JP2009530348A5 - - Google Patents
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- Publication number
- JP2009530348A5 JP2009530348A5 JP2009500854A JP2009500854A JP2009530348A5 JP 2009530348 A5 JP2009530348 A5 JP 2009530348A5 JP 2009500854 A JP2009500854 A JP 2009500854A JP 2009500854 A JP2009500854 A JP 2009500854A JP 2009530348 A5 JP2009530348 A5 JP 2009530348A5
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- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- convertible
- alkyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001153 fluoro group Chemical group F* 0.000 claims 13
- 238000000034 method Methods 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- -1 ethyloxy Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004093 cyano group Chemical class *C#N 0.000 claims 5
- 230000008878 coupling Effects 0.000 claims 4
- 238000010168 coupling process Methods 0.000 claims 4
- 238000005859 coupling reaction Methods 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
- 230000003551 muscarinic effect Effects 0.000 claims 3
- 230000001737 promoting effect Effects 0.000 claims 3
- 239000007818 Grignard reagent Substances 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- FXGFCGZYILBACL-JCNLHEQBSA-N C1C[C@@H](OCC)CC[C@@H]1N1CCC(N2C(NC3=C(F)C=C(C)C=C32)=O)CC1 Chemical compound C1C[C@@H](OCC)CC[C@@H]1N1CCC(N2C(NC3=C(F)C=C(C)C=C32)=O)CC1 FXGFCGZYILBACL-JCNLHEQBSA-N 0.000 claims 1
- QLNUDTKQNMQQSV-SAABIXHNSA-N C1C[C@@H](OCCC)CC[C@@H]1N1CCC(N2C(NC3=C(F)C=C(C)C=C32)=O)CC1 Chemical compound C1C[C@@H](OCCC)CC[C@@H]1N1CCC(N2C(NC3=C(F)C=C(C)C=C32)=O)CC1 QLNUDTKQNMQQSV-SAABIXHNSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 238000006751 Mitsunobu reaction Methods 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000008569 process Effects 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000009467 reduction Effects 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000005932 reductive alkylation reaction Methods 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0605785.5 | 2006-03-22 | ||
| GBGB0605785.5A GB0605785D0 (en) | 2006-03-22 | 2006-03-22 | Compounds |
| PCT/EP2007/052640 WO2007107567A1 (en) | 2006-03-22 | 2007-03-20 | Benzimidazoles which have activity at m1 receptor and their uses in medicine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009530348A JP2009530348A (ja) | 2009-08-27 |
| JP2009530348A5 true JP2009530348A5 (https=) | 2010-05-06 |
| JP5256189B2 JP5256189B2 (ja) | 2013-08-07 |
Family
ID=36383994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009500854A Expired - Fee Related JP5256189B2 (ja) | 2006-03-22 | 2007-03-20 | Ｍ１受容体で活性を有するベンズイミダゾールおよび医薬におけるその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110207777A1 (https=) |
| EP (1) | EP1996189B1 (https=) |
| JP (1) | JP5256189B2 (https=) |
| ES (1) | ES2395532T3 (https=) |
| GB (1) | GB0605785D0 (https=) |
| WO (1) | WO2007107567A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0706174D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706168D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706164D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706167D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706187D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| CA2755561A1 (en) * | 2009-03-26 | 2010-09-30 | Mapi Pharma Limited | Process for the preparation of alogliptin |
| CN110368375B (zh) * | 2019-07-02 | 2021-10-01 | 青岛大学附属医院 | 用于抑郁症及相关病症的缓释组合物及其制备方法 |
| WO2023114224A1 (en) | 2021-12-13 | 2023-06-22 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002515008A (ja) * | 1994-10-27 | 2002-05-21 | メルク エンド カンパニー インコーポレーテッド | ムスカリン・アンタゴニスト |
| US5691323A (en) * | 1995-05-12 | 1997-11-25 | Merck & Co., Inc. | Muscarine antagonists |
| US5574044A (en) * | 1994-10-27 | 1996-11-12 | Merck & Co., Inc. | Muscarine antagonists |
| WO1997016186A1 (en) * | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Muscarine agonists |
| ATE275141T1 (de) * | 1999-10-13 | 2004-09-15 | Banyu Pharma Co Ltd | Substituierte imidazolin-derivate |
| WO2004089942A2 (en) * | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| JP2005532361A (ja) * | 2002-06-17 | 2005-10-27 | メルク エンド カムパニー インコーポレーテッド | 高眼圧症の治療用の眼科用組成物 |
| GB0505304D0 (en) * | 2005-03-15 | 2005-04-20 | Ds Smith Plastics Ltd | Tap for liquid containers |
| WO2007036711A1 (en) * | 2005-09-30 | 2007-04-05 | Glaxo Group Limited | BENZIMIDAZOLONES WHICH HAVE ACTIVITY AT Ml RECEPTOR |
| BRPI0616609A2 (pt) * | 2005-09-30 | 2011-06-28 | Glaxo Group Ltd | compostos que têm atividade no receptor m1, composição farmacêutica contendo tais compostos, processo para preparação dos mesmos, bem como seus usos em medicina |
| GB0605784D0 (en) * | 2006-03-22 | 2006-05-03 | Glaxo Group Ltd | Compounds |
| GB0605786D0 (en) * | 2006-03-22 | 2006-05-03 | Glaxo Group Ltd | Compounds |
| GB0706189D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
-
2006
- 2006-03-22 GB GBGB0605785.5A patent/GB0605785D0/en not_active Ceased
-
2007
- 2007-03-20 EP EP07727117A patent/EP1996189B1/en active Active
- 2007-03-20 US US12/293,588 patent/US20110207777A1/en not_active Abandoned
- 2007-03-20 WO PCT/EP2007/052640 patent/WO2007107567A1/en not_active Ceased
- 2007-03-20 ES ES07727117T patent/ES2395532T3/es active Active
- 2007-03-20 JP JP2009500854A patent/JP5256189B2/ja not_active Expired - Fee Related
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