JP2009521483A5 - - Google Patents
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- JP2009521483A5 JP2009521483A5 JP2008547641A JP2008547641A JP2009521483A5 JP 2009521483 A5 JP2009521483 A5 JP 2009521483A5 JP 2008547641 A JP2008547641 A JP 2008547641A JP 2008547641 A JP2008547641 A JP 2008547641A JP 2009521483 A5 JP2009521483 A5 JP 2009521483A5
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- Prior art keywords
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- compound
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- optionally substituted
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- -1 cycloaliphatic Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000006168 tricyclic group Chemical group 0.000 claims description 8
- 102000014415 Muscarinic acetylcholine receptor family Human genes 0.000 claims description 7
- 108050003473 Muscarinic acetylcholine receptor family Proteins 0.000 claims description 7
- 125000005418 aryl aryl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000004429 atoms Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 102000005962 receptors Human genes 0.000 claims description 3
- 108020003175 receptors Proteins 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 2
- 125000005001 aminoaryl group Chemical group 0.000 claims 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000000051 modifying Effects 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 206010004938 Bipolar disease Diseases 0.000 claims 1
- 208000006218 Bradycardia Diseases 0.000 claims 1
- 206010057668 Cognitive disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 201000010374 Down syndrome Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000001786 Gonorrhea Diseases 0.000 claims 1
- 206010018612 Gonorrhoea Diseases 0.000 claims 1
- 201000001971 Huntington's disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 201000011585 Pick's disease Diseases 0.000 claims 1
- 206010061920 Psychotic disease Diseases 0.000 claims 1
- 206010040767 Sjogren's syndrome Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 206010044126 Tourette's disease Diseases 0.000 claims 1
- 230000001154 acute Effects 0.000 claims 1
- 230000036471 bradycardia Effects 0.000 claims 1
- 230000001684 chronic Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 201000003104 endogenous depression Diseases 0.000 claims 1
- 201000011240 frontotemporal dementia Diseases 0.000 claims 1
- 230000027119 gastric acid secretion Effects 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 230000004410 intraocular pressure Effects 0.000 claims 1
- 230000001404 mediated Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000002093 peripheral Effects 0.000 claims 1
- 201000010874 syndrome Diseases 0.000 claims 1
- 201000004810 vascular dementia Diseases 0.000 claims 1
- 200000000019 wound Diseases 0.000 claims 1
- 0 *C(CC1)CCN1c1cnccn1 Chemical compound *C(CC1)CCN1c1cnccn1 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 230000003551 muscarinic Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229930006677 A03BA01 - Atropine Natural products 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N Atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 Atropine Drugs 0.000 description 1
- WLVPJAPBRZNIRL-UHFFFAOYSA-N CC(CC1)CCN1C1=NCC(c2ccncc2)N=C1 Chemical compound CC(CC1)CCN1C1=NCC(c2ccncc2)N=C1 WLVPJAPBRZNIRL-UHFFFAOYSA-N 0.000 description 1
- NZXTTZCHGXRFGF-UHFFFAOYSA-N CC(CC1)CCN1c1cc(OC)ccc1 Chemical compound CC(CC1)CCN1c1cc(OC)ccc1 NZXTTZCHGXRFGF-UHFFFAOYSA-N 0.000 description 1
- PTMCNXVROIQJSS-UHFFFAOYSA-N CCC(CC1)CCN1c1cncnc1 Chemical compound CCC(CC1)CCN1c1cncnc1 PTMCNXVROIQJSS-UHFFFAOYSA-N 0.000 description 1
- KUHCKJQBOIUHMR-UHFFFAOYSA-N CCc(nc1)cnc1N1CCC(C)CC1 Chemical compound CCc(nc1)cnc1N1CCC(C)CC1 KUHCKJQBOIUHMR-UHFFFAOYSA-N 0.000 description 1
- SFLYLCSGHCILEF-UHFFFAOYSA-N CN(C1)C1C(CC1)CCN1c1ccccn1 Chemical compound CN(C1)C1C(CC1)CCN1c1ccccn1 SFLYLCSGHCILEF-UHFFFAOYSA-N 0.000 description 1
- QEFQAVCBWZDGPE-UHFFFAOYSA-N Cc(nc1)cnc1N(CC1)CCC1N Chemical compound Cc(nc1)cnc1N(CC1)CCC1N QEFQAVCBWZDGPE-UHFFFAOYSA-N 0.000 description 1
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QCHFTSOMWOSFHM-WPRPVWTQSA-N Pilopine HS Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- 230000003042 antagnostic Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010192 crystallographic characterization Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 1
