JP2010513393A5 - - Google Patents
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- JP2010513393A5 JP2010513393A5 JP2009542033A JP2009542033A JP2010513393A5 JP 2010513393 A5 JP2010513393 A5 JP 2010513393A5 JP 2009542033 A JP2009542033 A JP 2009542033A JP 2009542033 A JP2009542033 A JP 2009542033A JP 2010513393 A5 JP2010513393 A5 JP 2010513393A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- chlorophenyl
- pyrrolidinyl
- oxo
- phthalazinyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- NDXKEBLTUNOBOV-HXUWFJFHSA-N 3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]-n-ethylpropanamide Chemical compound CCNC(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 NDXKEBLTUNOBOV-HXUWFJFHSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- -1 (2R) -2-{[4-[(4-chlorophenyl) methyl] -1-oxopyrido [3,4-d] pyridazin-2 (1H) -yl] methyl} -1-pyrrolidinyl Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- VECKAPBFEODMSF-OAQYLSRUSA-N 3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]-n-ethyl-n-methylpropanamide Chemical compound CCN(C)C(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 VECKAPBFEODMSF-OAQYLSRUSA-N 0.000 claims 1
- JDIHBFWJHULKKO-LJQANCHMSA-N 3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]-n-methylpropanamide Chemical compound CNC(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JDIHBFWJHULKKO-LJQANCHMSA-N 0.000 claims 1
- MYWRTNYLYRSKNG-OAQYLSRUSA-N 3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]-n-propylpropanamide Chemical compound CCCNC(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MYWRTNYLYRSKNG-OAQYLSRUSA-N 0.000 claims 1
- WLYZNCAAPNKQIM-HXUWFJFHSA-N 3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]-n-ethyl-n-methylpropanamide Chemical compound CCN(C)C(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 WLYZNCAAPNKQIM-HXUWFJFHSA-N 0.000 claims 1
- JLDIINQMXPHQTO-HXUWFJFHSA-N 3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]-n-propylpropanamide Chemical compound CCCNC(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JLDIINQMXPHQTO-HXUWFJFHSA-N 0.000 claims 1
- QQFMHKBLTGTYDF-UHFFFAOYSA-N 3-[4-[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]piperidin-1-yl]-n-ethylpropanamide Chemical compound C1CN(CCC(=O)NCC)CCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 QQFMHKBLTGTYDF-UHFFFAOYSA-N 0.000 claims 1
- NZEFYLGMSWSUDH-JOCHJYFZSA-N 4-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]-n-propylbutanamide Chemical compound CCCNC(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 NZEFYLGMSWSUDH-JOCHJYFZSA-N 0.000 claims 1
- PZNIGNRZGFKNJS-JOCHJYFZSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-oxo-2-piperidin-1-ylethyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CC(=O)N2CCCCC2)CCC1 PZNIGNRZGFKNJS-JOCHJYFZSA-N 0.000 claims 1
- PSFDLUAPWJHDRQ-JOCHJYFZSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-morpholin-4-yl-3-oxopropyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCC(=O)N2CCOCC2)CCC1 PSFDLUAPWJHDRQ-JOCHJYFZSA-N 0.000 claims 1
- VMBMVCOIWROTNS-HSZRJFAPSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-oxo-3-piperidin-1-ylpropyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCC(=O)N2CCCCC2)CCC1 VMBMVCOIWROTNS-HSZRJFAPSA-N 0.000 claims 1
- WNOORGZBEQJEKX-JOCHJYFZSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-oxo-3-piperidin-1-ylpropyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CN=CC=C1C1=O)=NN1C[C@@H]1N(CCC(=O)N2CCCCC2)CCC1 WNOORGZBEQJEKX-JOCHJYFZSA-N 0.000 claims 1
- MEDLKULZWMDEKL-VGAJERRHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(2-oxopiperidin-3-yl)methyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CC2C(NCCC2)=O)CCC1 MEDLKULZWMDEKL-VGAJERRHSA-N 0.000 claims 1
- JJWUMKIRQORUCY-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(3-propyl-1,2,4-oxadiazol-5-yl)methyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCCC1=NOC(CN2[C@H](CCC2)CN2C(C3=CC=CC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 JJWUMKIRQORUCY-HXUWFJFHSA-N 0.000 claims 1
