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
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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
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 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
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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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- 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
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- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
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- 125000000335 thiazolyl 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)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material 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)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
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| US33438501P | 2001-11-30 | 2001-11-30 |
Publications (1)
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| JP (2) | JP4429724B2 (https=) |
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| CN (1) | CN1688581A (https=) |
| AR (1) | AR037681A1 (https=) |
| AT (1) | ATE358130T1 (https=) |
| AU (1) | AU2002352933A1 (https=) |
| CA (1) | CA2468658C (https=) |
| DE (1) | DE60219196T2 (https=) |
| ES (1) | ES2283625T3 (https=) |
| HU (1) | HUP0402324A3 (https=) |
| IL (1) | IL161573A0 (https=) |
| MX (1) | MXPA04005158A (https=) |
| PE (1) | PE20030653A1 (https=) |
| TW (1) | TW200300689A (https=) |
| WO (1) | WO2003048163A1 (https=) |
| ZA (1) | ZA200404168B (https=) |
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| IL161573A0 (en) * | 2001-11-30 | 2004-09-27 | Schering Corp | [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS |
| AR038366A1 (es) | 2001-11-30 | 2005-01-12 | Schering Corp | Compuestos de 1,2,4-triazolo [1,5-c] pirimidinas sustituidas, antagonistas del receptor de adenosina a2a, composiciones farmaceuticas, el uso de dichos compuestos para la manufactura de un medicamento para el tratamiento de enfermedades del sistema nervioso central y un kit que comprende combinacion |
| BR0308347A (pt) * | 2002-03-12 | 2005-01-25 | Wyeth Corp | Processo para fabricação de piperazinas 1,4-dissubstituìdas quirais |
| 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 |
| TWI331036B (en) * | 2002-12-19 | 2010-10-01 | Schering Corp | Adenosine a2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders |
| WO2004092177A1 (en) | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolopyrazines and methods of making and using the same |
| WO2004092173A2 (en) | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | A2a adenosine receptor antagonists |
| WO2004092172A2 (en) * | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosin e receptor antagonists |
| WO2004092170A2 (en) | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolotriazines and pyrazolotriazines useful as a2a adenosine receptor antagon ists |
| 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 |
| US20090124663A1 (en) * | 2005-06-08 | 2009-05-14 | Neurosearch A/S | Novel n-phenyl-piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| TW200803856A (en) | 2005-09-02 | 2008-01-16 | 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 |
| EP2274007B1 (en) | 2008-03-10 | 2016-12-14 | 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 |
| KR102633145B1 (ko) * | 2018-06-26 | 2024-02-05 | 쩌지앙 빔그린 파머슈티컬스, 엘티디 | A2a 수용체 길항제로서의 트리아졸로 트리아진 유도체 |
| WO2020227156A1 (en) * | 2019-05-03 | 2020-11-12 | Nektar Therapeutics | Adenosine 2 receptor antagonists |
| JP2023508182A (ja) * | 2019-12-26 | 2023-03-01 | チェジン ヴィムグリーン ファーマシューティカルズ リミテッド | トリアゾロトリアジン誘導体の疾患治療への応用 |
| 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. |
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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 |
| WO1995003806A1 (en) * | 1993-07-27 | 1995-02-09 | 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 |
| DE69820866T2 (de) * | 1997-03-24 | 2004-12-30 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-c]PYRIMIDIN-DERIVATE |
| 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 |
| AU2639299A (en) * | 1998-02-24 | 1999-09-15 | Kyowa Hakko Kogyo Co. Ltd. | Remedies/preventives for parkinson's disease |
| WO2000017201A1 (en) * | 1998-09-22 | 2000-03-30 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-c]PYRIMIDINE DERIVATIVES |
| 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 |
| DE60110219T2 (de) | 2000-05-26 | 2006-03-09 | Schering Corp. | Adenosin a2a rezeptor antagonisten |
| KR100687954B1 (ko) * | 2001-10-15 | 2007-02-27 | 쉐링 코포레이션 | 아데노신 Ａ2ａ 수용체 길항제로서의이미다조（4,3-ｅ）-1,2,4-트리아졸로（1,5-ｃ） 피리미딘 |
| IL161573A0 (en) * | 2001-11-30 | 2004-09-27 | Schering Corp | [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS |
-
2002
- 2002-11-26 IL IL16157302A patent/IL161573A0/xx unknown
- 2002-11-26 KR KR1020047007953A patent/KR20050044600A/ko not_active Withdrawn
- 2002-11-26 EP EP02789893A patent/EP1453836B1/en not_active Expired - Lifetime
- 2002-11-26 US US10/304,939 patent/US6875772B2/en not_active Expired - Lifetime
- 2002-11-26 MX MXPA04005158A patent/MXPA04005158A/es active IP Right Grant
- 2002-11-26 CN CNA028239679A patent/CN1688581A/zh active Pending
- 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 AU AU2002352933A patent/AU2002352933A1/en not_active Abandoned
- 2002-11-26 HU HU0402324A patent/HUP0402324A3/hu unknown
- 2002-11-26 AT AT02789893T patent/ATE358130T1/de not_active IP Right Cessation
- 2002-11-26 ES ES02789893T patent/ES2283625T3/es not_active Expired - Lifetime
- 2002-11-26 DE DE60219196T patent/DE60219196T2/de not_active Expired - Lifetime
- 2002-11-26 JP JP2003549353A patent/JP4429724B2/ja not_active Expired - Fee Related
- 2002-11-27 AR ARP020104562A patent/AR037681A1/es unknown
- 2002-11-27 TW TW091134487A patent/TW200300689A/zh 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 |
|---|---|
| JP4429724B2 (ja) | 2010-03-10 |
| US20030191130A1 (en) | 2003-10-09 |
| KR20050044600A (ko) | 2005-05-12 |
| ES2283625T3 (es) | 2007-11-01 |
| JP2005511697A (ja) | 2005-04-28 |
| TW200300689A (en) | 2003-06-16 |
| AU2002352933A1 (en) | 2003-06-17 |
| CA2468658C (en) | 2009-04-14 |
| CN1688581A (zh) | 2005-10-26 |
| HK1064097A1 (en) | 2005-01-21 |
| DE60219196D1 (de) | 2007-05-10 |
| EP1453836B1 (en) | 2007-03-28 |
| MXPA04005158A (es) | 2004-08-11 |
| HUP0402324A2 (hu) | 2005-02-28 |
| PE20030653A1 (es) | 2003-08-04 |
| US7078408B2 (en) | 2006-07-18 |
| WO2003048163A1 (en) | 2003-06-12 |
| ATE358130T1 (de) | 2007-04-15 |
| IL161573A0 (en) | 2004-09-27 |
| JP2010018634A (ja) | 2010-01-28 |
| HUP0402324A3 (en) | 2008-09-29 |
| AR037681A1 (es) | 2004-12-01 |
| US6875772B2 (en) | 2005-04-05 |
| EP1453836A1 (en) | 2004-09-08 |
| US20050113380A1 (en) | 2005-05-26 |
| CA2468658A1 (en) | 2003-06-12 |
| DE60219196T2 (de) | 2008-01-03 |
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