JP2009524683A5 - - Google Patents
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- JP2009524683A5 JP2009524683A5 JP2008552474A JP2008552474A JP2009524683A5 JP 2009524683 A5 JP2009524683 A5 JP 2009524683A5 JP 2008552474 A JP2008552474 A JP 2008552474A JP 2008552474 A JP2008552474 A JP 2008552474A JP 2009524683 A5 JP2009524683 A5 JP 2009524683A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- methyl
- pyridin
- tetrahydro
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 67
- 125000001072 heteroaryl group Chemical group 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 25
- 125000001188 haloalkyl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000003107 substituted aryl group Chemical group 0.000 claims 21
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 20
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 20
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 19
- 125000004438 haloalkoxy group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims 17
- 239000000651 prodrug Substances 0.000 claims 15
- 229940002612 prodrug Drugs 0.000 claims 15
- 239000012453 solvate Substances 0.000 claims 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 14
- -1 benzoxdiazolyl Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- BWGOFNHLWWSJNB-UHFFFAOYSA-N 3-fluoro-n-[4-[4-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C1=NC=CS1 BWGOFNHLWWSJNB-UHFFFAOYSA-N 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- WRHLSTUAPDFNPE-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-(1,3-oxazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C1=NC=CO1 WRHLSTUAPDFNPE-UHFFFAOYSA-N 0.000 claims 2
- FGGBQDLVIIWCEN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C1=NC=CS1 FGGBQDLVIIWCEN-UHFFFAOYSA-N 0.000 claims 2
- SLEWYYKLCSEZDR-UHFFFAOYSA-N 2,6-difluoro-n-[5-[4-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]pyrimidin-2-yl]benzamide Chemical compound C1CC(C)=C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)CN1C1=NC=CS1 SLEWYYKLCSEZDR-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- FCFQVXYTQRVKCF-UHFFFAOYSA-N [3-[4-[(2,6-difluorobenzoyl)amino]phenyl]-2-methylbut-2-enyl] acetate Chemical compound C1=CC(C(C)=C(C)COC(=O)C)=CC=C1NC(=O)C1=C(F)C=CC=C1F FCFQVXYTQRVKCF-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- PEZZMFSRMFVCBV-UHFFFAOYSA-N ethyl 4-methyl-5-[4-[(3-methylpyridine-4-carbonyl)amino]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C PEZZMFSRMFVCBV-UHFFFAOYSA-N 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 125000005945 imidazopyridyl group Chemical group 0.000 claims 2
- 230000005931 immune cell recruitment Effects 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- CENMJSMNRVHHGR-UHFFFAOYSA-N n-[4-(cyclohexen-1-yl)phenyl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2CCCCC=2)C=C1 CENMJSMNRVHHGR-UHFFFAOYSA-N 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005888 tetrahydroindolyl group Chemical group 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- PCZNZIKVYULMCE-UHFFFAOYSA-N (4-nitrophenyl) 5-[4-[(3-fluoropyridine-4-carbonyl)amino]phenyl]-4-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C(=O)OC1=CC=C([N+]([O-])=O)C=C1 PCZNZIKVYULMCE-UHFFFAOYSA-N 0.000 claims 1
- OHWRUMYXZSGSLK-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-formylcyclohepten-1-yl)phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2CCCCCC=2C=O)C=C1 OHWRUMYXZSGSLK-UHFFFAOYSA-N 0.000 claims 1