- XMFXCLLSLWHJEZ-LJQANCHMSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-(3-ethyl-1,2,4-oxadiazol-5-yl)ethyl]pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCC1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=NC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 XMFXCLLSLWHJEZ-LJQANCHMSA-N 0.000 claims 1
- PQRFKJZYLKNASS-LJQANCHMSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CC1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=NC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 PQRFKJZYLKNASS-LJQANCHMSA-N 0.000 claims 1
- CYNLVWYGBRLDEK-OAQYLSRUSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)ethyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CC(C)C1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=CC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 CYNLVWYGBRLDEK-OAQYLSRUSA-N 0.000 claims 1
- GSHARYOMNHXZFI-OAQYLSRUSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-(3-propyl-1,2,4-oxadiazol-5-yl)ethyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCCC1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=CC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 GSHARYOMNHXZFI-OAQYLSRUSA-N 0.000 claims 1
- GQRSFSPUUMFUIL-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-(3-propyl-1,2,4-oxadiazol-5-yl)ethyl]pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCCC1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=NC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 GQRSFSPUUMFUIL-HXUWFJFHSA-N 0.000 claims 1
- YNHAJSIGCYHJDY-OAQYLSRUSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]ethyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound COCCC1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=CC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 YNHAJSIGCYHJDY-OAQYLSRUSA-N 0.000 claims 1
- VAQXQDOONVLQOZ-LJQANCHMSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[2-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]ethyl]pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound COCC1=NOC(CCN2[C@H](CCC2)CN2C(C3=CC=NC=C3C(CC=3C=CC(Cl)=CC=3)=N2)=O)=N1 VAQXQDOONVLQOZ-LJQANCHMSA-N 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- XUOSGOQBPBKQSX-UHFFFAOYSA-N n-(2,2-dimethylpropyl)acetamide Chemical compound CC(=O)NCC(C)(C)C XUOSGOQBPBKQSX-UHFFFAOYSA-N 0.000 claims 1
- PCTJWGABKFYNEZ-LJQANCHMSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-2,2,2-trifluoro-n-methylacetamide Chemical compound FC(F)(F)C(=O)N(C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 PCTJWGABKFYNEZ-LJQANCHMSA-N 0.000 claims 1
- GBSCUBRYBGFQFP-GOSISDBHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 GBSCUBRYBGFQFP-GOSISDBHSA-N 0.000 claims 1
- NQTWQWOEKLOBAF-OAQYLSRUSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 NQTWQWOEKLOBAF-OAQYLSRUSA-N 0.000 claims 1
- DCYQIGVQTQRWNC-LJQANCHMSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-3,3,3-trifluoropropanamide Chemical compound FC(F)(F)CC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 DCYQIGVQTQRWNC-LJQANCHMSA-N 0.000 claims 1
- PQIAGKTUPBWYLN-OAQYLSRUSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-3-hydroxy-2,2-dimethylpropanamide Chemical compound OCC(C)(C)C(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 PQIAGKTUPBWYLN-OAQYLSRUSA-N 0.000 claims 1
- JJKMOFKIYHXREY-JOCHJYFZSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-4-methoxybutanamide Chemical compound COCCCC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JJKMOFKIYHXREY-JOCHJYFZSA-N 0.000 claims 1
- VVYQHHROMNFSAO-OAQYLSRUSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]butanamide Chemical compound CCCC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 VVYQHHROMNFSAO-OAQYLSRUSA-N 0.000 claims 1
- CYYGASOTAKULED-XMMPIXPASA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]cyclohexanecarboxamide Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCNC(=O)C2CCCCC2)CCC1 CYYGASOTAKULED-XMMPIXPASA-N 0.000 claims 1
- PTVITZRFRXZZEA-HSZRJFAPSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]cyclopentanecarboxamide Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCNC(=O)C2CCCC2)CCC1 PTVITZRFRXZZEA-HSZRJFAPSA-N 0.000 claims 1
- AAGWAYIWKWJZAD-HSZRJFAPSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]oxane-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCNC(=O)C2CCOCC2)CCC1 AAGWAYIWKWJZAD-HSZRJFAPSA-N 0.000 claims 1
- ZXYGIZJEOXZXTM-LWMIZPGFSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]oxolane-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCNC(=O)C2COCC2)CCC1 ZXYGIZJEOXZXTM-LWMIZPGFSA-N 0.000 claims 1
- KGNWCYQCPGINGS-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]propanamide Chemical compound CCC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 KGNWCYQCPGINGS-HXUWFJFHSA-N 0.000 claims 1
- GBNPSWSBLLVCPP-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 GBNPSWSBLLVCPP-HXUWFJFHSA-N 0.000 claims 1
- GTCMLOYYRNAPNV-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 GTCMLOYYRNAPNV-HXUWFJFHSA-N 0.000 claims 1
- DUKSTJYLQMPEER-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]butanamide Chemical compound CCCC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 DUKSTJYLQMPEER-HXUWFJFHSA-N 0.000 claims 1
- AJBGJNBZNWLATB-LJQANCHMSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]propanamide Chemical compound CCC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 AJBGJNBZNWLATB-LJQANCHMSA-N 0.000 claims 1
- AIVQGEIVZVEKCZ-JOCHJYFZSA-N n-[3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]propyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 AIVQGEIVZVEKCZ-JOCHJYFZSA-N 0.000 claims 1
- VGFTVIBDPNBCFA-OAQYLSRUSA-N n-[3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]propyl]acetamide Chemical compound CC(=O)NCCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 VGFTVIBDPNBCFA-OAQYLSRUSA-N 0.000 claims 1
- JKUXSRYMCBMIKZ-OAQYLSRUSA-N n-[3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]propyl]propanamide Chemical compound CCC(=O)NCCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JKUXSRYMCBMIKZ-OAQYLSRUSA-N 0.000 claims 1
- SCPBDGVVEIOOMK-OAQYLSRUSA-N n-[3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]propyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 SCPBDGVVEIOOMK-OAQYLSRUSA-N 0.000 claims 1
- IAEBTHHFINNWGS-OAQYLSRUSA-N n-[3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]propyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 IAEBTHHFINNWGS-OAQYLSRUSA-N 0.000 claims 1
- PPTRQXLVZRNQLJ-HXUWFJFHSA-N n-[3-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]propyl]propanamide Chemical compound CCC(=O)NCCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 PPTRQXLVZRNQLJ-HXUWFJFHSA-N 0.000 claims 1
- ACYFWRHALJTSCF-UHFFFAOYSA-N n-tert-butylacetamide Chemical compound CC(=O)NC(C)(C)C ACYFWRHALJTSCF-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- KHDGSULFSVLOPM-UHFFFAOYSA-N oxane-3-carboxamide Chemical compound NC(=O)C1CCCOC1 KHDGSULFSVLOPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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| US87087506P | 2006-12-20 | 2006-12-20 | |
| US97844707P | 2007-10-09 | 2007-10-09 | |
| US99122707P | 2007-11-30 | 2007-11-30 | |
| PCT/EP2007/064140 WO2008074803A2 (en) | 2006-12-20 | 2007-12-18 | 4-benzyl-l ( 2h) -phthalazinones as h1 receptor antagonists |
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| JP2010513393A JP2010513393A (ja) | 2010-04-30 |
| JP2010513393A5 true JP2010513393A5 (https=) | 2011-02-03 |
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| US (1) | US20100184770A1 (https=) |
| EP (1) | EP2091538B1 (https=) |
