1 Hz, 1H), 7.26 (d, J = 8,7 Hz, 1H), 6.90 (d, J = 2,6 Hz, 1H), 6.81 (dd, J = 8,7, 2,8 Hz, 1H), 6.23 (dd, J = 5,8, 1,7 Hz, 1H), 5.95 (s, 1H), 5.07 (s, 2H), 3.89 (t, J = 6,5 Hz, 2H), 2.15 (s, 3H), 1.73 - 1.58 (m, 7H), 1.28 - 1.08 (m, 6H), 0.93 - 0.79 (m, 2H) + [M+H] = 431.1 1 200 H NMR (400 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.45 (d, J = 7,2 Hz, 2H), 7.40 (t, J = 7,4 Hz, 3H), 7.38 - 7.26 (m, 3H), 6.90 (d, J = 2,8 Hz, 1H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.01 (d, J = 7,9 Hz, 1H), 5.96 (d, J = 7,8 Hz, 1H), 5.07 (s, 2H), 4.06 (t, J = 6,8 Hz, 2H), 2.17 (s, 3H), 1.63 (dq, J = 14,6, 8,6, 6,6 Hz, 7H), 1.27 - 1.09 (m, 6H), 0.91 - 0.79 (m, 2H) + [M+H] = 431.1 1 201 H NMR (400 MHz, DMSO-d6) δ 8.82 (s, 1H), 8.66 (dd, J = 16,8, 2,4 Hz, 2H), 7.24 (s, 1H), 7.08 (d, J = 8,6 Hz, 1H), 6.97 (t, 2H), 6.86 (dd, J = 8,6, 2,9 Hz, 1H), 6.22 (dd, J = 11.7, 8.5 Hz, 2H), 6.16 (d, J = 1.9 Hz, 1H), 5.23 (s, 2H), 3.82 (t, J = 6.5 Hz, 2H), 2.14 (s, 3H), 1.73 - 1.57 (m, 7H), 1.31 - 1.07 (m, 6H), 0.86 (q, J = 10.2, 8.9 Hz, 2H) 35 + [M+H] = 432.2 90 Sample Characterizations 1 202 H NMR (400 MHz, DMSO-d6) δ 9.46 (s, 1H), 7.56 (s, 1H), 7.46 (d, J = 7.2 Hz, 2H), 7.43 - 7.31 (m, 4H), 7.16 (t, J = 9.2 Hz, 1H), 7.03 - 6.95 (m, 2H), 6.81 (dd, J = 8.8, 2.4 Hz, 1H), 6.50 – 6.42 (m, 1H), 5.09 (s, 2H), 2.34 (t, J = 7.6 Hz, 2H), 1.74 to 1.56 (m, 5H), 1.46 (q, J = 7.1 Hz, 2H), 1.26 to 1.08 (m, 4H), 0.94 to 0.81 (m, 2H) + [M+H] = 465.2 1 203 H NMR (300 MHz, CDCl ) δ 8.60 (d, J = 4.7 Hz, 1H), 7.81 (t, J = 3.8 Hz, 1H), 3 7.73 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,8 Hz, 1H), 7.39 (t, J = 1,6 Hz, 1H), 7.27 - 7.21 (m, 2H), 7.14 (d, J = 7,7 Hz, 1H), 7.08 (d, J = 8,9 Hz, 2H), 7.00 (dd, J = 8,0, 1,5 Hz, 1H), 6.95 (d, J = 8,9 Hz, 2H), 5.19 (s, 2H), 3.66 (t, J = 9,3 Hz, 4H), 3.54 (dd, J = 11,5, 5,7 Hz, 2H), 2.53 (t, J = 5,7 Hz, 2H), 2.47 (t, J = 9,3 Hz, 4H), 1.77 (dt, J = 11,5, 5,7 Hz, 3H) + [M+H] = 447.3 1 204 H NMR (300 MHz, CDCl ) δ 8.64 (d, J = 4,4 Hz, 1H), 7.83 (td, J = 7,7, 1,7 Hz, 3 1H), 7.58 - 7.50 (m, 2H), 7.36 (d, J = 7,0 Hz, 1H), 7.33 - 7.26 (m, 2H), 6.98 (d, J = 8,6 Hz, 1H), 6.93 (dd, J = 8,1, 1,6 Hz, 1H), 6.46 (dd, J = 8,6, 2,9 Hz, 1H), 6.37 (d, J = 2,8 Hz, 1H), 5.61 (bs, 1H), 5.11 (s, 2H), 1.83 - 1.74 (m, 1H), 0.83 - 0.76 (m, 2H), 0.49 - 0.43 (m, 2H) + [M+H] = 385.4 1 205 H NMR (400 MHz, DMSO-d6) δ 8.37 (d, J = 7,8 Hz, 1H), 7.46 - 7.42 (m, 2H), 7.42 - 7.36 (m, 2H), 7.35 - 7.29 (m, 1H), 7.09 - 6.99 (m, 2H), 6.80 (dd, J = 8,7, 2,9 Hz, 1H), 6.70 (s, 1H), 6.66 - 6.59 (m, 2H), 6.39 (d, J = 7,7 Hz, 1H), 5.05 (s, 2H), 4.19 - 4.06 (m, 1H), 2.02 - 1.92 (m, 1H), 1.85 - 1.74 (m, 1H), 1.14 (d, J = 6,6 Hz, 6H), 0.91 - 0.81 (m, 4H), 0.66 - 0.61 (m, 2H), 0.61 - 0.56 (m, 2H) + [M+H] = 441.2 1 206 H NMR (400 MHz, DMSO-d6) δ 8.51 (d, J = 7,9 Hz, 1H), 7.47 - 7.29 (m, 5H), 7.14 - 7.04 (m, 2H), 6.86 - 6.75 (m, 3H), 6.62 - 6.56 (m, 2H), 5.06 (s, 2H), 4.15 - 4.04 (m, 1H), 1.86 - 1.77 (m, 1H), 1.15 (d, J = 6.6 Hz, 6H), 0.89 - 0.81 (m, 2H), 0.63 - 0.55 (m, 2H) + [M+H] = 435.2 The following examples are provided as illustration and do not encompass the scope of this invention in any way. It does not restrict it in this way. The following examples illustrate in detail the preparation of certain compounds according to the invention. The structures of the obtained products were confirmed by NMR spectra. EXAMPLES Example 1: Compound (39) in Table I 35 91 According to route (I), 4-nitro-5-methylphenol (3.06 g, 20 mmol, 1 equivalent), K₂CO₃ (8.3 g, 60 mmol, 2 3 3 equivalents) were placed in N,N-dimethylformamide (15 mL). 2-(bromomethyl)pyridine After the addition of hydrobromide (5.06 g, 20 mmol, 1 equivalent), the reaction mixture It was heated to 90 °C and stirred for 24 hours under an inert argon atmosphere. After being cooled to room temperature, the reaction mixture is placed under low pressure. It was concentrated, and the resulting residue was separated between dichloromethane and water. After decantation, the organic phase was washed with a saturated aqueous saline solution. Dried over MgSO, filtered and 2-(3-methyl-4-nitrophenoxymethyl)pyridine 4 It was concentrated under low pressure to yield (4.5 g, 92%). 1 H NMR (300 MHz, CDCl) δ 8.65 - 8.60 (m, 1H), 8.07 (d, J = 9.8 Hz, 1H), 7.75 (td, J = 3 7.7, 1.7 Hz, 1H), 7.48 (d, J = 7.7 Hz, 1H), 7.27 (t, J = 6.2 Hz, 1H), 6.90 - 6.87 (m, 2H), 2.62 (s, 3H). According to route (C), 2-(3-methyl-4-nitrophenoxymethyl)pyridine (4.5 g, 18.4 mmol, 1 equivalent) and Tin (II) chloride dihydrate (20.8 g, 92 mmol, 5 equivalents) was placed in EtOH (184 mL). The reaction mixture was heated to 60 °C and kept under an inert argon atmosphere for 14 hours. The reaction mixture was then concentrated under low pressure. and the resulting residue was diluted with dichloromethane. The organic phase was diluted with 1N NaOH. It was washed with an aqueous solution, and then with a saturated aqueous saline solution. Dried over MgSO, filtered, and processed into 2-methyl-4-(pyridin-2-ylmethoxy)aniline. 4 It was concentrated under low pressure to give (2.0 g, 51%). 1 H NMR (300 MHz, CDCl) δ 8.58 (d, J = 4.3 Hz, 1H), 7.70 (td, J = 7.7, 1.7 Hz, 1H), 7.52 3 (d, J = 7.7 Hz, 1H), 7.20 (dd, J = 6.9, 5.5 Hz, 1H), 6.76 (d, J = 2.7 Hz, 1H), 6.69 (dd, J = 8.5, 2.7 Hz, 1H), 6.60 (d, J = 8.5 Hz, 1H), 5.13 (s, 2H), 3.37 (s, 2H), 2.15 (s, 3H). 2-Cyclopentylethanol-1-amine hydrochloride (1.3 g, 8.7 mmol, 1.1 equivalents) in 3N NaOH aqueous solution It was placed in the solution (5.9 mL) and dichloromethane (1.5 mL) was added to the solution. The reaction mixture was cooled to 0 °C in an ice bath and dichloromethane (2.4 mL) by adding the 3-bromobenzoyl chloride solution (1.0 mL, 7.9 mmol, 1.0 equivalent) inside drop by drop added. The reaction mixture was then placed in an inert argon atmosphere at room temperature. It was stirred for 18 hours under the following conditions. Upon decantation, the organic phase became saturated. The aqueous solution was washed with saline solution, dried over MgSO, and filtered. 4 35 92 and to give 3-bromo-N-(2-cyclopentylethyl)benzamide (1.8 g, 77%) at low pressure It is concentrated below. 1 H NMR (300 MHz, CDCl) δ 7.89 (t, J = 1.7 Hz, 1H), 7.67 (d, J = 7.9 Hz, 1H), 7.65 - 3 7.58 (m, 1H), 7.31 (t, J = 7.9 Hz, 1H), 6.07 (s, 1H), 3.46 (dt, J = 7.4, 5.9 Hz, 2H), 1.88 - 1.79 (m, 3H), 1.67 - 1.47 (m, 6H), 1.18 - 1.13 (m, 2H). According to route (A), a 3-bromo-N-(2-cyclopentylethyl)benzamide in BuOH (11.2 mL) (830 mg, 2.8 mmol, 1 equivalent), 2-methyl-4-(pyridin-2-ylmethoxy)aniline (600 mg, 2.8 mmol, 1 equivalent), Pd (dba) (258 mg, 282 µmol, 10 mol%), XPhos (266 mg, 559 µmol, 20%) 2 3 The reaction mixture of K₂CO₃ (1.55 g, 11.2 mmol, 4 equivalents) and K₂CO₃ (1.55 g, 11.2 mmol, 4 equivalents) was heated at 90 °C. 2 3 and stirred for 88 hours under an inert argon atmosphere. The reaction mixture then It was then concentrated under low pressure, and the resulting residue was treated with dichloromethane. It was diluted. The organic phase was washed with a saturated aqueous saline solution, MgSO4. 4 It has been dried, filtered, and concentrated under low pressure. The resulting residue is N-(2-cyclopentylethyl)-3-{[2- after trituration in diethyl ether. giving methyl-4-(pyridin-2-ylmethoxy)phenyl]amino}benzamide (39) (734 mg, 61%) The fraction was purified by column chromatography on silica gel to obtain the fraction. 1 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4,3 Hz, 1H), 8.26 (t, J = 5,5 Hz, 1H), 7.85 6 (td, J = 7,7, 1,6 Hz, 1H), 7.54 (d, J = 7,7 Hz, 1H), 7.47 (s, 1H), 7.35 (dd, J = 6,9, 5,5 Hz, 1H), 7.20 - 7.05 (m, 4H), 6.97 (d, J = 2,7 Hz, 1H), 6.85 (dd, J = 8,6, 2,7 Hz, 1H), 6.75 (d, J = 7,7 Hz, 1H), 5.16 (s, 2H), 3.21 (dd, J = 13,4, 6,5 Hz, 2H), 2.14 (s, 3H), 1.82 - 1.70 (m, 2H), 1.64 - 1.39 (m, 6H), 1.12 - 1.07 (m, 3H). 13 C NMR (75 MHz, d -DMSO) δ 165.1, 155.5, 153.2, 147.6, 145.4, 135.5, 134.4, 132.7, 6 132.3, 127.3, 123.6, 121.5, 120.1, 115.6, 114.6, 114.2, 111.3, 111.2, 68.9, 37.1, 35.9, 34.0, 30.7, 23.2, 16.6 + [M+H] = 430.3 Örnek 2: Tablo I'deki bileşik (50) According to route (I), 4-nitrophenol (1.4 g, 10 mmol, 1 equivalent), K₂CO₃ (4.2 g, 30 mmol, 3 2 3 N,N-dimethylformamide (7.7 mL) was placed in (equivalent) 2-fluorobenzyl bromide. 35 93 After the addition of (1.2 mL, 10 mmol, 1 equivalent), the reaction mixture was heated to 90 °C. and stirred for 16 hours under an inert argon atmosphere. At room temperature. After cooling, the reaction mixture was concentrated under low pressure and The resulting residue is divided between ethyl acetate and water. Upon decantation, The organic phase was washed with a saturated aqueous saline solution, on MgSO4. 4 Dried, filtered and 1-fluoro-2-(4-nitrophenoxymethyl)benzene (2.0 g, 81%) It is concentrated under low pressure to provide the desired result. 1 H NMR (300 MHz, CDCl) δ 8.22 (d, J = 9.3 Hz, 2H), 7.47 (t, J = 7.5 Hz, 1H), 7.37 3 (dd, J = 13.6, 5.8 Hz, 1H), 7.19 (t, J = 7.5 Hz, 1H), 7.16 - 7.10 (m, 1H), 7.05 (d, J = 9.3 Hz, 2H), 5.23 (s, 2H). According to route (C), 1-[(2-fluorophenyl)methoxy]-4-nitrobenzene (1.0 g, 4.0 mmol, 1 equivalent) and Tin (II) chloride dihydrate (4.6 g, 20 mmol, 5 equivalents) was placed in EtOH (40 mL). The reaction mixture was heated to 60 °C and kept under an inert argon atmosphere for 14 hours. The reaction mixture was then concentrated under low pressure. The resulting residue was diluted with dichloromethane. The organic phase was diluted with 1N NaOH aqueous solution. It was washed with a solution, then with saturated aqueous saline solution, MgSO4. 4 It has been dried, filtered and processed into 4-[(2-fluorophenyl)methoxy]aniline (836 mg, 95%). It is concentrated under low pressure to provide the desired result. 