ZA200404168B - Ä1,2,4Ü-Triazole bicyclic adenosing A2a receptor antagonists. - Google Patents
Ä1,2,4Ü-Triazole bicyclic adenosing A2a receptor antagonists. Download PDFInfo
- Publication number
- ZA200404168B ZA200404168B ZA200404168A ZA200404168A ZA200404168B ZA 200404168 B ZA200404168 B ZA 200404168B ZA 200404168 A ZA200404168 A ZA 200404168A ZA 200404168 A ZA200404168 A ZA 200404168A ZA 200404168 B ZA200404168 B ZA 200404168B
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- South Africa
- Prior art keywords
- alkyl
- compound
- composition
- alkoxy
- disease
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- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- BKXPKNYXXNYCBX-UHFFFAOYSA-N ethyl 3-oxohept-6-enoate Chemical compound CCOC(=O)CC(=O)CCC=C BKXPKNYXXNYCBX-UHFFFAOYSA-N 0.000 description 1
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- GJMCGNNIEYHGHC-UHFFFAOYSA-N n,2,4-trifluoro-n-methylaniline Chemical compound CN(F)C1=CC=C(F)C=C1F GJMCGNNIEYHGHC-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
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- 230000002829 reductive effect Effects 0.000 description 1
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- 150000003378 silver Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61P25/14—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
- A61P25/24—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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33438501P | 2001-11-30 | 2001-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200404168B true ZA200404168B (en) | 2005-09-02 |
Family
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Family Applications (1)
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| ZA200404168A ZA200404168B (en) | 2001-11-30 | 2004-05-27 | Ä1,2,4Ü-Triazole bicyclic adenosing A2a receptor antagonists. |
Country Status (18)
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|---|---|
| US (2) | US6875772B2 (enExample) |
| EP (1) | EP1453836B1 (enExample) |
| JP (2) | JP4429724B2 (enExample) |
| KR (1) | KR20050044600A (enExample) |
| CN (1) | CN1688581A (enExample) |
| AR (1) | AR037681A1 (enExample) |
| AT (1) | ATE358130T1 (enExample) |
| AU (1) | AU2002352933A1 (enExample) |
| CA (1) | CA2468658C (enExample) |
| DE (1) | DE60219196T2 (enExample) |
| ES (1) | ES2283625T3 (enExample) |
| HU (1) | HUP0402324A3 (enExample) |
| IL (1) | IL161573A0 (enExample) |
| MX (1) | MXPA04005158A (enExample) |
| PE (1) | PE20030653A1 (enExample) |
| TW (1) | TW200300689A (enExample) |
| WO (1) | WO2003048163A1 (enExample) |
| ZA (1) | ZA200404168B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| MXPA04005158A (es) * | 2001-11-30 | 2004-08-11 | Schering Corp | Antagonistas receptores de adenosina a2a biciclica de (1.2.4]- triazol. |
| PE20030739A1 (es) | 2001-11-30 | 2003-08-28 | Schering Corp | Antagonistas del receptor de adenosina a2a |
| TW200304825A (en) * | 2002-03-12 | 2003-10-16 | Wyeth Corp | Process for making chiral 1,4-disubstituted piperazines |
| WO2004029056A1 (ja) * | 2002-09-24 | 2004-04-08 | Kyowa Hakko Kogyo Co., Ltd. | [１，２，４]トリアゾロ[１，５−ｃ]ピリミジン誘導体 |
| WO2005044245A1 (en) * | 2002-12-19 | 2005-05-19 | Schering Corporation | USES OF ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US7285550B2 (en) | 2003-04-09 | 2007-10-23 | Biogen Idec Ma Inc. | Triazolotriazines and pyrazolotriazines and methods of making and using the same |
