JP2010540562A5 - - Google Patents
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- Publication number
- JP2010540562A5 JP2010540562A5 JP2010527249A JP2010527249A JP2010540562A5 JP 2010540562 A5 JP2010540562 A5 JP 2010540562A5 JP 2010527249 A JP2010527249 A JP 2010527249A JP 2010527249 A JP2010527249 A JP 2010527249A JP 2010540562 A5 JP2010540562 A5 JP 2010540562A5
- Authority
- JP
- Japan
- Prior art keywords
- ylmethyl
- indole
- carboxylate
- quinuclidin
- heptan
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 35
- 150000003839 salts Chemical class 0.000 claims 25
- 239000012453 solvate Substances 0.000 claims 25
- 125000001475 halogen functional group Chemical group 0.000 claims 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 19
- 208000024827 Alzheimer disease Diseases 0.000 claims 16
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 12
- 206010012289 Dementia Diseases 0.000 claims 12
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 12
- 208000010877 cognitive disease Diseases 0.000 claims 12
- 208000028698 Cognitive impairment Diseases 0.000 claims 8
- 208000028017 Psychotic disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 201000000980 schizophrenia Diseases 0.000 claims 8
- -1 Quinuclidin-4-ylmethyl 1H-indole-3-carboxylate Chemical compound 0.000 claims 6
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 6
- 230000004770 neurodegeneration Effects 0.000 claims 6
- 208000024891 symptom Diseases 0.000 claims 6
- IHPXOQDYLTYWAR-UHFFFAOYSA-N (3-oxo-1-azabicyclo[2.2.2]octan-4-yl)methyl 1h-indole-3-carboxylate Chemical compound C1=CC=C2C(C(OCC34CCN(CC3)CC4=O)=O)=CNC2=C1 IHPXOQDYLTYWAR-UHFFFAOYSA-N 0.000 claims 5
- SEDHPUZKCQBANK-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 1h-indole-3-carboxylate Chemical compound C1=CC=C2C(C(OCC34CCN(CC3)C4)=O)=CNC2=C1 SEDHPUZKCQBANK-UHFFFAOYSA-N 0.000 claims 5
- AMLBBMMFMLVCAJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 5-(difluoromethoxy)-1h-indole-3-carboxylate Chemical compound C12=CC(OC(F)F)=CC=C2NC=C1C(=O)OCC1(C2)CCN2CC1 AMLBBMMFMLVCAJ-UHFFFAOYSA-N 0.000 claims 5
- YNUMJLHUOOGLJA-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 5-chloro-1h-indole-3-carboxylate Chemical compound C12=CC(Cl)=CC=C2NC=C1C(=O)OCC1(C2)CCN2CC1 YNUMJLHUOOGLJA-UHFFFAOYSA-N 0.000 claims 5
- QZAHPOTXRJLXFT-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 5-fluoro-1h-indole-3-carboxylate Chemical compound C12=CC(F)=CC=C2NC=C1C(=O)OCC1(C2)CCN2CC1 QZAHPOTXRJLXFT-UHFFFAOYSA-N 0.000 claims 5
- BYCMSLAAWXLXLI-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 5-methoxy-1h-indole-3-carboxylate Chemical compound C12=CC(OC)=CC=C2NC=C1C(=O)OCC1(C2)CCN2CC1 BYCMSLAAWXLXLI-UHFFFAOYSA-N 0.000 claims 5
- OUCGTTDCRABIMA-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 6-(difluoromethoxy)-1h-indole-3-carboxylate Chemical compound FC(F)OC1=CC=C2C(C(=O)OCC34CCN(CC3)C4)=CNC2=C1 OUCGTTDCRABIMA-UHFFFAOYSA-N 0.000 claims 5
- KHNZERYFIOUCKX-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-4-ylmethyl 6-methoxy-1h-indole-3-carboxylate Chemical compound COC1=CC=C2C(C(=O)OCC34CCN(CC3)C4)=CNC2=C1 KHNZERYFIOUCKX-UHFFFAOYSA-N 0.000 claims 5
- GFXKYBZVBAFFEB-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 1h-indazole-3-carboxylate Chemical compound C1=CC=C2C(C(OCC34CCN(CC3)CC4)=O)=NNC2=C1 GFXKYBZVBAFFEB-UHFFFAOYSA-N 0.000 claims 5
- WCVKQCWPYGAONY-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 2-methyl-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=C(C)NC2=CC=CC=C21 WCVKQCWPYGAONY-UHFFFAOYSA-N 0.000 claims 5
- VIMBZXPMHGSCMR-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-(cyclopropylmethoxy)-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C(C1=C2)=CNC1=CC=C2OCC1CC1 VIMBZXPMHGSCMR-UHFFFAOYSA-N 0.000 claims 5
