JP2007538011A5 - - Google Patents
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- JP2007538011A5 JP2007538011A5 JP2007511654A JP2007511654A JP2007538011A5 JP 2007538011 A5 JP2007538011 A5 JP 2007538011A5 JP 2007511654 A JP2007511654 A JP 2007511654A JP 2007511654 A JP2007511654 A JP 2007511654A JP 2007538011 A5 JP2007538011 A5 JP 2007538011A5
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- diazabicyclo
- alkyl
- ylcarbonyl
- substituted
- 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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- 125000004432 carbon atom Chemical group C* 0.000 claims 211
- 125000000217 alkyl group Chemical group 0.000 claims 121
- 229910005965 SO 2 Inorganic materials 0.000 claims 106
- 150000001875 compounds Chemical class 0.000 claims 73
- -1 Cyano, Hydroxyl Chemical group 0.000 claims 65
- 229910052794 bromium Inorganic materials 0.000 claims 57
- 229910052801 chlorine Inorganic materials 0.000 claims 57
- 229910052740 iodine Inorganic materials 0.000 claims 57
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 56
- 229910052731 fluorine Inorganic materials 0.000 claims 56
- 125000003545 alkoxy group Chemical group 0.000 claims 51
- 125000004663 dialkyl amino group Chemical group 0.000 claims 40
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 150000002367 halogens Chemical class 0.000 claims 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 239000000203 mixture Substances 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000004043 oxo group Chemical group O=* 0.000 claims 22
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 12
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 238000011282 treatment Methods 0.000 claims 11
- 150000001350 alkyl halides Chemical class 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 8
- 125000006413 ring segment Chemical group 0.000 claims 8
- AODOOQSKPNKDGP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CS1 AODOOQSKPNKDGP-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- NNYZNICVOLLXNV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-methoxy-1,2-benzothiazol-3-yl)methanone Chemical compound N=1SC2=CC(OC)=CC=C2C=1C(=O)N1CCN2CCC1CC2 NNYZNICVOLLXNV-UHFFFAOYSA-N 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 5
- FGRJCFQXMBBUHZ-UHFFFAOYSA-N (6-cyclopropyl-1,2-benzothiazol-3-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NSC1=CC=2C1CC1 FGRJCFQXMBBUHZ-UHFFFAOYSA-N 0.000 claims 4
- YRXUTSNTOGXCAG-UHFFFAOYSA-N 1,2-benzothiazol-3-yl(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound N=1SC2=CC=CC=C2C=1C(=O)N1CCN2CCC1CC2 YRXUTSNTOGXCAG-UHFFFAOYSA-N 0.000 claims 4
- RPUVSGFFSWSZSP-UHFFFAOYSA-N 1,2-benzoxazol-3-yl(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound N=1OC2=CC=CC=C2C=1C(=O)N1CCN2CCC1CC2 RPUVSGFFSWSZSP-UHFFFAOYSA-N 0.000 claims 4
- BPQJXXAKRZXHNG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl(1h-indazol-4-yl)methanone Chemical compound C=1C=CC=2NN=CC=2C=1C(=O)N1CCN2CCC1CC2 BPQJXXAKRZXHNG-UHFFFAOYSA-N 0.000 claims 4
- WFYGCMBOSHFWFP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-ethoxy-1,2-benzothiazol-3-yl)methanone Chemical compound N=1SC2=CC(OCC)=CC=C2C=1C(=O)N1CCN2CCC1CC2 WFYGCMBOSHFWFP-UHFFFAOYSA-N 0.000 claims 4
- KEKCXZWFFSZCOB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(7-methoxy-1,2-benzothiazol-3-yl)methanone Chemical compound N=1SC=2C(OC)=CC=CC=2C=1C(=O)N1CCN2CCC1CC2 KEKCXZWFFSZCOB-UHFFFAOYSA-N 0.000 claims 4
- WCMSQISELPQCRY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(3,6-dihydro-2h-pyran-4-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2C1=CCOCC1 WCMSQISELPQCRY-UHFFFAOYSA-N 0.000 claims 4
- WNESJIBHOMFZCK-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(4-methyl-1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound CC1=CSC(C=2C=C3C(C(=O)N4C5CCN(CC5)CC4)=NNC3=CC=2)=N1 WNESJIBHOMFZCK-UHFFFAOYSA-N 0.000 claims 4
- DTPPKDHXUUFAIV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(5-methyl-1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound S1C(C)=CN=C1C1=CC=C(NN=C2C(=O)N3C4CCN(CC4)CC3)C2=C1 DTPPKDHXUUFAIV-UHFFFAOYSA-N 0.000 claims 4
- CSTWCHMJLKAATQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(oxan-4-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2C1CCOCC1 CSTWCHMJLKAATQ-UHFFFAOYSA-N 0.000 claims 4
- SZTYPRKMELXJFS-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(trifluoromethoxy)-1h-indazol-3-yl]methanone Chemical compound C12=CC(OC(F)(F)F)=CC=C2NN=C1C(=O)N1CCN2CCC1CC2 SZTYPRKMELXJFS-UHFFFAOYSA-N 0.000 claims 4
- PYWOMPMOIRJAPM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(1,3-oxazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CO1 PYWOMPMOIRJAPM-UHFFFAOYSA-N 0.000 claims 4
- CEBJANFQKVFHBE-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CS1 CEBJANFQKVFHBE-UHFFFAOYSA-N 0.000 claims 4
- KANQNVPNTJPKED-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(4-methyl-1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound CC1=CSC(C=2C=C3NN=C(C3=CC=2)C(=O)N2C3CCN(CC3)CC2)=N1 KANQNVPNTJPKED-UHFFFAOYSA-N 0.000 claims 4
- LBDTVZWQTUGWFQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(5-methyl-1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound S1C(C)=CN=C1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 LBDTVZWQTUGWFQ-UHFFFAOYSA-N 0.000 claims 4
- ZKMAUIPCWKPPMA-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(oxan-4-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2C1CCOCC1 ZKMAUIPCWKPPMA-UHFFFAOYSA-N 0.000 claims 4
- COMJGIONTGURMB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(trifluoromethoxy)-1,2-benzothiazol-3-yl]methanone Chemical compound N=1SC2=CC(OC(F)(F)F)=CC=C2C=1C(=O)N1CCN2CCC1CC2 COMJGIONTGURMB-UHFFFAOYSA-N 0.000 claims 4
- NWQFDFPTWNATRN-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(trifluoromethoxy)-1h-indazol-3-yl]methanone Chemical compound N=1NC2=CC(OC(F)(F)F)=CC=C2C=1C(=O)N1CCN2CCC1CC2 NWQFDFPTWNATRN-UHFFFAOYSA-N 0.000 claims 4
- BYUQALRPZHQOMF-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-6-methoxychromen-4-one Chemical compound O=C1C2=CC(OC)=CC=C2OC=C1CN1CCN2CCC1CC2 BYUQALRPZHQOMF-UHFFFAOYSA-N 0.000 claims 4
- 230000004913 activation Effects 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 230000007074 memory dysfunction Effects 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- AVMFLZIPPMJCNT-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-5-methoxychromen-4-one Chemical compound O=C1C=2C(OC)=CC=CC=2OC=C1CN1CCN2CCC1CC2 AVMFLZIPPMJCNT-UHFFFAOYSA-N 0.000 claims 3