| JP (1) | JP2010513393A (https=) |
| AR (1) | AR064424A1 (https=) |
| AT (1) | ATE459358T1 (https=) |
| DE (1) | DE602007005167D1 (https=) |
| ES (1) | ES2341813T3 (https=) |
| PE (1) | PE20081657A1 (https=) |
| TW (1) | TW200831493A (https=) |
| WO (1) | WO2008074803A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006115221A1 (ja) * | 2005-04-21 | 2006-11-02 | Nippon Shinyaku Co., Ltd. | フタラジノン誘導体及びその医薬 |
| US8466150B2 (en) * | 2006-12-28 | 2013-06-18 | Abbott Laboratories | Inhibitors of poly(ADP-ribose)polymerase |
| DK2120579T3 (da) * | 2006-12-28 | 2014-02-03 | Abbvie Inc | Inhibitorer af poly(ADP-ripose)polymerase |
| ES2369320T3 (es) * | 2007-10-11 | 2011-11-29 | Glaxo Group Limited | Compuestos de ftalazina y pirido(3,4-d)piridazina como antagonistas del receptor h1. |
| WO2009150101A1 (en) * | 2008-06-09 | 2009-12-17 | Glaxo Group Limited | Pharmaceutical compositions comprising n-[2-((2r)-2-{[4-[(4-chlorophenyl)methyl]-l-oxo-2(ih)-phthalaz inyl]methyl}-l- pyrrolidinyl)ethyl]-4-(methyloxy)butanamide |
| JP5529131B2 (ja) * | 2008-08-13 | 2014-06-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | キマーゼ阻害薬 |
| WO2012045729A1 (en) | 2010-10-05 | 2012-04-12 | Glaxo Group Limited | Imidazo [1, 2 -a] pyridine and pyrazolo [1, 5 -a] pyridine derivatives as trpv1 antagonists |
| WO2012072512A1 (en) | 2010-11-29 | 2012-06-07 | Glaxo Group Limited | N-cyclobutyl-imidazopyridine or -pyrazolopyridine carboxamides as trpv1 antagonists |
| JP2014510768A (ja) | 2011-04-11 | 2014-05-01 | グラクソ グループ リミテッド | Ｔｒｐｖ１アンタゴニストとしてのｎ−シクロブチルイミダゾピリジンメチルアミン |
| KR20240013792A (ko) * | 2021-05-27 | 2024-01-30 | 슈뢰딩거, 인크. | 헤테로시클릭 화합물 및 사용 방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3677322D1 (de) * | 1985-11-11 | 1991-03-07 | Asta Pharma Ag | 4-benzyl-1-(2h)-phthalazinon-derivate. |
| DE3634942A1 (de) * | 1985-11-11 | 1987-05-14 | Asta Werke Ag Chem Fab | Neue 4-benzyl-1-(2h)-phthalazinon-derivate |
| CZ199593A3 (en) * | 1992-10-02 | 1994-04-13 | Asta Medica Ag | Phthalazinone derivatives exhibiting anti-arrhythmic and analgesic activity and eliminating resistance to a plurality of medicaments (mdr) |
| EP0997474B1 (en) * | 1998-08-14 | 2003-10-29 | Pfizer Inc. | Antithrombotic agents |
| EE05386B1 (et) * | 2001-02-15 | 2011-02-15 | ALTANA�Pharma�AG | Ftalasinoon-piperidinoderivaadid,ÁnendeÁkasutamineÁjaÁravim |
| TWI347845B (en) * | 2002-03-06 | 2011-09-01 | Nycomed Gmbh | Pharmaceutical compositions,combinations,and kits for the treatment of respiratory diseases and use of the same |
| WO2004082682A1 (en) * | 2003-03-18 | 2004-09-30 | Merck & Co. Inc. | Amino cyclobutylamide modulators of chemokine receptor activity |
| EP1642898B1 (en) * | 2003-06-27 | 2013-03-27 | Msd K.K. | Heteroaryloxy nitrogenous saturated heterocyclic derivative |
| WO2006115221A1 (ja) * | 2005-04-21 | 2006-11-02 | Nippon Shinyaku Co., Ltd. | フタラジノン誘導体及びその医薬 |
| EA200801996A1 (ru) * | 2006-04-20 | 2009-04-28 | Глаксо Груп Лимитед | 2-замещенные производные 4-бензилфталазинонов в качестве гистаминовых h1- и h3-антагонистов |
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2007
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- 2007-12-18 TW TW096148520A patent/TW200831493A/zh unknown
- 2007-12-18 ES ES07857765T patent/ES2341813T3/es active Active
- 2007-12-18 WO PCT/EP2007/064140 patent/WO2008074803A2/en not_active Ceased
- 2007-12-18 DE DE602007005167T patent/DE602007005167D1/de active Active
- 2007-12-18 US US12/065,775 patent/US20100184770A1/en not_active Abandoned
- 2007-12-18 JP JP2009542033A patent/JP2010513393A/ja active Pending
- 2007-12-18 AR ARP070105701A patent/AR064424A1/es unknown
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2008
- 2008-01-02 PE PE2008000040A patent/PE20081657A1/es not_active Application Discontinuation
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