KR100822602B1 - 페닐-치환된 사이클로프로판아민 화합물 - Google Patents
페닐-치환된 사이클로프로판아민 화합물 Download PDFInfo
- Publication number
- KR100822602B1 KR100822602B1 KR1020067027016A KR20067027016A KR100822602B1 KR 100822602 B1 KR100822602 B1 KR 100822602B1 KR 1020067027016 A KR1020067027016 A KR 1020067027016A KR 20067027016 A KR20067027016 A KR 20067027016A KR 100822602 B1 KR100822602 B1 KR 100822602B1
- Authority
- KR
- South Korea
- Prior art keywords
- triazolo
- formula
- amino
- pyrimidin
- apci
- 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 - Lifetime
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- -1 Phenyl-substituted cyclopropanamine compounds Chemical class 0.000 title claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 114
- 238000000034 method Methods 0.000 abstract description 45
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- 239000003814 drug Substances 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 6
- GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 59
- 239000000047 product Substances 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 229940093499 ethyl acetate Drugs 0.000 description 28
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
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- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 5
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- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 description 4
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- COEHCPYENSUXFK-WDEREUQCSA-N tert-butyl n-[(1r,4s)-4-hydroxycyclopent-2-en-1-yl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)[C@@H]1C[C@H](O)C=C1 COEHCPYENSUXFK-WDEREUQCSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9804211A SE9804211D0 (sv) | 1998-12-04 | 1998-12-04 | Novel compounds |
| SE9804211-2 | 1998-12-04 | ||
| SE9901271A SE9901271D0 (sv) | 1999-04-09 | 1999-04-09 | Novel compounds |
| SE9901271-8 | 1999-04-09 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067015291A Division KR100776484B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로[4,5-ｄ]피리미딘 화합물 |
Publications (2)
| Publication Number | Publication Date |
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| KR20070007971A KR20070007971A (ko) | 2007-01-16 |
| KR100822602B1 true KR100822602B1 (ko) | 2008-04-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020067015291A Expired - Lifetime KR100776484B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로[4,5-ｄ]피리미딘 화합물 |
| KR1020017006907A Expired - Lifetime KR100742924B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로 [4,5-ｄ]피리미딘 화합물 |
| KR1020077014185A Expired - Lifetime KR100764417B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로[4,5-ｄ]피리미딘 화합물 |
| KR1020067027016A Expired - Lifetime KR100822602B1 (ko) | 1998-12-04 | 1999-12-02 | 페닐-치환된 사이클로프로판아민 화합물 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020067015291A Expired - Lifetime KR100776484B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로[4,5-ｄ]피리미딘 화합물 |
| KR1020017006907A Expired - Lifetime KR100742924B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로 [4,5-ｄ]피리미딘 화합물 |
| KR1020077014185A Expired - Lifetime KR100764417B1 (ko) | 1998-12-04 | 1999-12-02 | 신규한 트리아졸로[4,5-ｄ]피리미딘 화합물 |
Country Status (36)
