JP2005537313A5 - - Google Patents
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- JP2005537313A5 JP2005537313A5 JP2004530142A JP2004530142A JP2005537313A5 JP 2005537313 A5 JP2005537313 A5 JP 2005537313A5 JP 2004530142 A JP2004530142 A JP 2004530142A JP 2004530142 A JP2004530142 A JP 2004530142A JP 2005537313 A5 JP2005537313 A5 JP 2005537313A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- methyl
- phenyl
- hydrogen
- 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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- -1 cyano, hydroxy Chemical group 0.000 claims 250
- 229910052739 hydrogen Inorganic materials 0.000 claims 60
- 239000001257 hydrogen Substances 0.000 claims 60
- 150000002431 hydrogen Chemical group 0.000 claims 48
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 150000002367 halogens Chemical group 0.000 claims 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 24
- 229910052757 nitrogen Inorganic materials 0.000 claims 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 16
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 12
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 10
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 6
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 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 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004544 purin-8-yl group Chemical group N1=CN=C2N=C(NC2=C1)* 0.000 claims 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 3
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical group OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- ZEVNGXMSXKCTGA-PQUUEDNTSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-(3,4,4a,5-tetrahydro-1H-isoquinoline-2-carboximidoyl)benzamide Chemical compound C1N(CCC2CC=CC=C12)C(=N)NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O ZEVNGXMSXKCTGA-PQUUEDNTSA-N 0.000 claims 1
- MZIOFBWJQAQWBK-DNQXCXABSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-(3,5-dimethylpyrazole-1-carboximidoyl)benzamide Chemical compound CC1=NN(C(=C1)C)C(=N)NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O MZIOFBWJQAQWBK-DNQXCXABSA-N 0.000 claims 1
- PTUONTLZUVQGNT-JWQCQUIFSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-(4-acetylpiperazine-1-carboximidoyl)benzamide Chemical compound C(C)(=O)N1CCN(CC1)C(N)=NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O PTUONTLZUVQGNT-JWQCQUIFSA-N 0.000 claims 1
- PXCBFHNABYEDMU-DHIUTWEWSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino(thiomorpholin-4-yl)methylidene]benzamide Chemical compound CCOc1cc2[C@H]3CN(C)CC[C@H]3N=C(c3ccc(cc3)C(=O)N=C(N)N3CCSCC3)c2cc1OC PXCBFHNABYEDMU-DHIUTWEWSA-N 0.000 claims 1
- ZSYZVBSWYMMVEL-LOYHVIPDSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino-(4-benzylpiperazin-1-yl)methylidene]benzamide Chemical compound NC(N1CCN(CC1)CC1=CC=CC=C1)=NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O ZSYZVBSWYMMVEL-LOYHVIPDSA-N 0.000 claims 1
- AUPZCBBRPGYOAX-FIRIVFDPSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino-(4-benzylpiperidin-1-yl)methylidene]benzamide Chemical compound CCOc1cc2[C@H]3CN(C)CC[C@H]3N=C(c3ccc(cc3)C(=O)N=C(N)N3CCC(Cc4ccccc4)CC3)c2cc1OC AUPZCBBRPGYOAX-FIRIVFDPSA-N 0.000 claims 1
- COEFGZZFDBPVFM-FQLXRVMXSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino-(4-cyclohexylpiperazin-1-yl)methylidene]benzamide Chemical compound NC(N1CCN(CC1)C1CCCCC1)=NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O COEFGZZFDBPVFM-FQLXRVMXSA-N 0.000 claims 1
