CA2359008C - Triazolo-pyridazine derivatives as ligands for gaba receptors - Google Patents
Triazolo-pyridazine derivatives as ligands for gaba receptors Download PDFInfo
- Publication number
- CA2359008C CA2359008C CA002359008A CA2359008A CA2359008C CA 2359008 C CA2359008 C CA 2359008C CA 002359008 A CA002359008 A CA 002359008A CA 2359008 A CA2359008 A CA 2359008A CA 2359008 C CA2359008 C CA 2359008C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pharmaceutically acceptable
- formula
- triazolo
- triazol
- 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.)
- Expired - Fee Related
Links
- 239000003446 ligand Substances 0.000 title abstract description 10
- CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical class N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 title description 4
- 102000005915 GABA Receptors Human genes 0.000 title description 2
- 108010005551 GABA Receptors Proteins 0.000 title description 2
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 13
- 230000036506 anxiety Effects 0.000 claims abstract description 11
- 230000002265 prevention Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 122
- 150000003839 salts Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 239000004160 Ammonium persulphate Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
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- NQFZRBJDRTUSRM-UHFFFAOYSA-N 7-tert-butyl-3-(2,5-difluorophenyl)-6-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CCN1N=CN=C1COC(C(=C1)C(C)(C)C)=NN2C1=NN=C2C1=CC(F)=CC=C1F NQFZRBJDRTUSRM-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- LDGXFPTUGULLJC-UHFFFAOYSA-N 5h-[1,2,4]triazolo[4,3-b]pyridazin-6-one Chemical compound N1C(=O)C=CC2=NN=CN21 LDGXFPTUGULLJC-UHFFFAOYSA-N 0.000 claims description 2
- WUWBLFOIBOCSJK-UHFFFAOYSA-N 7-tert-butyl-3-(2,6-difluorophenyl)-6-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CCN1N=CN=C1COC(C(=C1)C(C)(C)C)=NN2C1=NN=C2C1=C(F)C=CC=C1F WUWBLFOIBOCSJK-UHFFFAOYSA-N 0.000 claims description 2
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- NLPXMPSTTIFCJL-UHFFFAOYSA-N 7-tert-butyl-6-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound CN1N=CN=C1COC(C(=C1)C(C)(C)C)=NN2C1=NN=C2C1=C(F)C=CC(F)=C1F NLPXMPSTTIFCJL-UHFFFAOYSA-N 0.000 claims description 2
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- 108090000839 GABA-A Receptors Proteins 0.000 abstract 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9901743.6A GB9901743D0 (en) | 1999-01-27 | 1999-01-27 | Therapeutic agents |
| GB9901743.6 | 1999-01-27 | ||
| GBGB9901744.4A GB9901744D0 (en) | 1999-01-27 | 1999-01-27 | Therapeutic agents |
| GB9901744.4 | 1999-01-27 | ||
| GBGB9912429.9A GB9912429D0 (en) | 1999-05-27 | 1999-05-27 | Therapeutic agents |
| GB9912429.9 | 1999-05-27 | ||
| PCT/GB2000/000183 WO2000044752A1 (en) | 1999-01-27 | 2000-01-19 | Triazolo-pyridazine derivatives as ligands for gaba receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2359008A1 CA2359008A1 (en) | 2000-08-03 |
| CA2359008C true CA2359008C (en) | 2008-05-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002359008A Expired - Fee Related CA2359008C (en) | 1999-01-27 | 2000-01-19 | Triazolo-pyridazine derivatives as ligands for gaba receptors |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6500828B1 (enExample) |
| EP (1) | EP1149102B1 (enExample) |
| JP (1) | JP2002535407A (enExample) |
| AT (1) | ATE284403T1 (enExample) |
| AU (1) | AU772947B2 (enExample) |
| CA (1) | CA2359008C (enExample) |
| DE (1) | DE60016566T2 (enExample) |
| ES (1) | ES2232416T3 (enExample) |
| WO (1) | WO2000044752A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0000564D0 (en) * | 2000-01-11 | 2000-03-01 | Merck Sharp & Dohme | Therapeutic agents |
| WO2002083675A2 (en) | 2001-04-10 | 2002-10-24 | Merck Sharp & Dohme Limited | Inhibitors of akt activity |