- 239000000472 muscarinic agonist Substances 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75318705P | 2005-12-22 | 2005-12-22 | |
| PCT/US2006/049141 WO2007076070A2 (en) | 2005-12-22 | 2006-12-22 | Modulators of muscarinic receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009521483A JP2009521483A (ja) | 2009-06-04 |
| JP2009521483A5 true JP2009521483A5 (US07794700-20100914-C00152.png) | 2010-02-18 |
Family
ID=38138812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008547641A Pending JP2009521483A (ja) | 2005-12-22 | 2006-12-22 | ムスカリン受容体のモジュレーター |
Country Status (12)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2290731A1 (en) * | 1999-11-26 | 2001-05-26 | D. Jed Harrison | Apparatus and method for trapping bead based reagents within microfluidic analysis system |
| JP2003294742A (ja) | 2002-03-29 | 2003-10-15 | Inst Of Physical & Chemical Res | ハイブリダイゼーション用基板及びその使用方法 |
| US7786141B2 (en) * | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| AU2007221220A1 (en) * | 2006-02-22 | 2007-09-07 | Vertex Pharmaceuticals Incorporated | Spiro condensed piperidnes as modulators of muscarinic receptors |
| WO2008121066A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | Novel tricyclic spiropiperidines or spiropyrrolidines and their use as modulators of chemokine receptors |
| KR20140139125A (ko) * | 2007-08-31 | 2014-12-04 | 퍼듀 퍼머 엘피 | 치환-퀴녹살린-형 피페리딘 화합물 및 그의 용도 |
| NZ586872A (en) * | 2008-02-06 | 2012-03-30 | Astrazeneca Ab | Spirocyclic amide compounds |
| BR112012024380A2 (pt) | 2010-03-25 | 2015-09-15 | Glaxosmithkline Llc | compostos químicos |
| TWI543984B (zh) * | 2010-07-09 | 2016-08-01 | 艾伯維公司 | 作為s1p調節劑的螺-哌啶衍生物 |
| JP6083818B2 (ja) | 2011-11-18 | 2017-02-22 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ１受容体アゴニスト |
| DK2897948T3 (en) | 2012-09-18 | 2016-12-05 | Heptares Therapeutics Ltd | BICYCLIC AZA RELATIONS AS MUSCARIN M1 RECEPTOR AGONISTS |
| GB2519470A (en) * | 2013-09-18 | 2015-04-22 | Heptares Therapeutics Ltd | Bicyclic aza compounds as muscarinic M1 receptor agonists |
| AU2015213900B2 (en) | 2014-02-06 | 2018-12-13 | Nxera Pharma Uk Limited | Bicyclic aza compounds as muscarinic M1 receptor and/or M4 receptor agonists |
| GB201404922D0 (en) * | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| CN107531660A (zh) | 2015-03-13 | 2018-01-02 | 福马治疗股份有限公司 | 作为HDAC8抑制剂的α‑肉桂酰胺化合物和组合物 |
| GB201504675D0 (en) * | 2015-03-19 | 2015-05-06 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| TW201711999A (zh) | 2015-09-03 | 2017-04-01 | 佛瑪治療公司 | ﹝６，６﹞稠合雙環組蛋白脫乙醯基酶８（ｈｄａｃ８）抑制劑 |
| WO2017112719A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 6,7-dihydro-5h-pyrrolo[3,4-b]pyridin-5-one allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| WO2018112840A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6, 5-fused heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2019000237A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000236A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000238A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | 5- (PYRIDIN-3-YL) OXAZOLE ALLOSTERIC MODULATORS OF M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| GB201810245D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| WO2022032073A2 (en) * | 2020-08-07 | 2022-02-10 | Casma Therapeutics, Inc. | Trpml modulators |
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-
2006
- 2006-12-22 WO PCT/US2006/049141 patent/WO2007076070A2/en active Application Filing
- 2006-12-22 RU RU2008130094/14A patent/RU2008130094A/ru not_active Application Discontinuation
- 2006-12-22 JP JP2008547641A patent/JP2009521483A/ja active Pending
- 2006-12-22 EP EP06848092A patent/EP1973543A2/en not_active Withdrawn
- 2006-12-22 AU AU2006330866A patent/AU2006330866A1/en not_active Abandoned
- 2006-12-22 CA CA002634456A patent/CA2634456A1/en not_active Abandoned
- 2006-12-22 KR KR1020087017741A patent/KR20080087841A/ko not_active Application Discontinuation
- 2006-12-22 CN CNA2006800529466A patent/CN101374519A/zh active Pending
- 2006-12-22 US US11/644,124 patent/US7858635B2/en not_active Expired - Fee Related
-
2008
- 2008-06-19 IL IL192327A patent/IL192327A0/en unknown
- 2008-07-03 NO NO20083011A patent/NO20083011L/no not_active Application Discontinuation
- 2008-07-10 ZA ZA200806028A patent/ZA200806028B/xx unknown
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