TW200904799A - Trans-3-aza-bicyclo[3.1.0]hexane derivatives - Google Patents

Info

Publication number

TW200904799A

TW200904799A TW097128494A TW97128494A TW200904799A TW 200904799 A TW200904799 A TW 200904799A TW 097128494 A TW097128494 A TW 097128494A TW 97128494 A TW97128494 A TW 97128494A TW 200904799 A TW200904799 A TW 200904799A

Authority

TW

Taiwan

Prior art keywords

bicyclo

aza

methyl

carboxylic acid

hex

Prior art date

2007-07-27

Links

• Espacenet
• Global Dossier
• Discuss

• HGWUUOXXAIISDB-WHFBIAKZSA-N (1R,5R)-3-azabicyclo[3.1.0]hexane Chemical class C1NC[C@@H]2C[C@H]21 HGWUUOXXAIISDB-WHFBIAKZSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 95
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 239000003814 drug Substances 0.000 claims abstract description 12
• -1 trimethyl Chemical group 0.000 claims description 346
• 239000002253 acid Substances 0.000 claims description 215
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 87
• 125000000217 alkyl group Chemical group 0.000 claims description 84
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 81
• 125000001424 substituent group Chemical group 0.000 claims description 81
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 71
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 57
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 50
• 125000003118 aryl group Chemical group 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 44
• 125000003545 alkoxy group Chemical group 0.000 claims description 42
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 42
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
• 125000005605 benzo group Chemical group 0.000 claims description 35
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 34
• 150000001412 amines Chemical class 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 239000007789 gas Substances 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• VFMGOJUUTAPPDA-UHFFFAOYSA-N 2-ethyl-5-methylpyrazole-3-carboxylic acid Chemical compound CCN1N=C(C)C=C1C(O)=O VFMGOJUUTAPPDA-UHFFFAOYSA-N 0.000 claims description 24
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 20
• 239000011734 sodium Substances 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 235000001968 nicotinic acid Nutrition 0.000 claims description 18
• 239000011664 nicotinic acid Substances 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 17
• 150000002576 ketones Chemical class 0.000 claims description 17
• WFAPIZKLEVLUMX-UHFFFAOYSA-N 1-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1C=CO2 WFAPIZKLEVLUMX-UHFFFAOYSA-N 0.000 claims description 16
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 claims description 16
• YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 claims description 15
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 15
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 229910052708 sodium Inorganic materials 0.000 claims description 12
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 11
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 10
• CHDSHBWEGSCEDX-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1CCO2 CHDSHBWEGSCEDX-UHFFFAOYSA-N 0.000 claims description 10
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
• 150000002923 oximes Chemical class 0.000 claims description 10
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
• 210000003296 saliva Anatomy 0.000 claims description 9
• QCGMEWVZBGQOFN-UHFFFAOYSA-N 1,3-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CO1 QCGMEWVZBGQOFN-UHFFFAOYSA-N 0.000 claims description 8
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 8
• DKNFZZUEJPOIBQ-UHFFFAOYSA-N C(C)N1N=C(C=C1C(=O)O)S Chemical compound C(C)N1N=C(C=C1C(=O)O)S DKNFZZUEJPOIBQ-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 208000019116 sleep disease Diseases 0.000 claims description 8
• 208000011580 syndromic disease Diseases 0.000 claims description 8
• AVVACPBRCFXZMR-UHFFFAOYSA-N 2,2-dimethyl-3h-1-benzofuran-7-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2OC(C)(C)CC2=C1 AVVACPBRCFXZMR-UHFFFAOYSA-N 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 239000000796 flavoring agent Substances 0.000 claims description 7
• IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 claims description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
• 230000007958 sleep Effects 0.000 claims description 7
• HVRCLXXJIQTXHC-UHFFFAOYSA-N 1-methylindole-3-carboxylic acid Chemical compound C1=CC=C2N(C)C=C(C(O)=O)C2=C1 HVRCLXXJIQTXHC-UHFFFAOYSA-N 0.000 claims description 6
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 6
• IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 6
• ZOPXUHDPGGHISS-UHFFFAOYSA-N 5-fluoro-1-methylindole-2-carboxylic acid Chemical compound FC1=CC=C2N(C)C(C(O)=O)=CC2=C1 ZOPXUHDPGGHISS-UHFFFAOYSA-N 0.000 claims description 6
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
• 239000004305 biphenyl Substances 0.000 claims description 6
• JHTQTAYWCUAENJ-UHFFFAOYSA-N 1,3-benzoxazole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1OC=N2 JHTQTAYWCUAENJ-UHFFFAOYSA-N 0.000 claims description 5
• YALJPBXSARRWTA-UHFFFAOYSA-N 1,3-dimethylpyrazole-4-carboxylic acid Chemical compound CC1=NN(C)C=C1C(O)=O YALJPBXSARRWTA-UHFFFAOYSA-N 0.000 claims description 5
• MFROEIZTMRFRFV-UHFFFAOYSA-N 2-methyl-1,3-benzoxazole-4-carboxylic acid Chemical compound C1=CC=C2OC(C)=NC2=C1C(O)=O MFROEIZTMRFRFV-UHFFFAOYSA-N 0.000 claims description 5
• KDPOFQJHFWJFCB-UHFFFAOYSA-N 2-methyl-1,3-benzoxazole-7-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2OC(C)=NC2=C1 KDPOFQJHFWJFCB-UHFFFAOYSA-N 0.000 claims description 5
• OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 claims description 5
• 208000010877 cognitive disease Diseases 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
• 238000011084 recovery Methods 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• ITEWRYWRNQCNHT-UHFFFAOYSA-N 4-methylfuro[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=CC2=C1C=C(C(O)=O)N2C ITEWRYWRNQCNHT-UHFFFAOYSA-N 0.000 claims description 4
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• 208000025966 Neurological disease Diseases 0.000 claims description 4
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 230000035622 drinking Effects 0.000 claims description 4
• 235000005686 eating Nutrition 0.000 claims description 4
• 230000007937 eating Effects 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 claims description 4
• 229910052707 ruthenium Inorganic materials 0.000 claims description 4
• 150000003573 thiols Chemical class 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
• XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 235000007586 terpenes Nutrition 0.000 claims description 3
• GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
• ZGDGZMOKXTUMEV-UHFFFAOYSA-N 2,1,3-benzothiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NSN=C12 ZGDGZMOKXTUMEV-UHFFFAOYSA-N 0.000 claims description 2
• NGPYWZBQSYAKKK-UHFFFAOYSA-N 2,1,3-benzoxadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NON=C12 NGPYWZBQSYAKKK-UHFFFAOYSA-N 0.000 claims description 2
• DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 claims description 2
• XBGXGCOLWCMVOI-UHFFFAOYSA-N 3-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBGXGCOLWCMVOI-UHFFFAOYSA-N 0.000 claims description 2
• OOUHKHKJVKRHPI-UHFFFAOYSA-N 7-chloro-2-methoxy-2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound ClC1=CC=C(C(O)=O)C2=C1OC(OC)C2 OOUHKHKJVKRHPI-UHFFFAOYSA-N 0.000 claims description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
• IJFZUDQTZIVOOI-UHFFFAOYSA-N C1=C(N(NC1=S)S)C(=O)O Chemical compound C1=C(N(NC1=S)S)C(=O)O IJFZUDQTZIVOOI-UHFFFAOYSA-N 0.000 claims description 2
• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 2
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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• FBKMPSHMRCDIHD-UHFFFAOYSA-N 2-ethyl-1H-pyrazole-5-thione Chemical compound CCn1ccc(=S)[nH]1 FBKMPSHMRCDIHD-UHFFFAOYSA-N 0.000 claims 2
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• DJFHTJUMVKJIQG-UHFFFAOYSA-N 1H-carbazole-1-carboxylic acid Chemical compound C1(C=CC=C2C3=CC=CC=C3N=C12)C(=O)O DJFHTJUMVKJIQG-UHFFFAOYSA-N 0.000 claims 1
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• VSTDRKAQOCCOLF-UHFFFAOYSA-N 2-chloro-1H-benzo[g]indole Chemical compound ClC=1NC2=C3C(=CC=C2C=1)C=CC=C3 VSTDRKAQOCCOLF-UHFFFAOYSA-N 0.000 claims 1
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