| EP1618109A2 (en) * | 2003-04-09 | 2006-01-25 | Biogen Idec MA Inc. | Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists |
| EP1633756B1 (en) | 2003-04-09 | 2008-12-24 | Biogen Idec MA Inc. | A2a adenosine receptor antagonists |
| WO2004092177A1 (en) | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolopyrazines and methods of making and using the same |
| TW200507850A (en) | 2003-07-25 | 2005-03-01 | Kyowa Hakko Kogyo Kk | Pharmaceutical composition |
| WO2006129626A1 (ja) * | 2005-05-30 | 2006-12-07 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]トリアゾロ[1,5-c]ピリミジン誘導体の製造法 |
| EP2258372B8 (en) | 2005-06-07 | 2012-12-19 | Kyowa Hakko Kirin Co., Ltd. | A2A antagonists for use in the treatment of motor disorders |
| WO2006131524A1 (en) * | 2005-06-08 | 2006-12-14 | Neurosearch A/S | Novel n-phenyl-piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| WO2007027987A2 (en) * | 2005-09-02 | 2007-03-08 | Mount Cook Biosciences, Inc. | Method of treating parkinson's disease with diarylmethylpiperazine compounds exhibiting delta receptor agonist activity |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| US7615556B2 (en) * | 2006-01-27 | 2009-11-10 | Bristol-Myers Squibb Company | Piperazinyl derivatives as modulators of chemokine receptor activity |
| US20110064671A1 (en) | 2008-03-10 | 2011-03-17 | Cornell University | Modulation of blood brain barrier permeability |
| WO2010008775A1 (en) * | 2008-06-23 | 2010-01-21 | Ligand Pharmaceuticals Inc. | Aminopyridopyrazinone derivatives for treating neurodegenerative diseases |
| GB201214106D0 (en) * | 2012-08-07 | 2012-09-19 | Univ Strathclyde | Immunomodulatory compounds |
| EP3436013A4 (en) | 2016-03-31 | 2019-11-13 | Versi Group, LLC | DELTA OPIOID AGONIST, MU OPIOID ANTAGONIST COMPOSITIONS AND METHOD FOR TREATING MORBUS PARKINSON |
| CN106866582A (zh) * | 2017-01-10 | 2017-06-20 | 广州隽沐生物科技有限公司 | 一种氟班色林中间体的制备方法 |
| EP3814355A4 (en) | 2018-06-26 | 2022-06-08 | Zhejiang Vimgreen Pharmaceuticals, Ltd | PYRAZOLOTRIAZOLOPYRIMIDE DERIVATIVES AS A2A RECEPTOR ANTAGONISTS |
| WO2020227156A1 (en) * | 2019-05-03 | 2020-11-12 | Nektar Therapeutics | Adenosine 2 receptor antagonists |
| US20230048888A1 (en) * | 2019-12-26 | 2023-02-16 | Zhejiang Vimgreen Pharmaceuticals, Ltd. | Use of triazolotriazine derivative in treatment of diseases |
| MX2023012338A (es) * | 2021-04-23 | 2023-10-30 | Chong Kun Dang Pharmaceutical Corp | Compuesto como antagonista del receptor de adenosina a2a y composicion farmaceutica que comprende al mismo. |
Family Cites Families (12)
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| IT1264901B1 (it) | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| AU7237294A (en) * | 1993-07-27 | 1995-02-28 | Kyowa Hakko Kogyo Co. Ltd. | Remedy for parkinson's disease |
| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| JP4195729B2 (ja) * | 1997-03-24 | 2008-12-10 | 協和醗酵工業株式会社 | ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| WO1999043678A1 (en) | 1998-02-24 | 1999-09-02 | Kyowa Hakko Kogyo Co., Ltd. | Remedies/preventives for parkinson's disease |