1 H NMR (300 MHz, CDCl3) δ 7.50 (td, J = 7.5, 1.0 Hz, 1H), 7.33 - 7.27 (m, 1H), 7.14 (td, J = 7.5, 1.0 Hz, 1H), 7.10 - 7.03 (m, 1H), 6.82 (d, J = 8.8 Hz, 2H), 6.64 (d, J = 8.8 Hz, 2H), 5.06 (s, 2H), 3.43 (s, 2H). 2-Cyclopentylethanol-1-amine hydrochloride (3.0 g, 19.1 mmol, 1.1 equivalents) in 3N NaOH aqueous solution It was placed in the solution (13 mL) and dichloromethane (3.2 mL) was added to the solution. The reaction mixture was cooled to 0 °C in an ice bath and dichloromethane (5.5 mL) by adding the 3-bromobenzoyl chloride solution (2.3 mL, 17.4 mmol, 1 equivalent) drop by drop added. The reaction mixture was then placed in an inert argon atmosphere at room temperature. It was stirred for 18 hours under the following conditions. Upon decantation, the organic phase became saturated. The aqueous solution was washed with saline solution, dried over MgSO, and filtered. 4 and to give 3-bromo-N-(2-cyclopentylethyl)benzamide (4.6 g, 89%) at low pressure It is concentrated below. 35 94 1 H NMR (300 MHz, CDCl) δ 7.89 (t, J = 1.7 Hz, 1H), 7.67 (d, J = 7.9 Hz, 1H), 7.62 3 (d, J = 7.9 Hz, 1H), 7.30 (t, J = 7.9 Hz, 1H), 6.07 (s, 1H), 3.46 (dd, J = 7.4, 5.9 Hz, 2H), 1.90 - 1.76 (m, 3H), 1.67 - 1.52 (m, 6H), 1.20 - 1.09 (m, 2H). According to route (A), a 3-bromo-N-(2-cyclopentylethyl)benzamide in t-BuOH (4 mL) (296 mg, 1 mmol, 1 equivalent), 4-[(2-fluorophenyl)methoxy]aniline (217 mg, 1 mmol, 1 equivalent) equivalent), Pd (dba) (92 mg, 100 µmol, 10 mol%), XPhos (95 mg, 200 µmol, 20 mol%) 2 3 and the reaction mixture of K₂CO₃ (553 mg, 4 mmol, 4 equivalents) was heated to 90 °C and a 2 3 The reaction mixture was stirred for 14 hours under an inert argon atmosphere. concentrated under low pressure, and the resulting residual dichloromethane It was diluted. The organic phase was washed with a saturated aqueous saline solution, MgSO4. 4 It has been dried, filtered, and concentrated under low pressure. The resulting residue, after trituration in diethyl ether, is N-(2-cyclopentylethyl)-3-({4- [(2-fluorofenil)metoksi]fenil}amino)benzamid (50) (168 mg, 39%) It also means that the color of the chromatography is safe. 1 H NMR (300 MHz, d -DMSO) δ 8.31 (t, J = 5.6 Hz, 1H), 8.05 (s, 1H), 7.57 (td, J = 7.4, 6 1.5 Hz, 1H), 7.47 - 7.36 (m, 2H), 7.30 - 7.19 (m, 3H), 7.15 (d, J = 7.7 Hz, 1H), 7.07 (d, J = 9.0 Hz, 2H), 7.05 - 7.0 (m, 1H), 6.98 (d, J = 9.0 Hz, 2H), 5.10 (s, 2H), 3.23 (dd, J = 13.8, 6.3 Hz, 2H), 1.86 - 1.72 (m, 3H), 1.62 - 1.45 (m, 6H), 1.11 - 1.04 (m, 2H). 13 C NMR (75 MHz, d6-DMSO) δ 164.6, 160.2, 156.9, 151.1, 143.3, 134.4, 134.2, 128.9, 128.8, 128.4, 127.1, 122.7, 122.7, 122.4, 122.2, 118.7, 117.4, 115.3, 114.9, 113.8 113.4, 111.8, 78.0, 62.0, 35.6, 33.7, 30.4, 22.9 Example 3: Compound (60) in Table I According to route (I), 3-nitro-4-nitrophenol (1.7 g, 7.9 mmol, 1 equivalent), K CO (3.3 g, 23.7 mmol, 2 3 3 equivalents) were placed in N,N-dimethylformamide (6 mL). 2-(bromomethyl)pyridine After the addition of hydrobromide (2.0 g, 7.9 mmol, 1 equivalent), the reaction mixture It was heated to 90 °C and stirred for 24 hours under an inert argon atmosphere. Chamber After being cooled to its temperature, the reaction mixture is concentrated under low pressure. and the resulting residue was separated between dichloromethane and water. Decantation The organic phase was washed with a saturated aqueous saline solution, on MgSO4. 4 35 95 Dried, filtered and 2-(3-bromo-4-nitrophenoxymethyl)pyridine (2.4 g, 98%) It is concentrated under low pressure to provide the desired result. 1 H NMR (300 MHz, CDCl) δ 8.63 (d, J = 4.8 Hz, 1H), 7.97 (d, J = 9.1 Hz, 1H), 7.76 3 (td, J = 7.7, 1.7 Hz, 1H), 7.47 (d, J = 7.7 Hz, 1H), 7.35 (d, J = 2.7 Hz, 1H), 7.32 - 7.27 (m, 1H), 7.01 (dd, J = 9.1, 2.7 Hz, 1H), 5.27 (s, 2H). According to route (J), 2-(3-bromo-4-nitrophenoxymethyl)pyridine (2.4 g, 7.8 mmol, 1 equivalent), Pd(dppf)Cl .CH Cl (634 mg, 0.78 mmol, 0.1 equivalent) into 1,4-dioxane (28 mL) 2 2 2 It contains K₂PO₄ (6.6 g, 31 mmol, 4 equivalents) and cyclopropylboronic acid (2.0 g, 3 4 After the addition of 23.3 mmol, 3 equivalents, the reaction mixture was heated to 100 °C and The reaction mixture was stirred for 20 hours under an inert argon atmosphere. It was concentrated under low pressure and the resulting residue is 2-(3-cyclopropyl-4- column on silica gel to dispense nitrophenoxymethyl)pyridine (1.5 g, 71%) It was purified by chromatography. 1 H NMR (300 MHz, CDCl) δ 8.62 (d, J = 4.2 Hz, 1H), 7.94 (d, J = 9.0 Hz, 1H), 7.74 3 (td, J = 7.7, 1.7 Hz, 1H), 7.47 (d, J = 7.7 Hz, 1H), 7.30 - 7.22 (m, 2H), 6.84 (dd, J = 9.0, 2.7 Hz, 1H), 6.72 (d, J = 2.7 Hz, 1H), 5.24 (s, 2H), 2.54 (tt, J = 8.5, 5.5 Hz, 1H), 1.06 (q, J = 4.8 Hz, 2H), 0.67 (q, J = 4.8 Hz, 2H). According to route (C), 2-(3-cyclopropyl-4-nitrophenoxymethyl)pyridine (1.5 g, 5.6 mmol, 1 equivalent) and tin (II) chloride dihydrate (6.3 g, 28 mmol, 5 equivalents) to EtOH (56 mL) The reaction mixture was heated to 60 °C and placed in an inert argon atmosphere. The reaction mixture was stirred for 64 hours. The reaction mixture was then removed under low pressure. It was concentrated and the resulting residue was diluted with dichloromethane. The organic phase, with a 1N NaOH aqueous solution, then with a saturated aqueous saline solution. It has been washed, dried over MgSO, filtered, and 2-cyclopropyl-4-(pyridine-2- 4 It was concentrated under low pressure to give ylmethoxy)aniline (1.1 g, 82%). 1 H NMR (300 MHz, CDCl) δ 8.58 (d, J = 4.2 Hz, 1H), 7.70 (td, J = 7.7, 1.7 Hz, 1H), 3 7.52 (d, J = 7.7 Hz, 1H), 7.20 (dd, J = 6.9, 5.4 Hz, 1H), 6.73 (t, J = 2.7 Hz, 1H), 6.69 (d, J = 2.7 Hz, 1H), 6.61 (d, J = 8.3 Hz, 1H), 5.12 (s, 2H), 3.71 (s, 2H), 1.74 - 1.65 (m, 1H), 0.90 (q, J = 4.1 Hz, 2H), 0.58 (q, J = 4.1 Hz, 2H). 35 96 2-Cyclopentylethanol-1-amine hydrochloride (1.3 g, 8.7 mmol, 1.1 equivalents) in 3N NaOH aqueous solution It was placed in the solution (5.9 mL) and dichloromethane (1.5 mL) was added to the solution. The reaction mixture was cooled to 0 °C in an ice bath and dichloromethane (2.4 mL) by adding the 3-bromobenzoyl chloride solution (1.0 mL, 7.9 mmol, 1.0 equivalent) inside drop by drop added. The reaction mixture was then placed in an inert argon atmosphere at room temperature. It was stirred for 18 hours under the following conditions. Upon decantation, the organic phase became saturated. The aqueous solution was washed with saline solution, dried over MgSO, and filtered. 4 and to give 3-bromo-N-(2-cyclopentylethyl)benzamide (1.8 g, 77%) at low pressure It is concentrated below. 1 H NMR (300 MHz, CDCl) δ 7.89 (t, J = 1.7 Hz, 1H), 7.67 (d, J = 7.9 Hz, 1H), 7.65 - 3 7.58 (m, 1H), 7.31 (t, J = 7.9 Hz, 1H), 6.07 (s, 1H), 3.46 (dt, J = 7.4, 5.9 Hz, 2H), 1.88 - 1.79 (m, 3H), 1.67 - 1.47 (m, 6H), 1.18 - 1.13 (m, 2H). According to route (A), a 3-bromo-N-(2-cyclopentylethyl)benzamide in t-BuOH (2 mL) (148 mg, 0.5 mmol, 1 equivalent), 2-cyclopropyl-4-(pyridin-2-ylmethoxy)aniline (120 mg, 0.5 mmol, 1 equiv), Pd (dba) (46 mg, 50 µmol, 10 mol%), XPhos (48 mg, 2 3 reaction mixture of 100 µmol, 20 mol%) and K₂CO₃ (277 mg, 2.0 mmol, 4 equivalents). 2 3 It was heated to 90 °C and stirred for 14 hours under an inert argon atmosphere. The reaction mixture was then concentrated under low pressure, and the following was obtained: The resulting residue was diluted with dichloromethane. The organic phase was a saturated aqueous brine. It was washed with solution, dried over MgSO4, filtered, and placed at low temperature. It was concentrated under pressure. The resulting residue is N-(2-cyclopentylethyl)-3-{[2- cyclopropyl-4-(pyridin-2-ylmethoxy)phenyl]amino}benzamide (60) (190 mg, 83%) It was purified by column chromatography on silica gel. 1 H NMR (300 MHz, CDCl) δ 8.61 (d, J = 4.2 Hz, 1H), 7.73 (td, J = 7.7, 1.7 Hz, 1H), 7.54 3 (d, J = 7.7 Hz, 1H), 7.26 - 7.19 (m, 3H), 7.16 (d, J = 8.6 Hz, 1H), 7.08 (d, J = 7.7 Hz, 1H), 6.95 (dd, J = 7.7, 1.7 Hz, 1H), 6.78 (dd, J = 8.6, 2.9 Hz, 1H), 6.68 (d, J = 2.9 Hz, 1H), 6.03 (s, 1H), 5.71 (s, 1H), 5.18 (s, 2H), 3.43 (dd, J = 9.8, 4.7 Hz, 2H), 1.90 - 1.78 (m, 5H), 1.66 - 1.51 (m, 4H), 1.17 - 1.09 (m, 3H), 0.94 - 0.87 (m, 2H), 0.67 - 0.59 (m, 2H). 13 C NMR (75 MHz, CDCl) δ 165.4, 155.1, 152.7, 146.9, 143.9, 135.4, 134.5, 133.8, 3 132.2, 127.0, 120.9, 120.3, 119.0, 115.3, 114.4, 111.8, 111.2, 110.0, 68.6, 37.2, 35.6, 33.6, 30.4, 22.8, 9.3, 4.9 35 97 + [M+H] = 456.4 Example 4: Compound (68) in Table I According to route (I), 4-nitro-5-methylphenol (3.06 g, 20 mmol, 1 equivalent), K₂CO₃ (8.3 g, 60 mmol, 2 3 3 equivalents) were placed in N,N-dimethylformamide (15 mL). 2-(bromomethyl)pyridine After the addition of hydrobromide (5.06 g, 20 mmol, 1 equivalent), the reaction mixture It was heated to 90 °C and stirred for 24 hours under an inert argon atmosphere. After being cooled to room temperature, the reaction mixture is placed under low pressure. It was concentrated, and the resulting residue was separated between dichloromethane and water. After decantation, the organic phase was washed with a saturated aqueous saline solution. Dried over MgSO, filtered and 2-(3-methyl-4-nitrophenoxymethyl)pyridine 4 It was concentrated under low pressure to yield (4.5 g, 92%). 1 H NMR (300 MHz, CDCl) δ 8.65 - 8.60 (m, 1H), 8.07 (d, J = 9.8 Hz, 1H), 7.75 (td, J = 7.7, 3 1.7 Hz, 1H), 7.48 (d, J = 7.7 Hz, 1H), 7.30 - 7.24 (m, 1H), 6.90 - 6.87 (m, 2H), 2.62 (s, 3H). According to route (C), 2-(3-methyl-4-nitrophenoxymethyl)pyridine (4.5 g, 18.4 mmol, 1 equivalent) and Tin (II) chloride dihydrate (20.8 g, 92 mmol, 5 equivalents) was placed in EtOH (184 mL). The reaction mixture was heated to 60 °C and kept under an inert argon atmosphere for 14 hours. The reaction mixture was then concentrated under low pressure. and the resulting residue was diluted with dichloromethane. The organic phase was diluted with 1N NaOH. It was washed with an aqueous solution, and then with a saturated aqueous saline solution. Dried over MgSO, filtered, and processed into 2-methyl-4-(pyridin-2-ylmethoxy)aniline. 