122results about "Ketal steroids" patented technology

The present invention relates, inter alia, to compounds having the general formula:

in which: R¹ is a member selected from the group consisting of —OCH₃, —SCH₃, —N(CH₃)₂, —NHCH₃, —NC₄H₈, —NC₅H₁₀, —NC₄H₈O, —CHO, —CH(OH)CH₃, —C(O)CH₃, —O(CH₂)₂N(CH₃)₂, and —O(CH₂)₂NC₅H₁₀; R² is a member selected from the group consisting of hydrogen, halogen, alkyl, acyl, hydroxy, alkoxy (e.g., methoxy, ethoxy, vinyloxy, ethynyloxy, cyclopropyloxy, etc.), acyloxy (e.g., acetoxy, glycinate, etc.), alkylcarbonate, cypionyloxy, S-alkyl, —SCN, S-acyl and —OC(O)R⁶, wherein R⁶ is a functional group including, but not limited to, alkyl (e.g., methyl, ethyl, etc.), alkoxy ester (e.g., —CH₂OCH₃) and alkoxy (—OCH₃); R³ is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R⁴ is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ═O and ═N—OR⁵, wherein R⁵ is a member selected from the group consisting of hydrogen and alkyl.

In addition to providing the compounds of Formula I, the present invention provides methods wherein the compounds of Formula I are advantageously used, inter alia, to antagonize endogenous progesterone; to induce menses; to treat endometriosis; to treat dysmenorrhea; to treat endocrine hormone-dependent tumors; to treat meningiomas; to treat uterine leiomyomas; to treat uterine fibroids; to inhibit uterine endometrial proliferation; to induce cervical ripening; to induce labor; and for contraception.

A compound having the general formula:

in which: R¹ is a member selected from the group consisting of —OCH₃, —SCH₃, —N(CH₃)₂, —NHCH₃, —CHO, —COCH₃ and —CHOHCH₃; R² is a member selected from the group consisting of halogen, alkyl, acyl, hydroxy, alkoxy, acyloxy, alkyl carbonate, cypionyloxy, S-alkyl and S-acyl; R³ is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R⁴ is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ═O and ═N—OR⁵, wherein R⁵ is a member selected from the group consisting of hydrogen and alkyl.

In addition to providing the compounds of Formula I, the present invention provides methods wherein the compounds of Formula I are advantageously used, inter alia, to antagonize endogenous progesterone; to induce menses; to treat endometriosis; to treat dysmenorrhea; to treat endocrine hormone-dependent tumors; to treat uterine fibroids; to inhibit uterine endometrial proliferation; to induce labor; and for contraception.

Certain benzopyran antiestrogens are disclosed for treating estrogen sensitive diseases such as breast cancer. Prodrug forms provide ease of manufacturing, good shelf life, and bioavailability, and preferred stereoisomers are shown to be more effective than racemic mixtures.

The present invention relates to a new industrial process for the synthesis of solvate- free 17a-acetoxy-11ss-[4-(N,N-dimethyl-amino)-phenyl]-19-norpregna-4,9-diene-3,20-dione [CDB -2914] of formula (I) which is a strong antiprogestogene and antiglucocorticoid agent. The invention also relates to compounds of formula (VII) and (VIII) used as intermediates in the process. The process according to the invention is the following: i) 3-(ethylene-dioxy)-estra-5(10),9(11)-diene-17-one of formula (X) is reacted with potassium acetilyde formed in situ in dry tetrahydrofuran by known method, ii) the obtained 3-(ethylene-dioxy)-17a-ethynyl-17ss-hydroxy-estra-5(10),9(11)-diene of formula (IX) is reacted with phenylsulfenyl chloride in dichloromethane in the presence of triethylamine and acetic acid, iii) the obtained isomeric mixture of 3-(ethylene-dioxy)-21-(phenyl-sulfinyl)-19-norpregna-5(10),9(11),17(20),20-tetraene of formula (VIII) is reacted first with sodium methoxide in methanol, then with trimethyl phosphite, iv) the obtained 3-(ethylene-dioxy)-17a-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene of formula (VII) is reacted with hydrogen chloride in methanol, then v) the obtained 3-(ethylene-dioxy)-17a-hydroxy-19-norpregna-5(10),9(11l); -diene-20- one of formula (VI) is reacted with ethylene glycol hi dichloromethane in the presence of trimethyl orthoformate and p-toluenesulfonic acid by known method, vi) the obtained 3,3,20,20-bis(ethylene-dioxy)-17a-hydroxy-19-norpregna- 5(10),9(11)-diene of formula (V) is reacted with hydrogen peroxide in a mixture of pyridine and dichloromethane in the presence of hexachloroacetone by known method, vii) the obtained 3,3,20,20-bis(ethylene-dioxy)-17a-hydroxy-5,10-epoxy-19-norpregn-9(11)-ene of formula (IV), containing approximately a 1:1 mixture of 5a,10a- and 5ss,10ss-epoxides, is isolated from the solution and reacted with a Grignard reagent obtained from 4-bromo-N,N-dimethyl-aniline in tetrahydrofuran.