Families Citing this family (126)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI229674B (en) | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| SE9903290D0 (sv) | 1999-09-15 | 1999-09-15 | Astra Pharma Prod | Novel compounds |
| SE9904129D0 (sv) | 1999-11-15 | 1999-11-15 | Astra Pharma Prod | Novel compounds |
| SE9904377D0 (sv) * | 1999-12-01 | 1999-12-01 | Astra Pharma Prod | Pharmaceutical combinations |
| GB0013407D0 (en) * | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Forms of a chemical compound |
| AR028110A1 (es) * | 2000-06-02 | 2003-04-23 | Astrazeneca Ab | Nuevo proceso |
| GB0013488D0 (en) * | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Chemical compound |
| US6897201B2 (en) | 2000-08-21 | 2005-05-24 | Inspire Pharmaceuticals, Inc. | Compositions and methods for the treatment of glaucoma or ocular hypertension |
| US7018985B1 (en) | 2000-08-21 | 2006-03-28 | Inspire Pharmaceuticals, Inc. | Composition and method for inhibiting platelet aggregation |
| US7452870B2 (en) | 2000-08-21 | 2008-11-18 | Inspire Pharmaceuticals, Inc. | Drug-eluting stents coated with P2Y12 receptor antagonist compound |
| US7115585B2 (en) | 2000-08-21 | 2006-10-03 | Inspire Pharmaceuticals, Inc. | Compositions for treating epithelial and retinal tissue diseases |
| US7132408B2 (en) | 2000-08-21 | 2006-11-07 | Inspire Pharmaceuticals, Inc. | Composition and method for inhibiting platelet aggregation |
| SE0101932D0 (sv) * | 2001-05-31 | 2001-05-31 | Astrazeneca Ab | Pharmaceutical combinations |
| US7435724B2 (en) | 2002-02-27 | 2008-10-14 | Inspire Pharmaceutical, Inc. | Degradation-resistant mononucleoside phosphate compounds |
| KR20060041254A (ko) | 2003-07-24 | 2006-05-11 | 아스텔라스세이야쿠 가부시키가이샤 | 퀴놀론 유도체 또는 그의 염 |
| SE0400873D0 (sv) * | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
| SE0401001D0 (sv) | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
| EP1598354A1 (en) * | 2004-05-18 | 2005-11-23 | Vasopharm Biotech GmbH | Compounds containing a N-heteroaryl moiety linked to fused ring moieties for the inhibition of NAD(P)H oxidases and platelet activation |
| WO2007020935A1 (ja) * | 2005-08-17 | 2007-02-22 | Ono Pharmaceutical Co., Ltd. | Ｐ２ｙ１２受容体および／またはｐ２ｙ１４受容体ブロッカーを含有してなる疼痛治療剤 |
| TWI391378B (zh) | 2006-03-16 | 2013-04-01 | Astellas Pharma Inc | 喹啉酮衍生物或其製藥學上可被容許之鹽 |
| GB0615620D0 (en) | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | A process for the preparation of optically active intermediates |
| TWI482772B (zh) | 2006-08-21 | 2015-05-01 | Astrazeneca Ab | 適合口服且包含三唑并[4,5-d]嘧啶衍生物之組合物 |
| WO2008024044A1 (en) * | 2006-08-21 | 2008-02-28 | Astrazeneca Ab | Compositions, suitable for oral administration, comprising a triazolo [4, 5] pyrimidin derivate |
| JP2010508350A (ja) | 2006-10-31 | 2010-03-18 | ヤンセン ファーマシューティカ エヌ．ベー． | Ａｄｐｐ２ｙ１２レセプターアンタゴニストとしてのトリアゾロピリミジン誘導体 |
| TWI496776B (zh) * | 2007-11-15 | 2015-08-21 | Astrazeneca Ab | 製備(3aR,4S,6R,6aS)-6-胺基-2,2-二甲基四氫-3aH-環戊并[d][1,3]二氧雜環戊烯-4-醇之純非對映異構性之二苯甲醯-L-酒石酸鹽之方法 |
| UA100864C2 (uk) * | 2007-12-03 | 2013-02-11 | Астразенека Аб | Спосіб лікування або запобігання аневризмі черевної аорти |
| TWI389913B (zh) * | 2008-09-08 | 2013-03-21 | Lg Life Sciences Ltd | 并合雜環化合物 |
