RU2386633C2 - 1h-индазолы, бензотиазолы, 1, 2-бензоизоксазолы, 1, 2-бензоизотиазолы и хромоны и их получение и применения - Google Patents
1h-индазолы, бензотиазолы, 1, 2-бензоизоксазолы, 1, 2-бензоизотиазолы и хромоны и их получение и применения Download PDFInfo
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- RU2386633C2 RU2386633C2 RU2006143153/04A RU2006143153A RU2386633C2 RU 2386633 C2 RU2386633 C2 RU 2386633C2 RU 2006143153/04 A RU2006143153/04 A RU 2006143153/04A RU 2006143153 A RU2006143153 A RU 2006143153A RU 2386633 C2 RU2386633 C2 RU 2386633C2
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- RU
- Russia
- Prior art keywords
- compound
- diazabicyclo
- ylcarbonyl
- indazole
- hydroformate
- Prior art date
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- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical class C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000004777 chromones Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 118
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 16
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims abstract 10
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 7
- 201000010099 disease Diseases 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- -1 tetrahydropyranyloxy Chemical group 0.000 claims abstract 5
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 230000004913 activation Effects 0.000 claims abstract 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 239000011737 fluorine Substances 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical group 0.000 claims abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 2
- 230000002950 deficient Effects 0.000 claims abstract 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 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 8
- 206010012289 Dementia Diseases 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 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 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
- 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 4
- 208000000044 Amnesia Diseases 0.000 claims 4
- 208000026139 Memory disease Diseases 0.000 claims 4
- 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 3
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 230000009225 memory damage Effects 0.000 claims 3
- 230000006984 memory degeneration Effects 0.000 claims 3
- 208000023060 memory loss Diseases 0.000 claims 3
- 208000027061 mild cognitive impairment Diseases 0.000 claims 3
- 230000002265 prevention Effects 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 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
- 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 2
- 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 2
- 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 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
- 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 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
- 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 2
- 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 2
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
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- 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
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
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| US62646904P | 2004-11-10 | 2004-11-10 | |
| US60/626,469 | 2004-11-10 | ||
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| US7582631B2 (en) * | 2004-01-14 | 2009-09-01 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| WO2007135122A1 (en) * | 2006-05-23 | 2007-11-29 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonane derivatives and their medical use |
| JP5160764B2 (ja) * | 2006-10-13 | 2013-03-13 | 全薬工業株式会社 | 特定の構造の複素環化合物を含む抗鬱剤、脳保護剤、アミロイドβ沈着抑制剤または老化抑制剤 |
| EP2121654A1 (en) * | 2007-01-10 | 2009-11-25 | Albany Molecular Research, Inc. | 5-pyridinone substituted indazoles |
| KR20100044225A (ko) * | 2007-07-21 | 2010-04-29 | 알바니 몰레큘라 리써치, 인크. | 5-피리디논 치환된 인다졸 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| CN101910170A (zh) * | 2007-10-22 | 2010-12-08 | 记忆药物公司 | 用于治疗疾病的烟碱性乙酰胆碱受体的(1,4-二氮杂双环[3.2.2]壬-6-烯-4-基)-杂环基-甲酮配体 |
| US8697722B2 (en) | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| FR2931677B1 (fr) * | 2008-06-02 | 2010-08-20 | Sanofi Aventis | Association d'un agoniste partiel des recepteurs nicotiniques et d'un inhibiteur d'acetylcholinesterase, composition la contenant et son utilisation dans le traitement des troubles cognitifs |
| EP2346833B1 (en) | 2008-10-13 | 2013-03-27 | F. Hoffmann-La Roche AG | Diazonium-free method to make an indazole intermediate in the synthesis of bicyclic 5-(trifluormethoxy)-1h-3-indazolecarboxylic acid amides |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| CA2787063C (en) | 2010-01-11 | 2018-11-27 | Astraea Therapeutics, Llc | Nicotinic acetylcholine receptor modulators |
| US20110172428A1 (en) | 2010-01-12 | 2011-07-14 | Shan-Ming Kuang | Methods for the preparation of indazole-3-carboxylic acid and n-(s)-1-azabicyclo[2.2.2]oct-3-yl-1h-indazole-3-carboxamide hydrochloride salt |
| CA2799154A1 (en) | 2010-05-12 | 2011-11-17 | Abbvie Inc. | Indazole inhibitors of kinase |
| US8242276B2 (en) | 2010-06-30 | 2012-08-14 | Hoffmann-La Roche Inc. | Methods for the preparation of N-(S)-1-azabicyclo[2.2.2]oct-3-yl-1H-indazole-3-carboxamide hydrochloride salt |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| ES2712211T3 (es) | 2013-06-20 | 2019-05-09 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas |
| US9783527B2 (en) * | 2014-09-16 | 2017-10-10 | Abbvie Inc. | Indazole ureas and method of use |
| WO2018102885A1 (en) * | 2016-12-09 | 2018-06-14 | Bionomics Limited | Modulators of nicotinic acetylcholine receptors and uses thereof |
| 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 |
| WO2022125377A1 (en) * | 2020-12-08 | 2022-06-16 | Disarm Therapeutics, Inc. | Benzopyrazole inhibitors of sarm1 |
| EP4441034A4 (en) * | 2021-11-30 | 2025-10-29 | Merck Sharp & Dohme Llc | USE OF FUSIONIZED PYRAZOLE UREA ANALOGUES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS |
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- 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
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2006
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Also Published As
| Publication number | Publication date |
|---|---|
| US20050272735A1 (en) | 2005-12-08 |
| AU2005243147A1 (en) | 2005-11-24 |
| BRPI0510212A (pt) | 2007-10-16 |
| JP2007538011A (ja) | 2007-12-27 |
| EP1745046B1 (en) | 2011-04-13 |
| US20090325939A1 (en) | 2009-12-31 |
| KR20070015607A (ko) | 2007-02-05 |
| CA2565984A1 (en) | 2005-11-24 |
| RU2006143153A (ru) | 2008-06-20 |
| WO2005111038A2 (en) | 2005-11-24 |
| ATE505470T1 (de) | 2011-04-15 |
| WO2005111038A3 (en) | 2006-08-31 |
| IL179033A0 (en) | 2007-03-08 |
| EP1745046A2 (en) | 2007-01-24 |
| US7632831B2 (en) | 2009-12-15 |
| MXPA06012880A (es) | 2007-01-26 |
| NO20065622L (no) | 2007-02-02 |
| NZ551712A (en) | 2010-07-30 |
| DE602005027452D1 (de) | 2011-05-26 |
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