| BR9914040A (pt) * | 1998-09-22 | 2002-01-15 | Kyowa Hakko Kogyo Kk | Derivados de [1,2,4]triazolo[1,5-c]pirimidina e seu uso, medicamento, antagonista, agente para prevenir ou tratar doenças, bem como processo para prevenção ou tratamento de distúrbios |
| US6355653B1 (en) | 1999-09-06 | 2002-03-12 | Hoffmann-La Roche Inc. | Amino-triazolopyridine derivatives |
| JP2002037787A (ja) * | 2000-05-16 | 2002-02-06 | Kyowa Hakko Kogyo Co Ltd | ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体の製造法 |
| JP4574112B2 (ja) | 2000-05-26 | 2010-11-04 | シェーリング コーポレイション | アデノシンａ２ａレセプターアンタゴニスト |
| JP4545437B2 (ja) | 2001-10-15 | 2010-09-15 | シェーリング コーポレイション | アデノシンａ２ａ受容体アンタゴニストとしてのイミダゾ（４，３−ｅ）−１，２，４−トリアゾロ（１，５−ｃ）ピリミジン |
| MXPA04005158A (es) * | 2001-11-30 | 2004-08-11 | Schering Corp | Antagonistas receptores de adenosina a2a biciclica de (1.2.4]- triazol. |
-
2002
- 2002-11-26 MX MXPA04005158A patent/MXPA04005158A/es active IP Right Grant
- 2002-11-26 US US10/304,939 patent/US6875772B2/en not_active Expired - Lifetime
- 2002-11-26 AT AT02789893T patent/ATE358130T1/de not_active IP Right Cessation
- 2002-11-26 KR KR1020047007953A patent/KR20050044600A/ko not_active Withdrawn
- 2002-11-26 WO PCT/US2002/037915 patent/WO2003048163A1/en not_active Ceased
- 2002-11-26 CA CA002468658A patent/CA2468658C/en not_active Expired - Fee Related
- 2002-11-26 HU HU0402324A patent/HUP0402324A3/hu unknown
- 2002-11-26 AU AU2002352933A patent/AU2002352933A1/en not_active Abandoned
- 2002-11-26 ES ES02789893T patent/ES2283625T3/es not_active Expired - Lifetime
- 2002-11-26 EP EP02789893A patent/EP1453836B1/en not_active Expired - Lifetime
- 2002-11-26 CN CNA028239679A patent/CN1688581A/zh active Pending
- 2002-11-26 JP JP2003549353A patent/JP4429724B2/ja not_active Expired - Fee Related
- 2002-11-26 IL IL16157302A patent/IL161573A0/xx unknown
- 2002-11-26 DE DE60219196T patent/DE60219196T2/de not_active Expired - Lifetime
- 2002-11-27 TW TW091134487A patent/TW200300689A/zh unknown
- 2002-11-27 AR ARP020104562A patent/AR037681A1/es unknown
- 2002-11-28 PE PE2002001149A patent/PE20030653A1/es not_active Application Discontinuation
-
2004
- 2004-05-27 ZA ZA200404168A patent/ZA200404168B/en unknown
- 2004-10-26 US US10/973,642 patent/US7078408B2/en not_active Expired - Lifetime
-
2009
- 2009-10-26 JP JP2009245977A patent/JP2010018634A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050044600A (ko) | 2005-05-12 |
| US6875772B2 (en) | 2005-04-05 |
| JP4429724B2 (ja) | 2010-03-10 |
| HUP0402324A2 (hu) | 2005-02-28 |
| HK1064097A1 (en) | 2005-01-21 |
| US20030191130A1 (en) | 2003-10-09 |
| DE60219196D1 (de) | 2007-05-10 |
| TW200300689A (en) | 2003-06-16 |
| JP2005511697A (ja) | 2005-04-28 |
| ES2283625T3 (es) | 2007-11-01 |
| AR037681A1 (es) | 2004-12-01 |
| WO2003048163A1 (en) | 2003-06-12 |
| EP1453836B1 (en) | 2007-03-28 |
| HUP0402324A3 (en) | 2008-09-29 |
| CA2468658A1 (en) | 2003-06-12 |
| ATE358130T1 (de) | 2007-04-15 |
| DE60219196T2 (de) | 2008-01-03 |
| JP2010018634A (ja) | 2010-01-28 |
| PE20030653A1 (es) | 2003-08-04 |
| IL161573A0 (en) | 2004-09-27 |
| MXPA04005158A (es) | 2004-08-11 |
| CA2468658C (en) | 2009-04-14 |
| US7078408B2 (en) | 2006-07-18 |
| AU2002352933A1 (en) | 2003-06-17 |
| EP1453836A1 (en) | 2004-09-08 |
| CN1688581A (zh) | 2005-10-26 |
| US20050113380A1 (en) | 2005-05-26 |
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