| SI2340252T1 (sl) | 2008-09-09 | 2016-02-29 | Astrazeneca Ab | Postopek priprave (1S-)1-alfa, 2-alfa, 3-beta(1S*,2R*)5-beta))-3-(7-(2-(3,4-difluorofenil)-ciklopropilamino)-5- (propiltio)-3H-1,2,3-triazolo(4,5-D)pirimidin-3-il)-5-(2-hidroksietoksi) ciklopentan-1,2-diola in njegovih vmesnih spojin |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| WO2010084160A1 (en) | 2009-01-21 | 2010-07-29 | Oryzon Genomics S.A. | Phenylcyclopropylamine derivatives and their medical use |
| CA2768043A1 (en) | 2009-07-27 | 2011-02-10 | Auspex Pharmaceuticals, Inc. | Cyclopropyl modulators of p2y12 receptor |
| EP2305376A1 (en) | 2009-09-23 | 2011-04-06 | Lonza Ltd. | Process and catalyst for the catalytic hydrogenation of aromatic and heteroaromatic nitro compounds |
| MX338041B (es) | 2009-09-25 | 2016-03-30 | Oryzon Genomics Sa | Inhibidores de demetilasa-1 especificos de lisina y su uso. |
| WO2011042217A1 (en) | 2009-10-09 | 2011-04-14 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
| WO2011067571A1 (en) | 2009-12-03 | 2011-06-09 | Astrazeneca Ab | Co - crystals of a triazolo [4,5 - d] pyrimidine platelet aggregation inhibitor |
| ES2548845T3 (es) | 2009-12-23 | 2015-10-21 | Ratiopharm Gmbh | Forma de dosificación farmacéutica sólida de ticagrelor y ácido acetilsalicílico |
| AU2011216991A1 (en) | 2010-02-16 | 2012-08-30 | Actavis Group Ptc Ehf | Improved processes for preparing ticagrelor intermediate, 4,6-dichloro-5-nitro-2-(propylthio)pyrimidine |
| WO2011106105A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| AU2011244325B2 (en) | 2010-04-19 | 2015-12-17 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| EP2560939A2 (en) | 2010-04-20 | 2013-02-27 | Actavis Group Ptc Ehf | Novel process for preparing phenylcyclopropylamine derivatives using novel intermediates |
| JP2013530209A (ja) | 2010-06-30 | 2013-07-25 | アクタビス・グループ・ピーティーシー・イーエイチエフ | フェニルシクロプロピルアミン誘導体の新規調製方法及びチカグレロルを調製するためのそれらの使用 |
| ES2674747T3 (es) | 2010-07-29 | 2018-07-03 | Oryzon Genomics, S.A. | Inhibidores de demetilasa LSD1 basados en arilciclopropilamina y sus usos médicos |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| US9061966B2 (en) | 2010-10-08 | 2015-06-23 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012063126A2 (en) | 2010-11-09 | 2012-05-18 | Actavis Group Ptc Ehf | Improved processes for preparing pure (3ar,4s,6r,6as)-6-amino-2,2-dimethyltetrahdro-3ah-cyclopenta[d] [1,3]-dioxol-4-ol and its key starting material |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| US20130317220A1 (en) * | 2010-12-20 | 2013-11-28 | Actavis Group Ptc Ehf | NOVEL PROCESSES FOR PREPARING TRIAZOLO[4, 5-d]PYRIMIDINE DERIVATIVES AND INTERMEDIATES THEREOF |
| WO2012107498A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| CN102653539B (zh) * | 2011-03-01 | 2014-09-17 | 秦引林 | 一种抗血小板聚集化合物及其药物组合 |
| EP2694514A2 (en) | 2011-04-06 | 2014-02-12 | Teva Pharmaceutical Industries Ltd. | New intermediates and processes for preparing ticagrelor |
| CN102731510B (zh) * | 2011-04-07 | 2015-12-16 | 博瑞生物医药（苏州）股份有限公司 | 替卡格雷的衍生物、制备方法及其药物用途 |
| CZ2011229A3 (cs) * | 2011-04-19 | 2012-08-15 | Zentiva, K.S. | Opticky aktivní soli (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyklopenta-[d][1,3]dioxol-4-olu a zpusob jejich prípravy |
| SG194585A1 (en) * | 2011-05-13 | 2013-12-30 | Astrazeneca Ab | A process for the preparation of benzyl [(3as,4r,6s,6ar)-6-hydroxy-2,2-dimethyltetrahydro-3ah-cyclopenta[d][1,3]dioxol]-4-yl]carbamate and intermediates in theprocess |