| US6958334B2 (en) | 2001-04-10 | 2005-10-25 | Merck & Co., Inc. | Inhibitors of Akt activity |
| WO2002083139A1 (en) | 2001-04-10 | 2002-10-24 | Merck & Co., Inc. | Inhibitors of akt activity |
| DE60315876T2 (de) * | 2002-11-28 | 2008-05-21 | Neurosearch A/S | Verfahren zum screening für verbindungen mit sedativer oder anxiolytischer potenz |
| WO2006061428A2 (en) * | 2004-12-10 | 2006-06-15 | Universität Zürich | Gaba-a alpha 2 and alpha 3 receptor agonists for treating neuropathic, inflammatory and migraine associated pain |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| AU2006282896A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| JP2009513672A (ja) | 2005-10-31 | 2009-04-02 | ブレインセルス，インコーポレイティド | 神経発生のｇａｂａ受容体媒介調節 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7998971B2 (en) | 2006-09-08 | 2011-08-16 | Braincells Inc. | Combinations containing a 4-acylaminopyridine derivative |
| CN102176826B (zh) * | 2008-08-29 | 2014-08-20 | 康瑟特制药公司 | 取代的三唑并哒嗪衍生物 |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| EP2454259A1 (en) | 2009-06-23 | 2012-05-23 | Concert Pharmaceuticals Inc. | Deuterium-modified triazolo-pyridazine derivatives as gaba-a receptor modulators |
| WO2011047315A1 (en) | 2009-10-15 | 2011-04-21 | Concert Pharmaceuticals, Inc. | Subsitituted benzimidazoles |
| US20150158870A1 (en) * | 2012-05-11 | 2015-06-11 | Concert Pharmaceuticals Inc. | Polymorphs of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| US20150119398A1 (en) * | 2012-05-11 | 2015-04-30 | Concert Pharmaceuticals Inc. | Form 2 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| WO2013170243A1 (en) * | 2012-05-11 | 2013-11-14 | Concert Pharmaceuticals, Inc. | Form 5 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| WO2015095549A1 (en) * | 2013-12-18 | 2015-06-25 | Concert Pharmaceuticals, Inc. | Dosage regimen for gabaa receptor subtype selective drug |
| JP7353663B2 (ja) | 2018-09-13 | 2023-10-02 | サニオナ エー／エス | Ｇａｂａａ受容体リガンド |
| EP4511025A1 (en) * | 2022-04-20 | 2025-02-26 | Engrail Therapeutics, Inc. | GABAa RECEPTOR MODULATOR SALTS, PARTICLES, AND USES THEREOF |
| CN115837022B (zh) * | 2023-02-20 | 2023-04-25 | 中山大学附属第八医院（深圳福田） | 1,2,4三唑并4,3-b哒嗪衍生物在制备抗衰老药物中的应用 |
| WO2025141131A1 (en) | 2023-12-27 | 2025-07-03 | Saniona A/S | A gabaa receptor ligand and the use thereof in medicine, in particular in the treatment of epilepsy |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU2899A (sh) * | 1996-07-25 | 2000-03-21 | Merck Sharp & Dohme Limited | Supstituisani triazolo-piridazin derivati kao ligandi za gaba receptore |
-
2000
- 2000-01-19 ES ES00900748T patent/ES2232416T3/es not_active Expired - Lifetime
- 2000-01-19 WO PCT/GB2000/000183 patent/WO2000044752A1/en not_active Ceased
- 2000-01-19 AT AT00900748T patent/ATE284403T1/de not_active IP Right Cessation
- 2000-01-19 EP EP00900748A patent/EP1149102B1/en not_active Expired - Lifetime
- 2000-01-19 DE DE60016566T patent/DE60016566T2/de not_active Expired - Fee Related
- 2000-01-19 AU AU30669/00A patent/AU772947B2/en not_active Ceased
- 2000-01-19 JP JP2000596008A patent/JP2002535407A/ja not_active Withdrawn
- 2000-01-19 CA CA002359008A patent/CA2359008C/en not_active Expired - Fee Related
- 2000-01-19 US US09/890,000 patent/US6500828B1/en not_active Expired - Fee Related
-
2002
- 2002-12-20 US US10/324,968 patent/US20030158203A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ES2232416T3 (es) | 2005-06-01 |
| ATE284403T1 (de) | 2004-12-15 |
| WO2000044752A1 (en) | 2000-08-03 |
| AU772947B2 (en) | 2004-05-13 |
| EP1149102B1 (en) | 2004-12-08 |
| DE60016566T2 (de) | 2005-12-15 |
| US6500828B1 (en) | 2002-12-31 |
| JP2002535407A (ja) | 2002-10-22 |
| US20030158203A1 (en) | 2003-08-21 |
| EP1149102A1 (en) | 2001-10-31 |
| CA2359008A1 (en) | 2000-08-03 |
| AU3066900A (en) | 2000-08-18 |
| DE60016566D1 (de) | 2005-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |