JP2012510515A5 - - Google Patents
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- JP2012510515A5 JP2012510515A5 JP2011539569A JP2011539569A JP2012510515A5 JP 2012510515 A5 JP2012510515 A5 JP 2012510515A5 JP 2011539569 A JP2011539569 A JP 2011539569A JP 2011539569 A JP2011539569 A JP 2011539569A JP 2012510515 A5 JP2012510515 A5 JP 2012510515A5
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- JP
- Japan
- Prior art keywords
- acid
- carbonyl
- oxo
- carboxylic acid
- ethyl
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 44
- 150000003839 salts Chemical class 0.000 claims 37
- 239000002253 acid Substances 0.000 claims 35
- 125000005907 alkyl ester group Chemical group 0.000 claims 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- -1 piperazino Chemical group 0.000 claims 8
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical group OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims 7
- 239000005711 Benzoic acid Substances 0.000 claims 6
- ZXVJCGPNCXIZLN-UHFFFAOYSA-N 4-(piperazine-1-carbonyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C(=O)N1CCNCC1 ZXVJCGPNCXIZLN-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 229910052757 nitrogen Chemical group 0.000 claims 5
- PLXSTIPOOXOJGU-UHFFFAOYSA-N 2-(piperazine-1-carbonyl)cyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1C(=O)N1CCNCC1 PLXSTIPOOXOJGU-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- BOYBTBKKHLEPFD-UHFFFAOYSA-N benzyl 4-(piperazine-1-carbonyl)cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)N2CCNCC2)CCC1C(=O)OCC1=CC=CC=C1 BOYBTBKKHLEPFD-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- IWZDDBJDSAIODB-UHFFFAOYSA-N 2-(piperidine-1-carbonyl)cyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1C(=O)N1CCCCC1 IWZDDBJDSAIODB-UHFFFAOYSA-N 0.000 claims 2
- WVUXHDNUHWDIKB-DEOSSOPVSA-N 4-[(3s)-3-[4-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]phenoxy]pyrrolidin-1-yl]benzoic acid Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)NC(=O)C=2N(CC)C=3C=CC=C(C=3C=2)OCC)CN1C1=CC=C(C(O)=O)C=C1 WVUXHDNUHWDIKB-DEOSSOPVSA-N 0.000 claims 2
- YAVUNRHXIJSNGZ-UHFFFAOYSA-N 4-[4-[4-[(4,5-dichloro-1-ethylindole-2-carbonyl)amino]phenyl]piperazin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C2=C(Cl)C(Cl)=CC=C2N(CC)C=1C(=O)NC(C=C1)=CC=C1N1CCN(C(=O)CC(C)(C)C(O)=O)CC1 YAVUNRHXIJSNGZ-UHFFFAOYSA-N 0.000 claims 2
- FLPOVELHQSTQKA-UHFFFAOYSA-N 4-[4-[4-[(7-methoxy-3-methyl-1h-indole-2-carbonyl)amino]phenyl]piperazin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N1C=2C(OC)=CC=CC=2C(C)=C1C(=O)NC(C=C1)=CC=C1N1CCN(C(=O)CC(C)(C)C(O)=O)CC1 FLPOVELHQSTQKA-UHFFFAOYSA-N 0.000 claims 2
- DGPLDFKTNYFQTQ-UHFFFAOYSA-N 4-[4-[4-[(7-methoxy-3-methyl-1h-indole-2-carbonyl)amino]phenyl]piperazine-1-carbonyl]cyclohexane-1-carboxylic acid Chemical compound N1C=2C(OC)=CC=CC=2C(C)=C1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1C(=O)C1CCC(C(O)=O)CC1 DGPLDFKTNYFQTQ-UHFFFAOYSA-N 0.000 claims 2
- KBQYYFGSUVNTEY-UHFFFAOYSA-N 4-[4-[4-[(7-methoxy-3-methyl-1h-indole-2-carbonyl)amino]phenyl]piperidine-1-carbonyl]cyclohexane-1-carboxylic acid Chemical compound N1C=2C(OC)=CC=CC=2C(C)=C1C(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCC(C(O)=O)CC1 KBQYYFGSUVNTEY-UHFFFAOYSA-N 0.000 claims 2
- VRWKTDOYQKJOPX-UHFFFAOYSA-N 4-[4-[5-[(1-ethyl-4-methoxyindole-2-carbonyl)amino]pyridin-2-yl]piperazine-1-carbonyl]cyclohexane-1-carboxylic acid Chemical compound C=1C2=C(OC)C=CC=C2N(CC)C=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C(=O)C1CCC(C(O)=O)CC1 VRWKTDOYQKJOPX-UHFFFAOYSA-N 0.000 claims 2
- OXSSDSAVLVULAO-UHFFFAOYSA-N 4-[4-[5-[(4,5-dichloro-1-ethylindole-2-carbonyl)amino]pyridin-2-yl]piperazin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C2=C(Cl)C(Cl)=CC=C2N(CC)C=1C(=O)NC(C=N1)=CC=C1N1CCN(C(=O)CC(C)(C)C(O)=O)CC1 OXSSDSAVLVULAO-UHFFFAOYSA-N 0.000 claims 2
- ZRQFAPVDBTWLEI-UHFFFAOYSA-N 4-[4-[5-[(4-chloro-1-benzothiophene-2-carbonyl)amino]pyridin-2-yl]piperazin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1CN(C(=O)CC(C)(C)C(O)=O)CCN1C(N=C1)=CC=C1NC(=O)C1=CC2=C(Cl)C=CC=C2S1 ZRQFAPVDBTWLEI-UHFFFAOYSA-N 0.000 claims 2
- FYOWTZPCCQWRFB-UHFFFAOYSA-N 4-[4-[5-[(5-bromo-1-benzothiophene-2-carbonyl)amino]pyridin-2-yl]piperazin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1CN(C(=O)CC(C)(C)C(O)=O)CCN1C(N=C1)=CC=C1NC(=O)C1=CC2=CC(Br)=CC=C2S1 FYOWTZPCCQWRFB-UHFFFAOYSA-N 0.000 claims 2
- LVJVKXNZGUVQRW-XYPYZODXSA-N C1C[C@@H](C(=O)O)CC[C@@H]1C(=O)N1CCCCC1 Chemical group C1C[C@@H](C(=O)O)CC[C@@H]1C(=O)N1CCCCC1 LVJVKXNZGUVQRW-XYPYZODXSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- GTWJOFRXPOJPEL-UHFFFAOYSA-N ethyl 3-[4-[(7-methoxy-3-methyl-1h-indole-2-carbonyl)amino]phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1OC(C=C1)=CC=C1NC(=O)C1=C(C)C2=CC=CC(OC)=C2N1 GTWJOFRXPOJPEL-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- UNOWQHZNDSZLOU-UHFFFAOYSA-N n-[4-[4-[2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetyl]piperazin-1-yl]phenyl]-4-ethoxy-1-ethylindole-2-carboxamide Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1C(=O)CC1SC(=O)NC1=O UNOWQHZNDSZLOU-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- PLXSTIPOOXOJGU-RKDXNWHRSA-N (1r,2r)-2-(piperazine-1-carbonyl)cyclopentane-1-carboxylic acid Chemical group OC(=O)[C@@H]1CCC[C@H]1C(=O)N1CCNCC1 PLXSTIPOOXOJGU-RKDXNWHRSA-N 0.000 claims 1
- XKOMNLKTFULJEY-DHIUTWEWSA-N (1r,2r)-2-[4-[4-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]phenyl]piperazine-1-carbonyl]cyclopentane-1-carboxylic acid Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1C(=O)[C@@H]1CCC[C@H]1C(O)=O XKOMNLKTFULJEY-DHIUTWEWSA-N 0.000 claims 1
- IZNDPWGXKJQXEP-UHFFFAOYSA-N 1-(2-oxoethyl)-2-piperidin-1-ylcyclopentane-1-carboxylic acid Chemical compound O=CCC1(C(=O)O)CCCC1N1CCCCC1 IZNDPWGXKJQXEP-UHFFFAOYSA-N 0.000 claims 1
- MHJADBJNRMTDHI-UHFFFAOYSA-N 1-ethyl-4-methylindole-2-carboxylic acid Chemical compound C1=CC=C2N(CC)C(C(O)=O)=CC2=C1C MHJADBJNRMTDHI-UHFFFAOYSA-N 0.000 claims 1
- QEUUVQIEPWTBDL-UHFFFAOYSA-N 1-ethyl-5-methoxy-n-[6-[2-methoxyethyl(methyl)amino]pyridin-3-yl]indole-2-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2N(CC)C=1C(=O)NC1=CC=C(N(C)CCOC)N=C1 QEUUVQIEPWTBDL-UHFFFAOYSA-N 0.000 claims 1
- AMNGBHKKUGMHDI-UHFFFAOYSA-N 1-ethyl-n-[6-[2-methoxyethyl(methyl)amino]pyridin-3-yl]-5-(trifluoromethoxy)indole-2-carboxamide Chemical compound C=1C2=CC(OC(F)(F)F)=CC=C2N(CC)C=1C(=O)NC1=CC=C(N(C)CCOC)N=C1 AMNGBHKKUGMHDI-UHFFFAOYSA-N 0.000 claims 1
- SHTDSBFOFATFQY-UHFFFAOYSA-N 2,2-dimethyl-4-oxo-3-piperazin-1-ylbutanoic acid Chemical group OC(=O)C(C)(C)C(C=O)N1CCNCC1 SHTDSBFOFATFQY-UHFFFAOYSA-N 0.000 claims 1
- PQYVGDNGRKIOOF-UHFFFAOYSA-N 2,2-dimethyl-4-oxo-3-piperidin-1-ylbutanoic acid Chemical group OC(=O)C(C)(C)C(C=O)N1CCCCC1 PQYVGDNGRKIOOF-UHFFFAOYSA-N 0.000 claims 1
- XKOMNLKTFULJEY-UHFFFAOYSA-N 2-[4-[4-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]phenyl]piperazine-1-carbonyl]cyclopentane-1-carboxylic acid Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1C(=O)C1CCCC1C(O)=O XKOMNLKTFULJEY-UHFFFAOYSA-N 0.000 claims 1
- WRRSKNIOOMGGMH-UHFFFAOYSA-N 2-[4-[4-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]phenyl]piperidine-1-carbonyl]cyclopentane-1-carboxylic acid Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCCC1C(O)=O WRRSKNIOOMGGMH-UHFFFAOYSA-N 0.000 claims 1
- UODYGVCEZCTHFE-UHFFFAOYSA-N 3-methyl-2-(2-oxoethyl)-2-piperazin-1-ylbutanoic acid Chemical compound O=CCC(C(C)C)(C(O)=O)N1CCNCC1 UODYGVCEZCTHFE-UHFFFAOYSA-N 0.000 claims 1
- LVJVKXNZGUVQRW-UHFFFAOYSA-N 4-(piperidine-1-carbonyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C(=O)N1CCCCC1 LVJVKXNZGUVQRW-UHFFFAOYSA-N 0.000 claims 1
- NHYBBVCRPJJRSG-NRFANRHFSA-N 4-[(3s)-3-[4-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]phenoxy]pyrrolidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=C1)=CC=C1O[C@H]1CCN(C(=O)CC(C)(C)C(O)=O)C1 NHYBBVCRPJJRSG-NRFANRHFSA-N 0.000 claims 1
- ONNIQKISGPUDJA-UHFFFAOYSA-N 4-[4-[5-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]pyridin-2-yl]piperazin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=N1)=CC=C1N1CCN(C(=O)CC(C)(C)C(O)=O)CC1 ONNIQKISGPUDJA-UHFFFAOYSA-N 0.000 claims 1
- BUUFUGUKARDXGU-UHFFFAOYSA-N 4-oxo-2-phenyl-2-piperidin-1-ylbutanoic acid Chemical compound C=1C=CC=CC=1C(CC=O)(C(=O)O)N1CCCCC1 BUUFUGUKARDXGU-UHFFFAOYSA-N 0.000 claims 1
- XUVOUVXBUAVCAL-UHFFFAOYSA-N 4-oxo-2-piperazin-1-ylbutanoic acid Chemical compound O=CCC(C(=O)O)N1CCNCC1 XUVOUVXBUAVCAL-UHFFFAOYSA-N 0.000 claims 1
- ARPXJCWWVVEBSW-UHFFFAOYSA-N 5-(1-acetylpiperazin-2-yl)-1,3-thiazolidine-2,4-dione Chemical compound CC(=O)N1CCNCC1C1C(=O)NC(=O)S1 ARPXJCWWVVEBSW-UHFFFAOYSA-N 0.000 claims 1
- SMHQZIFZMIBTIY-UHFFFAOYSA-N 5-chloro-n-[6-[cyclopropyl(methyl)amino]pyridin-3-yl]-1-ethylindole-2-carboxamide Chemical compound C=1C2=CC(Cl)=CC=C2N(CC)C=1C(=O)NC(C=N1)=CC=C1N(C)C1CC1 SMHQZIFZMIBTIY-UHFFFAOYSA-N 0.000 claims 1
- ZXVJCGPNCXIZLN-MGCOHNPYSA-N C1C[C@@H](C(=O)O)CC[C@@H]1C(=O)N1CCNCC1 Chemical group C1C[C@@H](C(=O)O)CC[C@@H]1C(=O)N1CCNCC1 ZXVJCGPNCXIZLN-MGCOHNPYSA-N 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- YKECJJQBSZRUAY-UHFFFAOYSA-N benzyl 4-[4-[5-[(1-ethyl-4-methoxyindole-2-carbonyl)amino]pyridin-2-yl]piperazine-1-carbonyl]cyclohexane-1-carboxylate Chemical compound C=1C2=C(OC)C=CC=C2N(CC)C=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C(=O)C(CC1)CCC1C(=O)OCC1=CC=CC=C1 YKECJJQBSZRUAY-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- LVUWSTNMCPSYOZ-SFHVURJKSA-N ethyl (3s)-3-[[5-[(1-ethyl-4-methylindole-2-carbonyl)amino]pyridin-2-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CC[C@@H]1NC(N=C1)=CC=C1NC(=O)C1=CC2=C(C)C=CC=C2N1CC LVUWSTNMCPSYOZ-SFHVURJKSA-N 0.000 claims 1
- GIVSKGUZUKUWMF-AWEZNQCLSA-N ethyl (3s)-3-[[5-[(4-chloro-1-benzothiophene-2-carbonyl)amino]pyridin-2-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CC[C@@H]1NC(N=C1)=CC=C1NC(=O)C1=CC2=C(Cl)C=CC=C2S1 GIVSKGUZUKUWMF-AWEZNQCLSA-N 0.000 claims 1
- PCQLQVZIJBOEGW-UHFFFAOYSA-N ethyl 3-[[5-[(1-ethyl-4,6-dimethoxyindole-2-carbonyl)amino]pyridin-2-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1NC(N=C1)=CC=C1NC(=O)C1=CC2=C(OC)C=C(OC)C=C2N1CC PCQLQVZIJBOEGW-UHFFFAOYSA-N 0.000 claims 1
- GLOXXTFQHFWBLO-UHFFFAOYSA-N ethyl 3-[[5-[(1-ethyl-5-methoxyindole-2-carbonyl)amino]pyridin-2-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1NC(N=C1)=CC=C1NC(=O)C1=CC2=CC(OC)=CC=C2N1CC GLOXXTFQHFWBLO-UHFFFAOYSA-N 0.000 claims 1
- IKVJVKBGHHRAOE-UHFFFAOYSA-N ethyl 3-[[5-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]pyridin-2-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1NC(N=C1)=CC=C1NC(=O)C1=CC2=C(OCC)C=CC=C2N1CC IKVJVKBGHHRAOE-UHFFFAOYSA-N 0.000 claims 1
- MOBWCOUYBAWJLP-UHFFFAOYSA-N ethyl 3-[[5-[(5-bromo-1-ethylindole-2-carbonyl)amino]pyridin-2-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1NC(N=C1)=CC=C1NC(=O)C1=CC2=CC(Br)=CC=C2N1CC MOBWCOUYBAWJLP-UHFFFAOYSA-N 0.000 claims 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical group CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- KCUNWYMCPOOKCY-IBGZPJMESA-N n-[6-[[(3s)-1-(tert-butylcarbamoyl)pyrrolidin-3-yl]amino]pyridin-3-yl]-1-ethyl-4-methylindole-2-carboxamide Chemical compound C=1C2=C(C)C=CC=C2N(CC)C=1C(=O)NC(C=N1)=CC=C1N[C@H]1CCN(C(=O)NC(C)(C)C)C1 KCUNWYMCPOOKCY-IBGZPJMESA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- ZSKGQRPHVHCUPB-UHFFFAOYSA-N tert-butyl 4-[5-[(1-ethyl-4,6-dimethoxyindole-2-carbonyl)amino]pyridin-2-yl]piperazine-1-carboxylate Chemical compound C=1C2=C(OC)C=C(OC)C=C2N(CC)C=1C(=O)NC(C=N1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 ZSKGQRPHVHCUPB-UHFFFAOYSA-N 0.000 claims 1
- WANQRFBUYIQKFK-UHFFFAOYSA-N tert-butyl 4-[5-[(4-chloro-1-benzothiophene-2-carbonyl)amino]pyridin-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(N=C1)=CC=C1NC(=O)C1=CC2=C(Cl)C=CC=C2S1 WANQRFBUYIQKFK-UHFFFAOYSA-N 0.000 claims 1
