OA12970A - 2-aminocarbonyl-quinoline compounds as platelet adenosine diphosphate receptor antagonists. - Google Patents

2-aminocarbonyl-quinoline compounds as platelet adenosine diphosphate receptor antagonists. Download PDF

Info

Publication number: OA12970A
Authority: OA; OAPI
Prior art keywords: alkyl; hydrogen; aminocarbonyl; aralkyl; carboxy
Prior art date: 2002-12-11

Application number

OA1200500175A

Other languages

English (en)

Inventor

Judi Bryant

Brad Buckman

Imadul Islam

Raju Mohan

Michael Morrissey

Guo Ping Wei

Wei Xu

Shendong Yuan

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-12-11

Filing date

2003-12-09

Publication date

2006-10-13

2003-12-09 Application filed by Schering Ag filed Critical Schering Ag

2006-10-13 Publication of OA12970A publication Critical patent/OA12970A/en

Links

150000001875 compounds Chemical class 0.000 abstract description 262
238000000034 method Methods 0.000 abstract description 45
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 abstract description 29
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 abstract description 28
230000008569 process Effects 0.000 abstract description 5
239000003146 anticoagulant agent Substances 0.000 abstract description 4
239000008194 pharmaceutical composition Substances 0.000 abstract description 4
229960004676 antithrombotic agent Drugs 0.000 abstract description 3
239000003112 inhibitor Substances 0.000 abstract description 3
230000002194 synthesizing effect Effects 0.000 abstract 1
-1 aralkoxycarbonyl Chemical group 0.000 description 240
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 111
229910052739 hydrogen Inorganic materials 0.000 description 101
239000001257 hydrogen Substances 0.000 description 101
125000004435 hydrogen atom Chemical group [H]* 0.000 description 99
125000000217 alkyl group Chemical group 0.000 description 95
150000003254 radicals Chemical class 0.000 description 76
ZTQNUTNKGQGWCM-UHFFFAOYSA-N 2-methoxyquinoline Chemical compound C1=CC=CC2=NC(OC)=CC=C21 ZTQNUTNKGQGWCM-UHFFFAOYSA-N 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
125000003710 aryl alkyl group Chemical group 0.000 description 60
125000001188 haloalkyl group Chemical group 0.000 description 51
239000000203 mixture Substances 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000011541 reaction mixture Substances 0.000 description 46
125000003118 aryl group Chemical group 0.000 description 40
125000005843 halogen group Chemical group 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
125000004181 carboxyalkyl group Chemical group 0.000 description 32
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
125000001424 substituent group Chemical group 0.000 description 31
125000004453 alkoxycarbonyl group Chemical group 0.000 description 29
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 26
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
IDPWXVBDDIYDKT-UHFFFAOYSA-N 2-phenoxyquinoline Chemical compound C=1C=C2C=CC=CC2=NC=1OC1=CC=CC=C1 IDPWXVBDDIYDKT-UHFFFAOYSA-N 0.000 description 24
101000621371 Homo sapiens WD and tetratricopeptide repeats protein 1 Proteins 0.000 description 24
101000892274 Human adenovirus C serotype 2 Adenovirus death protein Proteins 0.000 description 24
101000820656 Rattus norvegicus Seminal vesicle secretory protein 4 Proteins 0.000 description 24
102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000002253 acid Substances 0.000 description 18
125000002947 alkylene group Chemical group 0.000 description 18
208000007536 Thrombosis Diseases 0.000 description 16
229940093499 ethyl acetate Drugs 0.000 description 16
235000019439 ethyl acetate Nutrition 0.000 description 16
125000002768 hydroxyalkyl group Chemical group 0.000 description 16
230000001732 thrombotic effect Effects 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
201000010099 disease Diseases 0.000 description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
239000000651 prodrug Substances 0.000 description 15
229940002612 prodrug Drugs 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
239000007787 solid Substances 0.000 description 15
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 14
125000003545 alkoxy group Chemical group 0.000 description 14
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
125000004093 cyano group Chemical group *C#N 0.000 description 14
125000004356 hydroxy functional group Chemical group O* 0.000 description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
239000002904 solvent Substances 0.000 description 14
208000010110 spontaneous platelet aggregation Diseases 0.000 description 14
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
150000005840 aryl radicals Chemical class 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
125000004448 alkyl carbonyl group Chemical group 0.000 description 11
239000012267 brine Substances 0.000 description 11
125000004663 dialkyl amino group Chemical group 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
NWIAYUZWWLSLBI-UHFFFAOYSA-N 2-phenylmethoxyquinoline Chemical compound C=1C=C2C=CC=CC2=NC=1OCC1=CC=CC=C1 NWIAYUZWWLSLBI-UHFFFAOYSA-N 0.000 description 10
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
241000700159 Rattus Species 0.000 description 10
238000003556 assay Methods 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
238000002955 isolation Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
VGJWVEYTYIBXIA-UHFFFAOYSA-N 2,2,2-trifluoroethane-1,1-diol Chemical compound OC(O)C(F)(F)F VGJWVEYTYIBXIA-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
102000007466 Purinergic P2 Receptors Human genes 0.000 description 9
108010085249 Purinergic P2 Receptors Proteins 0.000 description 9
230000002776 aggregation Effects 0.000 description 9
238000004220 aggregation Methods 0.000 description 9
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 description 9
238000009739 binding Methods 0.000 description 9
125000005111 carboxyalkoxy group Chemical group 0.000 description 9
125000004438 haloalkoxy group Chemical group 0.000 description 9
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
239000000725 suspension Substances 0.000 description 9
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 8
239000000010 aprotic solvent Substances 0.000 description 8
230000027455 binding Effects 0.000 description 8
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 8
125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 8
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
108010035532 Collagen Proteins 0.000 description 7
102000008186 Collagen Human genes 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
125000005097 aminocarbonylalkyl group Chemical group 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
229920001436 collagen Polymers 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
229940073584 methylene chloride Drugs 0.000 description 7
230000010118 platelet activation Effects 0.000 description 7
239000000047 product Substances 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
239000000126 substance Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
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SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
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210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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238000001727 in vivo Methods 0.000 description 6
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
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239000002244 precipitate Substances 0.000 description 6
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238000005160 1H NMR spectroscopy Methods 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
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238000009835 boiling Methods 0.000 description 5
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JYASQADVXZBDBP-UHFFFAOYSA-N ethyl 4-[2-amino-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(C(=O)C(N)CCC(=O)OC(C)(C)C)CC1 JYASQADVXZBDBP-UHFFFAOYSA-N 0.000 description 5
238000000605 extraction Methods 0.000 description 5
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125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
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238000012360 testing method Methods 0.000 description 5
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 5
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
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WLMZTKAZJUWXCB-JLOOSCHCSA-N [(2r,3s,4r,5r)-5-(6-amino-2-methylsulfanylpurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydroxyphosphoryl hydrogen phosphate Chemical compound C12=NC(SC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO[33P](O)(=O)O[33P](O)(O)=O)[C@@H](O)[C@H]1O WLMZTKAZJUWXCB-JLOOSCHCSA-N 0.000 description 4
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150000007530 organic bases Chemical class 0.000 description 4
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238000004007 reversed phase HPLC Methods 0.000 description 4
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GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
VUKHRCOPMVPBJV-UHFFFAOYSA-N 7-methyl-4-oxo-1h-quinoline-2-carboxylic acid Chemical compound OC1=CC(C(O)=O)=NC2=CC(C)=CC=C21 VUKHRCOPMVPBJV-UHFFFAOYSA-N 0.000 description 3
ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 3
239000005552 B01AC04 - Clopidogrel Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 3
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KPWMOVKJWMPHGC-UHFFFAOYSA-N ethyl 4-[5-[(2-methylpropan-2-yl)oxy]-5-oxo-2-(phenylmethoxycarbonylamino)pentanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)C(CCC(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1 KPWMOVKJWMPHGC-UHFFFAOYSA-N 0.000 description 3
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239000010410 layer Substances 0.000 description 3
KDNMQEWSPXSMDB-UHFFFAOYSA-N methyl 6-chloro-7-methyl-4-oxo-3h-quinoline-2-carboxylate Chemical compound CC1=C(Cl)C=C2C(=O)CC(C(=O)OC)=NC2=C1 KDNMQEWSPXSMDB-UHFFFAOYSA-N 0.000 description 3
PNQIEWPPSCIQJF-UHFFFAOYSA-N methyl 7-methyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=CC(C)=CC2=NC(C(=O)OC)=CC(O)=C21 PNQIEWPPSCIQJF-UHFFFAOYSA-N 0.000 description 3
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125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
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MWDJRMIHHQKFDX-UHFFFAOYSA-N methyl 4-oxo-7-(trifluoromethoxy)-1h-quinoline-2-carboxylate Chemical compound C1=CC(OC(F)(F)F)=CC2=NC(C(=O)OC)=CC(O)=C21 MWDJRMIHHQKFDX-UHFFFAOYSA-N 0.000 description 1
HXMSYFTWUSYAPH-UHFFFAOYSA-N methyl 4-oxo-7-(trifluoromethyl)-1h-quinoline-2-carboxylate Chemical compound C1=CC(C(F)(F)F)=CC2=NC(C(=O)OC)=CC(O)=C21 HXMSYFTWUSYAPH-UHFFFAOYSA-N 0.000 description 1
VLZYGTRQYVQNHJ-UHFFFAOYSA-N methyl 4-oxo-7-phenylmethoxy-1h-quinoline-2-carboxylate Chemical compound C=1C2=NC(C(=O)OC)=CC(O)=C2C=CC=1OCC1=CC=CC=C1 VLZYGTRQYVQNHJ-UHFFFAOYSA-N 0.000 description 1
ZXHCYCLBSVNODY-UHFFFAOYSA-N methyl 4-oxo-7-propoxy-1h-quinoline-2-carboxylate Chemical compound OC1=CC(C(=O)OC)=NC2=CC(OCCC)=CC=C21 ZXHCYCLBSVNODY-UHFFFAOYSA-N 0.000 description 1
DXSRVGHSPKNIAB-UHFFFAOYSA-N methyl 5-(4-ethoxy-4-oxobutoxy)-4-oxo-1h-quinoline-2-carboxylate Chemical compound COC(=O)C1=CC(O)=C2C(OCCCC(=O)OCC)=CC=CC2=N1 DXSRVGHSPKNIAB-UHFFFAOYSA-N 0.000 description 1
LYBGSHMYWHJYRI-UHFFFAOYSA-N methyl 5-(diacetylamino)-4-oxo-1h-quinoline-2-carboxylate Chemical compound CC(=O)N(C(C)=O)C1=CC=CC2=NC(C(=O)OC)=CC(O)=C21 LYBGSHMYWHJYRI-UHFFFAOYSA-N 0.000 description 1
OFVIWZAPAWYJOU-UHFFFAOYSA-N methyl 5-(hydroxymethoxy)-4-oxo-1h-quinoline-2-carboxylate Chemical compound OCOC1=CC=CC2=NC(C(=O)OC)=CC(O)=C21 OFVIWZAPAWYJOU-UHFFFAOYSA-N 0.000 description 1
OXTVUJAXIVALGT-UHFFFAOYSA-N methyl 5-acetamido-4-oxo-1h-quinoline-2-carboxylate Chemical compound CC(=O)NC1=CC=CC2=NC(C(=O)OC)=CC(O)=C21 OXTVUJAXIVALGT-UHFFFAOYSA-N 0.000 description 1
USRGKPYANAVHOW-UHFFFAOYSA-N methyl 5-amino-4-oxo-1h-quinoline-2-carboxylate Chemical compound NC1=CC=CC2=NC(C(=O)OC)=CC(O)=C21 USRGKPYANAVHOW-UHFFFAOYSA-N 0.000 description 1
UOFBKHDWDOWCBE-UHFFFAOYSA-N methyl 5-hydroxy-4-oxo-1h-quinoline-2-carboxylate Chemical compound OC1=CC=CC2=NC(C(=O)OC)=CC(O)=C21 UOFBKHDWDOWCBE-UHFFFAOYSA-N 0.000 description 1
ZOKUJNGBPSXUEN-UHFFFAOYSA-N methyl 5-nitro-4-oxo-1h-quinoline-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=CC2=NC(C(=O)OC)=CC(O)=C21 ZOKUJNGBPSXUEN-UHFFFAOYSA-N 0.000 description 1
IAOJNGHTHOBUPV-UHFFFAOYSA-N methyl 6,7-difluoro-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(F)C(F)=CC2=NC(C(=O)OC)=CC(O)=C21 IAOJNGHTHOBUPV-UHFFFAOYSA-N 0.000 description 1
SRRWUPWAZYFBKK-UHFFFAOYSA-N methyl 6-(diethylaminomethyl)-4-oxo-1h-quinoline-2-carboxylate Chemical compound N1=C(C(=O)OC)C=C(O)C2=CC(CN(CC)CC)=CC=C21 SRRWUPWAZYFBKK-UHFFFAOYSA-N 0.000 description 1
POWMRSDSYBXKTH-UHFFFAOYSA-N methyl 6-(dimethylamino)-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(N(C)C)C=CC2=NC(C(=O)OC)=CC(O)=C21 POWMRSDSYBXKTH-UHFFFAOYSA-N 0.000 description 1
QKMURGWSCDSNMN-UHFFFAOYSA-N methyl 6-acetyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound CC(=O)C1=CC=C2NC(C(=O)OC)=CC(=O)C2=C1 QKMURGWSCDSNMN-UHFFFAOYSA-N 0.000 description 1
LTCKDZAUNSZESX-UHFFFAOYSA-N methyl 6-amino-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(N)C=CC2=NC(C(=O)OC)=CC(O)=C21 LTCKDZAUNSZESX-UHFFFAOYSA-N 0.000 description 1
QULFUAQYCCSQAG-UHFFFAOYSA-N methyl 6-carbamoyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(C(N)=O)C=CC2=NC(C(=O)OC)=CC(O)=C21 QULFUAQYCCSQAG-UHFFFAOYSA-N 0.000 description 1
HESVUOITGSAKKR-UHFFFAOYSA-N methyl 6-chloro-4-oxo-1h-quinoline-2-carboxylate Chemical compound ClC1=CC=C2NC(C(=O)OC)=CC(=O)C2=C1 HESVUOITGSAKKR-UHFFFAOYSA-N 0.000 description 1
RVQKBOJONGSIDH-UHFFFAOYSA-N methyl 6-chloro-5-methyl-4-oxo-3h-quinoline-2-carboxylate Chemical compound C1=C(Cl)C(C)=C2C(=O)CC(C(=O)OC)=NC2=C1 RVQKBOJONGSIDH-UHFFFAOYSA-N 0.000 description 1
IMSQMUNVQFYCPF-UHFFFAOYSA-N methyl 6-ethoxy-4-oxo-1h-quinoline-2-carboxylate Chemical compound N1=C(C(=O)OC)C=C(O)C2=CC(OCC)=CC=C21 IMSQMUNVQFYCPF-UHFFFAOYSA-N 0.000 description 1
PBNYNLXOQRWFDR-UHFFFAOYSA-N methyl 6-ethyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound N1=C(C(=O)OC)C=C(O)C2=CC(CC)=CC=C21 PBNYNLXOQRWFDR-UHFFFAOYSA-N 0.000 description 1
BESDSRIEDPEFRN-UHFFFAOYSA-N methyl 6-fluoro-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(F)C=CC2=NC(C(=O)OC)=CC(O)=C21 BESDSRIEDPEFRN-UHFFFAOYSA-N 0.000 description 1
KDMHMHBQWSJHSI-UHFFFAOYSA-N methyl 6-methoxy-4-oxo-1h-quinoline-2-carboxylate Chemical compound COC1=CC=C2NC(C(=O)OC)=CC(=O)C2=C1 KDMHMHBQWSJHSI-UHFFFAOYSA-N 0.000 description 1
OFNPBZVQMSFLIS-UHFFFAOYSA-N methyl 6-nitro-4-oxo-1h-quinoline-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2NC(C(=O)OC)=CC(=O)C2=C1 OFNPBZVQMSFLIS-UHFFFAOYSA-N 0.000 description 1
BKSHXXHCHOZUDL-UHFFFAOYSA-N methyl 7-[2-(diethylamino)ethoxy]-4-oxo-1h-quinoline-2-carboxylate Chemical compound OC1=CC(C(=O)OC)=NC2=CC(OCCN(CC)CC)=CC=C21 BKSHXXHCHOZUDL-UHFFFAOYSA-N 0.000 description 1
OKHLVOCPJRTOQQ-UHFFFAOYSA-N methyl 7-acetyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=CC(C(C)=O)=CC2=NC(C(=O)OC)=CC(O)=C21 OKHLVOCPJRTOQQ-UHFFFAOYSA-N 0.000 description 1
HNKLSMKAQAVMKQ-UHFFFAOYSA-N methyl 7-bromo-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=CC(Br)=CC2=NC(C(=O)OC)=CC(O)=C21 HNKLSMKAQAVMKQ-UHFFFAOYSA-N 0.000 description 1
QHPKUXTUEVUQAZ-UHFFFAOYSA-N methyl 7-chloro-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(Cl)C=C2NC(C(=O)OC)=CC(=O)C2=C1 QHPKUXTUEVUQAZ-UHFFFAOYSA-N 0.000 description 1
WFEYMCITSCYMSP-UHFFFAOYSA-N methyl 7-chloro-6-fluoro-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(F)C(Cl)=CC2=NC(C(=O)OC)=CC(O)=C21 WFEYMCITSCYMSP-UHFFFAOYSA-N 0.000 description 1
MPAAKJHSTVGSHE-UHFFFAOYSA-N methyl 7-chloro-6-methoxy-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(OC)C(Cl)=CC2=NC(C(=O)OC)=CC(O)=C21 MPAAKJHSTVGSHE-UHFFFAOYSA-N 0.000 description 1
HSZVCJOLXPSIQI-UHFFFAOYSA-N methyl 7-chloro-6-methyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=C(C)C(Cl)=CC2=NC(C(=O)OC)=CC(O)=C21 HSZVCJOLXPSIQI-UHFFFAOYSA-N 0.000 description 1
FJIHNTFXUYMFRI-UHFFFAOYSA-N methyl 7-cyano-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=CC(C#N)=CC2=NC(C(=O)OC)=CC(O)=C21 FJIHNTFXUYMFRI-UHFFFAOYSA-N 0.000 description 1
XGTZLBOMFGBSAL-UHFFFAOYSA-N methyl 7-ethyl-4-oxo-1h-quinoline-2-carboxylate Chemical compound OC1=CC(C(=O)OC)=NC2=CC(CC)=CC=C21 XGTZLBOMFGBSAL-UHFFFAOYSA-N 0.000 description 1
GWISOUSAPFLHLI-UHFFFAOYSA-N methyl 7-fluoro-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=CC(F)=CC2=NC(C(=O)OC)=CC(O)=C21 GWISOUSAPFLHLI-UHFFFAOYSA-N 0.000 description 1
MUJXVVHLAUTTHP-UHFFFAOYSA-N methyl 7-methoxy-4-oxo-1h-quinoline-2-carboxylate Chemical compound C1=CC(OC)=CC2=NC(C(=O)OC)=CC(O)=C21 MUJXVVHLAUTTHP-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
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Pharmacology & Pharmacy (AREA)
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Diabetes (AREA)
Urology & Nephrology (AREA)
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Heart & Thoracic Surgery (AREA)
Oncology (AREA)
Neurosurgery (AREA)
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Biomedical Technology (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
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OA1200500175A 2002-12-11 2003-12-09 2-aminocarbonyl-quinoline compounds as platelet adenosine diphosphate receptor antagonists. OA12970A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US43279202P	2002-12-11	2002-12-11