- NFWLUMRZUPPTIF-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-formylcyclopenten-1-yl)phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2CCCC=2C=O)C=C1 NFWLUMRZUPPTIF-UHFFFAOYSA-N 0.000 claims 1
- FMGXJYPTSJRXFX-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-methyl-1-phenylprop-1-enyl)phenyl]benzamide Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2F)F)C=CC=1C(=C(C)C)C1=CC=CC=C1 FMGXJYPTSJRXFX-UHFFFAOYSA-N 0.000 claims 1
- HCCSCLWFYLZEFW-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-methylcyclohexen-1-yl)phenyl]benzamide Chemical compound C1CCCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F HCCSCLWFYLZEFW-UHFFFAOYSA-N 0.000 claims 1
- IQSDJWBNMBDLOL-UHFFFAOYSA-N 2,6-difluoro-n-[4-(4-methyl-1-pyrimidin-2-yl-3,6-dihydro-2h-pyridin-5-yl)phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C1=NC=CC=N1 IQSDJWBNMBDLOL-UHFFFAOYSA-N 0.000 claims 1
- FCUGJUKRPROMRY-UHFFFAOYSA-N 2,6-difluoro-n-[4-(5-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl]benzamide Chemical compound C1CNCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F FCUGJUKRPROMRY-UHFFFAOYSA-N 0.000 claims 1
- DCJOXMRZUKKAOO-UHFFFAOYSA-N 2,6-difluoro-n-[4-[1-(2-methoxyphenyl)-2-methylprop-1-enyl]phenyl]benzamide Chemical compound COC1=CC=CC=C1C(=C(C)C)C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F DCJOXMRZUKKAOO-UHFFFAOYSA-N 0.000 claims 1
- GCXIQYBFNAURFP-UHFFFAOYSA-N 2,6-difluoro-n-[4-[1-(3-methoxyphenyl)-2-methylprop-1-enyl]phenyl]benzamide Chemical compound COC1=CC=CC(C(=C(C)C)C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 GCXIQYBFNAURFP-UHFFFAOYSA-N 0.000 claims 1
- XWMVWCGAMMPIKF-UHFFFAOYSA-N 2,6-difluoro-n-[4-[1-(4-methoxyphenyl)-2-methylprop-1-enyl]phenyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=C(C)C)C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F XWMVWCGAMMPIKF-UHFFFAOYSA-N 0.000 claims 1
- BCAVVFXLQGBVTM-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(1,3-oxazol-5-yl)cyclohepten-1-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2CCCCCC=2C=2OC=NC=2)C=C1 BCAVVFXLQGBVTM-UHFFFAOYSA-N 0.000 claims 1
- ILNAEDUKNAAFAS-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(1,3-oxazol-5-yl)cyclohexen-1-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2CCCCC=2C=2OC=NC=2)C=C1 ILNAEDUKNAAFAS-UHFFFAOYSA-N 0.000 claims 1
- FEFXYVMHIAVMSM-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(1,3-oxazol-5-yl)cyclopenten-1-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2CCCC=2C=2OC=NC=2)C=C1 FEFXYVMHIAVMSM-UHFFFAOYSA-N 0.000 claims 1
- AYEAKPSSARDRRD-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(hydroxymethyl)cyclohepten-1-yl]phenyl]benzamide Chemical compound C1CCCCC(CO)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F AYEAKPSSARDRRD-UHFFFAOYSA-N 0.000 claims 1
- XYUCDYGPJJSDHS-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(hydroxymethyl)cyclohexen-1-yl]phenyl]benzamide Chemical compound C1CCCC(CO)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F XYUCDYGPJJSDHS-UHFFFAOYSA-N 0.000 claims 1
- SIDRMAFBYIMMQE-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(hydroxymethyl)cyclopenten-1-yl]phenyl]benzamide Chemical compound C1CCC(CO)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F SIDRMAFBYIMMQE-UHFFFAOYSA-N 0.000 claims 1