4 It was concentrated under low pressure to give (2.0 g, 51%). 1 H NMR (300 MHz, CDCl) δ 8.58 (d, J = 4.3 Hz, 1H), 7.70 (td, J = 7.7, 1.7 Hz, 1H), 3 7.52 (d, J = 7.7 Hz, 1H), 7.23 - 7.17 (m, 1H), 6.76 (d, J = 2.7 Hz, 1H), 6.69 (dd, J = 8.5, 2.7 Hz, 1H), 6.60 (d, J = 8.5 Hz, 1H), 5.13 (s, 2H), 3.37 (s, 2H), 2.15 (s, 3H). 3-Bromophenyl isocyanate (624 μL, 5.0 mmol, 1.0 equivalent) and triethylamine (695 μL, 5.0 mmol, 1.0 equivalent) was placed in dichloromethane (5 mL) and dichloromethane (2 mL) by dropping a solution of 3-methylbutane-1-amine (580 μL, 5.0 mmol, 1.0 equivalent) into it added. The reaction mixture was then placed in an inert argon atmosphere at room temperature. 35 98 The reaction mixture was stirred for 16 hours under low pressure. It was concentrated and the resulting residue was diluted with ethyl acetate. The organic phase was a 1N It was washed with an aqueous solution of HCl, and then with a saturated aqueous saline solution. MgSO4 was dried, filtered, and concentrated under low pressure. 4 The resulting residue was 1-(3-bromophenyl)-3-(3-methylbutyl)urea (1.06 g, 74%). To achieve this, it was purified by column chromatography on silica gel. 1 H NMR (300 MHz, CDCl) δ 7.54 (s, 1H), 7.49 (t, J = 1.9 Hz, 1H), 7.18 (dt, J = 7.2, 3 1.9 Hz, 1H), 7.13 - 7.03 (m, 2H), 5.56 (t, J = 5.3 Hz, 1H), 3.20 (dt, J = 7.5, 5.8 Hz, 2H), 1.60 - 1.54 (m, 1H), 1.36 - 1.30 (m, 2H), 0.86 (d, J = 6.6 Hz, 6H). According to route (A), 1-(3-bromophenyl)-3-(3-methylbutyl)urea (285 mg, in t-BuOH (4 mL, 1.0 mmol, 1 equivalent), 2-methyl-4-(pyridin-2-ylmethoxy)aniline (214 mg, 1.0 mmol, 1 equivalent), Pd (dba) (92 mg, 100 µmol, 10 mol%), XPhos (95 mg, 200 µmol, 20 mol%) 2 3 and the reaction mixture of K₂CO₃ (553 mg, 4.0 mmol, 4 equivalents) was heated to 90 °C and a 2 3 The reaction mixture was stirred for 24 hours under an inert argon atmosphere. concentrated under low pressure, and the resulting residual dichloromethane It was diluted. The organic phase was washed with a saturated aqueous saline solution, MgSO4. 4 It has been dried, filtered, and concentrated under low pressure. The resulting residue is 1-isopentyl-3-(3-((2-methyl-4- after trituration in diethyl ether. to give a fraction that gives (pyridine-2-ylmethoxy)phenyl)amino)phenyl)urea (68) (76 mg, 18%). It was purified by column chromatography on silica gel. 1 H NMR (300 MHz, d -DMSO) δ 8.59 (d, J = 4.5 Hz, 1H), 8.15 (s, 1H), 7.85 (td, J = 7.9, 6 1.5 Hz, 1H), 7.54 (d, J = 7.9 Hz, 1H), 7.39 - 7.31 (m, 1H), 7.18 (s, 1H), 7.06 (d, J = 8.6 Hz, 1H), 6.96 - 6.90 (m, 2H), 6.82 (dd, J = 8.6, 2.8 Hz, 1H), 6.73 (s, 1H), 6.67 (d, J = 7.9 Hz, 1H), 6.21 (d, J = 7.9 Hz, 1H), 5.92 (t, J = 5.4 Hz, 1H), 5.14 (s, 2H), 3.06 (dd, J = 13.3, 6.7 Hz, 2H), 2.14 (s, 3H), 1.57 (td, J = 13.3, 6.7 Hz, 1H), 1.33 - 1.25 (m, 2H), 0.88 (d, J = 6.7 Hz, 6H). + [M+H] = 419.4 Example 5: Compound (73) in Table I According to route (I), 4-nitrophenol (2.75 g, 19.8 mmol, 1 equivalent), K₂CO₃ (8.2 g, 59.3 mmol, 3 2 3 N,N-dimethylformamide (15 mL) was placed in (equivalent) 2-(bromomethyl)pyridine. 35 99 After the addition of hydrobromide (5.0 g, 19.8 mmol, 1 equivalent), the reaction mixture It was heated to 90 °C and stirred for 16 hours under an inert argon atmosphere. After being cooled to room temperature, the reaction mixture is placed under low pressure. It was concentrated, and the resulting residue was separated between ethyl acetate and water. Upon decantation, the organic phase was washed with a saturated aqueous saline solution. MgSO4 was dried, filtered, and concentrated under low pressure. 4 The resulting residue was processed to give 2-(4-nitrophenoxymethyl)pyridine (3.1 g, 68%). 1 Purified by column chromatography on silica gel. 1H NMR (300 MHz, CDCl ) δ 8.63 (d, J = 4.8 Hz, 1H), 8.25 - 8.16 (m, 2H), 7.75 (td, J = 7.7, 1.7 Hz, 1H), 3 7.48 (d, J = 7.7 Hz, 1H), 7.31 - 7.26 (m, 1H), 7.11 - 7.03 (m, 2H), 5.30 (s, 2H). According to route (C), 2-(4-nitrophenoxymethyl)pyridine (2.0 g, 8.7 mmol, 1 equivalent) and tin (II) Chloride dihydrate (9.8 g, 43 mmol, 5 equivalents) was placed in EtOH (87 mL). The reaction... The mixture was heated to 60 °C and stirred for 14 hours under an inert argon atmosphere. Subsequently, the reaction mixture was concentrated under low pressure, and the resulting The residue was diluted with ethyl acetate. The organic phase was then diluted with a 1N NaOH aqueous solution, further... It was then washed with a saturated aqueous saline solution, on MgSO4. 4 It has been dried, filtered, and concentrated under low pressure. The resulting... residue, 4-(pyridin-2-ylmethoxy)aniline (1.1 g, 63%) on silica gel column 1 was purified by chromatography. H NMR (300 MHz, CDCl) δ 8.58 (d, J = 4.3 Hz, 3 1H), 7.70 (td, J = 7.7, 1.7 Hz, 1H), 7.52 (d, J = 7.7 Hz, 1H), 7.20 (dd, J = 7.2, 5.2 Hz, 1H), 6.85 - 6.79 (m, 2H), 6.67 - 6.61 (m, 2H), 5.13 (s, 2H), 3.43 (br s, 2H). Cyclopentanepropanol (2.0 g, 15.6 mmol, 1 equivalent) and triethylamine (2.8 mL, 20.1 mmol, 1.3 The solution was placed in dichloromethane (9.1 mL) (equivalent). The solution was heated to 0 °C in an ice bath. It was refrigerated and 4-toluenesulfonyl chloride (2.6 g, 13.6 mmol) in dichloromethane (4.6 mL). 0.9 equivalents of the solution were added dropwise. The reaction mixture was then placed in room temperature. It was stirred for 24 hours under an inert argon atmosphere at a certain temperature. The organic phase was It was washed with a 1N aqueous HCl solution, then with a saturated aqueous NaHCO3 solution, 3 It was dried over MgSO, filtered, and concentrated under low pressure. 4 The resulting residue was to give 3-cyclopentylpropyl 4-methylbenzene-1-sulfonate (3.2 g, 83%). It was purified by column chromatography on silica gel. 1 H NMR (300 MHz, CDCl) δ 7.79 (d, J = 8.1 Hz, 2H), 7.34 (d, J = 8.1 Hz, 2H), 4.02 (t, J = 3 6.6 Hz, 1H), 2.45 (s, 2H), 1.75 - 1.43 (m, 11H), 1.34 - 1.23 (m, 2H), 1.05 - 0.95 (m, 2H). 35 100 3-Bromophenol (613 mg, 3.5 mmol, 1 equivalent), Cs CO (3.5 g, 10.7 mmol, 3 equivalents) with N,N- 2 3 Dimethylformamide (25 mL) is placed in 3-cyclopentylpropyl 4-methylbenzene-1-sulfonate. After the addition of (1.0 g, 3.5 mmol, 1 equivalent), the reaction mixture was heated to 90 °C and It was stirred for 14 hours under an inert argon atmosphere. It was then cooled to room temperature. The reaction mixture is then concentrated under low pressure, and the resulting residue, It is divided between ethyl acetate and water. Upon decantation, the organic phase becomes a saturated aqueous. It was washed with NH4Cl solution and then with a saturated aqueous saline solution, 4 Dried over MgSO, filtered and 1-bromo-3-(3-cyclopentylpropoxy)benzene 4 1 Concentrated under low pressure to give (716 mg, 71%). 1H NMR (300 MHz, CDCl ) δ 7.14 - 7.10 (m, 1H), 7.07 - 7.03 (m, 2H), 6.82 (ddd, J = 8.1, 2.3, 1.2 Hz, 1H), 3.92 3 (t, J = 6.6 Hz, 2H), 1.86 - 1.70 (m, 6H), 1.69 - 1.40 (m, 7H), 1.18 - 1.03 (m, 2H). According to route (A), a 1-bromo-3-(3-cyclopentylpropoxy)benzene in t-BuOH (4 mL) (282 mg, 1.0 mmol, 1 equivalent), 4-(pyridin-2-ylmethoxy)aniline (200 mg, 1.0 mmol, 1 equivalent), Pd (dba) (92 mg, 100 µmol, 10 mol%), XPhos (95 mg, 200 µmol, 20 mol%) and 2 3 The reaction mixture K₂CO₃ (553 mg, 4.0 mmol, 4 equivalents) was heated to 90 °C and placed in an inert 2 3 The reaction mixture was stirred for 64 hours under an argon atmosphere. The reaction mixture was then lowered. It was concentrated under pressure, and the resulting residue was diluted with dichloromethane. The organic phase was washed with a saturated aqueous saline solution, based on MgSO4. 4 It has been dried, filtered, and concentrated under low pressure. The resulting... residue, 3-(3-cyclopentylpropoxy)-N-(4-(pyridin-2-ylmethoxy)phenyl)aniline (73) (94 mg, 23%) It was purified by column chromatography on silica gel to give the desired result. 1 H NMR (300 MHz, CDCl) δ 8.59 (d, J = 5.2 Hz, 1H), 7.71 (td, J = 7.7, 1.7 Hz, 1H), 7.53 3 (d, J = 7.7 Hz, 1H), 7.21 (dd, J = 7.0, 5.2 Hz, 1H), 7.12 - 7.03 (m, 3H), 6.96 - 6.89 (m, 2H), 6.50 - 6.44 (m, 2H), 6.38 (dd, J = 7.7, 1.7 Hz, 1H), 5.55 (br s, 1H), 5.18 (s, 2H), 3.88 (t, J = 6.6 Hz, 2H), 1.82 - 1.68 (m, 7H), 1.66 - 1.46 (m, 5H), 1.17 - 1.04 (m, 3H). Example 6: Compound (93) in Table I According to procedure (A1), an N-(3-bromophenyl)-3- in anhydrous DMF (1.3 mL) cyclohexylmepropanamide (113 mg, 0.423 mmol, 1.2 equivalents), 4-(benzyloxy)-2-(cyclopent-1- en-1-yl)aniline (100 mg, 0.351 mmol, 1.0 equivalent), BrettPhos Pd G3 (6.4 mg, 7.0 μmol, 2% reaction mixture of Cs CO (171 mg, 0.526 mmol, 1.5 equivalents) with argon gas 35 2 3101 It was purified and heated at 80 °C for 75 minutes under an inert atmosphere. The reaction The mixture was then cooled to room temperature, filtered through a cellulose pad, and The pad was washed with EtOAc. Then saturated aqueous saline solution was added to the filtrate. The mixture was extracted with EtOAc. Combined organic phases were placed on MgSO4. 4 It has been dried, filtered, and concentrated under low pressure. The resulting... residue, N-(3-{[4-(benzyloxy)-2-(cyclopent-1-en-1-yl)phenyl]amino}phenyl)-3-cyclohexylpropanamide Purified by column chromatography on silica gel to yield (131 mg, 76%). 1 H NMR (400 MHz, d -DMSO) δ 7.52 - 7.22 (m, 5H), 6.76 - 6.53 (m, 3H), 6.01 (s, 1H), 6 4.97 (p, 2H), 4.50 (p, 2H), 2.62 (t, J = 6.6 Hz, 2H), 1.89 (p, J = 7.5 Hz, 2H). + [M+H] = 495.3 A 0.025 M N-(3-{[4-(benzyloxy)-2-(cyclopent-1-en-1- in MeOH:THF (1:1) 1)phenyl]amino}phenyl)-3-cyclohexylpropanamide (100 mg, 0.202 mmol, 1.0 equivalent) solution through an H-cube apparatus (cartridge Pd / C 30 mm, 30 °C, 2 bar, 1 mL / min). The solvent has been passed through. The solvent was then concentrated under low pressure. The resulting... residue, N-(3-{[4-(benzyloxy)-2-cyclopentylphenyl]amino}phenyl)-3-cyclohexylpropanamide (93) Purified by column chromatography on silica gel to yield (50.0 mg, 50%). 1 H NMR (400 MHz, d -DMSO) δ 9.55 (s, 1H), 7.55 - 7.27 (m, 5H), 7.17 (s, 1H), 7.08 - 6.73 6 (m, 6H), 6.27 (d, J = 8.9 Hz, 1H), 5.08 (s, 2H), 3.26 - 3.13 (m, 1H), 2.28 - 2.15 (m, 2H), 1.89 (d, J = 6.1 Hz, 2H), 1.79 - 1.36 (m, 14H), 1.28 - 1.04 (m, 4H), 0.87 (q, J = 10.4, 8.9 Hz, 2H). + [M+H] = 497.3 Example 7: Compound (101) in Table I According to route (I), 4-amino-3-tert-butylphenol (100 mg, 0.581 mmol, 1 equivalent), Cs CO (227 mg, 2 3 0.697 mmol, 1.2 equivalents) was placed in N,N-dimethylformamide (2 mL). Upon addition of bromomethylbenzene (75.9 μL, 0.639 mmol, 1 equivalent), the reaction mixture, The mixture was stirred for 16 hours at room temperature under an inert argon atmosphere. The reaction took place in a 1 M aqueous humor. It was quenched with hydrochloric acid and extracted with ethyl acetate. Combined organic. The phases were dried on magnesium sulfate, filtered, and O and N poly-benzylated. The products are concentrated under low pressure to provide a mixture. Residue 35 102 methanol (15 mL) was placed in an H-cube apparatus (Pd / C 10%, 1 bar hydrogen pressure, The solvent was hydrogenated using a flow rate of 1 mL / minute. The solvent was then hydrogenated under low pressure. It is concentrated below. The resulting residue is 4-(benzyloxy)-2-tert-butylaniline. Purified by column chromatography on silica gel to yield (23.8 mg, 21%). 1 H NMR (400 MHz, d -DMSO) δ 7.42 (d, J = 6.9 Hz, 2H), 7.37 (t, J = 7.3 Hz, 2H), 7.31 6 (d, J = 7.0 Hz, 1H), 6.72 (d, J = 2.7 Hz, 1H), 6.61 (d, J = 2.7 Hz, 1H), 6.58 (d, J = 8.5 Hz, 1H), 4.94 (s, 2H), 4.32 (s, 2H), 1.31 (s, 9H). According to procedure (A1), one methyl 2-bromobenzoate (11.0 mL) in anhydrous toluene (1.0 mL) μL, 78.3 μmol, 1.0 equivalent), 4-(benzyloxy)-2-tert-butylaniline (20.0 mg, 78.3 μmol, 1.0 equivalent), Pd(OAc) (0.53 mg, 2.3 μmol, 3% mol), rac-BINAP (0.98 mg, 1.6 μmol, 2% mol) 2 reaction mixture of μM (235 μmol, 3 equivalents) and K₂CO₃ (32.5 mg, 235 μmol, 3 equivalents) with N₂ gas 2 3 2 It was purified and heated at 110 °C for 75 minutes under an inert atmosphere. The reaction... The mixture was cooled to room temperature, filtered through a cellulose pad, and the pad, It was washed with EtOAc. Then saturated aqueous saline solution was added to the filtrate and The mixture was extracted with EtOAc. Combined organic phases were placed on MgSO4. 4 It has been dried, filtered, and processed into methyl 2-{[4-(benzyloxy)-2-tert-butylphenyl]amino}benzoate. It was concentrated under low pressure to give (50.0 mg, 47% purity, 77%). Methyl 2-{ [4-(benzyloxy)-2-tert-butylphenyl] amino}benzoate (50.0 mg, 47% purity, 60.3 μmol, 1 equivalent) was placed in methanol (2 mL) and a 2 M aqueous solution of NaOH (151 μL, 302 μmol, 5 equivalents) solution was added. The reaction mixture was heated to 80 °C and 3 The mixture was stirred for hours. It was then concentrated under low pressure and a 2 M solution was obtained. extracted with dichloromethane after addition of aqueous HCl (10 equivalents) solution Combined organic phases were dried on magnesium sulfate. filtered and 2-{[4-(benzyloxy)-2-tert-butylphenyl]amino}benzoic acid (28.0 mg, 42%) It was concentrated under low pressure to give a purity of 52%. 2-{[4-(benzyloxy)-2-tert-butylphenyl]amino}benzoic acid (28.0 mg, 42% purity, 74.6 μmol, 1 (equivalent) and 2-cyclohexylathanamine (12.5 μL, 89.5 μmol, 1.2 equivalents) anhydrous N,N- Dimethylformamide (1.0 mL) was placed in HATU (44.3 mg, 112 μmol, 1.5 equivalents) and DIPEA (39.1 μL, 224 μmol, 3 equivalents) was added and the resulting reaction mixture was placed in room temperature. The mixture was stirred at [temperature] for 16 hours. The reaction was quenched with 1 M aqueous hydrochloric acid. and extracted with ethyl acetate. Combined organic phases on magnesium sulfate. 35 103 It has been dried, filtered, and concentrated under low pressure. The resulting product... residue, 2-{ [4-(benzyloxy)-2-tert-butylphenyl]amino}-N-(2-cyclohexylethyl)benzamide (101) It was purified by column chromatography on silica gel to give (5.1 mg, 14%). 1 H NMR (400 MHz, d -DMSO) δ 9.47 (s, 1H), 8.40 (s, 1H), 7.61 (d, J = 6.9 Hz, 1H), 6 7.48 (d, J = 7.1 Hz, 2H), 7.41 (t, J = 7.4 Hz, 2H), 7.34 (t, J = 7.2 Hz, 1H), 7.16 (t, J = 7.7 Hz, 1H), 7.06 (d, J = 8.6 Hz, 1H), 7.00 (d, J = 2.8 Hz, 1H), 6.90 (dd, J = 8.6, 2.8 Hz, 1H), 6.61 (t, J = 7.4 Hz, 1H), 6.49 (d, J = 8.4 Hz, 1H), 5.09 (s, 2H), 3.27 (d, J = 6.8 Hz, 2H), 1.74 (d, J = 12.2 Hz, 2H), 1.64 (dd, J = 20.5, 11.1 Hz, 3H), 1.44 (q, J = 6.9 Hz, 2H), 1.31 (s, 9H), 1.26 - 1.13 (m, 4H), 0.90 (q, J = 13.3, 12.5 Hz, 2H). + [M+H] = 485.3 Pharmacologic vari Example 8: Chikungunya Virus Vaccines, therapy and vaccine against Chikungunya virus infection suitable as active substances for prevention, inhibition or treatment. They have been subjected to pharmacological tests which have shown that they are effective. MATERIALS AND PROCEDURES Inhibition of Chikungunya virus (CHIKV) production in infected HEK293T cell line. The compounds' ability to inhibit viral replication is demonstrated when infected cells are formulated at 1 μM. It was evaluated in an experiment in which it was treated with compounds belonging to (Ie). Ribavirin has been used as a positive control for the inhibition of Chikungunya. The toxicity of the compounds was evaluated in parallel. • Cell amplification Human embryonic kidney cells 293T (HEK293T, CRL-11268), 10% fetal bovine serum (FBS), Dulbecco modified Eagle Medium supplemented with penicillin and streptomycin. (DMEM, 31966-021, Thermo Fisher Scientific) stored in. The environment 35 104 2+ After removal, the cells remove all traces of serum using Ca and 2+ It was washed with a magnesium-free saline solution. From the aspiration of the washing solution... Next, the cells were separated with a 0.25% trypsin-EDTA solution and stored at a minimum of 37 °C. The cell suspension was incubated in an incubator for 30 seconds. The cell suspension concentration was adjusted automatically. Determined by cell counter (EVE, NanoEntek) and supplemented with 10% FBS if necessary. 6 It was adjusted to 0.33 × 10 cells / mL with DMEM medium. • Preparation of compounds 100 μL of the cell suspension was placed in a ViewPlate-96 Black (6005182, PerkinElmer) and It was transferred to a transparent 96-well cell culture plate (655180, Greiner bio-one). 24 After incubation at 37 °C under 5% CO2 for 7 hours, the compounds are suitable. 2 It has been added in a specific concentration. • Scanning at 1 μM Stock solution was mixed with 2 mM DMSO (D8418, Sigma) in a 96-well V-bottom microplate. An intermediate dilution was prepared with: One μL of the 50 mM stock library is mixed in 25 μL of DMSO. 2 μL of the mM stock library is mixed in 25 μL of DMSO. • Determining IC values 50 Stock solution was mixed with 25 mM DMSO (D8418, 96-well V-bottom microplate) An intermediate dilution was prepared using Sigma: 2 μL of the 50 mM stock library is mixed in 2 μL of DMSO. Serial dilution is performed 13 times in 2 μL DMSO to reach 0.0015 mM. Table III continues as follows: Table III 35 105 Concentration (mM) DMSO Volume 100% (μL) Solution volume A 12.5 μL 50 mM solution B 6.25 2 2 μL solution A C 3,125 2 2 μL solution B D 1.56 2 2 μL solution C E 0.78 2 2 μL solution D F 0.39 2 2 μL solution E G 0.195 2 2 μL solution F H 0.0976 2 2 μL solution G I 0.0488 2 2 μL solution H J 0.0244 2 2 μL solution I K 0.0122 2 2 μL solution J L 0.0061 2 2 μL solution K M 0.0030 2 2 μL solution L N 0.0015 2 2 μL solution M For both screening and determination of IC, 1 μL of each solution, 50 One 1 mL Masterblock 96 cell (Greiner bio-one, 780261) containing 1 mL of DMEM medium. 5 μL of 80 mM Ribavirin solution (R9644, Sigma) was added as a positive control. 1 mL of DMEM is added. On the other hand, DMSO is used as a negative control. • Infection Cells with GFP modification within 5' (CHIK 5'LR) were involved in the La Réunion outbreak (LR2006- OPY1) was infected with 30 μL of CHIKV strain (for Vector Proficiency Studies). (https: / / www.european-virus-archive.com / nucleic-acid / chikv-lr-5gfp-infectious-clone) Tsetsarkin K, Higgs S, McGee CE, De Lamballerie X, Charrel RN, available at [address] Vanlandingham D.L. Infectious Clones of Chikungunya Virus (La Réunion Isolate - Ref- SKU: 001N-EVA249 (PMID: 17187566). Vector Borne Zoonotic Dis. 2006; 6(4)). This The modified virus, CHIKV, was used to infect cells at an MOI of 0.1. The LR2006-OPY1 strain (CHIKV-LR) was developed at the University of Texas Medical Branch, Galveston, Texas. 35 106 Obtained from the World Reference Centre for Arboviruses. This strain was originally from La. It was isolated from the serum of a feverish French patient returning from Réunion Island. • Cell lysis The medium was removed after 22 hours at 37°C under 5% CO2, and the cells were as described above. 2 Washed as described. 60 μL RIPA buffer (50 mM Tris-HCl pH 8, 100 mM NaCl, 1 mM MgCl₂ (1% Triton X-100) was added to the cells and the fluorescent signal was read before... 2 Incubated for at least 20 minutes. Normalizing the fluorescent signal according to protein amount. Pierce 660 nm Protein Analysis Reagent (22660, Thermo scientific) was used for this purpose. ® CellTiter 96 AQueous One Solution is used to control the toxicity of compounds in cells. Proliferation Analysis (MTS) (G3581, Promega) was used. 20 μL MTS solution It was added and the absorbance was read at 492 nm after one hour. Results - The inhibition results are calculated as follows, through the steps below: A first experimental round was conducted in which the results were expressed as a percentage: 1. Fluorescence intensity (FI) / Absorbance 660 nm (A660) = A This ratio allows the infection to be considered based on the amount of GFP virus protein. 