Publications (1)

Publication Number	Publication Date
OA12970A true OA12970A (en)	2006-10-13

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ID=32507994

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500175A OA12970A (en)	2002-12-11	2003-12-09	2-aminocarbonyl-quinoline compounds as platelet adenosine diphosphate receptor antagonists.

Country Status (23)

Country	Link
US (2)	US7056923B2 (pl)
EP (1)	EP1578423B1 (pl)
JP (1)	JP4662777B2 (pl)
KR (1)	KR20050085580A (pl)
CN (1)	CN1747732A (pl)
AP (1)	AP2005003363A0 (pl)
AT (1)	ATE477800T1 (pl)
AU (1)	AU2003297763A1 (pl)
BR (1)	BR0317222A (pl)
CA (1)	CA2507657C (pl)
DE (1)	DE60333866D1 (pl)
EA (1)	EA200500899A1 (pl)
EC (1)	ECSP055912A (pl)
ES (1)	ES2348942T3 (pl)
MX (1)	MXPA05006302A (pl)
NO (1)	NO20053335L (pl)
NZ (1)	NZ540872A (pl)
OA (1)	OA12970A (pl)
PL (1)	PL377053A1 (pl)
RS (1)	RS20050450A (pl)
UA (1)	UA83648C2 (pl)
WO (1)	WO2004052366A1 (pl)
ZA (1)	ZA200505492B (pl)

