ES2395532T3 - BENCIMIDAZOLES que tienen actividad en el receptor M1 y sus usos en medicina - Google Patents
BENCIMIDAZOLES que tienen actividad en el receptor M1 y sus usos en medicina Download PDFInfo
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- ES2395532T3 ES2395532T3 ES07727117T ES07727117T ES2395532T3 ES 2395532 T3 ES2395532 T3 ES 2395532T3 ES 07727117 T ES07727117 T ES 07727117T ES 07727117 T ES07727117 T ES 07727117T ES 2395532 T3 ES2395532 T3 ES 2395532T3
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- 239000003814 drug Substances 0.000 title claims description 35
- 230000000694 effects Effects 0.000 title claims description 34
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- 101150073075 Chrm1 gene Proteins 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 271
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 71
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 239000012453 solvate Substances 0.000 claims abstract description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical group 0.000 claims abstract description 20
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- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
- -1 Ethyloxy Chemical group 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 60
- 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 description 45
- 238000006243 chemical reaction Methods 0.000 claims description 41
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 22
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
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- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 14
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- 230000017105 transposition Effects 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
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- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- DVMZIAXGARTAAQ-FZNQNYSPSA-N C1C[C@@H](OC)CC[C@H]1N1CCC(N2C(NC3=C(F)C=C(C)C=C32)=O)CC1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1CCC(N2C(NC3=C(F)C=C(C)C=C32)=O)CC1 DVMZIAXGARTAAQ-FZNQNYSPSA-N 0.000 claims description 2
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
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- 239000008096 xylene Substances 0.000 claims description 2
- 238000003747 Grignard reaction Methods 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 6
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- 239000000203 mixture Substances 0.000 description 120
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 208000016686 tic disease Diseases 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 206010046947 vaginismus Diseases 0.000 description 1
- 208000008918 voyeurism Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- JOLJIIDDOBNFHW-UHFFFAOYSA-N xanomeline Chemical compound CCCCCCOC1=NSN=C1C1=CCCN(C)C1 JOLJIIDDOBNFHW-UHFFFAOYSA-N 0.000 description 1
- 229950006755 xanomeline Drugs 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 229940039925 zyprexa Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0605785 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| ES2395532T3 true ES2395532T3 (es) | 2013-02-13 |
Family
ID=36383994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07727117T Active ES2395532T3 (es) | 2006-03-22 | 2007-03-20 | BENCIMIDAZOLES que tienen actividad en el receptor M1 y sus usos en medicina |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110207777A1 (enExample) |
| EP (1) | EP1996189B1 (enExample) |
| JP (1) | JP5256189B2 (enExample) |
| ES (1) | ES2395532T3 (enExample) |
| GB (1) | GB0605785D0 (enExample) |
| WO (1) | WO2007107567A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0706167D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706187D0 (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 |
| GB0706174D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| WO2010109468A1 (en) * | 2009-03-26 | 2010-09-30 | Mapi Pharma Hk 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 |
| EP4447953A1 (en) | 2021-12-13 | 2024-10-23 | 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 |
|---|---|---|---|---|
| US5691323A (en) * | 1995-05-12 | 1997-11-25 | Merck & Co., Inc. | Muscarine antagonists |
| EP0786997A4 (en) * | 1994-10-27 | 1998-03-11 | Merck & Co Inc | MUSCARINE ANTAGONISTS |
| US5574044A (en) * | 1994-10-27 | 1996-11-12 | Merck & Co., Inc. | Muscarine antagonists |
| AU7478396A (en) * | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Muscarine agonists |
| DE60013464T2 (de) * | 1999-10-13 | 2005-09-15 | Banyu Pharmaceutical 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 |
| WO2007036715A2 (en) * | 2005-09-30 | 2007-04-05 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| US8288413B2 (en) * | 2005-09-30 | 2012-10-16 | Glaxo Group Limited | Benzimidazolones which have activity at M1 receptor |
| GB0605786D0 (en) * | 2006-03-22 | 2006-05-03 | Glaxo Group Ltd | Compounds |
| GB0605784D0 (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 ES ES07727117T patent/ES2395532T3/es active Active
- 2007-03-20 JP JP2009500854A patent/JP5256189B2/ja not_active Expired - Fee Related
- 2007-03-20 EP EP07727117A patent/EP1996189B1/en active Active
- 2007-03-20 WO PCT/EP2007/052640 patent/WO2007107567A1/en not_active Ceased
- 2007-03-20 US US12/293,588 patent/US20110207777A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1996189A1 (en) | 2008-12-03 |
| JP2009530348A (ja) | 2009-08-27 |
| JP5256189B2 (ja) | 2013-08-07 |
| US20110207777A1 (en) | 2011-08-25 |
| GB0605785D0 (en) | 2006-05-03 |
| WO2007107567A1 (en) | 2007-09-27 |
| EP1996189B1 (en) | 2012-09-26 |
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