TW200300686A - Adenosine A2a receptor antagonists - Google Patents
Adenosine A2a receptor antagonists Download PDFInfo
- Publication number
- TW200300686A TW200300686A TW091134178A TW91134178A TW200300686A TW 200300686 A TW200300686 A TW 200300686A TW 091134178 A TW091134178 A TW 091134178A TW 91134178 A TW91134178 A TW 91134178A TW 200300686 A TW200300686 A TW 200300686A
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- Prior art keywords
- alkyl
- group
- alkoxy
- cvc6
- mmol
- Prior art date
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- 229940123702 Adenosine A2a receptor antagonist Drugs 0.000 title description 2
- 239000002467 adenosine A2a receptor antagonist Substances 0.000 title description 2
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- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 125000002181 pyridoxine group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003942 tert-butylamines Chemical class 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- UBORTCNDUKBEOP-UUOKFMHZSA-N xanthosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(NC(=O)NC2=O)=C2N=C1 UBORTCNDUKBEOP-UUOKFMHZSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- 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
- 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)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33429301P | 2001-11-30 | 2001-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200300686A true TW200300686A (en) | 2003-06-16 |
Family
ID=23306533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091134178A TW200300686A (en) | 2001-11-30 | 2002-11-25 | Adenosine A2a receptor antagonists |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7041666B2 (https=) |
| EP (1) | EP1453835B1 (https=) |
| JP (2) | JP4284181B2 (https=) |
| KR (1) | KR20050044607A (https=) |
| CN (1) | CN1596258A (https=) |
| AR (1) | AR038366A1 (https=) |
| AT (1) | ATE317844T1 (https=) |
| AU (1) | AU2002346572A1 (https=) |
| CA (1) | CA2468681C (https=) |
| DE (1) | DE60209251T2 (https=) |
| ES (1) | ES2258164T3 (https=) |
| HU (1) | HUP0402270A3 (https=) |
| IL (1) | IL161572A0 (https=) |
| MX (1) | MXPA04005156A (https=) |
| PE (1) | PE20030739A1 (https=) |
| TW (1) | TW200300686A (https=) |
| WO (1) | WO2003048164A2 (https=) |
| ZA (1) | ZA200404160B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1544200A1 (en) * | 2002-09-24 | 2005-06-22 | Kyowa Hakko Kogyo Co., Ltd. | 1,2,4 -TRIAZOLO 1,5-c PYRIMIDINE DERIVATIVE |
| JP2006514697A (ja) | 2002-12-19 | 2006-05-11 | 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の使用 |
| US20060106040A1 (en) | 2002-12-19 | 2006-05-18 | Michael Grzelak | Adenosine A2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders |
| US20070010522A1 (en) * | 2003-04-09 | 2007-01-11 | Chi Vu | Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists |
| JP4800216B2 (ja) * | 2003-10-24 | 2011-10-26 | エグゼリクシス， インコーポレイテッド | ｐ７０Ｓ６キナーゼモジュレーターおよび使用方法 |
| AR050926A1 (es) * | 2004-09-03 | 2006-12-06 | Astrazeneca Ab | Derivados de benzamida como inhibidores de la histonadesacetilasa(hdac) |
| 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 |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| US8835631B2 (en) | 2007-05-24 | 2014-09-16 | Mitsubishi Tanabe Pharma Corporation | Therapeutic agent for cerebral infarction |
| JP2010531364A (ja) * | 2007-06-25 | 2010-09-24 | ニューロジェン・コーポレーション | ピペラジニルオキソアルキルテトラヒドロ−β−カルボリンおよび関連類似体 |
| US20100093756A1 (en) * | 2008-10-13 | 2010-04-15 | Berbay J Kent | HETEROARYL SUBSTITUTED THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US20100093764A1 (en) * | 2008-10-13 | 2010-04-15 | Devraj Chakravarty | AMINES AND SULFOXIDES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| KR101211338B1 (ko) | 2008-11-25 | 2012-12-11 | 닛산 지도우샤 가부시키가이샤 | 도전 부재 및 이것을 사용한 고체 고분자형 연료 전지 |
| EP2424840B1 (en) * | 2009-04-27 | 2014-08-06 | Boehringer Ingelheim International GmbH | Cxcr3 receptor antagonists |
| US8952004B2 (en) | 2010-01-07 | 2015-02-10 | Boehringer Ingelheim International Gmbh | CXCR3 receptor antagonists |
| CN103261202B (zh) * | 2010-09-24 | 2016-01-20 | 阿迪维纳斯疗法有限公司 | 作为腺苷受体拮抗剂的稠合三环化合物 |
| WO2012127472A1 (en) * | 2011-03-22 | 2012-09-27 | Mapi Pharma Ltd. | Process and intermediates for the preparation of preladenant and related compounds |
| PL3611174T3 (pl) * | 2017-04-07 | 2022-08-08 | Medshine Discovery Inc. | Pochodne [1,2,4]triazolo[1,5-c]pirymidyny jako inhibitor receptora a2a |