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US7335648B2 (en) *	2003-10-21	2008-02-26	Inspire Pharmaceuticals, Inc.	Non-nucleotide composition and method for inhibiting platelet aggregation
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DE102006020385A1 (de) *	2006-04-28	2007-10-31	Dade Behring Marburg Gmbh	Verfahren und Vorrichtung zur Bestimmung der Thrombozytenfunktion unter Flussbedingungen
CL2007002920A1 (es) *	2006-10-13	2008-06-06	Actelion Pharmaceuticals Ltd	Compuestos derivados de 2-aminocarbonilpiridina; composicion farmaceutica; y uso para el tratamiento de trastornos vasculares oclusivos.
CL2007003038A1 (es)	2006-10-25	2008-06-06	Actelion Pharmaceuticals Ltd	Compuestos derivados de 2-fenil-6-aminocarbonil-pirimidina; composicion farmaceutica; y uso en el tratamiento de trastornos vasculares oclusivos.
CA2684644A1 (en) *	2007-04-23	2008-10-30	Sanofi-Aventis	Quinoline-carboxamide derivatives as p2y12 antagonists
CA2690243A1 (en)	2007-06-18	2008-12-24	Sanofi-Aventis	Pyrrole derivatives as p2y12 antagonists
BRPI0819696B1 (pt)	2007-11-29	2018-10-23	Actelion Pharmaceuticals Ltd	compostos de derivados de 2-fenil-pirimidina, composição farmacêutica e uso de um composto
AR071652A1 (es) *	2008-04-11	2010-07-07	Actelion Pharmaceuticals Ltd	Derivados 2- fenil-piridina substituidos
AR071653A1 (es)	2008-04-11	2010-07-07	Actelion Pharmaceuticals Ltd	Derivados 2-fenil-4-ciclopropil-pirimidina
WO2010116328A2 (en)	2009-04-08	2010-10-14	Actelion Pharmaceuticals Ltd	6-(3-aza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-pyrimidines
KR101728180B1 (ko)	2009-04-22	2017-04-18	액테리온 파마슈티칼 리미티드	티아졸 유도체들 및 ｐ2ｙ12 수용체 길항제로서 이들의 용도
CN102304108B (zh) *	2011-06-28	2013-11-06	中国药科大学	五元杂环双羰基衍生物及其抗多药耐药细菌上的用途
CN104151235B (zh) *	2014-08-07	2016-01-20	南阳师范学院	一种喹啉衍生物制备方法
HUE057772T2 (hu)	2016-09-22	2022-06-28	Idorsia Pharmaceuticals Ltd	Kristályos formák
US11179390B2 (en)	2017-03-15	2021-11-23	Idorsia Pharmaceuticals Ltd	Subcutaneous administration of a P2Y12 receptor antagonist
CN112062687B (zh) *	2020-09-02	2023-11-21	上海信谊万象药业股份有限公司	一种盐酸阿扎司琼中间体3-氨基-5-氯-2-羟基苯甲酸甲酯的合成方法
CN112920181A (zh) *	2021-01-29	2021-06-08	中国医科大学	N-(5-苯基-1,3,4-噻二唑-2-基)苯甲酰胺类化合物

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GB1334705A (en)	1970-06-19	1973-10-24	Ici Ltd	Pharmaceutical compositions containing kynurenic acid derivatives
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JPH05503300A (ja)	1990-11-15	1993-06-03	ペンタファルム　アクチェンゲゼルシャフト	メタ置換フェニルアラニン誘導体
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2003
- 2003-12-09 CA CA2507657A patent/CA2507657C/en not_active Expired - Fee Related
- 2003-12-09 UA UAA200506729A patent/UA83648C2/ru unknown
- 2003-12-09 US US10/731,815 patent/US7056923B2/en not_active Expired - Fee Related
- 2003-12-09 DE DE60333866T patent/DE60333866D1/de not_active Expired - Lifetime
- 2003-12-09 CN CNA2003801096637A patent/CN1747732A/zh active Pending
- 2003-12-09 PL PL377053A patent/PL377053A1/pl not_active Application Discontinuation
- 2003-12-09 AT AT03796831T patent/ATE477800T1/de not_active IP Right Cessation
- 2003-12-09 ES ES03796831T patent/ES2348942T3/es not_active Expired - Lifetime
- 2003-12-09 BR BR0317222-8A patent/BR0317222A/pt not_active IP Right Cessation
- 2003-12-09 OA OA1200500175A patent/OA12970A/en unknown
- 2003-12-09 KR KR1020057010688A patent/KR20050085580A/ko not_active Withdrawn
- 2003-12-09 AU AU2003297763A patent/AU2003297763A1/en not_active Abandoned
- 2003-12-09 EP EP03796831A patent/EP1578423B1/en not_active Expired - Lifetime
- 2003-12-09 MX MXPA05006302A patent/MXPA05006302A/es active IP Right Grant
- 2003-12-09 AP AP2005003363A patent/AP2005003363A0/xx unknown
- 2003-12-09 EA EA200500899A patent/EA200500899A1/ru unknown
- 2003-12-09 NZ NZ540872A patent/NZ540872A/en unknown
- 2003-12-09 RS YUP-2005/0450A patent/RS20050450A/sr unknown
- 2003-12-09 WO PCT/US2003/039079 patent/WO2004052366A1/en not_active Ceased
- 2003-12-09 JP JP2004558607A patent/JP4662777B2/ja not_active Expired - Fee Related
2005
- 2005-07-08 NO NO20053335A patent/NO20053335L/no not_active Application Discontinuation
- 2005-07-11 EC EC2005005912A patent/ECSP055912A/es unknown
2006
- 2006-01-12 US US11/331,621 patent/US7084142B2/en not_active Expired - Fee Related
- 2006-01-17 ZA ZA200505492A patent/ZA200505492B/en unknown