- OPXNIJUNTMAHGQ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-formyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2CN(CCC=2C=O)C=2SC=CN=2)C=C1 OPXNIJUNTMAHGQ-UHFFFAOYSA-N 0.000 claims 1
- PYJXEYPSJIICDC-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-(1-methyltetrazol-5-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C1=NN=NN1C PYJXEYPSJIICDC-UHFFFAOYSA-N 0.000 claims 1
- BCCCDCGGLAACJU-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-(2-methyltetrazol-5-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C=1N=NN(C)N=1 BCCCDCGGLAACJU-UHFFFAOYSA-N 0.000 claims 1
- FGQWROFZDNQBQR-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-(2h-tetrazol-5-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C1=NN=NN1 FGQWROFZDNQBQR-UHFFFAOYSA-N 0.000 claims 1
- XFZBUOXFDFLOFN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-(4-methyl-1,3-oxazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound CC1=COC(N2CC(=C(C)CC2)C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=N1 XFZBUOXFDFLOFN-UHFFFAOYSA-N 0.000 claims 1
- UFGAQYIQKKZPBB-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-1-[1-(pyridine-3-carbonyl)cyclopropanecarbonyl]-3,6-dihydro-2h-pyridin-5-yl]phenyl]benzamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C(=O)C1(C(=O)C=2C=NC=CC=2)CC1 UFGAQYIQKKZPBB-UHFFFAOYSA-N 0.000 claims 1
- WCUYMUUHBDNDNR-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]benzamide Chemical compound C1C(C)=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CCN1C1=NC=CS1 WCUYMUUHBDNDNR-UHFFFAOYSA-N 0.000 claims 1
- RYGSHTKQDOFFJY-UHFFFAOYSA-N 2,6-difluoro-n-[5-[4-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]pyridin-2-yl]benzamide Chemical compound C1CC(C)=C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)CN1C1=NC=CS1 RYGSHTKQDOFFJY-UHFFFAOYSA-N 0.000 claims 1
- SZOAENAZGYLCMV-UHFFFAOYSA-N 3-fluoro-n-[4-(2-methylcyclohexen-1-yl)phenyl]pyridine-4-carboxamide Chemical compound C1CCCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F SZOAENAZGYLCMV-UHFFFAOYSA-N 0.000 claims 1
- WMMXBXCBCSCCSM-UHFFFAOYSA-N 3-fluoro-n-[4-(3-methylbut-2-en-2-yl)phenyl]pyridine-4-carboxamide Chemical compound C1=CC(C(C)=C(C)C)=CC=C1NC(=O)C1=CC=NC=C1F WMMXBXCBCSCCSM-UHFFFAOYSA-N 0.000 claims 1
- XZKPCEQWUYPFBH-UHFFFAOYSA-N 3-fluoro-n-[4-(4-methyl-1-pyridin-2-yl-3,6-dihydro-2h-pyridin-5-yl)phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C1=CC=CC=N1 XZKPCEQWUYPFBH-UHFFFAOYSA-N 0.000 claims 1
- XMLPJOCFLNCNEA-UHFFFAOYSA-N 3-fluoro-n-[4-(4-methyl-1-pyrimidin-5-yl-3,6-dihydro-2h-pyridin-5-yl)phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C1=CN=CN=C1 XMLPJOCFLNCNEA-UHFFFAOYSA-N 0.000 claims 1
- IRTFINFJAQMYSR-QGZVFWFLSA-N 3-fluoro-n-[4-[(5r)-2-methyl-5-prop-1-en-2-ylcyclohexen-1-yl]phenyl]pyridine-4-carboxamide Chemical compound C1[C@H](C(=C)C)CCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F IRTFINFJAQMYSR-QGZVFWFLSA-N 0.000 claims 1
- DASYPMKDRQCGGX-HNNXBMFYSA-N 3-fluoro-n-[4-[(5s)-2-methyl-5-prop-1-en-2-ylcyclohexen-1-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound C1[C@@H](C(=C)C)CCC(C)=C1C1=CC=NC(NC(=O)C=2C(=CN=CC=2)F)=C1 DASYPMKDRQCGGX-HNNXBMFYSA-N 0.000 claims 1
- RAYVZRVLHBVZJA-UHFFFAOYSA-N 3-fluoro-n-[4-[2-(1,3-oxazol-5-yl)cyclohexen-1-yl]phenyl]pyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2CCCCC=2C=2OC=NC=2)C=C1 RAYVZRVLHBVZJA-UHFFFAOYSA-N 0.000 claims 1