| US20140329833A1 (en) * | 2011-05-19 | 2014-11-06 | Oryzon Genomics, S.A | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| US20140296255A1 (en) * | 2011-05-19 | 2014-10-02 | Oryzong Genomics, S.A. | Lysine demethylase inhibitors for thrombosis and cardiovascular diseases |
| CN103764149A (zh) | 2011-06-01 | 2014-04-30 | 阿斯利康(瑞典)有限公司 | 新型替卡格雷共晶 |
| US20140206867A1 (en) | 2011-06-15 | 2014-07-24 | Actavis Group Ptc Ehf | Process for Preparing Cyclopentylamine Derivatives and Intermediates Thereof |
| CN102924457A (zh) * | 2011-08-12 | 2013-02-13 | 上海恒瑞医药有限公司 | 三唑并嘧啶类衍生物、其制备方法及其用途 |
| WO2013037942A1 (en) | 2011-09-14 | 2013-03-21 | Lek Pharmaceuticals D.D. | Synthesis of triazolopyrimidine compounds |
| EP2570405A1 (en) | 2011-09-14 | 2013-03-20 | LEK Pharmaceuticals d.d. | Synthesis of Triazolopyrimidine Compounds |
| EP4074695A1 (en) | 2011-10-20 | 2022-10-19 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| BR112014009306B1 (pt) | 2011-10-20 | 2021-07-20 | Oryzon Genomics S.A. | Compostos de (hetero)aril ciclopropilamina como inibidores de lsd1 |
| EP2586773A1 (en) | 2011-10-27 | 2013-05-01 | LEK Pharmaceuticals d.d. | Synthesis of Triazolopyrimidine Compounds |
| HUE036244T2 (hu) * | 2011-10-27 | 2018-06-28 | Lek Pharmaceuticals | Triazolo-pirimidin vegyületek szintézise |
| EP2589587A1 (en) | 2011-11-04 | 2013-05-08 | Chemo Ibérica, S.A. | Synthesis of nitrogen substituted cyclopropanes |
| BR112014013085A2 (pt) | 2011-11-30 | 2017-06-13 | Actavis Group Ptc Ehf | forma cristalina do ticagrelor, processo para a preparação da forma cristalina do ticagrelor, composição farmacêutica e processo para preparar uma composição farmacêutica |
| CN104114542B (zh) * | 2011-12-23 | 2017-11-14 | 力奇制药公司 | 三唑并嘧啶化合物的合成 |
| EP2607355A1 (en) * | 2011-12-23 | 2013-06-26 | LEK Pharmaceuticals d.d. | Synthesis of triazolopyrimidine compounds |
| EP2628721A1 (en) | 2012-02-20 | 2013-08-21 | LEK Pharmaceuticals d.d. | Synthesis of 2-(3,4-difluorophenyl)cyclopropanecarboxylic acid |
| CN104603098B (zh) | 2012-03-30 | 2016-06-29 | 桑多斯股份公司 | 2-(3,4-二氟苯基)环丙胺衍生物和盐的合成 |
| EP2644590A1 (en) | 2012-03-30 | 2013-10-02 | LEK Pharmaceuticals d.d. | Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts |
| US9233966B2 (en) | 2012-04-05 | 2016-01-12 | Dr. Reddy's Laboratories Limited | Preparation of ticagrelor |
| WO2013163892A1 (en) * | 2012-05-02 | 2013-11-07 | Sunshine Lake Pharma Co., Ltd. | Novel triazolo pyrimidine compounds and a process of preparation thereof |
| CN102659815B (zh) * | 2012-05-04 | 2013-07-17 | 开原亨泰制药股份有限公司 | 一种制备选择性抗凝血药替卡格雷及其中间体的方法 |
| EP2666771A1 (en) | 2012-05-24 | 2013-11-27 | LEK Pharmaceuticals d.d. | Synthesis of Aminocyclopentanetriol Derivatives |
| ITMI20121142A1 (it) * | 2012-06-28 | 2013-12-29 | Chemo Iberica Sa | Processo chemoenzimatico per la produzione di fenil ciclopropilammine |
| BR112014032085A2 (pt) | 2012-06-29 | 2017-06-27 | Zentiva Ks | solvato de ticagrelor, processos para a preparação de um solvato e para a preparação de um cocristal, cocristal de ticagrelor, e, usos de um solvato e de um cocristal |
| CN104640864B (zh) * | 2012-07-04 | 2016-11-16 | 力奇制药公司 | 替格瑞洛与二价金属盐的加合物 |
| CN103626743B (zh) * | 2012-08-23 | 2018-06-08 | 广东东阳光药业有限公司 | 替卡格雷的新型中间体及其制备方法 |
| CN102875537A (zh) * | 2012-09-10 | 2013-01-16 | 常州制药厂有限公司 | 一种新的抗血栓药物的制备方法 |
| CZ2012705A3 (cs) | 2012-10-16 | 2014-04-23 | Zentiva, K.S. | Pevná orální farmaceutická formulace obsahující ticagrelor |
| WO2014083139A1 (en) | 2012-11-29 | 2014-06-05 | Actavis Group Ptc Ehf | Novel amorphous form of ticagrelor |
| WO2014102830A1 (en) | 2012-12-31 | 2014-07-03 | Megafine Pharma (P) Ltd. | A process for preparation of ticagrelor and intermediates thereof |
| CN104045620B (zh) * | 2013-03-12 | 2017-05-10 | 博瑞生物医药（苏州）股份有限公司 | 一种替卡格雷中间体的制备方法 |
| CZ307217B6 (cs) | 2013-03-14 | 2018-04-04 | Zentiva, K.S. | Zlepšený způsob výroby a nové intermediáty syntézy ticagreloru |
| IN2013MU01111A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 2013-03-25 | 2015-05-01 | Glenmark Generics Ltd | |
| ITMI20130487A1 (it) | 2013-03-29 | 2014-09-30 | Chemo Res S L | Alchilazione selettiva di ciclopentilalcoli |
| CN104098553B (zh) | 2013-04-10 | 2017-11-28 | 江苏恒瑞医药股份有限公司 | 替格瑞洛的中间体及其制备方法和替格瑞洛的制备方法 |
| EP2813216A1 (en) | 2013-06-10 | 2014-12-17 | Zentiva, a.s. | Stabilized amorphous ticagrelor |
| WO2014170026A1 (en) | 2013-04-18 | 2014-10-23 | Zentiva, K.S. | Stabilized amorphous ticagrelor |
| CN104230818B (zh) * | 2013-06-06 | 2018-01-12 | 郝聪梅 | 替卡格雷中间体的改进制备方法 |
| EP2816043A1 (en) | 2013-06-21 | 2014-12-24 | LEK Pharmaceuticals d.d. | Spherical ticagrelor particles |
| WO2014206187A1 (zh) | 2013-06-24 | 2014-12-31 | 苏州明锐医药科技有限公司 | 替卡格雷及其中间体的制备方法 |
| CN104250251B (zh) * | 2013-06-25 | 2017-05-17 | 上海京新生物医药有限公司 | 一种替格瑞洛的制备方法 |
| WO2015001489A1 (en) | 2013-07-01 | 2015-01-08 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of ticagrelor |
| CZ2013866A3 (cs) | 2013-11-08 | 2015-05-20 | Zentiva, K.S. | Způsob výroby a nová krystalická forma intermediátu syntézy ticagreloru |
| WO2015110952A1 (en) | 2014-01-21 | 2015-07-30 | Wockhardt Limited | Solid oral pharmaceutical compositions comprising ticagrelor or salt thereof |
| CN103992323B (zh) * | 2014-04-18 | 2017-03-29 | 南通常佑药业科技有限公司 | 一种替格瑞洛的制备方法 |
| WO2015162630A1 (en) | 2014-04-25 | 2015-10-29 | Anlon Chemical Research Organization | Novel processes for preparing triazolo [4,5-d]- pyrimidines, including ticagrelor, vianew intermediates and new route of synthesis. |
| DE102014108210A1 (de) | 2014-06-11 | 2015-12-17 | Dietrich Gulba | Rodentizid |
| WO2015193165A1 (en) | 2014-06-18 | 2015-12-23 | Flamma Spa | Process for the preparation of triazolo[4,5-d] pyrimidine cyclopentane compounds |
| CN105272985B (zh) * | 2014-06-24 | 2017-11-21 | 珠海联邦制药股份有限公司 | 三唑并[4,5‑d]嘧啶化合物及其合成方法、用途、组合物 |
| WO2016001851A1 (en) * | 2014-07-02 | 2016-01-07 | Dr. Reddy's Laboratories Limited | Preparation of ticagrelor |
| EP3201235A1 (en) * | 2014-10-01 | 2017-08-09 | Medimmune Limited | Antibodies to ticagrelor and methods of use |
| WO2016116942A1 (en) | 2015-01-20 | 2016-07-28 | Anlon Chemical Research Organization | Novel pharmaceutical compounds comprising ticagrelor with salts of aspirin |
| CN105985346B (zh) * | 2015-03-06 | 2019-10-18 | 苏州朗科生物技术股份有限公司 | 一种新的替格瑞洛化合物制备方法及其中间体化合物 |
| US9789087B2 (en) | 2015-08-03 | 2017-10-17 | Thomas Jefferson University | PAR4 inhibitor therapy for patients with PAR4 polymorphism |
| CN105237540B (zh) * | 2015-09-21 | 2017-10-03 | 南京正大天晴制药有限公司 | 一种替格瑞洛有关物质的制备方法、检测方法及用途 |
| US20190002471A1 (en) | 2016-01-05 | 2019-01-03 | Amneal Pharmaceuticals Company Gmbh | Crystalline Form Of Ticagrelor |
| TR201601835A2 (tr) | 2016-02-12 | 2017-08-21 | Ali Raif Ilac Sanayi Ve Ticaret Anonim Sirketi | Ti̇kagrelor i̇çeren formülasyonlar i̇çi̇n üreti̇m yöntemi̇ |