- NMCVBHGCGQCGTA-FQLXRVMXSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino-(4-phenylpiperazin-1-yl)methylidene]benzamide Chemical compound NC(N1CCN(CC1)C1=CC=CC=C1)=NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O NMCVBHGCGQCGTA-FQLXRVMXSA-N 0.000 claims 1
- FQXQCGJTGJJWDJ-VSGBNLITSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino-[4-(2-methoxyphenyl)piperazin-1-yl]methylidene]benzamide Chemical compound CCOc1cc2[C@H]3CN(C)CC[C@H]3N=C(c3ccc(cc3)C(=O)N=C(N)N3CCN(CC3)c3ccccc3OC)c2cc1OC FQXQCGJTGJJWDJ-VSGBNLITSA-N 0.000 claims 1
- BOWWBAUOPMWYBN-KAYWLYCHSA-N 4-[(4aR,10bS)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-[amino-[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]methylidene]benzamide Chemical compound NC(N1CCN(CC1)CCOCCO)=NC(C1=CC=C(C=C1)C1=N[C@@H]2CCN(C[C@@H]2C2=C1C=C(C(=C2)OCC)OC)C)=O BOWWBAUOPMWYBN-KAYWLYCHSA-N 0.000 claims 1
- BLOXCQJLLFAOPS-FGZHOGPDSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[(e)-n'-(4-methyl-1,3-thiazol-2-yl)carbamimidoyl]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)N\C(N)=N\C1=NC(C)=CS1 BLOXCQJLLFAOPS-FGZHOGPDSA-N 0.000 claims 1
- IQJVESWCXAEULU-FIRIVFDPSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[[4-(4-acetylphenyl)piperazin-1-yl]-aminomethylidene]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)N=C(N)N(CC1)CCN1C1=CC=C(C(C)=O)C=C1 IQJVESWCXAEULU-FIRIVFDPSA-N 0.000 claims 1
- KBQIZRVBKBVLBH-JWQCQUIFSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino(anilino)methylidene]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)N=C(N)NC1=CC=CC=C1 KBQIZRVBKBVLBH-JWQCQUIFSA-N 0.000 claims 1
- OSDITUJPDREPII-CLJLJLNGSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino(azocan-1-yl)methylidene]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)N=C(N)N1CCCCCCC1 OSDITUJPDREPII-CLJLJLNGSA-N 0.000 claims 1
- DUBIPMHMELWMDP-DHIUTWEWSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino-(1h-benzimidazol-2-ylamino)methylidene]benzamide Chemical compound C1=CC=C2NC(NC(N)=NC(=O)C3=CC=C(C=C3)C3=N[C@@H]4CCN(C)C[C@@H]4C=4C=C(C(=CC=43)OC)OCC)=NC2=C1 DUBIPMHMELWMDP-DHIUTWEWSA-N 0.000 claims 1
- AUVVMOHYFDVDJQ-VSGBNLITSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)methylidene]benzamide Chemical compound C1CC2=CC(OC)=C(OC)C=C2CN1C(N)=NC(=O)C(C=C1)=CC=C1C1=N[C@@H]2CCN(C)C[C@@H]2C2=C1C=C(OC)C(OCC)=C2 AUVVMOHYFDVDJQ-VSGBNLITSA-N 0.000 claims 1
- KYVKZRRUECDXCK-WOJBJXKFSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino-(cyanoamino)methylidene]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N=C(N)NC#N)C=C1 KYVKZRRUECDXCK-WOJBJXKFSA-N 0.000 claims 1
- NYFHYIHORPMRGI-XRKRLSELSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino-(naphthalen-1-ylamino)methylidene]benzamide Chemical compound C1=CC=C2C(NC(N)=NC(=O)C3=CC=C(C=C3)C3=N[C@@H]4CCN(C)C[C@@H]4C=4C=C(C(=CC=43)OC)OCC)=CC=CC2=C1 NYFHYIHORPMRGI-XRKRLSELSA-N 0.000 claims 1
- ASFYKLUBNAMNGE-FQLXRVMXSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]methylidene]benzamide Chemical compound C1=C2OCOC2=CC(CN2CCN(CC2)C(N)=NC(=O)C2=CC=C(C=C2)C2=N[C@@H]3CCN(C)C[C@@H]3C=3C=C(C(=CC=32)OC)OCC)=C1 ASFYKLUBNAMNGE-FQLXRVMXSA-N 0.000 claims 1
- UKAOXXMANKNUNB-FQLXRVMXSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[amino-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methylidene]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)N=C(N)N(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 UKAOXXMANKNUNB-FQLXRVMXSA-N 0.000 claims 1
- NAMFPJABTYKEOL-JWQCQUIFSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[n'-(2-morpholin-4-ylethyl)carbamimidoyl]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)NC(N)=NCCN1CCOCC1 NAMFPJABTYKEOL-JWQCQUIFSA-N 0.000 claims 1
- PBNPSLCUNSIJEW-LNYUQPRGSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[n'-[(1r)-1-phenylethyl]carbamimidoyl]benzamide Chemical compound C1([C@@H](C)N=C(N)NC(=O)C2=CC=C(C=C2)C2=N[C@@H]3CCN(C)C[C@@H]3C=3C=C(C(=CC=32)OC)OCC)=CC=CC=C1 PBNPSLCUNSIJEW-LNYUQPRGSA-N 0.000 claims 1
- PBNPSLCUNSIJEW-MHBGZZOHSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[n'-[(1s)-1-phenylethyl]carbamimidoyl]benzamide Chemical compound C1([C@H](C)N=C(N)NC(=O)C2=CC=C(C=C2)C2=N[C@@H]3CCN(C)C[C@@H]3C=3C=C(C(=CC=32)OC)OCC)=CC=CC=C1 PBNPSLCUNSIJEW-MHBGZZOHSA-N 0.000 claims 1
- KYCGRWSNMVWCKF-CLJLJLNGSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n-[n'-[(3,4-dimethoxyphenyl)methyl]carbamimidoyl]benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)NC(N)=NCC1=CC=C(OC)C(OC)=C1 KYCGRWSNMVWCKF-CLJLJLNGSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical group FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02018529 | 2002-08-17 | ||
| PCT/EP2003/008996 WO2004018465A2 (en) | 2002-08-17 | 2003-08-13 | Benzonaphthyridines with pde 3/4 inhibiting activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005537313A JP2005537313A (ja) | 2005-12-08 |
| JP2005537313A5 true JP2005537313A5 (enExample) | 2006-10-05 |
Family
ID=31896838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004530142A Withdrawn JP2005537313A (ja) | 2002-08-17 | 2003-08-13 | 新規のベンゾナフチリジン |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20060113968A1 (enExample) |
| EP (1) | EP1581533A2 (enExample) |
| JP (1) | JP2005537313A (enExample) |
| AU (1) | AU2003263216A1 (enExample) |
| CA (1) | CA2495603A1 (enExample) |
| HR (1) | HRP20050227A2 (enExample) |
| IS (1) | IS7729A (enExample) |
| PL (1) | PL373598A1 (enExample) |
| RS (1) | RS20050117A (enExample) |
| WO (1) | WO2004018465A2 (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
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| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| ES2337083T3 (es) | 2005-03-02 | 2010-04-20 | Nycomed Gmbh | (2r,4ar,10br)-6-(2,6-dimetoxipiridin-3-il)-9-exoti-8-metoxi-1,2,3,4,4a,10b-hexahidrofenantridin-2-ol, sal de hc1. |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
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| EP2532677A1 (en) | 2005-10-21 | 2012-12-12 | Novartis AG | Human antibodies against il13 and therapeutic uses |
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| HRP20120494T1 (hr) | 2006-04-21 | 2012-08-31 | Novartis Ag | Derivati purina za uporabu kao agonista adenozin a2a receptora |
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| AU2007342223B2 (en) | 2007-01-10 | 2011-02-24 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
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| BRPI0820669A2 (pt) | 2007-12-10 | 2020-08-04 | Novartis Ag | compostos orgânicos |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
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| ES2396023T3 (es) | 2009-01-29 | 2013-02-18 | Novartis Ag | Bencimidazoles sustituidos para el tratamiento de astrocitomas |
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| BR112012003262A8 (pt) | 2009-08-12 | 2016-05-17 | Novartis Ag | compostos de hidrazona heterocíclica e seus usos para tratar câncer e inflamação |
| UA111579C2 (uk) | 2009-08-17 | 2016-05-25 | Інтеллікіне Ллк | ГЕТЕРОЦИКЛІЧНІ ПОХІДНІ 2-АМІНОБЕНЗО[d]ОКСАЗОЛУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ НА ЇХ ОСНОВІ ТА ЇХ ЗАСТОСУВАННЯ ДЛЯ ЛІКУВАННЯ ЗАХВОРЮВАННЯ, ПОВ'АНОГО З РІ3-КІНАЗОЮ |
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| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