- OWUNKIPWLBWUAI-UHFFFAOYSA-N 3-fluoro-n-[4-[4-methyl-1-(1,3-oxazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C1=NC=CO1 OWUNKIPWLBWUAI-UHFFFAOYSA-N 0.000 claims 1
- LHZRDXHNDGFXRP-UHFFFAOYSA-N 3-fluoro-n-[4-[4-methyl-1-(1-methyltetrazol-5-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C1=NN=NN1C LHZRDXHNDGFXRP-UHFFFAOYSA-N 0.000 claims 1
- GTCZZGBKBPGJGH-UHFFFAOYSA-N 3-fluoro-n-[4-[4-methyl-1-(2-methyltetrazol-5-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C=1N=NN(C)N=1 GTCZZGBKBPGJGH-UHFFFAOYSA-N 0.000 claims 1
- KKDPVJPVRYNODQ-UHFFFAOYSA-N 3-fluoro-n-[4-[4-methyl-1-(2h-tetrazol-5-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)CN1C1=NN=NN1 KKDPVJPVRYNODQ-UHFFFAOYSA-N 0.000 claims 1
- AFDKXHAZFATUIU-UHFFFAOYSA-N 3-methyl-n-[4-(2-methyl-1-phenylprop-1-enyl)phenyl]pyridine-4-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(=CN=CC=2)C)C=CC=1C(=C(C)C)C1=CC=CC=C1 AFDKXHAZFATUIU-UHFFFAOYSA-N 0.000 claims 1
- AWSHFQZQWJQKNZ-LJQANCHMSA-N 3-methyl-n-[4-[(5r)-2-methyl-5-prop-1-en-2-ylcyclohexen-1-yl]phenyl]pyridine-4-carboxamide Chemical compound C1[C@H](C(=C)C)CCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C AWSHFQZQWJQKNZ-LJQANCHMSA-N 0.000 claims 1
- AWSHFQZQWJQKNZ-IBGZPJMESA-N 3-methyl-n-[4-[(5s)-2-methyl-5-prop-1-en-2-ylcyclohexen-1-yl]phenyl]pyridine-4-carboxamide Chemical compound C1[C@@H](C(=C)C)CCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C AWSHFQZQWJQKNZ-IBGZPJMESA-N 0.000 claims 1
- JQKBHOXSGUGZPJ-UHFFFAOYSA-N 3-methyl-n-[4-[4-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyridine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)CN1C1=NC=CS1 JQKBHOXSGUGZPJ-UHFFFAOYSA-N 0.000 claims 1
- OOCVOTJHZNTWKH-UHFFFAOYSA-N 4-chloro-n-[4-(2-methylcyclohexen-1-yl)phenyl]-1,3-thiazole-5-carboxamide Chemical compound C1CCCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=C(Cl)N=CS1 OOCVOTJHZNTWKH-UHFFFAOYSA-N 0.000 claims 1
- RUBQGFPSWXWDGF-UHFFFAOYSA-N 4-methyl-n-[4-(2-methylcyclohexen-1-yl)phenyl]pyrimidine-5-carboxamide Chemical compound C1CCCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=CN=CN=C1C RUBQGFPSWXWDGF-UHFFFAOYSA-N 0.000 claims 1
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 claims 1
- POOBBEQIUWWXCI-UHFFFAOYSA-N 4-o-ethyl 1-o-methyl 5-[4-[(2,6-difluorobenzoyl)amino]phenyl]-2,3,6,7-tetrahydroazepine-1,4-dicarboxylate Chemical compound C1CN(C(=O)OC)CCC(C(=O)OCC)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F POOBBEQIUWWXCI-UHFFFAOYSA-N 0.000 claims 1
- YOUWHBCVHXEKMR-UHFFFAOYSA-N 5-methyl-n-[4-(2-methylcyclohexen-1-yl)phenyl]pyrimidine-4-carboxamide Chemical compound C1CCCC(C)=C1C(C=C1)=CC=C1NC(=O)C1=NC=NC=C1C YOUWHBCVHXEKMR-UHFFFAOYSA-N 0.000 claims 1
- UGWOIYHQWUMROA-UHFFFAOYSA-N 5-methyl-n-[4-[4-methyl-1-(1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]pyrimidine-4-carboxamide Chemical compound C1CC(C)=C(C=2C=CC(NC(=O)C=3C(=CN=CN=3)C)=CC=2)CN1C1=NC=CS1 UGWOIYHQWUMROA-UHFFFAOYSA-N 0.000 claims 1
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- 2007-01-25 JP JP2008552474A patent/JP2009524683A/ja active Pending
- 2007-01-25 US US11/699,002 patent/US7816535B2/en not_active Expired - Fee Related
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2014
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