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

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

Inactive Publication Date: 2008-04-02
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

[0186] [Preparation method of the compound of the present invention]

[0187] Compounds of the present invention represented by formula (I) can be prepared by, for example, the following methods:

[0188] [I] In the compound shown in formula (I), R 1 for C 1-4 Alkyl, C 2-4 The compound of alkenyl or benzyl is the compound shown in the following formula (IA)

[0189]

[0190] (where, R 1A for C 1-4 Alkyl, C 2-4 Alkenyl or benzyl, the meaning of other symbols is the same as above) can be prepared by the following method:

[0191] (a) In formula (IA), E represents -C(=O)- or -S(O) 2 The compound of - is formula (IA-1) compound

[0192]

[0193] (where, E A for -C(=O)- or -S(O) 2 -, the meaning of other symbols is the same as above) can be prepared by the following method: formula (II-1) compound

[0194]

[0195] (where, R 2-1 with R 2 have the same meaning, but R 2-1 The hydroxyl or amino group represented is protected when necessary; R 4-1 is a hydrogen at...

Embodiment approach

[0334] The following Reference Examples and Examples are used to illustrate the present invention but not to limit the present invention.

[0335] In chromatographic separation or TLC, the solvents in parentheses represent eluents or developing solvents, and the ratios of solvents used are volume ratios. In NMR, solvents in parentheses are solvents for measurement.

[0336] Reference Example 1: N-formyl-2-fluoroaniline

[0337] To acetic anhydride (15.5 mL) was added dropwise formic acid (6.1 mL) at 0°C under an argon atmosphere, followed by stirring at 50°C for 2 hours. After cooling the reaction mixture 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 the mixture was stirred at room temperature for 1 hr. Concentration of the reaction mixture afforded the title compound having the following physicochemical data. The resulting title c...

Embodiment 1

[0375] Example 1: 3-(4-((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-ylmethoxy)benzoylamino)benzene Methyl acetate

[0376]

[0377] To a solution of the compound prepared in Reference Example 9 (165 mg) in dichloromethane (2 mL) was added pyridine (161 µl) under argon protection. To this mixture was added dropwise a solution of the compound prepared in Reference Example 8 (350 mg) in dichloromethane (2.5 mL) under ice-cooling, and stirred at 0°C for 15 minutes. Methanol and water were added to the mixture. It was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated to give the title compound (447 mg) having the following physical data.

[0378] TLC: Rf0.23 (hexane:ethyl acetate=2:1).

[0379] Embodiment 1(1)~1(15)

[0380] In the same manner as in Example 1, using the corresponding amine instead of the compound prepared in Ref...

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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) Carboxylic acid compounds and nontoxic salts thereof shown in formula (I): [0003] [0004] (In the formula, all symbols have the same meanings as those described later), [0005] (2) methods for preparing the above-mentioned compounds and non-toxic salts thereof, 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 Produced primarily in and released primarily from mast cells. and is known to release PGD 2 Causes bronchoconstriction, enhanced vascular permeability, vasod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/36A61K31/538A61P1/04A61P7/00A61P9/10A61P11/00A61P17/00A61P25/06A61P25/20A61P29/00A61P37/08A61P43/00C07D209/12C07D307/80C07D319/20C07D327/06
CPCC07D265/36C07D319/20C07D327/06C07D307/80C07D209/12A61P1/04A61P1/16A61P11/00A61P11/02A61P11/06A61P11/08A61P17/00A61P17/04A61P17/10A61P19/02A61P25/00A61P25/06A61P25/20A61P27/02A61P27/14A61P29/00A61P37/00A61P37/06A61P37/08A61P39/00A61P43/00A61P7/00A61P7/02A61P9/00A61P9/10
Inventor 岩桥摩纪小林馨南部文男
Owner ONO PHARMA CO LTD
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