- ZFLYDIAWYSRYSC-UHFFFAOYSA-N tert-butyl 4-[5-[(4-ethoxy-1-ethylindole-2-carbonyl)amino]pyridin-2-yl]piperazine-1-carboxylate Chemical compound C=1C=2C(OCC)=CC=CC=2N(CC)C=1C(=O)NC(C=N1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 ZFLYDIAWYSRYSC-UHFFFAOYSA-N 0.000 claims 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical group CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11946708P | 2008-12-03 | 2008-12-03 | |
| US61/119,467 | 2008-12-03 | ||
| PCT/US2009/064971 WO2010065310A1 (en) | 2008-12-03 | 2009-11-18 | Inhibitors of diacylglycerol acyltransferase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012510515A JP2012510515A (ja) | 2012-05-10 |
| JP2012510515A5 true JP2012510515A5 (OSRAM) | 2013-01-10 |
Family
ID=42231833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011539569A Withdrawn JP2012510515A (ja) | 2008-12-03 | 2009-11-18 | ジアシルグリセロールアシルトランスフェラーゼの阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8124766B2 (OSRAM) |
| EP (1) | EP2367817A4 (OSRAM) |
| JP (1) | JP2012510515A (OSRAM) |
| CN (1) | CN102239165A (OSRAM) |
| AU (1) | AU2009322774A1 (OSRAM) |
| CA (1) | CA2744152A1 (OSRAM) |
| IL (1) | IL212916A0 (OSRAM) |
| WO (1) | WO2010065310A1 (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8115011B2 (en) | 2007-05-22 | 2012-02-14 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8153644B2 (en) | 2007-05-22 | 2012-04-10 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8211884B2 (en) | 2008-08-06 | 2012-07-03 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| JP4900361B2 (ja) * | 2008-10-21 | 2012-03-21 | ソニー株式会社 | 画像処理装置、画像処理方法およびプログラム |
| US8324385B2 (en) * | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| CA2745445A1 (en) | 2008-12-17 | 2010-07-08 | Via Pharmaceuticals, Inc. | Inhibitors of diacylglycerol aclytransferase |
| PA8854101A1 (es) | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
| AU2010211109B2 (en) | 2009-02-06 | 2014-11-27 | Cellzome Limited | Novel substituted bicyclic heterocyclic compounds as gamma secretase modulators |
| TWI461425B (zh) | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| MX2011011753A (es) | 2009-05-07 | 2011-11-29 | Janssen Pharmaceuticals Inc | Nuevos derivados sustitutos de indazol y aza-indazol como moduladores de la gamma secretasa. |
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| PH12012501381A1 (en) | 2010-01-15 | 2012-10-22 | Janssen Pharmaceuticals Inc | Novel substituted bicyclic triazole derivatives as gamma secretase modulators |
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| EA023045B1 (ru) | 2011-07-15 | 2016-04-29 | Янссен Фармасьютикалз, Инк. | Новые замещенные производные индола в качестве модуляторов гамма-секретазы |
| MX355164B (es) | 2012-05-16 | 2018-04-06 | Janssen Pharmaceuticals Inc | Derivados de 3,4-dihidro-2h-pirido[1,2-a]pirazin-1,6-diona sustituidos utiles para el tratamiento de la enfermedad de alzheimer (inter alia). |