| US20170296666A1 (en) | 2016-04-18 | 2017-10-19 | Amneal Pharmaceuticals Company Gmbh | Stable Pharmaceutical Composition Of Amorphous Ticagrelor |
| PL3445338T3 (pl) | 2016-04-21 | 2025-03-31 | Astrazeneca Ab | Tabletki rozpadające się w jamie ustnej |
| CA3034802A1 (en) * | 2016-08-26 | 2018-03-01 | Mitsubishi Tanabe Pharma Corporation | Bicyclic nitrogenated heterocyclic compound |
| EP3292867B1 (en) * | 2016-09-09 | 2019-05-15 | Université de Liège | Triazolo(4,5-d)pyrimidine derivatives for use in the prevention and treatment of bacterial infection |
| US10905691B2 (en) | 2016-09-09 | 2021-02-02 | Université de Liège | Use of triazolo(4,5-d)pyrimidine derivatives for prevention and treatment of bacterial infection |
| CN107814772A (zh) * | 2017-11-24 | 2018-03-20 | 常州沃腾化工科技有限公司 | 4,6‑二氯‑5‑氨基‑2‑丙硫基嘧啶酯的精制方法 |
| EP3527571A1 (en) * | 2018-02-14 | 2019-08-21 | Université de Liège | Pyrimidine derivatives for prevention and treatment of bacterial infection |
| WO2020021110A1 (en) | 2018-07-27 | 2020-01-30 | Krka, D.D., Novo Mesto | Pharmaceutical composition of ticagrelor |
| CN109761785A (zh) * | 2019-02-16 | 2019-05-17 | 安徽诺全药业有限公司 | 一种(1r，2r）-2-(3,4-二氟苯基)环丙烷羧酸的合成方法 |
| GB201910656D0 (en) | 2019-07-25 | 2019-09-11 | Univ Liege | New use of triazolo(4,5-d)Pyrimidine deerivatives |
| EP3919497A1 (en) | 2020-06-04 | 2021-12-08 | Zaklady Farmaceutyczne Polpharma S.A. | Process for the preparation of ticagrelor |
| CN112876485A (zh) * | 2021-01-25 | 2021-06-01 | 郭丽伟 | 一种用于治疗子宫平滑肌高频率强直性收缩相关疾病的化合物 |
| EP4070658A1 (de) | 2021-04-06 | 2022-10-12 | BIORoxx GmbH | Verwendung von blutgerinnungshemmenden verbindungen als rodentizide |
| WO2023213198A1 (zh) * | 2022-05-04 | 2023-11-09 | 华东师范大学 | 芳香稠环化合物作为trek-1激活剂的用途、包含其的药物组合物、镇痛剂 |
| CN119080782A (zh) * | 2024-10-10 | 2024-12-06 | 重庆普佑生物医药有限公司 | 替卡格雷的合成方法 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3106578A (en) | 1960-09-16 | 1963-10-08 | Smith Kline French Lab | Nu-phenethyl-2-phenylcyclopropylamine derivatives |
| SE329623B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-08 | 1970-10-19 | C F Boehringer Soehne Gmbh | |
| DE1670265A1 (de) | 1967-08-25 | 1971-01-28 | Boehringer Mannheim Gmbh | 2-Amino-Adenosinderivate und Verfahren zu deren Herstellung |
| CH558137A (de) | 1971-05-17 | 1975-01-31 | Ciba Geigy Ag | Mittel zur beeinflussung des pflanzenwachstums. |
| US4016204A (en) * | 1975-10-31 | 1977-04-05 | Nelson Research & Development Company | Method of synthesis of trans-2-phenylcyclopropylamine |
| US4543255A (en) | 1984-05-10 | 1985-09-24 | Southern Research Institute | Carbocyclic analogs of purine 2'-deoxyribofuranosides |
| US4742064A (en) | 1985-09-10 | 1988-05-03 | Regents Of The University Of Minnesota | Antiviral carbocyclic analogs of xylofuranosylpurines |
| DE3901502C2 (de) | 1988-01-20 | 2002-06-13 | Univ Minnesota | Didesoxydehydrocarbocyclische Nucleoside, diese enthaltende pharmazeutische Formulierungen und Pyrimidinylamino-cyclopentenylcarbinol-Derivate |
| EP0452360A4 (en) | 1988-12-12 | 1992-05-20 | Peter M. Palese | Methods and compositions for the prophylaxis and treatment of hepatitis b virus infections |
| US5110933A (en) | 1989-11-13 | 1992-05-05 | Board Of Regents Of Oklahoma State University | Salts of 3-azabicyclo[3.3.1]nonanes as antiarrhythmic agents, and precursors thereof |