- PAUBQJDZIFBTBK-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-(difluoromethoxy)-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC=C(OC(F)F)C=C21 PAUBQJDZIFBTBK-UHFFFAOYSA-N 0.000 claims 5
- TUCUBBVRRKXMII-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-(trifluoromethoxymethyl)-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC=C(COC(F)(F)F)C=C21 TUCUBBVRRKXMII-UHFFFAOYSA-N 0.000 claims 5
- CQPWZYTUOGSVFZ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-carbamoyl-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC=C(C(=O)N)C=C21 CQPWZYTUOGSVFZ-UHFFFAOYSA-N 0.000 claims 5
- MDDRPRHJXXDKKV-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-chloro-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC=C(Cl)C=C21 MDDRPRHJXXDKKV-UHFFFAOYSA-N 0.000 claims 5
- GCEPLXYEEIJUJZ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-cyano-1h-indole-3-carboxylate Chemical compound C1=C(C#N)C=C2C(C(OCC34CCN(CC3)CC4)=O)=CNC2=C1 GCEPLXYEEIJUJZ-UHFFFAOYSA-N 0.000 claims 5
- TVBLCSQOLNHLAF-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-methoxy-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC=C(OC)C=C21 TVBLCSQOLNHLAF-UHFFFAOYSA-N 0.000 claims 5
- OHANUTMZXQOBOM-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-methoxy-2-methyl-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=C(C)NC2=CC=C(OC)C=C21 OHANUTMZXQOBOM-UHFFFAOYSA-N 0.000 claims 5
- OEIJNTVNSOQULQ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 5-propan-2-yloxy-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC=C(OC(C)C)C=C21 OEIJNTVNSOQULQ-UHFFFAOYSA-N 0.000 claims 5
- GUKIAYZQCGKGEC-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 6-(difluoromethoxy)-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC(OC(F)F)=CC=C21 GUKIAYZQCGKGEC-UHFFFAOYSA-N 0.000 claims 5
- XIQPDIUHKIOZOL-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-ylmethyl 6-methoxy-1h-indole-3-carboxylate Chemical compound C1CN(CC2)CCC12COC(=O)C1=CNC2=CC(OC)=CC=C21 XIQPDIUHKIOZOL-UHFFFAOYSA-N 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- PKBVKBLTOFEJGO-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-1,2-benzothiazole-3-carboxamide Chemical compound C1=CC=C2C(C(NCC34CCN(CC3)CC4)=O)=NSC2=C1 PKBVKBLTOFEJGO-UHFFFAOYSA-N 0.000 claims 5
- IMRMDIBVFXYZFZ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(NCC34CCN(CC3)CC4)=O)=NNC2=C1 IMRMDIBVFXYZFZ-UHFFFAOYSA-N 0.000 claims 5
- CWKWTCNBOIXQKP-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(NCC34CCN(CC3)CC4)=O)=CNC2=C1 CWKWTCNBOIXQKP-UHFFFAOYSA-N 0.000 claims 5
- QAYPIHUQZWFFNR-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-5-fluoro-1h-indazole-3-carboxamide Chemical compound C1CN(CC2)CCC12CNC(=O)C1=NNC2=CC=C(F)C=C21 QAYPIHUQZWFFNR-UHFFFAOYSA-N 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 208000030507 AIDS Diseases 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims 4
- 208000032841 Bulimia Diseases 0.000 claims 4
- 206010006550 Bulimia nervosa Diseases 0.000 claims 4
- 201000010374 Down Syndrome Diseases 0.000 claims 4
- 208000012661 Dyskinesia Diseases 0.000 claims 4
- 208000027534 Emotional disease Diseases 0.000 claims 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 4
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 4
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 4
- 208000010412 Glaucoma Diseases 0.000 claims 4
- 208000023105 Huntington disease Diseases 0.000 claims 4
- 208000019022 Mood disease Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 4
- 206010036631 Presenile dementia Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 206010039966 Senile dementia Diseases 0.000 claims 4
- 206010040070 Septic Shock Diseases 0.000 claims 4
- 208000000323 Tourette Syndrome Diseases 0.000 claims 4
- 208000016620 Tourette disease Diseases 0.000 claims 4
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 4
- 230000002159 abnormal effect Effects 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 4
- 208000022531 anorexia Diseases 0.000 claims 4
- 231100000871 behavioral problem Toxicity 0.000 claims 4
- 230000003542 behavioural effect Effects 0.000 claims 4
- 208000030963 borderline personality disease Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 230000001149 cognitive effect Effects 0.000 claims 4
- 231100000870 cognitive problem Toxicity 0.000 claims 4
- 206010061428 decreased appetite Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 230000037406 food intake Effects 0.000 claims 4
- 235000012631 food intake Nutrition 0.000 claims 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 4
- 210000004558 lewy body Anatomy 0.000 claims 4
- 208000002780 macular degeneration Diseases 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 230000036651 mood Effects 0.000 claims 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 4
- 230000005586 smoking cessation Effects 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 230000009529 traumatic brain injury Effects 0.000 claims 4
- 230000029663 wound healing Effects 0.000 claims 4
- 238000009472 formulation Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 206010002198 Anaphylactic reaction Diseases 0.000 claims 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 2
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010392 Bone Fractures Diseases 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 206010063094 Cerebral malaria Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 241000701022 Cytomegalovirus Species 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 206010013754 Drug withdrawal syndrome Diseases 0.000 claims 2
- 206010017076 Fracture Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 206010020164 HIV infection CDC Group III Diseases 0.000 claims 2
- 208000007514 Herpes zoster Diseases 0.000 claims 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims 2
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 2
- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010028289 Muscle atrophy Diseases 0.000 claims 2
- 208000000112 Myalgia Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 208000010191 Osteitis Deformans Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 208000027868 Paget disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000024571 Pick disease Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 208000033464 Reiter syndrome Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000034189 Sclerosis Diseases 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000009205 Tinnitus Diseases 0.000 claims 2
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims 2
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims 2
- 230000036783 anaphylactic response Effects 0.000 claims 2
- 208000003455 anaphylaxis Diseases 0.000 claims 2
- 210000001367 artery Anatomy 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000003143 atherosclerotic effect Effects 0.000 claims 2
- 208000019664 bone resorption disease Diseases 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000035876 healing Effects 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 206010022000 influenza Diseases 0.000 claims 2
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 2
- 208000027202 mammary Paget disease Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 208000002574 reactive arthritis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 241000701161 unidentified adenovirus Species 0.000 claims 2
- 241001529453 unidentified herpesvirus Species 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97672407P | 2007-10-01 | 2007-10-01 | |
| US60/976,724 | 2007-10-01 | ||
| PCT/US2008/078320 WO2009046025A1 (en) | 2007-10-01 | 2008-09-30 | Quinuclidin-4-ylmethyl 1h-indole-3-carboxylate derivatives as alpha 7 nicotinic acetylcholine receptor ligands for the treatment of alzheimer's disease |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010540562A JP2010540562A (ja) | 2010-12-24 |
| JP2010540562A5 true JP2010540562A5 (enExample) | 2011-11-17 |
| JP5022494B2 JP5022494B2 (ja) | 2012-09-12 |
Family
ID=40344599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010527249A Expired - Fee Related JP5022494B2 (ja) | 2007-10-01 | 2008-09-30 | アルツハイマー病治療用のα７ニコチン性アセチルコリン受容体リガンドとしてのキヌクリジン−４−イルメチル１Ｈ−インドール−３−カルボキシレート誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8114891B2 (enExample) |
| EP (1) | EP2217597B1 (enExample) |
| JP (1) | JP5022494B2 (enExample) |
| KR (1) | KR101565469B1 (enExample) |
| CN (2) | CN101883771A (enExample) |
| AT (1) | ATE503754T1 (enExample) |
| CA (1) | CA2701126A1 (enExample) |
| DE (1) | DE602008005928D1 (enExample) |
| DK (1) | DK2217597T3 (enExample) |
| ES (1) | ES2362326T3 (enExample) |
| MX (1) | MX2010003375A (enExample) |
| WO (1) | WO2009046025A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| CN105687190A (zh) | 2008-11-19 | 2016-06-22 | 福拉姆医药股份有限公司 | 用(R)-7-氯-N-(奎宁环-3-基)苯并[b]噻吩-2-甲酰胺及其可药用盐治疗认知障碍 |
| PE20120324A1 (es) * | 2009-05-11 | 2012-04-17 | Envivo Pharmaceuticals Inc | Combinacion que comprende (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida y donezepilo como moduladora de trastornos cognitivos |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| KR20180101641A (ko) | 2010-05-17 | 2018-09-12 | 포럼 파마슈티칼즈 인크. | (R)-7-클로로-N-(퀴누클리딘-3-일)벤조[b]티오펜-2-카르복사미드 히드로클로리드 모노히드레이트의 결정질 형태 |
| US20130197028A1 (en) * | 2010-06-25 | 2013-08-01 | Oklahoma Medical Research Foundation | nAChRalpha7 Agonists and nAChRalpha7 Antagonists for Treating Ulcerative Colitis (UC) and Crohn's Disease (CD) |
| AU2012279298A1 (en) * | 2011-07-01 | 2014-01-23 | Envivo Pharmaceuticals, Inc. | Methods of treatment of Limited Cognitive Impairment |
| RU2014144951A (ru) * | 2012-04-10 | 2016-06-10 | Сумитомо Дайниппон Фарма Ко., Лтд. | Новое 1-замещенное производное индазола |
| EP3461481A1 (en) | 2012-05-08 | 2019-04-03 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| JP6261048B2 (ja) * | 2012-12-05 | 2018-01-17 | 国立大学法人 新潟大学 | 破骨細胞が関与する疾患の予防又は治療剤 |
| KR102243637B1 (ko) | 2013-03-14 | 2021-04-26 | 리커리엄 아이피 홀딩스, 엘엘씨 | 바이사이클릭 진통 화합물 |
| JP6427197B2 (ja) | 2013-10-03 | 2018-11-21 | クラ オンコロジー， インコーポレイテッド | Ｅｒｋの阻害剤および使用方法 |
| EP3080072A4 (en) | 2013-12-12 | 2017-07-19 | Kalyra Pharmaceuticals, inc. | Bicyclic alkyl compounds and synthesis |
| WO2015134710A1 (en) | 2014-03-07 | 2015-09-11 | Kalyra Pharmaceuticals, Inc. | Propellane derivates and synthesis |
| EP3166940A4 (en) | 2014-07-11 | 2018-04-25 | Alpharmagen, LLC | Quinuclidine compounds for modulating alpha7 -nicotinic acetylcholine receptor activity |
| WO2016044331A1 (en) | 2014-09-17 | 2016-03-24 | Kalyra Pharmaceuticals, Inc. | Bicyclic compounds |
| WO2017120532A1 (en) * | 2016-01-08 | 2017-07-13 | Alpharmagen, Llc | Polymorphs of a phosphate salt of quinuclidin-4-ylmethyl 4-methyl-1h-indole-3-carboxylate and uses thereof |
| US20190083460A1 (en) * | 2016-03-16 | 2019-03-21 | Zeno Royalties & Milestones, LLC | Analgesic compounds |
| MX389668B (es) | 2017-05-15 | 2025-03-20 | Recurium Ip Holdings Llc | Compuestos biciclo[1.1.1]pentilo sustituidos y uso de los mismos para el tratamiento del dolor y fiebre. |
| EP3520803A1 (en) * | 2018-01-31 | 2019-08-07 | Zarodex Therapeutics Limited | Novel uses |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1223873A (en) | 1982-04-14 | 1987-07-07 | Francis D. King | Pharmaceutically active compounds |
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- 2008-09-30 ES ES08835512T patent/ES2362326T3/es active Active
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- 2008-09-30 WO PCT/US2008/078320 patent/WO2009046025A1/en not_active Ceased