Methods of using 7α,11β-dimethyl-17β-hydroxyestra-4,14-dien-3-one (III)

and 17 esters thereof for various hormonal therapies, oral and parenteral dosage forms comprising these actives, and processes for their preparation.

Methods for treating sex steroid-dependent diseases by inhibiting sex steroid activity include administration of novel compounds which include an androgenic nucleus substituted at a ring carbon with at least one substituent specified herein. Such compounds may function by inhibiting sex steroid synthesis (both estrogen and androgen synthesis) and/or by antagonistically blocking androgen receptors.

Described herein are methods of using compounds that inhibit leukemia inhibitory factor (LIF) and/or block of the leukemia inhibitory factor receptor for treatment of liver fibrosis, proliferation of spinal tumors, and in combination therapy with an immunotherapeutic agent.

(3alpha,3beta)-disubstituted 17beta steroidal compounds, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, are provided for the prevention and treatment of a variety of CNS-related conditions.

Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein -------, R¹, R², R⁵, A and L are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

The present disclosure is generally directed to neuroactive 13,17-substituted steroids as referenced herein, and pharmaceutically acceptable salts thereof, for use as, for example, an anesthetic, and/or in the treatment of disorders relating to GABA function and activity. The present disclosure is further directed to pharmaceutical compositions comprising such compounds.

The instant invention provides potent antiandrogen compounds, such as 3β-acetoxyandrost-1,5-diene-17-ethylene ketal and 3β-hydroxyandrost-1,5-diene-17-ethylene ketal, and methods for their use in the prevention and treatment of biological conditions mediated by androgen receptors. Thus, for example, compounds of the invention are useful in the prevention and treatment of prostrate cancer. Furthermore, it has been discovered that compounds of the invention are useful in the prevention and treatment of androgen-independent cancers such as androgen-independent prostrate cancer. Finally, inventive compounds may be used to treat antiandrogen induced withdrawal syndrome.

Provided herein are inhibitors of CYP11B, CYP17, and/or CYP21 enzymes of Formula (Z), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII). Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions. Formula (Z).

The invention discloses a preparation method of a dydrogesterone intermediate. The preparation method is characterized by comprising the following steps: dissolving 5,7-diene steroid compound in an organic solvent to obtain a solution as a raw material; and carrying out a photocatalytic reaction and separating to obtain the dydrogesterone intermediate, wherein the 5,7-diene steroid compound is 7-dehydropregnenolone acetate, pregna-5,7-diene-3,20-diketodivinyl ketal, 7-dehydropregnenolone, ergosterol or pregna-5,7-diene-3,20-diketo-3-vinyl ketal, and a lamp used in the photocatalytic reaction comprises an LED ultraviolet lamp with the wavelength range of 295-335 nm. The preparation method of the dydrogesterone intermediate is high in yield, low in cost, safer in preparation and friendlier to environment.

The invention discloses a preparation method of a steroid intermediate. The preparation method comprises the following steps: adding a first solvent, a first acid solution, water and 17-alpha-hydroxypregnenolone steroid-4,9-diene-3,20-diketone acetate into a first reaction tank, and uniformly stirring; adding a bromination agent in four times at 2-4 DEG C, maintaining the temperature for reactingfor 2h, and carrying out thin-layer chromatography analysis until the reaction of the raw materials is finished; and regulating the pH value to be more than 7, regulating the pH value back to 6, carrying out reduced pressure concentration until the first solvent is completely concentrated, adding water, cooling to 5 DEG C, and carrying out centrifugation, cleaning, spin-drying and drying, so as toobtain the steroid intermediate, namely cortisone. According to the preparation method, an oxidant and a catalyst which contain heavy metal ions are not used, the used solvent can be recycled and reused, wastewater does not contain heavy metal ions in the production process, the method belongs to an environment-friendly process and has very good process prospects, and the yield and purity of theproduct are high.

The invention relates to a gas separation flow system and a gas separation flow method for photochemical synthesis of 9-beta,10-alpha-dehydroprogesterone ketal. The method is characterized in that 9-beta,10-alpha-dehydroprogesterone ketal is synthesized in one step or two steps by utilizing ultraviolet light with different wave bands, a raw material 9-alpha,10-beta-dehydroprogesterone ketal reaction solution is separated by gas doing not participate in a reaction, the internal disturbance of the reaction solution is enhanced, and the retention time of the reaction solution in a tubular reactoris ensured to be consistent. The method has the advantages of being continuous, stable, high in light energy utilization rate, low in production cost, easy and convenient to operate and controllablein process, and has huge prospect in the industrial production of 9-beta,10-alpha-dehydroprogesterone ketal through photochemical synthesis.

The invention discloses a synthesis method of ursodeoxycholic acid, and the method comprises the following steps: by using a botanical compound BA as a raw material, carrying out ethylene glycol protection, oxidation, side chain extension reaction, ethylene glycol removal protection, reduction, hydrolysis and the like to synthesize the ursodeoxycholic acid. Raw materials for synthesizing the ursodeoxycholic acid are cheap and easy to obtain, synthesis steps are easy and convenient to operate, the yield is high, environmental friendliness is achieved, and industrial production is facilitated.