2. A' = A - background noise of the uninfected plate, 3. B = Fluorescence intensity (FI) / Infected but untreated plates absorbance (660 nm) (A660), 35 107 4. C = A' / B, This then shows infection after treatment compared to the untreated sample. It is converted as a percentage and then as an infection percentage. For example, The value of 100 in Table IV below represents the signal attributed to GFP fluorescence after treatment. This means it has been eliminated, a condition associated with the absence of infection. 5. C' = 100 - C This value corresponds to the percentage of inhibition. Table IV below shows the mean and corresponding standard deviation of the two experiments above. It includes the aforementioned C' value for some compounds, as calculated. Some values ​​are initially above 100. In such cases, the value is set back to 100. This has been reduced. This indicates that some molecules also have an effect on the viability of cells. This means that, in other words, the A value can be lower than the background noise. Additionally, for each measurement, the test was performed with Ribavirin as a control. The percentage of inhibition was checked and given as 100%. Table IV % CHIKV inhibition Sample Mean (n = 2) Standard Deviation (n = 2) 36 99 0 37 100 0 38 99 2 39 98 1 35 40 99 1 108 % CHIKV inhibition Sample Mean (n = 2) Standard Deviation (n = 2) 41 99 1 43 100 0 45 99 2 46 99 2 47 96 1 48 98 1 49 98 3 50 100 0 51 100 0 52 99 1 73 100 0 - A second round of experiments was conducted, with the results presented as IC values. 50 IC values ​​range from 0.1 nM to 1 μM, especially between 0.5 and 500 nM, and even higher. 50 It varies very specifically between 1 and 400 nM, for example, between 1 and 200 nM. For example compounds (36)-(41), (53), (54), (57), (58), (60)-(62), (64), (68), (70) and (71), 1 to 400 nM It has an IC value that varies between [range]. 50 Conclusion Based on previous results, compounds belonging to the formula (Ie) are effective against group IV RNA viruses, more commonly, alphavirus infections, and especially Chikungunya virus. treatment of RNA virus infections caused by infections and / or It can be concluded that there are suitable chemical compounds for prevention. Example 9: RSV virus The compounds derived from this invention may be used in therapy, and in particular in the prevention and inhibition of RSV virus infection. suitable as active substances for the treatment or cure 35 It has been subjected to pharmacological tests which have shown results. 109 MATERIALS AND PROCEDURES RSV inhibition and cytotoxicity were investigated using Viral ToxGlo analysis. Protocol for screening antiviral compounds HEp-2 cells, 2 mM L-glutamine, 10% fetal bovine serum, 100 U / ml penicillin, and 100 Earle BSS, adjusted to contain μg / ml streptomycin, and Eagle's minimum It was preserved in its essential medium (EMEM). The purposes of the screening analysis. Accordingly, these were amplified to 90% confusion levels, affecting your tripsins. It has been processed and recovered. Trypsin has been neutralized with cell culture medium and The cells were processed after the removal of the supernatant and in analysis medium (2 mM L-glutamine, 2% fetal bovine). serum and formulated to contain 100 U / ml penicillin and 100 μg / ml streptomycin. Earle BSS (EMEM) cell pellet was resuspended for 5 minutes before resuspension. The cells were centrifuged at 150 x g. The cells were then placed in 96-well plates and 384-well plates, respectively. 4 3 White, transparent, with densities of 1.5 x 10⁶ cells / eye in 50 μl and 4 x 10⁶ cells / eye in 25 μl. seeded into cell culture plates. Medium / background control column analysis. Only the medium has been added. The cell plates are placed in a humid compartment and It was incubated overnight at 37 °C / 5% CO2. After incubation overnight... 2 The cells were checked for confusion and a healthy appearance. Test substances were treated at a maximum DMSO concentration of 10% (final analysis The concentration was prepared at a maximum of 1% DMSO (10x test concentration) and The cell plates were prepared in volumes of 10 μl for 96-well plates and 5 μl for 384-well plates. Added. Test substance solvent only for cell control and virus control eyes. Viruses or cytotoxicity test kits have been added for cytotoxicity test eyes and medium / cell control eyes. The analysis medium was at an MOI of 0.5, 40, or 20 μl for 96-well and 384-well plates, respectively. It was added immediately after the test materials. Virus suspension, RSV A2. Thawing of frozen stocks and plaque formation on ice in the analysis environment. It is prepared by diluting the units to the required concentration. The cell plates were also stored in a humid compartment at 37 °C / %5CO₂ for 72 hours as pi. 2' They were incubated throughout the period. After the incubation period, the cells were subjected to virus control. the characteristic cytopathic effect in their eyes and the healthy cells in the cell control eyes They were observed under a microscope to check. The plates were brought to room temperature. 35 110 After adjustment, 20 / 40 μl Viral was added to each cell of 384 / 96-cell plates. ToxGlo (Promega) was added. The plates were incubated at room temperature, one Before measuring luminescence on the spectrophotometer (Biotek Synergy HTX), 20 For a few minutes, it was protected from the light on a plate shaker. RSV inhibition is expressed as a percentage of cytopathic effect inhibition relative to virus control, and Cytotoxicity is the percentage of cell survival compared to cell control eyes. This has been calculated. This applies to every instance where viral inhibition or cytotoxic dose response is identified. It has allowed the calculation of EC values ​​for a test substance. 50 EC values ​​ranging from 0.001 µM to 2.5 µM have been found, and this is particularly true for... 50 compounds (36), (38), (39), (45), (46), (47), (54), (57), (60), (61), (64), (68), (70), (71), (72), It is valid for (75)-(80), (82)-(86), (88)-(142), (147)-(156), (164)-(166) and (179). Table V Example EC (nM) 50 36 232 38,281 39 185 45 280 46 199 47 182 54 177 57 26 60 67 61 54 64 341 68 144 70 660 71 185 72 158 35 75 25 111 Example EC (nM) 50 76 14 77 124 78 58 79 33 80 21 82 4 83 9 84,637 85 8 86,567 88,461 89 140 90 92 91 2 92 4 93 4 94 7 95 8 96 10 97 10 98 12 99 13 100 16 101 21 102 22 103 24 104 29 105 31 35 112 Example EC (nM) 50 106 33 107 36 108 41 109 48 110 59 111 62 112 67 113 69 114 71 115 83 116 93 117 98 118 103 119 107 120 110 121 116 122 116 123 120 124 126 125 130 126 133 127 148 128 156 129 175 130 198 131 204 132 228 133 230 35 113 Example EC (nM) 50 134 281 135 292 136 295 137,300 138 312 139 329 140 349 141 352 142 370 147 414 148,532 149,555 150 597 151 671 152 802 153 809 154 810 155 1031 156 1059 164 1325 165 2357 166 2490 179 721 Conclusion Based on previous results, compounds belonging to the formula (Ie) are effective against group V RNA viruses, especially pneumovirus infections, and most commonly RSV virus treatment of RNA virus infections caused by infections and / or 35 It can be concluded that there are suitable chemical compounds for prevention. 114 Example 10: Dengue 2 virus The compounds derived from this invention are used in therapy and, in particular, in the prevention of Dengue 2 virus infection. suitable as active substances for inhibition or treatment It has been subjected to pharmacological tests which have shown results. MATERIALS AND PROCEDURES DENV-2 inhibition and cytotoxicity were investigated using viral ToxGlo analysis. Protocol for screening antiviral compounds A549 cells, 10% fetal bovine serum, 100 U / ml penicillin, and 100 μg / ml streptomycin It is stored in Dulbecco Modified Eagle Medium (DMEM) supplemented with... For the purposes of screening analysis, these reach up to 90% consensus levels. It was grown, trypsinized, and recovered. Trypsin, cell culture medium. neutralized with and cells, after the removal of the supernatant and in the analysis medium (%2 fetal DMEM supplemented with bovine serum and 100 U / ml penicillin and 100 μg / ml streptomycin) The cell pellet was heated at 150 x g for 5 minutes before being resuspended. Centrifuged. The cells were collected in 96-cell white plasma at a density of 1.0 x 10⁴ cells / cell per 50 μl. Seeded into clear-bottom cell culture plates. Medium / background control column Only the medium was added for the analysis. The cell plates were placed in a humidified compartment. and incubated overnight at 37 °C / 5% CO2. After incubation overnight... The cells were checked for confusion and a healthy appearance. Test compounds were analyzed at a maximum DMSO concentration of 1% (final analysis The concentration was prepared with a maximum of 0.1% DMSO to a final concentration of 10 μM. and added to cell plates in 10 μl volumes. Cell control and virus control eyes. Only the test substance solvent was added. As a positive inhibition control, in 3 eyes 7-Deaza-2'-C-methyladenosine was added at 100 μM. Cytotoxicity test was performed on eyes and medium / cells. The virus (DENV-2 strain 16681) was applied to control eyes or analytical medium, 96 eyes respectively. For the plates, it was added immediately after the test substances at an MOI of 0.5 and 40. Virus suspension, thawing of DENV-2 frozen stocks and plate in the analysis medium It is prepared by diluting the constituent units to the required concentration. 