JP2002003370A5 - - Google Patents
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- JP2002003370A5 JP2002003370A5 JP2000290357A JP2000290357A JP2002003370A5 JP 2002003370 A5 JP2002003370 A5 JP 2002003370A5 JP 2000290357 A JP2000290357 A JP 2000290357A JP 2000290357 A JP2000290357 A JP 2000290357A JP 2002003370 A5 JP2002003370 A5 JP 2002003370A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- methyl
- nmr
- ethyl acetate
- melting point
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
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- 239000002904 solvent Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 18
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- -1 N- [4-[(E) -3-amino-3-oxo-1-propenyl] phenyl] [1,1'-biphenyl] -4-carboxamide (E) -3- [4-[([1,1′-biphenyl] -4-ylcarbonyl) amino] phenyl] -2-propenoic acid Chemical compound 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XZLDYCLPZPAZGE-UHFFFAOYSA-N 6-(pyrrolidin-1-ylmethyl)-7,8-dihydronaphthalen-2-amine Chemical compound C1CC2=CC(N)=CC=C2C=C1CN1CCCC1 XZLDYCLPZPAZGE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CKEVHPNLWBHDMY-UHFFFAOYSA-N tert-butyl 3-[(4-aminophenyl)methyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1CC1=CC=C(N)C=C1 CKEVHPNLWBHDMY-UHFFFAOYSA-N 0.000 description 3
- QARVELJVEBLWGK-UHFFFAOYSA-N 1-methyl-3,5-dinitropyridin-2-one Chemical compound CN1C=C([N+]([O-])=O)C=C([N+]([O-])=O)C1=O QARVELJVEBLWGK-UHFFFAOYSA-N 0.000 description 2
- HBFBJEXFVBHLIC-UHFFFAOYSA-N 3-nitro-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=CC([N+](=O)[O-])=CN=C21 HBFBJEXFVBHLIC-UHFFFAOYSA-N 0.000 description 2
- TWPLWCXWCQSEAX-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-7,8-dihydronaphthalen-2-amine Chemical compound C1=C(N)C=C2CCC(CN(C)C)=CC2=C1 TWPLWCXWCQSEAX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 2
- IIHPMDBETUITGI-UHFFFAOYSA-N n-[6-[(dimethylamino)methyl]-7,8-dihydronaphthalen-2-yl]-4-(4-fluorophenyl)piperidine-1-carboxamide Chemical compound C1=C2CCC(CN(C)C)=CC2=CC=C1NC(=O)N(CC1)CCC1C1=CC=C(F)C=C1 IIHPMDBETUITGI-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- LXWNTLBMNCXRQN-UHFFFAOYSA-N 4'-fluoro-1,1'-biphenyl-4-carboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1 LXWNTLBMNCXRQN-UHFFFAOYSA-N 0.000 description 1
- YADKGZRPAKKBSA-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-[hydroxy(piperidin-3-yl)methyl]phenyl]benzamide;hydrochloride Chemical compound Cl.C=1C=C(NC(=O)C=2C=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=CC=1C(O)C1CCCNC1 YADKGZRPAKKBSA-UHFFFAOYSA-N 0.000 description 1
- ZEAIEARBYGKRGY-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[6-(pyrrolidin-1-ylmethyl)-7,8-dihydronaphthalen-2-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)NC=2C=C3CCC(CN4CCCC4)=CC3=CC=2)CC1 ZEAIEARBYGKRGY-UHFFFAOYSA-N 0.000 description 1
- FIMRRWLTRBEAOM-UHFFFAOYSA-N 4-(4-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 FIMRRWLTRBEAOM-UHFFFAOYSA-N 0.000 description 1
- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- PSQLDJRMAWPCKZ-UHFFFAOYSA-N Cc(cc1)ccc1-c(nc1)ccc1C(Nc1ccc(C=C(CN2CCCC2)CC2)c2c1)=O Chemical compound Cc(cc1)ccc1-c(nc1)ccc1C(Nc1ccc(C=C(CN2CCCC2)CC2)c2c1)=O PSQLDJRMAWPCKZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- UNSKMEXFKFPMGP-UHFFFAOYSA-N [[4-[[4-(4-chlorophenyl)benzoyl]amino]phenyl]-piperidin-3-ylmethyl] acetate Chemical compound C=1C=C(NC(=O)C=2C=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=CC=1C(OC(=O)C)C1CCCNC1 UNSKMEXFKFPMGP-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- KBMQNOPPULBLKM-UHFFFAOYSA-N n-(5,6,7,8-tetrahydroquinolin-3-yl)acetamide Chemical compound C1CCCC2=CC(NC(=O)C)=CN=C21 KBMQNOPPULBLKM-UHFFFAOYSA-N 0.000 description 1
- OMYWBXYAOJZMNR-SNAWJCMRSA-N n-[4-[(e)-2-cyanoethenyl]phenyl]-4-phenylbenzamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NC1=CC=C(\C=C\C#N)C=C1 OMYWBXYAOJZMNR-SNAWJCMRSA-N 0.000 description 1
- YGUGFXJFVANLAS-UHFFFAOYSA-N n-[6-[(dimethylamino)methyl]-7,8-dihydronaphthalen-2-yl]-4-(4-methylphenyl)piperidine-1-carboxamide Chemical compound C1=C2CCC(CN(C)C)=CC2=CC=C1NC(=O)N(CC1)CCC1C1=CC=C(C)C=C1 YGUGFXJFVANLAS-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MPEVRZKJUAVLCO-UHFFFAOYSA-N tert-butyl 3-[[4-[(4-phenylbenzoyl)amino]phenyl]methyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 MPEVRZKJUAVLCO-UHFFFAOYSA-N 0.000 description 1
- VTSUCRCHBMVCGY-UHFFFAOYSA-N tert-butyl 3-[[4-[[4-(4-chlorophenyl)benzoyl]amino]phenyl]methyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 VTSUCRCHBMVCGY-UHFFFAOYSA-N 0.000 description 1
- CZFDDPBEQHCBHG-UHFFFAOYSA-N tert-butyl 3-[[4-[[4-(4-fluorophenyl)benzoyl]amino]phenyl]methyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 CZFDDPBEQHCBHG-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000290357A JP2002003370A (ja) | 1999-09-20 | 2000-09-20 | メラニン凝集ホルモン拮抗剤 |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26629899 | 1999-09-20 | ||
| JP35788999 | 1999-12-16 | ||
| JP2000-126272 | 2000-04-20 | ||
| JP2000126272 | 2000-04-20 | ||
| JP11-357889 | 2000-04-20 | ||
| JP11-266298 | 2000-04-20 | ||
| JP2000290357A JP2002003370A (ja) | 1999-09-20 | 2000-09-20 | メラニン凝集ホルモン拮抗剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002003370A JP2002003370A (ja) | 2002-01-09 |
| JP2002003370A5 true JP2002003370A5 (ko) | 2007-09-06 |
Family
ID=27478766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000290357A Withdrawn JP2002003370A (ja) | 1999-09-20 | 2000-09-20 | メラニン凝集ホルモン拮抗剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002003370A (ko) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002352878B2 (en) * | 2001-11-27 | 2007-11-22 | Merck Sharp & Dohme Corp. | 2-Aminoquinoline compounds |
| EP2508204B1 (en) * | 2002-06-26 | 2014-09-24 | Ono Pharmaceutical Co., Ltd. | Remedies for diseases caused by vascular contraction or dilation |
| DE10233817A1 (de) * | 2002-07-25 | 2004-02-12 | Aventis Pharma Deutschland Gmbh | Substituierte Diarylheterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10250708A1 (de) * | 2002-10-31 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7727998B2 (en) | 2003-02-10 | 2010-06-01 | Banyu Pharmaceutical Co., Ltd. | Melanin-concentrating hormone receptor antagonists containing piperidine derivatives as the active ingredient |
| JP4630555B2 (ja) * | 2003-02-12 | 2011-02-09 | 武田薬品工業株式会社 | アミン誘導体 |
| WO2004103992A1 (ja) * | 2003-05-21 | 2004-12-02 | Banyu Pharmaceutical Co., Ltd. | ２－アミノキノリン誘導体 |
| AU2004247559B2 (en) | 2003-06-12 | 2009-08-27 | Astellas Pharma Inc. | Benzamide derivative or salt thereof |
| DE10360745A1 (de) * | 2003-12-23 | 2005-07-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| JPWO2005085200A1 (ja) * | 2004-03-05 | 2008-01-17 | 萬有製薬株式会社 | ピリドン誘導体 |
| DE102004017932A1 (de) * | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| EP1798221A4 (en) | 2004-10-01 | 2010-04-07 | Banyu Pharma Co Ltd | NITROGENIC HETEROCYCLIC 2-ARYLCARBOXYLENEAMIDE COMPOUND |
| MX2007004354A (es) * | 2004-10-14 | 2007-07-17 | Abbot Gmbh & Co Kg | Compuestos aromaticos biciclicos sustituidos con aminometilo adecuados para tratar trastornos que responden a la modulacion del receptor de dopamina d3. |
| EP1876179B1 (en) * | 2005-04-28 | 2015-03-25 | Takeda Pharmaceutical Company Limited | Thienopyrimidone compounds |
| JP2008542365A (ja) * | 2005-05-31 | 2008-11-27 | アストラゼネカ・アクチエボラーグ | 新規なｍｃｈｒ１アンタゴニスト並びにｍｃｈｒ１媒介状態及び障害の処置のためのそれらの使用 |
| CA2619770A1 (en) * | 2005-08-24 | 2007-03-01 | Banyu Pharmaceutical Co., Ltd. | Phenylpyridone derivative |
| AR056871A1 (es) * | 2005-10-04 | 2007-10-31 | Aventis Pharma Inc | Compuestos de pirimidina amida como inhibidores de pgds |
| CA2652524A1 (en) * | 2006-06-08 | 2007-12-21 | Eli Lilly And Company | Novel mch receptor antagonists |
| EA015127B1 (ru) * | 2006-06-08 | 2011-06-30 | Эли Лилли Энд Компани | Антагонисты мсн-рецепторов |
| WO2008041090A1 (en) * | 2006-10-06 | 2008-04-10 | Pfizer Limited | Malanin concentrating hormone receptor-1 antagonist pyridinones |
| EP2522657B1 (en) * | 2010-01-06 | 2016-08-03 | Takeda Pharmaceutical Company Limited | Indole derivative |
| CA2814768C (en) * | 2010-10-30 | 2019-02-12 | Lupin Limited | Oxazoline and isoxazoline derivatives as crac modulators |
| JP6510498B2 (ja) * | 2013-09-24 | 2019-05-08 | ウニヴェルジテート・ツー・ケルン | 腫瘍疾患の治療に有用な化合物 |
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2000
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