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Carboxylic acid compounds and drugs containing the compounds as the active ingredient

A carboxylic acid compound and compound technology, applied in the direction of medical preparations containing active ingredients, organic active ingredients, drug combinations, etc., can solve the problems of small toxic and side effects, weak combination, etc.

Inactive Publication Date: 2005-08-17
ONO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Now, if new compounds can be found that specifically bind to the DP receptor but to other prostaglandin receptors to a lesser extent, these compounds could become drugs with minimal toxic side effects, since they have no other effects

Method used

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  • Carboxylic acid compounds and drugs containing the compounds as the active ingredient
  • Carboxylic acid compounds and drugs containing the compounds as the active ingredient
  • Carboxylic acid compounds and drugs containing the compounds as the active ingredient

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0195] [Preparation method of the compound of the present invention]

[0196] The compound of the present invention represented by formula (I) can be prepared by, for example, the following method:

[0197] [I] In the compound represented by formula (I), R 1 Is C 1-4 Alkyl, C 2-4 Alkenyl or benzyl compounds are compounds represented by the following formula (IA)

[0198]

[0199] (In the formula, R 1A Is C 1-4 Alkyl, C 2-4 (Alkenyl or benzyl, other symbols have the same meaning as above) can be prepared by the following method:

[0200] (a) In formula (IA), E represents -C(=O)- or -S(O) 2 -The compound is the compound of formula (IA-1)

[0201]

[0202] (In the formula, E A Is -C(=O)- or -S(O) 2 -, the meaning of other symbols is the same as above) can be prepared by the following method: compound of formula (II-1)

[0203]

[0204] (In the formula, R 2-1 With R 2 Has the same meaning, but R 2-1 The indicated hydroxyl or amino group is protected when necessary; R 4-1 Is a hydr...

Embodiment approach

[0343] The following reference examples and examples are used to illustrate the present invention, but cannot be used to limit the present invention.

[0344]In chromatographic separation or TLC, the solvent in parentheses represents the eluent or developing agent, and the solvent ratio used is the volume ratio. In NMR, the solvent in parentheses is the solvent for measurement.

[0345] Reference Example 1: N-formyl-2-fluoroaniline

[0346] In an argon atmosphere at 0°C, formic acid (6.1 mL) was added dropwise to acetic anhydride (15.5 mL), and the mixture was stirred at 50°C for 2 hours. After the reaction mixture was cooled to room temperature, it was diluted with tetrahydrofuran (THF; 10 mL). To the above diluted solution was added a solution of 2-fluoroaniline (5.56 g) in THF (20 mL) at room temperature, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated to obtain the title compound with the following physical and chemical da...

Embodiment 1

[0384] Example 1: 3-(4-((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-ylmethoxy)benzoylamino)benzene Methyl acetate

[0385]

[0386]Under the protection of argon, pyridine (161 μl) was added to the dichloromethane (2 mL) solution of the compound (165 mg) prepared in Reference Example 9. Under ice cooling, a dichloromethane (2.5 mL) solution of the compound (350 mg) prepared in Reference Example 8 was added dropwise to the mixture, and the mixture was stirred at 0°C for 15 minutes. Methanol and water are added to this mixture. It was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride solution and saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated to obtain the title compound (447 mg) having the following physical data.

[0387] TLC: Rf 0.23 (hexane:ethyl acetate=2:1).

[0388] Examples 1(1)~1(15)

[0389] In the same manner as in Example 1, using the corresponding amine instead of...

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Abstract

A carboxylic acid compound represented by formula (I): (meanings of the symbols in the formula are as mentioned in the specification) and a pharmaceutical agent comprising the compound. <>Since the compound represented by formula (I) binds to a DP receptor and shows antagonistic activity for the DP receptor, it is useful for prevention and / or treatment of diseases such as allergic disease (such as allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma and food allergy), systemic mastocytosis, disorders accompanied by systemic mast cell activation, anaphylaxis shock, bronchoconstriction, urticaria, eczema, diseases accompanied by itch (such as atopic dermatitis and urticaria), diseases (such as cataract, retinal detachment, inflammation, infection and sleeping disorders) which is generated secondarily as a result of behavior accompanied by itch (such as scratching and beating), inflammation, chronic obstructive pulmonary diseases, ischemic reperfusion injury, cerebrovascular accident, chronic rheumatoid arthritis, pleurisy, ulcerative colitis and the like. Carboxylic acid compounds represented by the following general formula (I) (wherein each symbol is as defined in the description) and drugs containing these compounds: (I) Because of binding to DP receptor and antagonizing the same, the compounds represented by the general formula (I) are useful in preventing and / or treating allergic diseases (allergic nephritis, allergic conjunctivitis, atopic dermatitis, bronchial asthma, food allergy, etc.), systemic mast cell disease, systemic mast cell activation failure, anaphylactic shock, respiratory tract contraction, urticaria, eczema, diseases associated with itch (atopic dermatitis, urticaria, etc.), diseases (cataract, retinal detachment, inflammation, infection, sleep disorder, etc.) secondarily caused by behaviors associating itch (scratching, beating.

Description

Technical field [0001] The present invention relates to carboxylic acid compounds. More specifically, the present invention relates to: [0002] (1) The carboxylic acid compound represented by formula (I) and its non-toxic salt: [0003] [0004] (In the formula, all symbols have the same meaning as described later), [0005] (2) Methods of preparing the above-mentioned compounds and their non-toxic salts, and [0006] (3) Pharmaceutical preparations containing them as active ingredients. Background technique [0007] Known prostaglandin D 2 (Abbreviated as PGD 2 ) Is one of the metabolites produced through the arachidonic acid cascade, which is considered to be one of the chemical mediators involved in allergic diseases such as allergic rhinitis, bronchial asthma, and allergic conjunctivitis. Known PGD 2 Mainly produced in mast cells, and mainly released from mast cells. And it is known that the released PGD 2 Causes bronchoconstriction, enhanced vascular permeability, vasodil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P1/04A61P7/00A61P9/10A61P11/00A61P17/00A61P25/06A61P25/20A61P29/00A61P37/08A61P43/00C07D209/12C07D265/36C07D307/80C07D319/20C07D327/06
CPCC07D209/12C07D307/80C07D265/36C07D327/06C07D319/20A61P1/04A61P1/16A61P11/00A61P11/02A61P11/06A61P11/08A61P17/00A61P17/04A61P17/10A61P19/02A61P25/00A61P25/06A61P25/20A61P27/02A61P27/14A61P29/00A61P37/00A61P37/06A61P37/08A61P39/00A61P43/00A61P7/00A61P7/02A61P9/00A61P9/10
Inventor 岩桥摩纪小林馨南部文男
Owner ONO PHARMA CO LTD
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