- UUTOCJOHQATTTQ-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC=C(C2=O)C=1OC=C2CN1CCN2CCC1CC2 UUTOCJOHQATTTQ-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 201000004810 Vascular dementia Diseases 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 230000032683 aging Effects 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000004064 dysfunction Effects 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 206010027175 memory impairment Diseases 0.000 claims 3
- 208000027061 mild cognitive impairment Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 230000004936 stimulating effect Effects 0.000 claims 3
- 230000000638 stimulation Effects 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- QMOQIVAZETZFED-ACCUITESSA-N (3e)-3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethylidene)-5-methoxychromen-4-one Chemical compound O=C1C=2C(OC)=CC=CC=2OC\C1=C/N1CCN2CCC1CC2 QMOQIVAZETZFED-ACCUITESSA-N 0.000 claims 2
- QWLLJTBPGFFLMY-ACCUITESSA-N (3e)-3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethylidene)-6-methoxychromen-4-one Chemical compound O=C1C2=CC(OC)=CC=C2OC\C1=C/N1CCN2CCC1CC2 QWLLJTBPGFFLMY-ACCUITESSA-N 0.000 claims 2
- ZDXQIWPYXVYTHD-ACCUITESSA-N (3e)-3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethylidene)-7-methoxychromen-4-one Chemical compound C1OC2=CC(OC)=CC=C2C(=O)\C1=C\N1CCN2CCC1CC2 ZDXQIWPYXVYTHD-ACCUITESSA-N 0.000 claims 2
- DDAPYINAKKHJLC-UHFFFAOYSA-N (6-bromo-1,2-benzothiazol-3-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound N=1SC2=CC(Br)=CC=C2C=1C(=O)N1CCN2CCC1CC2 DDAPYINAKKHJLC-UHFFFAOYSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 2
- LNNJOENXHAEGRO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(1,3-oxazol-2-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CO1 LNNJOENXHAEGRO-UHFFFAOYSA-N 0.000 claims 2
- SEBNFUUMYPXTBI-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(difluoromethoxy)-1h-indazol-3-yl]methanone Chemical compound C12=CC(OC(F)F)=CC=C2NN=C1C(=O)N1CCN2CCC1CC2 SEBNFUUMYPXTBI-UHFFFAOYSA-N 0.000 claims 2
- RWCUXIYXZRHMQQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(oxan-4-yloxy)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2OC1CCOCC1 RWCUXIYXZRHMQQ-UHFFFAOYSA-N 0.000 claims 2
- YOSNUAVTCSGDDZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(3,6-dihydro-2h-pyran-4-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2C1=CCOCC1 YOSNUAVTCSGDDZ-UHFFFAOYSA-N 0.000 claims 2
- MTPZJIVGGBTVKG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(difluoromethoxy)-1h-indazol-3-yl]methanone Chemical compound N=1NC2=CC(OC(F)F)=CC=C2C=1C(=O)N1CCN2CCC1CC2 MTPZJIVGGBTVKG-UHFFFAOYSA-N 0.000 claims 2
- ZHASMQOOVFRFCQ-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonane-4-carbonyl)chromen-4-one Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C(=O)N1CCN2CCC1CC2 ZHASMQOOVFRFCQ-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- DRLIWCKHESTEFJ-UHFFFAOYSA-N [6-(cyclopropylmethoxy)-1,2-benzothiazol-3-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NSC1=CC=2OCC1CC1 DRLIWCKHESTEFJ-UHFFFAOYSA-N 0.000 claims 2
- 230000007000 age related cognitive decline Effects 0.000 claims 2
- 230000005540 biological transmission Effects 0.000 claims 2
- 230000001713 cholinergic effect Effects 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- AUMGOAPZEOFYNT-UHFFFAOYSA-N 1,3-benzothiazol-5-yl(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C=1C=C2SC=NC2=CC=1C(=O)N1CCN2CCC1CC2 AUMGOAPZEOFYNT-UHFFFAOYSA-N 0.000 claims 1
