Carboxylic acid derivatives and pharmaceutical agent comprising the same as active ingredient
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Abstract
A carboxylic acid derivative of formula (I):
wherein R1 is —COOH, —COOR6, etc.; A is a single bond, alkylene, etc.; R2 is alkyl, alkoxy, etc.; B is a carbocyclic ring or a heterocyclic ring; Q is alkylnene-Cyc2, etc.; D is a linking chain; and R3 is alkyl, a carbocyclic ring or a heterocyclic ring, or a non-toxic salt thereof. The compound of formula (I) binds to PGE2 receptor, especially subtypes EP3 and/or EP4 and show the antagonizing activity, are useful for the prevention and/or treatment of diseases induced pain, itch, urticaria, allergy, urinary frequency, urinary disturbance, Alzheimer'"'"'s disease, cancer, dysmenorrhea, endometriosis, etc.
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Citations
4 Claims
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1. A carboxylic acid derivative of formula (I):
- View Dependent Claims (2, 3, 4)
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2. The compound according to the claim 1, which is selected from
(1) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-ethoxyphenoxymethyl)phenyl)butanoic acid, (2) (2E)-3-(2-((2-(naphthalen-2-yl)acetyl)amino)-4-(pyrazol-1-ylmethyl)phenyl)-2-propenoic acid, (3) 2-(2-((4-methyl-2-(naphthalen-1-yl)pentanoyl)amino)-4-(pyrazol-1-ylmethyl)benzyl)benzoic acid, (4) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (5) 4-(2-((4-methyl-2-(naphthalen-1-yl)pentanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (6) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-oxopyridin-1-ylmethyl)phenyl)butanoic acid, (7) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(pyridin-3-yloxymethyl)phenyl)butanoic acid, (8) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenylthiomethylphenyl)butanoic acid, (9) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenylaminomethylphenyl)butanoic acid, (10) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenylsulfinylmethylphenyl)butanoic acid, (11) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenylsulfonylmethylphenyl)butanoic acid, (12) 3-(2-((4-methyl-2-(naphthalen-1-yl)pentanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (13) 4-(2-((4-methyl-2-(naphthalen-1-yl)pentanoyl)amino)-4-(pyrazol-1-ylmethyl)phenyl)butanoic acid, (14) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-benzoylaminomethylphenyl)butanoic acid, (15) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(pyridin-4-yloxymethyl)phenyl)butanoic acid, (16) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-phenoxyethyl)phenyl)butanoic acid, (17) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(pyridin-2-yloxymethyl)phenyl)butanoic acid, (18) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(N-methyl-N-phenylaminomethyl)phenyl)butanoic acid, (19) 4-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (20) 4-(2-((2-phenylpropanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (21) 3-(2-((4-methyl-2-phenylpentanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (22) 3-(2-((2-phenylpentanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (23) 3-(2-((2-phenylpropanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (24) 3-(2-((2-phenylbutanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (25) 4-(2-((2-phenylpropanoyl)amino)-4-phenylaminomethylphenyl)butanoic acid, (26) 4-(2-((2-phenylpropanoyl)amino)-4-benzoylaminomethylphenyl)butanoic acid, (27) 4-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-benzoylaminomethylphenyl)butanoic acid, (28) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenylsulfonylaminomethylphenyl)butanoic acid, (29) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-benzylaminomethylphenyl)butanoic acid, (30) 4-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-phenylaminomethylphenyl)butanoic acid, (31) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-cyanophenoxymethyl)phenyl)butanoic acid, phenylaminomethylphenyl)butanoic acid, (32) 2-(2-((2-phenylpropanoyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (33) 2-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (34) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(furan-2-ylcarbonylaminomethyl)phenyl)butanoic acid, (35) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-fluorobenzoylaminomethyl)phenyl)butanoic acid, (36) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-methoxybenzoylaminomethyl)phenyl)butanoic acid, (37) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-cyclopropylcarbonylaminomethylphenyl)butanoic acid, (38) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(thiophen-2-ylcarbonylaminomethyl)phenyl)butanoic acid, (39) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-methylbenzoylaminomethyl)phenyl)butanoic acid, (40) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-chlorobenzoylaminomethyl)phenyl)butanoic acid, (41) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-cyanobenzoylaminomethyl)phenyl)butanoic acid, (42) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-fluorobenzoylaminomethyl)phenyl)butanoic acid, (43) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-fluorobenzoylaminomethyl)phenyl)butanoic acid, (44) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-chloro-4-fluorobenzoylaminomethyl)phenyl)butanoic