| US5652366A (en) | 1990-09-25 | 1997-07-29 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | DI (1R)-(-)camphosulfonic acid) salt, preparation thereof and use thereof |
| WO1992012718A1 (en) | 1991-01-23 | 1992-08-06 | Gensia, Inc. | Adenosine kinase inhibitors |
| DK0508687T3 (da) | 1991-04-06 | 1996-02-05 | Astra Pharma Prod | ATP-analoger |
| EP0521463A3 (en) | 1991-07-04 | 1993-04-14 | Hoechst Aktiengesellschaft | Substituted cyclic cycloalkyltriols, process, intermediates for their preparation and their use as antiviral and antiparasitic agents |
| FI101150B (fi) | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| US5817660A (en) | 1991-12-06 | 1998-10-06 | Hoechst Marion Roussel, Inc. | Trans cyclopentanyl purine analogs useful as immunosuppressants |
| TW224044B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| US5338725A (en) | 1992-06-30 | 1994-08-16 | The Research Foundation Of The State University Of New York | Anti-aggregatory agents for platelets |
| IL108523A0 (en) | 1993-02-03 | 1994-05-30 | Gensia Inc | Pharmaceutical compositions containing adenosine kinase inhibitors for preventing or treating conditions involving inflammatory responses and pain |
| KR100315612B1 (ko) | 1993-02-10 | 2002-06-20 | 추후제출 | N-알킬-2-치환아데노신트리포스페이트동족체 |
| US5688774A (en) | 1993-07-13 | 1997-11-18 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| US5620676A (en) | 1994-03-08 | 1997-04-15 | The United States Of America As Represented By The Department Of Health And Human Services | Biologically active ATP analogs |
| US5831099A (en) | 1995-03-10 | 1998-11-03 | The United States Of America As Represented By The Secretary Of The Army | Compounds of 1,5-disubstituted-3,7 diaza bicyclo 3.3.0! octanes and products containing the same |
| US5712258A (en) | 1995-03-23 | 1998-01-27 | The Trustees Of The University Of Pennsylvania | Inotropic ADP and ATP analogues and their pharmaceutical compositions |
| US6143749A (en) | 1995-06-07 | 2000-11-07 | Abbott Laboratories | Heterocyclic substituted cyclopentane compounds |
| TW427996B (en) | 1995-07-11 | 2001-04-01 | Astra Pharma Prod | Novel triazolopyrimidines and their use as medicaments |
| EP0864572B1 (en) | 1995-09-01 | 2001-04-25 | Hokuriku Seiyaku Co., Ltd. | Crystal of hydrate and process for preparation thereof |
| CA2235627C (en) | 1995-11-21 | 2010-08-10 | Euroscreen S.A. | Receptor and nucleic acid molecule encoding said receptor |
| US5948437A (en) | 1996-05-23 | 1999-09-07 | Zeneca Limited | Pharmaceutical compositions using thiazepine |
| AU5501598A (en) | 1996-12-20 | 1998-07-17 | Astra Pharmaceuticals Limited | Triazolo{4,5-(d)}pyrimidinyl derivatives and their use as medicaments |
| JPH10258654A (ja) | 1997-03-18 | 1998-09-29 | Delta Tsuuring:Kk | リクライニングシート |
| SE9702772D0 (sv) * | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| SE9702773D0 (sv) | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| TW530058B (en) * | 1997-07-22 | 2003-05-01 | Astra Pharma Prod | Triazolo [4,5-d]pyrimidine compounos and their use and process for preparation |
| SE9702775D0 (sv) | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| SE9704709D0 (sv) | 1997-12-17 | 1997-12-17 | Astra Ab | Pharmaceutically active compounds |