| BR122023024273A2 (pt) * | 2018-02-27 | 2024-02-20 | Incyte Corporation | Compostos imidazopirimidinas e triazolopirimidinas, seus usos, método para inibir uma atividade de um receptor de adenosina e composição farmacêutica dos mesmos |
| CN112105617B (zh) * | 2018-04-28 | 2022-04-05 | 南京明德新药研发有限公司 | 一种三唑并嘧啶类化合物的晶型、盐型及其制备方法 |
| WO2019222677A1 (en) * | 2018-05-18 | 2019-11-21 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| GEP20237548B (en) | 2018-07-05 | 2023-10-10 | Incyte Corp | Fused pyrazine derivatives as a2a /a2b inhibitors |
| AR116315A1 (es) * | 2018-09-12 | 2021-04-21 | Dizal Jiangsu Pharmaceutical Co Ltd | Compuestos de triazolo-pirimidina y usos de los mismos |
| WO2020106560A1 (en) | 2018-11-20 | 2020-05-28 | Merck Sharp & Dohme Corp. | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| KR20210093964A (ko) * | 2018-11-20 | 2021-07-28 | 머크 샤프 앤드 돔 코포레이션 | 치환된 아미노 트리아졸로피리미딘 및 아미노 트리아졸로피라진 아데노신 수용체 길항제, 제약 조성물 및 그의 용도 |
| JP2022511778A (ja) | 2018-11-30 | 2022-02-01 | メルク・シャープ・アンド・ドーム・コーポレーション | アデノシン受容体拮抗薬としての７－、８－及び１０－置換されたアミノトリアゾロキナゾリン誘導体、医薬組成物及びそれらの使用 |
| TW202039496A (zh) | 2018-11-30 | 2020-11-01 | 美商默沙東藥廠 | 做為腺苷受體拮抗劑之9-經取代胺基三唑喹唑啉衍生物、醫藥組合物及其用途 |
| CA3124088A1 (en) | 2018-12-20 | 2020-06-25 | Incyte Corporation | Imidazopyridazine and imidazopyridine compounds as inhibitors of activin receptor-like kinase-2 |
| WO2020128036A1 (en) * | 2018-12-21 | 2020-06-25 | Ryvu Therapeutics S.A. | Modulators of the adenosine a2a receptor |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| 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 |
| EP0666079B1 (en) | 1993-07-27 | 2001-11-07 | 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 |
| IL142128A0 (en) * | 1998-09-22 | 2002-03-10 | Kyowa Hakko Kogyo Kk | [1,2,4] triazolo [1,5-c] pyrimidine derivatives |
| SI1283839T1 (https=) | 2000-05-26 | 2005-08-31 | Schering Corp | |
| JPWO2002079204A1 (ja) * | 2001-03-28 | 2004-07-22 | 協和醗酵工業株式会社 | ８−チアゾリル［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 |
| ES2283625T3 (es) | 2001-11-30 | 2007-11-01 | Schering Corporation | Antagonistas del receptopr a2a de adenosina de (1,2,4)-triazol biciclicos. |
-
2002
- 2002-11-25 PE PE2002001128A patent/PE20030739A1/es not_active Application Discontinuation
- 2002-11-25 TW TW091134178A patent/TW200300686A/zh unknown
- 2002-11-25 AR ARP020104528A patent/AR038366A1/es unknown
- 2002-11-26 AU AU2002346572A patent/AU2002346572A1/en not_active Abandoned
- 2002-11-26 IL IL16157202A patent/IL161572A0/xx unknown
- 2002-11-26 HU HU0402270A patent/HUP0402270A3/hu unknown
- 2002-11-26 DE DE60209251T patent/DE60209251T2/de not_active Expired - Lifetime
- 2002-11-26 CN CNA028239229A patent/CN1596258A/zh active Pending
- 2002-11-26 US US10/304,504 patent/US7041666B2/en not_active Expired - Lifetime
- 2002-11-26 KR KR1020047008031A patent/KR20050044607A/ko not_active Withdrawn
- 2002-11-26 CA CA2468681A patent/CA2468681C/en not_active Expired - Fee Related
- 2002-11-26 JP JP2003549354A patent/JP4284181B2/ja not_active Expired - Fee Related
- 2002-11-26 AT AT02784641T patent/ATE317844T1/de not_active IP Right Cessation
- 2002-11-26 MX MXPA04005156A patent/MXPA04005156A/es active IP Right Grant
- 2002-11-26 ES ES02784641T patent/ES2258164T3/es not_active Expired - Lifetime
- 2002-11-26 WO PCT/US2002/038134 patent/WO2003048164A2/en not_active Ceased
- 2002-11-26 EP EP02784641A patent/EP1453835B1/en not_active Expired - Lifetime
-
2004
- 2004-05-27 ZA ZA200404160A patent/ZA200404160B/en unknown
-
2008
- 2008-06-04 JP JP2008147394A patent/JP2008303217A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2468681C (en) | 2011-01-25 |
| AR038366A1 (es) | 2005-01-12 |
| IL161572A0 (en) | 2004-09-27 |
| US20030212080A1 (en) | 2003-11-13 |
| ES2258164T3 (es) | 2006-08-16 |
| EP1453835B1 (en) | 2006-02-15 |
| JP4284181B2 (ja) | 2009-06-24 |
| US7041666B2 (en) | 2006-05-09 |
| KR20050044607A (ko) | 2005-05-12 |
| EP1453835A2 (en) | 2004-09-08 |
| HUP0402270A3 (en) | 2008-09-29 |
| ATE317844T1 (de) | 2006-03-15 |
| DE60209251D1 (de) | 2006-04-20 |
| JP2005511698A (ja) | 2005-04-28 |
| CA2468681A1 (en) | 2003-06-12 |
| ZA200404160B (en) | 2005-04-08 |
| WO2003048164A3 (en) | 2003-10-16 |
| JP2008303217A (ja) | 2008-12-18 |
| WO2003048164A2 (en) | 2003-06-12 |
| AU2002346572A1 (en) | 2003-06-17 |
| DE60209251T2 (de) | 2006-11-09 |
| HUP0402270A2 (hu) | 2005-02-28 |
| PE20030739A1 (es) | 2003-08-28 |
| CN1596258A (zh) | 2005-03-16 |
| MXPA04005156A (es) | 2004-08-11 |
| HK1064100A1 (en) | 2005-01-21 |
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