acid, (45) 4-(2-((2-(2-chlorophenyl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (46) 4-(2-((2-(3-chlorophenyl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (47) 4-(2-((2-(4-chlorophenyl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (48) 4-(2-((2-(4-fluorophenyl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (49) 4-(2-((2-(4-methoxyphenyl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (50) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-ethoxybenzoylaminomethyl)phenyl)butanoic acid, (51) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3,5-difluorobenzoylaminomethyl)phenyl)butanoic acid, (52) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-fluorophenoxymethyl)phenyl)butanoic acid, (53) 4-(2-((2-(4-methylphenyl)propanoyl)amino)-4-phenoxymethylphenyl)butanoic acid, (54) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-cyano-2-methoxyphenoxymethyl)phenyl)butanoic acid, (55) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-acetylphenoxymethyl)phenyl)butanoic acid, (56) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-isopropyl-5-methylphenoxymethyl)phenyl)butanoic acid, (57) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2,4,6-trifluorophenoxymethyl)phenyl)butanoic acid, (58) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-trifluoromethylthiophenoxymethyl)phenyl)butanoic acid, (59) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-bromophenoxymethyl)phenyl)butanoic acid, (60) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-methoxyphenoxymethyl)phenyl)butanoic acid, (61) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-methoxyphenoxymethyl)phenyl)butanoic acid, (62) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-methylbenzothiazol-5-yloxymethyl)phenyl)butanoic acid, (63) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-(1,2,4-triazol-1-yl)phenoxymethyl)phenyl)butanoic acid, (64) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-ethoxyphenoxymethyl)phenyl)butanoic acid, (65) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-methoxy-5-methylphenoxymethyl)phenyl)butanoic acid, (66) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3,5-dimethoxyphenoxymethyl)phenyl)butanoic acid, (67) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-fluoro-6-methoxyphenoxymethyl)phenyl)butanoic acid, (68) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-isopropyloxyphenoxymethyl)phenyl)butanoic acid, (69) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-acetyl-5-methoxyphenoxymethyl)phenyl)butanoic acid, (70) 2-(2-((4-methyl-2-(naphthalen-1-yl)pentanoyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (71) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-chloro-4,5-dimethylphenoxymethyl)phenyl)butanoic acid, (72) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(1-oxo-1,2,3,4-tetrahydronaphthalen-6-yloxymethyl)phenyl)butanoic acid, (73) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-cyanophenoxymethyl)phenyl)butanoic acid, (74) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-chloro-5-methoxyphenoxymethyl)phenyl)butanoic acid, (75) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-ethyl-2-methoxyphenoxymethyl)phenyl)butanoic acid, (76) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-acetylamino-2-chlorophenoxymethyl)phenyl)butanoic acid, (77) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-methylthiophenoxymethyl)phenyl)butanoic acid, (78) 4-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(4-butanoylphenoxymethyl)phenyl)butanoic acid, (79) (2E)-3-(2-((4-methyl-2-phenylpentanoyl)amino)-4-phenoxymethylphenyl)-2-propenoic acid, (80) 4-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-(pyrazol-1-ylmethyl)phenyl)butanoic acid, (81) 3-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (82) 3-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-phenylaminomethylphenyl)propanoic acid, (83) 3-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-(pyrazol-1-ylmethyl)phenyl)propanoic acid, (84) 2-(2-((2-(4-fluoronaphthalen-1-yl)acetyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (85) 2-(2-((2-(4-fluoronaphthalen-1-yl)propanoyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (86) 2-(2-((4-methyl-2-phenylpentanoyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (87) 2-(2-((4-methyl-2-(3,5-dimethylphenyl)pentanoyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (88) 2-(2-((2-(naphthalen-1-yl)acetyl)amino)-4-phenoxymethylbenzyl)benzoic acid, (89) 3-(2-((4-methyl-2-(4-fluoro-3-methylphenyl)pentanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (90) 3-(2-((4-methyl-2-(3,5-dimethylphenyl)pentanoyl)amino)-4-phenoxymethylphenyl)propanoic acid, (91) 2-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-methylphenoxymethyl)benzyl)benzoic acid, (92) 2-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(2-chloro-5-methylphenoxymethyl)benzyl)benzoic acid, (93) 2-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(3-cyanophenoxymethyl)benzyl)benzoic acid, (94) 2-(2-((2-(naphthalen-1-yl)propanoyl)amino)-4-(pyridin-3-yloxymethyl)benzyl)benzoic acid, methyl ester thereof, ethyl ester therof or non-toxic salts thereof. -
3. A pharmaceutical composition, which comprises the compound of formula (I) according to claim 1, or a non-toxic salt thereof.