| TWI229674B (en) | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| EP1063231B1 (en) | 1999-06-21 | 2005-05-11 | Yamamoto Chemicals, Inc. | Polymethine compounds, method of producing the same, and use thereof |
| SE9903759D0 (sv) | 1999-10-18 | 1999-10-18 | Astra Ab | Pharmaceutically active compounds |
| CZ20021615A3 (cs) | 1999-11-12 | 2002-08-14 | Biogen, Inc. | Antagonisty adenosinového receptoru, způsoby jejich přípravy a způsoby jejich pouľití |
| GB0013407D0 (en) | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Forms of a chemical compound |
| US7040429B2 (en) | 2001-10-10 | 2006-05-09 | Invacare Corporation | Wheelchair suspension |
| WO2003053416A1 (en) | 2001-12-21 | 2003-07-03 | Pfizer Products Inc. | Directly compressible formulations of azithromycin |
| TWI482772B (zh) | 2006-08-21 | 2015-05-01 | Astrazeneca Ab | 適合口服且包含三唑并[4,5-d]嘧啶衍生物之組合物 |
| SI2340252T1 (sl) | 2008-09-09 | 2016-02-29 | Astrazeneca Ab | Postopek priprave (1S-)1-alfa, 2-alfa, 3-beta(1S*,2R*)5-beta))-3-(7-(2-(3,4-difluorofenil)-ciklopropilamino)-5- (propiltio)-3H-1,2,3-triazolo(4,5-D)pirimidin-3-il)-5-(2-hidroksietoksi) ciklopentan-1,2-diola in njegovih vmesnih spojin |
| AU2011216991A1 (en) | 2010-02-16 | 2012-08-30 | Actavis Group Ptc Ehf | Improved processes for preparing ticagrelor intermediate, 4,6-dichloro-5-nitro-2-(propylthio)pyrimidine |
| JP2013530209A (ja) | 2010-06-30 | 2013-07-25 | アクタビス・グループ・ピーティーシー・イーエイチエフ | フェニルシクロプロピルアミン誘導体の新規調製方法及びチカグレロルを調製するためのそれらの使用 |
| US20130317220A1 (en) | 2010-12-20 | 2013-11-28 | Actavis Group Ptc Ehf | NOVEL PROCESSES FOR PREPARING TRIAZOLO[4, 5-d]PYRIMIDINE DERIVATIVES AND INTERMEDIATES THEREOF |
| EP2694514A2 (en) | 2011-04-06 | 2014-02-12 | Teva Pharmaceutical Industries Ltd. | New intermediates and processes for preparing ticagrelor |
| US20140206867A1 (en) | 2011-06-15 | 2014-07-24 | Actavis Group Ptc Ehf | Process for Preparing Cyclopentylamine Derivatives and Intermediates Thereof |
| BR112014013085A2 (pt) | 2011-11-30 | 2017-06-13 | Actavis Group Ptc Ehf | forma cristalina do ticagrelor, processo para a preparação da forma cristalina do ticagrelor, composição farmacêutica e processo para preparar uma composição farmacêutica |
| US9233966B2 (en) | 2012-04-05 | 2016-01-12 | Dr. Reddy's Laboratories Limited | Preparation of ticagrelor |
| WO2014083139A1 (en) | 2012-11-29 | 2014-06-05 | Actavis Group Ptc Ehf | Novel amorphous form of ticagrelor |
| WO2014102830A1 (en) | 2012-12-31 | 2014-07-03 | Megafine Pharma (P) Ltd. | A process for preparation of ticagrelor and intermediates thereof |
| WO2014118808A2 (en) | 2013-02-04 | 2014-08-07 | Hetero Research Foundation | Ticagrelor solid dispersion |
| CN104098553B (zh) | 2013-04-10 | 2017-11-28 | 江苏恒瑞医药股份有限公司 | 替格瑞洛的中间体及其制备方法和替格瑞洛的制备方法 |
| WO2014195861A2 (en) | 2013-06-04 | 2014-12-11 | Dr. Reddy’S Laboratories Limited | Preparation of ticagrelor |
| WO2016001851A1 (en) | 2014-07-02 | 2016-01-07 | Dr. Reddy's Laboratories Limited | Preparation of ticagrelor |
| CN107530363A (zh) | 2015-01-27 | 2018-01-02 | 阿斯利康(瑞典)有限公司 | 治疗或预防具有心肌梗塞病史的患者的动脉粥样硬化血栓形成事件的方法 |
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-
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Non-Patent Citations (2)
| Title |
|---|
| Journal of Medicinal Chemistry, 1996, 39(7), 1485-93* |
| Journal of Neural Transmission, supplement, 1994, 41, pp. 155-63* |
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