35 115 The cell plates were also stored in a humid compartment at 37 °C / %5CO2 for 5 days as pi. They were incubated throughout the period. After the incubation period, the cells were subjected to virus control. the characteristic cytopathic effect in their eyes and the healthy cells in the cell control eyes They were observed under a microscope to check. The plates were brought to room temperature. After adjustment, 20 μl of Viral ToxGlo was added to each cell of the 96-cell plates. (Promega) was added. The plates were analyzed in a spectrophotometer (Envision, PerkinElmer). The samples were incubated at room temperature for 5 minutes before luminescence measurement. DENV-2 inhibition is expressed as a percentage of cytopathic effect inhibition relative to virus control, and Cytotoxicity is the percentage of cell survival compared to cell control eyes. It has been calculated. Table VI % DENV-2 inhibition Sample Mean (n = 3) 38 65 40 71 43 71 45 89 46 71 48 110 49 111 61 55 62 55 64 93 65 77 68 70 82 64 98 60 119 104 35 121 59 116 % DENV-2 inhibition Sample Mean (n = 3) 132 71 140 74 150 78 151 63 156 82 169 59 175 60 176 85 192 66 Conclusion Based on previous results, compounds belonging to the formula (Ie) are more effective against group IV RNA viruses. especially flavivirus infections, and most notably Dengue 2 virus treatment of RNA virus infections caused by infections and / or It can be concluded that there are suitable chemical compounds for prevention. The invention in question also includes at least one new compound, as defined above, or a combination thereof. any of the pharmaceutically acceptable salts or as defined above at least any of the compounds (36) to (206) or its pharmaceutical use any of the acceptable salts and also pharmaceutically acceptable It relates to a pharmaceutical compound containing at least one excipient. The pharmaceutical compositions of the invention, in any form described herein, may constitute one or more of the inventions. It may contain more compounds. Another purpose of the invention in question is to classify in a subject, according to the Baltimore classification An RNA virus infection caused by an RNA virus from group IV or group V. And for example, a Chikungunya infection, a Dengue infection, an Influenza infection a drug to prevent or treat an infection or RSV infection 35 The invention which is the subject of preparation is formulated as described above (Ie) 117 belonging to at least one compound and compounds (36) and (206) as defined herein or It consists of using one of their pharmaceutically acceptable salts. Therefore, the invention in question is an RNA virus infection, and as is most commonly preferred... an RNA virus infection from group IV or V, for example a Chikungunya infection, inhibiting a Dengue infection, an Influenza infection, or an RSV infection as an agent for the prevention or treatment of, as listed above a compound and compounds (36) to (206) or thereof belonging to the formula (Ie) as defined. It relates to one of the acceptable salts. Depending on the specific treatment, the therapy may be continuous or not. “Continuous treatment” means once a day, every three days, once a week, or every two weeks, or once a month. This refers to a long-term treatment that can be applied at various frequency intervals. According to one application, the compound belonging to the formula (Ie) or its pharmaceutical acceptance any of the available salts, ranging from 0.1 to 1000 mg, especially from 0.1 up to mg or, for example, from 10 to 200 mg or, for example It is administered in doses ranging from 200 to 1000 mg. Another aim of the invention is to produce a compound of the formula (Ie) as defined above. the therapeutic of compounds (36) to (206) or one of their acceptable salts an RNA virus in a subject to include the application of an effective amount infection and, as is most preferred, Baltimore classification group IV or Treating an RNA virus infection caused by a virus belonging to the V1 gene. It relates to a therapeutic approach aimed at prevention and / or prevention. In a specific application, the invention relates to a compound whose formula (Ie) is derived from or derived from the invention. a pharmaceutically acceptable salt of it or a pharmaceutically active one of it provides for the use of its derivative or a method according to the invention, where the compound belonging to the formula (Ie), the RNA virus infection in question, and most commonly group IV or V. RNA virus infection and, for example, Chikungunya infection, Dengue useful in treating infection, influenza infection or RSV infection. It will be administered in combination with an auxiliary agent. 35 118 Compounds can be administered via any route such as intramuscular, intravenous, intranasal, or oral, etc. It can be implemented via an application mode. The compounds of the invention in question, where appropriate, are those compounds to which the invention relates. They can be administered as prodrugs, such as esters. "Prodrugs" are metabolic pathways in vivo. (for example, through hydrolysis, reduction or oxidation) a modification of the invention in question It means a compound that can be converted into another compound. For example, a compound related to the invention in question. An ester prodrug of the compound can be converted back to the parent molecule via in vivo hydrolysis. (Subject) Suitable esters of the compounds of the invention, for example acetates, citrates, lactates, tartrates, malonates, oxalates, salicylates, propionates, succinates, fumarates, maleates, methylene-bis-β-hydroxynaphthoates, gentisates, isethionates, di-p- toluoyl tartrates, methanesulfonates, ethanesulfonates, benzenesulfonates, p- Examples include toluenesulfonates, cyclohexylsulfamates, and quinates. Examples of ester prodrugs include FJ. These are the details provided by Leinweber, Drug Metab. Res., 1987, 18, 379. As used, the references to the components of the invention in question are also It is also intended to include any form of prodrug or metabolite. The innovative compound also includes diluents, excipients, stabilizers, and preservatives. It may contain one or more additives. Such additives are specialized in the field. This is well known by many, and especially in “Ullmann's Encyclopedia of Industrial Chemistry, 6th Ed.” (various editors, 1989-1998, Marcel Dekker) and “Pharmaceutical Dosage Forms and This is explained in "Drug Delivery Systems" (ANSEL et al., 1994, WILLIAMS & WILKINS). The excipients mentioned above are selected according to the dosage form and the desired mode of administration. The components of this invention may be administered orally, parenterally, including but not limited to, sublingually, transdermally, vaginally, rectally, transmucosal as, topically, intranasally, by inhalation, buccal or intranasal. any through application or combination thereof It can be administered in the following ways. Parenteral administration, including but not limited to intravenous, intra-arterial, intra-peritoneal, subcutaneous, intramuscular, intra-thecal and intra-articular It includes. The compositions of this invention also feature slow release of the compounds. It can also be administered in the form of an implant, allowing for a slow, controlled intravenous infusion. 35 119 According to another interpretation, pharmaceutically acceptable compositions of this invention are: Administered orally to humans and other animals, depending on the severity of the infection being treated. rectal, parenteral, intrasisternal, intravaginal, intraperitoneal, topical (powders, ointments) (or via drops), buccally, as an oral or nasal spray, or similarly It can be implemented in this way. The components of the invention in question can be administered orally, parenterally, as an inhalation spray, or topically. as, rectally, nasally, buccally, vaginally, or via an implant. It can be administered via a reservoir. As used here, the term "parenteral" refers to subcutaneous administration. intravenous, intramuscular, intra-articular, intra-synovial, intrasternal, intrathecal, This includes intrahepatic, intralesional, and intracranial injection or infusion techniques. Preferably, the compounds are administered orally, intraperitoneally, or intravenously. This sterile injectable forms of the invention's components, aqueous or oleaginous suspension These suspensions may require suitable dispersing or wetting agents and suspending agents. It can be formulated according to known techniques in the field. Sterile and injectable. The preparation also contains a non-toxic, parenterally acceptable diluent or a sterile injectable solution in a solvent, for example, 1,3-butanediol It can be a solution or suspension. Acceptable means and solvents that can be used. These include water, Ringer's solution, and isotonic sodium chloride solution. In addition, Sterile, fixed oils are traditionally used as a solvent or suspension medium. For example, a compound with the formula (Ie) can have a daily dose of 0.1 to 1000 mg of the active substance. in doses that make its application possible, for example, plain or coated tablets, hard gelatin, soft-shell capsules and other capsules, suppositories or suspensions, drinkable elements such as syrups or injectable solutions or suspensions In its current form, it is administered enterally or parenterally in conjunction with appropriate excipients. It may be available in any pharmaceutical form suitable for that purpose. In a specific application, a compound with the formula (Ie) according to the invention is administered orally. For the prophylaxis or treatment of this invention, the oral route of administration is particularly preferred. 35