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4. The compound according to claim 1, which is
2-(2-((4-methyl-2-(naphthalen-1-yl)pentanoyl)amino)-4-(pyrazol-1-ylmethyl) benzyl)benzoic acid.
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2. The compound according to the claim 1, which is selected from
Specification
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Current AssigneeONO Pharmaceutical Company Limited
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Original AssigneeONO Pharmaceutical Company Limited
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InventorsNarita, Masami, Asada, Masaki, Ogawa, Mikio, Kobayashi, Kaoru, Tani, Kousuke
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Primary Examiner(s)Aulakh; Charanjit S
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Application NumberUS12/259,012Publication NumberTime in Patent Office673 DaysField of Search514/406, 514/383, 514/367, 514/546, 514/557, 548/375.1, 548/267.2, 548/152, 560/155, 562/400US Class Current514/406CPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 1/02 Stomatological preparations...A61P 1/04 for ulcers, gastritis or re...A61P 1/10 LaxativesA61P 1/16 for liver or gallbladder di...A61P 11/00 Drugs for disorders of the ...A61P 11/02 Nasal agents, e.g. deconges...A61P 13/00 Drugs for disorders of the ...A61P 13/10 of the bladderA61P 13/12 of the kidneysA61P 15/06 Antiabortive agents; Labour...A61P 17/00 Drugs for dermatological di...A61P 17/02 for treating wounds, ulcers...A61P 19/00 Drugs for skeletal disordersA61P 19/02 for joint disorders, e.g. a...A61P 19/10 for osteoporosisA61P 25/00 Drugs for disorders of the ...A61P 25/04 Centrally acting analgesics...A61P 25/18 Antipsychotics, i.e. neurol...A61P 25/20 Hypnotics; SedativesA61P 25/22 : AnxiolyticsA61P 25/28 : for treating neurodegenerat...A61P 27/02 : Ophthalmic agentsA61P 29/00 : Non-central analgesic, anti...A61P 29/02 : without antiinflammatory ef...A61P 3/14 : for calcium homeostasis vit...A61P 31/18 : for HIVA61P 35/00 : Antineoplastic agentsA61P 35/04 : specific for metastasisA61P 37/00 : Drugs for immunological or ...A61P 37/02 : ImmunomodulatorsA61P 37/06 : Immunosuppressants, e.g. dr...A61P 37/08 : Antiallergic agents antiast...A61P 43/00 : Drugs for specific purposes...A61P 5/24 : of the sex hormonesA61P 7/02 : Antithrombotic agents; Anti...A61P 9/00 : Drugs for disorders of the ...A61P 9/08 : Vasodilators for multiple i...A61P 9/10 : for treating ischaemic or a...A61P 9/12 : AntihypertensivesA61P 9/14 : Vasoprotectives; Antihaemor...C07C 229/34 : the carbon skeleton contain...C07C 309/66 : MethanesulfonatesC07C 309/67 : of an unsaturated carbon sk...C07C 309/73 : to carbon atoms of non-cond...C07C 311/06 : to acyclic carbon atoms of ...C07C 311/08 : having the nitrogen atom of...C07C 311/19 : to an acyclic carbon atom o...C07C 311/29 : having the sulfur atom of a...C07C 311/51 : Y being a hydrogen or a car...C07C 317/18 : with sulfone or sulfoxide g...C07C 317/22 : with sulfone or sulfoxide g...C07C 317/40 : Y being a hydrogen or a car...C07C 317/50 : at least one of the nitroge...C07C 323/19 : with singly-bound oxygen at...C07C 323/42 : Y being a carbon atom of a ...C07C 323/59 : with acylated amino groups ...C07C 323/60 : with the carbon atom of at ...C07C 59/68 : the oxygen atom of the ethe...C07C 69/734 : EthersC07C 69/736 : the hydroxy group of the es...C07C 69/738 : Esters of keto-carboxylic a...C07D 231/12 : with only hydrogen atoms, h...C07D 233/56 : with only hydrogen atoms or...C07D 249/08 : 1,2,4-Triazoles; Hydrogenat...