Also Published As

Publication number	Publication date
NZ540872A (en)	2007-08-31
MXPA05006302A (es)	2005-08-29
WO2004052366A1 (en)	2004-06-24
UA83648C2 (ru)	2008-08-11
EP1578423A1 (en)	2005-09-28
EA200500899A1 (ru)	2006-02-24
CN1747732A (zh)	2006-03-15
ATE477800T1 (de)	2010-09-15
WO2004052366A9 (en)	2005-06-23
KR20050085580A (ko)	2005-08-29
US20060122188A1 (en)	2006-06-08
NO20053335L (no)	2005-09-07
AU2003297763A1 (en)	2004-06-30
JP4662777B2 (ja)	2011-03-30
DE60333866D1 (de)	2010-09-30
US20040138229A1 (en)	2004-07-15
ES2348942T3 (es)	2010-12-17
JP2006511519A (ja)	2006-04-06
EP1578423B1 (en)	2010-08-18
RS20050450A (sr)	2007-08-03
US7084142B2 (en)	2006-08-01
BR0317222A (pt)	2005-11-01
US7056923B2 (en)	2006-06-06
CA2507657A1 (en)	2004-06-24
CA2507657C (en)	2011-05-31
NO20053335D0 (no)	2005-07-08
ECSP055912A (es)	2005-11-22
ZA200505492B (en)	2006-03-29
PL377053A1 (pl)	2006-01-23
AP2005003363A0 (en)	2005-09-30

Publication	Publication Date	Title
US7026323B2 (en)	2006-04-11	Platelet adenosine diphosphate receptor antagonists
US7056923B2 (en)	2006-06-06	Platelet adenosine diphosphate receptor antagonists
JP3507494B2 (ja)	2004-03-15	タキキニン拮抗薬
US7893279B2 (en)	2011-02-22	Cyclohexanecarboxylic acid compound
CN101151246B (zh)	2011-04-13	1-苄基吲哚-2-甲酰胺衍生物
JPH05503530A (ja)	1993-06-10	置換ベンジル成分を含むアンギオテンシン２拮抗物質
HU195220B (en)	1988-04-28	Process for production of new fluor-alkoxi-benzimidasole-derivatives and medical compositions containig them
JPH054984A (ja)	1993-01-14	カルボスチリル誘導体及びバソプレシン拮抗剤
WO2005060959A1 (en)	2005-07-07	Pyrazole derivatives and use thereof as orexin receptor antagonists
US6028081A (en)	2000-02-22	Substituted quinolone derivatives and pharmaceuticals containing the same
EA010392B1 (ru)	2008-08-29	Производные имидазолов, способ их получения и их применение в качестве лекарственного средства
AU2008264999B8 (en)	2013-10-31	Sulfonyl-quinoline derivatives
WO1999033822A1 (en)	1999-07-08	Indole derivatives useful a.o. for the treatment of osteoporosis
TWI787751B (zh)	2022-12-21	醯胺化合物的製備方法、其晶型及其鹽類
EP0536400A1 (en)	1993-04-14	Tetrazole derivative and medicine
SU1614760A3 (ru)	1990-12-15	Способ получени производных феноксиуксусной кислоты или их фармацевтически приемлемых солей