Claims

1. It is a compound with the formula (Ie): Here: ring and Both rings represent a phenylene group, 1 Y represents a phenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl group, or a pyrimidinyl group. It represents an aryl group selected from the group; that aryl group is optional. as a halogen atom, a (C-C)alkyl group, a cyano group, a (C-C)alkoxy group. 1 4 1 5 group, a trifluoromethyl group, a trifluoromethoxy group, an -SO -NR R group, a - 2 ab The SO₂H group, an -OH group, an -O-SO₄-OR group, or an -OP(=O)-(OR₂)(OR₂) 3 2 ccd It is substituted with one or two substituent(s) selected from its group. R, R, R, and R are independent of each hydrogen atom or a (C-C)alkyl group. abcd 1 4 represents the group, 2 X represents the following: an -O- group, a -NH- group, an -S- group, a -CO-NH- group, a -NH-CO-NH- group, 35 a group of -NH-CO-, 121 a -CH(OH)- group, a -CH(COOH)NH- group, a -CH(COOCH )NH- group, 3 a -C(OH)(CH OH)-, 2 group, containing 1, 2, 3 or 4 heteroatoms, such as a triazole, a tetrazole or an oxadiazole a divalent 5-membered heteroaromatic ring, a -SO- group, 2 or a -SO -NH- group, 2 n is 0, 1, 2, or 3. m and m' are independently 0, 1, or 2. 2 Y represents the following: a hydroxyl group, a (C-C) alkoxy group, 1 4 a -CHC(OH) , 2 a COOR, where R represents a hydrogen atom or an (C -C )alkyl group, ff 1 4 a morpholinyl group, a dihydropyranyl group, a group, One 35 group, 122 a -PO(OR )(OR' ) group, where R and R' are independent hydrogen atoms ffff or represents an (C-C)alkyl group, 1 4 an oxetanil group, a -Si(CH ) group, 3 3 a -NHCOO-(C -C )alkyl group, 1 4 or 1 2 3 1 2 3 a -CR RR group, where R, R and R are independent hydrogen atoms, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 1 2 hydrogen atoms, or R and R together with the carbon atoms that carry them. It is understood that it forms a (C-C)cycloalkyl group, the said (C-C)cycloalkyl group 3 8 3 8 Optionally, one or two (C-C)alkyl groups, halogen atoms, or (C-C)alkoxy groups. 1 4 1 4 is substituted with the group and the (C-C)cycloalkyl group in question is optional 3 8 1 2 the R and / or R in question is interrupted by an oxygen atom, 2 2 Alternatively, X -Y represents a -CONR R group, where R and CDC R, along with a nitrogen atom, can optionally be a hydroxyl group or a hydroxyl group. d It forms a heterocyclic group substituted with a (C-C)alkyl group. 1 4 R and R' independently represent the following: a (C-C)alkyl group, 1 4 a -S-(C -C )alkyl group, 1 4 a (C-C)cycloalkyl group, 3 6 a halogen atom, like a fluorine atom, a trifluoromethyl group, a -SO (C -C )alkyl group, 2 1 4 a (C-C)cycloalkenyl group, 3 6 a (C-C) alkoxy group, 1 5 a -SO -NR R group, 2 ab a -SO H or SO -CH group, 3 2 3 an -OH group, -CONHR, where R represents a hydrogen atom or a (C-C)alkyl group. gg 1 4 does, a -O-SO -OR group, 2 c an azetidinyl group, a morpholinyl group or a cyano group, 35 123 "R" is a hydrogen atom, optionally substituted with a -COOH group. It represents a (C-C) alkyl group. 1 4 or any of its pharmaceutically acceptable salts, Compounds are excluded: 35 124 2. According to claim 1, it is a compound with the formula (Ie), where R" is a hydrogen atom. or any of its pharmaceutically acceptable salts.

3. According to any of the previous requirements, it is a compound of the formula (Ie), where 1 Y stands for a phenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl, or a It represents an aryl group selected from a pyrimidinyl group; that aryl group Optionally, a halogen atom, a (C-C)alkyl group, a cyano group, 1 4 a (C-C) alkoxy group, a trifluoromethyl group, a trifluoromethoxy group or 1 5 selected from any of its pharmaceutically acceptable salts It is substituted with one or two substituent(s).

4. According to any of the previous requirements, it is a compound of the formula (Ie), where 2 X represents the following: an -O- group, a -NH- group, an -S- group, a -CO-NH- group, a -NH-CO-NH- group, a -NH-CO- group, containing 1, 2, 3 or 4 heteroatoms, such as a triazole, a tetrazole or an oxadiazole a divalent 5-membered heteroaromatic ring, a -SO- group, 2 or a -SO -NH- group, 2 or any of its pharmaceutically acceptable salts.

5. According to any of the previous requirements, the compound belonging to the formula (Ie) is where 2 Y represents a hydroxyl group, a -PO(OR )(R' ) group, where R and R' are independent hydrogen atoms ffff 35 or represents an (C-C)alkyl group, 1 4125 or 1 2 3 1 2 3 a -CR RR group, where R, R and R are independent hydrogen atoms, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 1 2 hydrogen atoms, or R and R together with the carbon atoms that carry them. It is understood that it forms a (C-C)cycloalkyl group, the said (C-C)cycloalkyl group 3 8 3 8 Optionally, one or two (C-C)alkyl groups, halogen atoms, or (C-C)alkoxy groups. 1 4 1 4 is substituted with the group and the (C-C)cycloalkyl group in question is optional 3 8 1 2 the R and / or an oxygen atom on R or its pharmaceutical equivalent It is interrupted by any of its acceptable salts.

6. According to any of the previous requirements, the compound belonging to the formula (Ie) is where R and R' independently represent the following: a (C-C)alkyl group, 1 4 a (C-C)cycloalkyl group, 3 6 a halogen atom, like a fluorine atom, a trifluoromethyl group or a -SO H or SO -CH group, 3 2 3 or any of its pharmaceutically acceptable salts.

7. According to any of the previous requirements, the compound belonging to the formula (Ie) is where "R" is a hydrogen atom, 1 Y stands for a phenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl, or a It represents an aryl group selected from a pyrimidinyl group; that aryl group Optionally, a halogen atom, a (C-C)alkyl group, a cyano group, 1 4 from a (C-C) alkoxy group, a trifluoromethyl group, a trifluoromethoxy group 1 5 It is substituted with one or two selected substituent(s). 2 X represents the following: an -O- group, a -CO-NH- group, a -NH-CO-NH- group, a -NH-CO- group, containing 1, 2, 3 or 4 heteroatoms, such as a triazole, a tetrazole or an oxadiazole a divalent 5-membered heteroaromatic ring, or a -SO -NH- group, 35 2126 2 Y represents the following: a hydroxyl group, a -PO(OR )(R' ) group, where R and R' are independent hydrogen atoms ffff or represents an (C-C)alkyl group, 1 4 or 1 2 3 1 2 3 a -CR RR group, where R, R and R are independent hydrogen atoms, a fluorine atom 1 2 3 It represents an atom or an (C-C)alkyl group, at most one of R, R and R. 1 4 1 2 hydrogen atoms, or R and R together with the carbon atoms that carry them. It is understood that it forms a (C-C)cycloalkyl group, the said (C-C)cycloalkyl group 3 8 3 8 Optionally, one or two (C-C)alkyl groups, halogen atoms, or (C-C)alkoxy groups. 1 4 1 4 is substituted with the group and the (C-C)cycloalkyl group in question is optional 3 8 1 2 the R and / or R in question is interrupted by an oxygen atom, And R and R' independently represent the following: a (C-C)alkyl group, 1 4 a (C-C)cycloalkyl group, 3 6 a halogen atom, like a fluorine atom, a trifluoromethyl group, a -SO H or SO -CH group or 3 2 3 a morpholinyl group, or any of its pharmaceutically acceptable salts.

8. Claims are a compound of the formula (Ie) according to any of 1 to 3, where "R" is a hydrogen atom, 1 Y represents either a phenyl group or a pyridyl group. 2 X represents the following: an -O- group, a -CO-NH- group, a -NH-CO- group, or two heteroatoms containing 1, 2, 3 or 4 heteroatoms, such as a triazole, tetrazole or an oxadiazole a 5-membered heteroaromatic ring with multiple valence, 2 Y represents the following: a -PO(OR )(R' ) group, where R and R' are independent hydrogen atoms ffff or represents an (C-C)alkyl group, 35 1 4127 or 1 2 3 gr 1 2 3 a -CR RR ubu, where R, R and R are independently a hydrogen atom, 1 2 3 It represents a fluorine atom or an (C-C)alkyl group, R, R and R of the most 1 4 1 2 one of them is a hydrogen atom, or R and R are carbon atoms carrying them. It is understood that it forms a (C -C )cycloalkyl group together with its atom, 3 8 And R and R' independently represent the following: a (C-C)alkyl group, 1 4 a (C-C)cycloalkyl group or 3 6 a morpholinyl group, or any of its pharmaceutically acceptable salts.

9. According to claim 1, a compound of the formula (Ie) is chosen from the following: 36 37 38 39 40 43 45 35 128 46 47 48 49 50 51 52 53 54 55 56 57 35 129 58 59 60 61 62 63 64 65 66 67 68 69 35 130 70 71 72 73 74 75 76 77 78 79 80 81 82 35 131 83 85 89 91 92 93 94 95 96 97 98 35 132 99 100 101 102 103 104 105 106 107 108 35 133 109 110 111 112 113 114 115 116 118 119 35 134 120 121 122 123 124 125 126 127 128 35 135 129 130 131 132 133 134 135 136 137 138 35 136 139 140 141 142 144 145 146 147 148 149 150 35 137 151 152 153 154 155 156 157 158 159 160 35 138 162 163 167 169 170 171 172 174 175 176 177 35 139 178 180 181 182 183 184 185 186 187 188 35 140 189 190 191 192 194 195 196 201 202 203 205 35 141 206 or any of its pharmaceutically acceptable salts.

10. It is a compound, selected from the following: 41 42 44 84 86 87 88 90 117 35 142 143 161 164 165 166 168 173 179 193 197 35 143 198 199 200 204 and any of its pharmaceutically acceptable salts.

11. A compound of the formula (Ie) or of any of the claims 1 to 8. any of the pharmaceutically acceptable salts or claims 9 or 10 any of the compounds (36) to (206) or thereof which are considered pharmaceutical It is one of the available salts and is intended for use as a medicine.

12. A compound or claim belonging to the formula (Ie) according to any of claims 1 to 8 or claims 9 or any of the compounds (36) to (206) according to 10 or its pharmaceutical any of the salts that can be considered as such, according to the Baltimore classification an RNA virus caused by an RNA virus belonging to group IV or V It is intended for use in the treatment and / or prevention of infection.

13. According to the previous request, it is a compound of the formula (Ie) intended for use, where Caused by an RNA virus belonging to group IV or V of the Baltimore classification. RNA virus infections include RSV, Chikungunya, influenza, and Dengue. fevers, and especially RSV, Chikungunya and Dengue fever. It is selected from among the fevers.

14. A pharmaceutical compound, as defined in any of Claims 1 to 8. at least one of its compounds or any of its pharmaceutically acceptable salts 35 one of the compounds (36) to (206) as defined in claims 9 or 10, at least 144 at least any of them or their pharmaceutically acceptable salts It contains any and also at least one pharmaceutically acceptable excipient.

15. A formula (Ie) as defined in any of claims 1 to 8. any of the compound or its pharmaceutically acceptable salts one of them or a compound as defined in claims 9 or 10 or thereof to produce any of its pharmaceutically acceptable salts It is a synthesis process aimed at, where requirements 1 through 8 are defined. a compound of the formula (Ie) or its pharmaceutically acceptable form any of its salts or one as defined in claim 9 or 10 the compound or any of its pharmaceutically acceptable salts to obtain it, in the presence of an inorganic base and a diphosphine and a a compound with formula (IIe) in the presence of an organometallic catalyst It includes at least one coupling step with a compound belonging to the formula (IIIe). 1 Here Y, R, R', m, m', n, ring, 35 145 2 2 The ring, X, YR and R are as defined above, X is a chlorine atom, YR is an iodine atom. ab 1 is an atom or a bromine atom, and Y is a phenyl group, a pyridine group, a pyrazine group. The group is either a pyridazine group or a pyrimidine group. 35