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| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| WO2012107500A1 (en) | 2011-02-10 | 2012-08-16 | Novartis Ag | [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
| WO2012116237A2 (en) | 2011-02-23 | 2012-08-30 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| BR112013021638A2 (pt) | 2011-02-25 | 2016-08-02 | Irm Llc | "compostos inibidores de trk, seu uso e composições que os compreendem" |
| EP2549638A1 (de) * | 2011-07-19 | 2013-01-23 | AEG Power Solutions B.V. | Stromversorgungsanordnung für einen Reaktor zur Polysiliciumherstellung mit einem Frequenzumrichter |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| UY34329A (es) | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| JP6165733B2 (ja) | 2011-09-16 | 2017-07-19 | ノバルティス アーゲー | Ｎ−置換ヘテロシクリルカルボキサミド類 |
| CN103946221B (zh) | 2011-09-16 | 2016-08-03 | 诺华股份有限公司 | 用于治疗囊性纤维化的杂环化合物 |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| MX371119B (es) | 2012-04-03 | 2020-01-17 | Novartis Ag | Productos de combinacion con los inhibidores de cinasa de tirosina y su uso. |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| HK1219421A1 (zh) | 2013-03-15 | 2017-04-07 | 因特利凯有限责任公司 | 激酶抑制剂的组合及其用途 |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
| KR20160145780A (ko) | 2014-04-24 | 2016-12-20 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 아미노 피리딘 유도체 |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| AU2014391610B2 (en) | 2014-04-24 | 2018-01-25 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| US10195208B2 (en) | 2014-07-31 | 2019-02-05 | Novartis Ag | Combination therapy |
| WO2018069210A1 (en) | 2016-10-10 | 2018-04-19 | Takeda Gmbh | Tetrahydrofuro[3,4-c]isoquinolines as inhibitors of pde4 |
| US20200383960A1 (en) | 2019-06-10 | 2020-12-10 | Novartis Ag | Pyridine and Pyrazine derivative for the Treatment of CF, COPD, and Bronchiectasis |
| KR20220052934A (ko) | 2019-08-28 | 2022-04-28 | 노파르티스 아게 | 치환 1,3-페닐 헤테로아릴 유도체 및 질환 치료에서의 이의 용도 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9027055D0 (en) * | 1990-12-13 | 1991-02-06 | Sandoz Ltd | Organic compounds |
| DK0937074T3 (da) * | 1996-11-11 | 2003-06-23 | Altana Pharma Ag | Benzonaphthyridiner som bronkiale terapeutiske midler |
| SI0968211T1 (en) * | 1997-03-07 | 2004-02-29 | Altana Pharma Ag | Tetrazole derivatives |
| CA2330738A1 (en) * | 1998-05-05 | 1999-11-11 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel n-oxides of benzonaphthyridines |
| SI1109810T1 (en) * | 1998-08-31 | 2004-12-31 | Altana Pharma Ag | Benzonaphthyridine-n-oxides comprising a pde3 and pde4 inhibiting activity |
| AU2001239550A1 (en) * | 2000-03-23 | 2001-10-03 | Takeda Chemical Industries Ltd. | Furoisoquinoline derivatives, process for producing the same and use thereof |
| US6936622B2 (en) * | 2001-02-21 | 2005-08-30 | Altana Pharma Ag | 6-phenylbenzonaphthyridines |
-
2003
- 2003-08-13 AU AU2003263216A patent/AU2003263216A1/en not_active Abandoned
- 2003-08-13 HR HR20050227A patent/HRP20050227A2/hr not_active Application Discontinuation
- 2003-08-13 WO PCT/EP2003/008996 patent/WO2004018465A2/en not_active Ceased
- 2003-08-13 EP EP03792314A patent/EP1581533A2/en not_active Withdrawn
- 2003-08-13 RS YUP-2005/0117A patent/RS20050117A/sr unknown
- 2003-08-13 CA CA002495603A patent/CA2495603A1/en not_active Abandoned
- 2003-08-13 US US10/524,638 patent/US20060113968A1/en not_active Abandoned
- 2003-08-13 JP JP2004530142A patent/JP2005537313A/ja not_active Withdrawn
- 2003-08-13 PL PL03373598A patent/PL373598A1/xx not_active Application Discontinuation
-
2005
- 2005-03-08 IS IS7729A patent/IS7729A/is unknown
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