| ES2608356T3 (es) | 2012-12-20 | 2017-04-10 | Janssen Pharmaceutica Nv | Novedosos derivados tricíclicos de 3,4-dihidro-2H-pirido[1,2-a]pirazin-1,6-diona como moduladores de la secretasa gamma |
| AU2014206834B2 (en) | 2013-01-17 | 2017-06-22 | Janssen Pharmaceutica Nv | Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| US10562897B2 (en) | 2014-01-16 | 2020-02-18 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| MX2022015793A (es) * | 2020-06-24 | 2023-02-27 | Pmv Pharmaceuticals Inc | Terapia de combinacion para tratamiento de cancer. |
| KR20230079427A (ko) * | 2020-10-08 | 2023-06-07 | 머크 샤프 앤드 돔 엘엘씨 | 신규 디아실글리세리드 o-아실트랜스퍼라제 2 억제제로서의 옥스인돌 유도체의 제조 |
| CN120826398A (zh) * | 2023-03-30 | 2025-10-21 | 微境生物医药科技(上海)有限公司 | 作为DGKζ抑制剂的化合物 |
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| US3250771A (en) * | 1962-12-17 | 1966-05-10 | Geigy Chem Corp | 5-monocarbocyclic aryl-n-lower alkyl-2-pyrrolidine carboxylic acid, esters, amides and derivatives thereof |
| DE2337461A1 (de) * | 1973-07-24 | 1975-02-06 | Boehringer Mannheim Gmbh | Neue indolderivate und verfahren zu deren herstellung |
| US4066654A (en) * | 1975-04-16 | 1978-01-03 | G. D. Searle & Co. | 1-triarylalkyl-4-phenyl-4-piperidine carboxylic acids and derivatives |
| US6495558B1 (en) * | 1999-01-22 | 2002-12-17 | Amgen Inc. | Kinase inhibitors |
| US6756374B2 (en) * | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
| PL208515B1 (pl) | 2001-08-31 | 2011-05-31 | Sanofi Aventis Deutschland | Pochodne diarylocykloalkilowe, środki lecznicze zawierające te związki oraz ich zastosowanie jako aktywatorów PPAR |
| US7553867B2 (en) | 2002-09-06 | 2009-06-30 | Takeda Pharmaceutical Company Limited | Furan or thiophene derivative and medicinal use thereof |
| RU2342388C2 (ru) * | 2002-11-22 | 2008-12-27 | Джапан Тобакко Инк. | Конденсированные бициклические азотсодержащие гетероциклы, обладающие dgat ингибирующим действием |
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| US20100093733A1 (en) * | 2007-02-15 | 2010-04-15 | Prosidion Limited | Amide and urea derivatives for the treatment of metabolic diseases |
| AU2008253118B2 (en) * | 2007-05-22 | 2013-11-21 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
-
2009
- 2009-11-18 US US12/621,109 patent/US8124766B2/en not_active Expired - Fee Related
- 2009-11-18 JP JP2011539569A patent/JP2012510515A/ja not_active Withdrawn
- 2009-11-18 AU AU2009322774A patent/AU2009322774A1/en not_active Abandoned
- 2009-11-18 WO PCT/US2009/064971 patent/WO2010065310A1/en not_active Ceased
- 2009-11-18 CA CA2744152A patent/CA2744152A1/en not_active Abandoned
- 2009-11-18 CN CN2009801482136A patent/CN102239165A/zh active Pending
- 2009-11-18 EP EP09830855A patent/EP2367817A4/en not_active Withdrawn
-
2011
- 2011-05-16 IL IL212916A patent/IL212916A0/en unknown
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