- MDRHONVJPBVFOF-UHFFFAOYSA-N 1,3-benzothiazol-6-yl(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C=1C=C2N=CSC2=CC=1C(=O)N1CCN2CCC1CC2 MDRHONVJPBVFOF-UHFFFAOYSA-N 0.000 claims 1
- ITAOYGYJHONWEY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)N1CCN2CCC1CC2 ITAOYGYJHONWEY-UHFFFAOYSA-N 0.000 claims 1
- MWNZYGCTYKNOGW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl(1h-indazol-6-yl)methanone Chemical compound C=1C=C2C=NNC2=CC=1C(=O)N1CCN2CCC1CC2 MWNZYGCTYKNOGW-UHFFFAOYSA-N 0.000 claims 1
- OVJSGHJLVRFCEB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(1,3-thiazol-2-yl)-1h-indazol-3-yl]methanone;hydrochloride Chemical compound Cl.C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2C1=NC=CS1 OVJSGHJLVRFCEB-UHFFFAOYSA-N 0.000 claims 1
- VSNNWIAGFYGKRM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(1,3-oxazol-2-yl)-1h-indazol-3-yl]methanone;hydrochloride Chemical compound Cl.C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CO1 VSNNWIAGFYGKRM-UHFFFAOYSA-N 0.000 claims 1
- UZKCXKGCVAZJRM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(3,6-dihydro-2h-pyran-4-yl)-1h-indazol-3-yl]methanone;hydrochloride Chemical compound Cl.C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2C1=CCOCC1 UZKCXKGCVAZJRM-UHFFFAOYSA-N 0.000 claims 1
- VTXJUEMYYUZZNS-UHFFFAOYSA-N 1-[3-(1,4-diazabicyclo[3.2.2]nonane-4-carbonyl)-1,2-benzothiazol-6-yl]-3-methylimidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(C(=NS2)C(=O)N3C4CCN(CC4)CC3)C2=C1 VTXJUEMYYUZZNS-UHFFFAOYSA-N 0.000 claims 1
- CDESTGLMGICAED-UHFFFAOYSA-N 1-[3-(1,4-diazabicyclo[3.2.2]nonane-4-carbonyl)-1,2-benzothiazol-6-yl]-3-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C(C)C)CCN1C1=CC=C(C(=NS2)C(=O)N3C4CCN(CC4)CC3)C2=C1 CDESTGLMGICAED-UHFFFAOYSA-N 0.000 claims 1
- JTPZTKBRUCILQD-UHFFFAOYSA-N 1-methylimidazolidin-2-one Chemical compound CN1CCNC1=O JTPZTKBRUCILQD-UHFFFAOYSA-N 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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| CN114230565B (zh) * | 2020-09-09 | 2023-10-27 | 成都奥睿药业有限公司 | 5-取代吲哚3-酰胺衍生物及其制备方法和用途 |
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-
2005
- 2005-05-06 JP JP2007511654A patent/JP2007538011A/ja active Pending
- 2005-05-06 US US11/123,219 patent/US7632831B2/en not_active Expired - Fee Related
- 2005-05-06 EP EP05747486A patent/EP1745046B1/en not_active Expired - Lifetime
- 2005-05-06 KR KR1020067025685A patent/KR20070015607A/ko not_active Ceased
- 2005-05-06 AU AU2005243147A patent/AU2005243147A1/en not_active Abandoned
- 2005-05-06 NZ NZ551712A patent/NZ551712A/en unknown
- 2005-05-06 AT AT05747486T patent/ATE505470T1/de active
- 2005-05-06 WO PCT/US2005/015937 patent/WO2005111038A2/en not_active Ceased
- 2005-05-06 DE DE602005027452T patent/DE602005027452D1/de not_active Expired - Lifetime
- 2005-05-06 MX MXPA06012880A patent/MXPA06012880A/es active IP Right Grant
- 2005-05-06 RU RU2006143153/04A patent/RU2386633C2/ru not_active IP Right Cessation
- 2005-05-06 BR BRPI0510212-0A patent/BRPI0510212A/pt not_active IP Right Cessation
- 2005-05-06 CA CA002565984A patent/CA2565984A1/en not_active Abandoned
-
2006
- 2006-11-02 IL IL179033A patent/IL179033A0/en unknown
- 2006-12-06 NO NO20065622A patent/NO20065622L/no not_active Application Discontinuation
-
2009
- 2009-09-03 US US12/553,538 patent/US20090325939A1/en not_active Abandoned
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