KR20030007827A - 시클로프로필 카르복실산 에스테르 및 그의 유도체의 제조방법 - Google Patents
시클로프로필 카르복실산 에스테르 및 그의 유도체의 제조방법 Download PDFInfo
- Publication number
- KR20030007827A KR20030007827A KR1020027016377A KR20027016377A KR20030007827A KR 20030007827 A KR20030007827 A KR 20030007827A KR 1020027016377 A KR1020027016377 A KR 1020027016377A KR 20027016377 A KR20027016377 A KR 20027016377A KR 20030007827 A KR20030007827 A KR 20030007827A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- difluorophenyl
- trans
- preparing
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/20—Compounds containing azido groups with azido groups acylated by carboxylic acids
- C07C247/22—Compounds containing azido groups with azido groups acylated by carboxylic acids with the acylating carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/66—Acyl halides with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (22)
- 하기 화학식 II의 화합물을 -10 ℃ 내지 90 ℃의 온도에서 용매의 존재하에 디메틸술폭소늄 메틸라이드와 접촉시키는 것을 포함하는, 하기 화학식 I의 화합물의 제조 방법.<화학식 I><화학식 II>식 중,R은 1개 이상의 할로겐으로 치환된 페닐이고,Y는 OR1이고, 이 때 R1은 직쇄 알킬, 분지쇄 알킬, 시클로알킬 또는 치환된 비시클로헵틸 기이다.
- 제1항에 있어서,i) 트리메틸술폭소늄 염을 주위 온도 또는 승온에서 디메틸 술폭시드 중의 고상 금속 수산화물과 반응시켜 디메틸술폭소늄 메틸라이드를 제조하는 단계; 및ii) 화학식 II의 화합물을 -10 ℃ 내지 90 ℃의 온도에서 용매의 존재하에디메틸술폭소늄 메틸라이드와 접촉시키는 단계를 포함하는 화학식 I의 화합물의 제조 방법.
- 제2항에 있어서, 금속 수산화물이 수산화나트륨인 방법.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 화학식 II의 화합물은 하기 화학식 III의 화합물을 0 내지 200 ℃의 온도에서 불활성 용매 및 촉매의 존재하에 염소화제와 반응시키고, 이어서 생성된 용액을 승온에서 YH 또는 Y-(여기서, Y는 제1항에 정의된 바와 같다)와 반응시킴으로써 제조되는 것인 방법.<화학식 III>식 중, R은 제1항에 정의된 바와 같다.
- 제4항에 있어서, 화학식 III의 화합물을 0 내지 200 ℃의 온도에서 불활성 용매 및 피리딘의 존재하에 염화티오닐과 반응시키고, 이어서 생성된 용액을 승온에서 YH 또는 Y-(여기서, Y는 제1항에 정의된 바와 같다)와 반응시키는 것인 방법.
- 제1항 내지 제5항 중 어느 한 항에 있어서, YH가 L-멘톨을 나타내는 방법.
- 제4항 내지 제6항 중 어느 한 항에 있어서, 하기 화학식 IV의 화합물을 승온에서 피리딘 및 피페리딘의 존재하에 말론산과 접촉시켜 화학식 III의 화합물을 제조하는 것인 방법.<화학식 IV>식 중, R은 제1항에 정의된 바와 같다.
- 화학식 I의 화합물를 염기 가수분해하는 것을 포함하는 하기 화학식 V의 화합물의 제조 방법.<화학식 V>식 중, R은 제1항에 정의된 바와 같다.
- 제8항에 있어서, 염기 가수분해가 10 내지 100 ℃에서 알칼리 금속 수산화물 및 용매를 사용하여 달성되는 방법.
- 화학식 V의 화합물을 0 내지 200 ℃에서 용매 및 촉매의 존재하에 염화티오닐과 반응시키는 것을 포함하는 하기 화학식 VI의 화합물의 제조 방법.<화학식 VI>식 중, R은 제1항에 정의된 바와 같다.
- 화학식 VI의 화합물을 상 이동 촉매, 수성 탄산칼륨 및 불활성 용매의 존재하에 알칼리 금속 아지드와 반응시키는 것을 포함하는 하기 화학식 VII의 화합물의 제조 방법.<화학식 VII>식 중, R은 제1항에 정의된 바와 같다.
- 화학식 VII의 화합물을 승온에서 톨루엔 중에서 전위(rearrangement)반응시키고, 이어서 승온에서 염산과 반응시키는 것을 포함하는 하기 화학식 VIII의 화합물의 제조 방법.<화학식 VIII>식 중, R은 제1항에 정의된 바와 같다.
- 화학식 VIII의 화합물의 염의 수용액을 pH 10 이상으로 조정하는 것을 포함하는 하기 화학식 IX의 화합물의 제조 방법.<화학식 IX>식 중, R은 제1항에 정의된 바와 같다.
- R-(-)-만델산을 주위 온도 또는 승온에서 제13항 기재의 화학식 IX의 화합물에 첨가하는 것을 포함하는 화학식 IX의 화합물의 만델산 염 화합물을 제조하는 방법.
- 제1항 내지 제14항 중 어느 한 항에 있어서, R이 1개 이상의 불소 원자에 의해 치환된 페닐인 방법.
- 제15항에 있어서, R이 3,4-디플루오로페닐인 방법.
- 제1항 내지 제16항 중 어느 한 항에 있어서, Y가 키랄인 방법.
- 제17항에 있어서, Y가 L-멘톡시인 방법.
- 제1항 내지 제18항 중 어느 한 항에 있어서, 화학식 I의 화합물을 결정화 또는 크로마토그래피 방법으로 분할하여 하기 화학식 Ia의 화합물을 수득하는 것인 방법.<화학식 Ia>식 중, R 및 Y는 제1항에 정의된 바와 같다.
- 제19항에 있어서, 화학식 I의 화합물을 헵탄중으로 추출하고, 이어서 헵탄 추출물로부터 결정함으로써 분할을 수행하는 것인 방법.
- 상기 화학식 I, Ia, II, III, V, Va, VI, VIa, VII, VIIa, VIII, VIIIa, IX 및 IXa의 중간체 화합물.
- (1R,2S,5R)-2-이소프로필-5-메틸시클로헥실 트랜스-2-(3,4-디플루오로페닐)시클로프로판카르복실레이트;(1R,2S,5R)-2-이소프로필-5-메틸시클로헥실 트랜스-(1R,2R)-2-(3,4-디플루오로페닐)시클로프로판 카르복실레이트;(1R,2S,5R)-2-이소프로필-5-메틸시클로헥실 (E)-3-(3,4-디플루오로페닐)-2-프로페노에이트;(E)-3-(3,4-디플루오로페닐)-2-프로펜산;(E)-3-(3,4-디플루오로페닐)-2-프로페노일 클로라이드;트랜스-(1R,2R)-2-(3,4-디플루오로페닐)시클로프로판카르복실산;트랜스-(1R,2R)-2-(3,4-디플루오로페닐)시클로프로판카르보닐 클로라이드;트랜스-(1R,2R)-2-(3,4-디플루오로페닐)시클로프로판카르보닐 아지드;트랜스-(1R,2S)-2-(3,4-디플루오로페닐)시클로프로필 아민; 및트랜스-(1R,2S)-2-(3,4-디플루오로페닐)시클로프로판아미늄(2R)-2-히드록시-2-페닐에타노에이트인 중간체 화합물.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0013487.4 | 2000-06-02 | ||
GB0013487A GB0013487D0 (en) | 2000-06-02 | 2000-06-02 | Novel process |
SE0002101A SE0002101D0 (sv) | 2000-06-06 | 2000-06-06 | Novel Process |
SE0002101-4 | 2000-06-06 | ||
PCT/SE2001/001240 WO2001092200A1 (en) | 2000-06-02 | 2001-05-31 | Process for the preparation of cyclopropyl carboxylic acid esters and derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20030007827A true KR20030007827A (ko) | 2003-01-23 |
KR100755170B1 KR100755170B1 (ko) | 2007-09-04 |
Family
ID=26244412
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020027016377A KR100755170B1 (ko) | 2000-06-02 | 2001-05-31 | 시클로프로필 카르복실산 에스테르 및 그의 유도체의 제조방법 |
Country Status (31)
Country | Link |
---|---|
US (4) | US7122695B2 (ko) |
EP (4) | EP2292591A3 (ko) |
JP (2) | JP4944344B2 (ko) |
KR (1) | KR100755170B1 (ko) |
CN (2) | CN1211344C (ko) |
AR (2) | AR028110A1 (ko) |
AT (1) | ATE386011T1 (ko) |
AU (2) | AU2001262875B2 (ko) |
BG (4) | BG65922B1 (ko) |
BR (2) | BRPI0111329B1 (ko) |
CA (3) | CA2746622C (ko) |
CY (1) | CY1108100T1 (ko) |
CZ (2) | CZ302384B6 (ko) |
DE (1) | DE60132771T2 (ko) |
DK (1) | DK1292561T3 (ko) |
EE (1) | EE05215B1 (ko) |
ES (1) | ES2300331T3 (ko) |
HK (1) | HK1052171B (ko) |
HU (1) | HU230303B1 (ko) |
IL (4) | IL152778A0 (ko) |
IS (1) | IS8828A (ko) |
MX (1) | MXPA02011794A (ko) |
MY (2) | MY140938A (ko) |
NO (1) | NO20025664L (ko) |
NZ (2) | NZ535112A (ko) |
PL (1) | PL205232B1 (ko) |
PT (1) | PT1292561E (ko) |
SI (1) | SI1292561T1 (ko) |
SK (1) | SK287215B6 (ko) |
TW (1) | TWI290549B (ko) |
WO (1) | WO2001092200A1 (ko) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR028110A1 (es) * | 2000-06-02 | 2003-04-23 | Astrazeneca Ab | Nuevo proceso |
JP2006265171A (ja) * | 2005-03-24 | 2006-10-05 | Toyotama Koryo Kk | 香料組成物及び芳香製品の芳香性を改良又は増強する新しい方法 |
GB0615619D0 (en) * | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | Chemical process for preparation of intermediates |
GB0615620D0 (en) * | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | A process for the preparation of optically active intermediates |
US7566722B2 (en) | 2006-10-31 | 2009-07-28 | Janssen Pharmaceutica, N.V. | Triazolopyrimidine derivatives as ADP P2Y12 receptor antagonists |
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 |
EP2560939A2 (en) | 2010-04-20 | 2013-02-27 | Actavis Group Ptc Ehf | Novel process for preparing phenylcyclopropylamine derivatives using novel intermediates |
BR112012033500A2 (pt) * | 2010-06-30 | 2016-11-29 | Actavis Group Hf | processo para a preparação de derivados de fenilciclopropilamina substiuídos, processo de vaso único para a preparação de derivados de fenilciclopropilamina substiuídos, formas de estado sólido de um sal de adição de ácido e processo para a preparação da forma de estado sólido de um sal de adição de ácido |
RS57331B1 (sr) * | 2010-07-29 | 2018-08-31 | Oryzon Genomics Sa | Inhibitori demetilaze za lsd1 zasnovani na arilciklopropilaminu i njihova medicinska upotreba |
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 |
CA2859743A1 (en) | 2010-12-20 | 2012-06-28 | Actavis Group Ptc Ehf | Novel processes for preparing triazolo[4,5-d]pyrimidine derivatives and intermediates thereof |
CN102249929A (zh) * | 2011-05-19 | 2011-11-23 | 博瑞生物医药技术(苏州)有限公司 | 反式-(1r,2s)-2-(3,4-二氟代苯基)环丙胺的合成方法 |
EP2721018A1 (en) | 2011-06-15 | 2014-04-23 | Actavis Group Ptc Ehf | Improved process for preparing cyclopentylamine derivatives and intermediates thereof |
EP2589587A1 (en) | 2011-11-04 | 2013-05-08 | Chemo Ibérica, S.A. | Synthesis of nitrogen substituted cyclopropanes |
EP2628721A1 (en) | 2012-02-20 | 2013-08-21 | LEK Pharmaceuticals d.d. | Synthesis of 2-(3,4-difluorophenyl)cyclopropanecarboxylic acid |
EP2644590A1 (en) | 2012-03-30 | 2013-10-02 | LEK Pharmaceuticals d.d. | Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts |
WO2013144295A1 (en) | 2012-03-30 | 2013-10-03 | Sandoz Ag | 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 |
CN103588674B (zh) * | 2012-08-14 | 2015-02-11 | 上海医药工业研究院 | 一种具有光学活性的环丙烷酰阱化合物、其制备和应用 |
CN102796007B (zh) * | 2012-08-14 | 2014-03-26 | 济南瑞丰医药科技有限公司 | 一种替卡格雷中间体的制备方法 |
CN102863341B (zh) * | 2012-10-22 | 2014-05-07 | 南通大学 | 一种(1r,2s)-2-芳基环丙胺衍生物的化学合成方法 |
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 |
CN103739483B (zh) * | 2013-12-23 | 2015-05-20 | 王桂霞 | 一种反式-(1r,2r)-2-(3,4-二氟苯基)-1-环丙烷甲酸的制备方法 |
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. |
US10011605B2 (en) | 2014-06-18 | 2018-07-03 | Flamma Spa | Process for the preparation of triazolo[4,5-D] pyrimidine cyclopentane compounds |
WO2018020366A1 (en) * | 2016-07-26 | 2018-02-01 | Glaxosmithkline Intellectual Property (No.2) Limited | Crystalline (r)-mandelate salt of (1r,2s)-2-phenylcyclopropylamine |
CN106496178A (zh) * | 2016-10-19 | 2017-03-15 | 青岛辰达生物科技有限公司 | 一种替卡格雷中间体及其制备方法 |
CN107141236B (zh) * | 2017-04-24 | 2019-03-22 | 台州职业技术学院 | 替卡格雷中间体(1r,2r)-2-(3,4-二氟代苯基)环丙烷腈的新合成方法 |
CN108863791B (zh) * | 2018-08-17 | 2023-12-01 | 淄博齐翔腾达化工股份有限公司 | 顺酐回收用溶剂再生装置及其工艺方法 |
CN110894184B (zh) * | 2019-11-25 | 2022-02-18 | 安徽一帆香料有限公司 | 一种基于绿色环保的替格瑞洛中间体的制备方法 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734904A (en) * | 1956-02-14 | Xcxnhxc-nh | ||
GB873018A (en) * | 1958-09-22 | 1961-07-19 | Smith Kline French Lab | Substituted phenylcyclopropylamines |
US3106578A (en) * | 1960-09-16 | 1963-10-08 | Smith Kline French Lab | Nu-phenethyl-2-phenylcyclopropylamine derivatives |
US3079403A (en) * | 1960-09-19 | 1963-02-26 | Smith Kline French Lab | Process for preparing amines |
DE1251755B (de) * | 1960-10-17 | 1967-10-12 | Smith Kline &. French Laboratories, Philadelphia, Pa (V St A) | Verfahren zur Herstellung von 2 Phenyl-cyclopropyl carbaminsaurederivaten |
US3134676A (en) * | 1961-06-21 | 1964-05-26 | Smith Kline French Lab | Animal feed compositions and methods for their administration |
US3207785A (en) * | 1963-01-17 | 1965-09-21 | Smith Kline French Lab | N-(2-phenylcyclopropyl) formamides |
DE3160641D1 (en) * | 1980-05-13 | 1983-08-25 | Ciba Geigy Ag | Process for the preparation of benzene or naphthalene alkenyl carboxylic acid derivatives |
JPS6025952A (ja) * | 1983-07-20 | 1985-02-08 | Sumitomo Chem Co Ltd | 光学活性2,2−ジメチルシクロプロパン−1−カルボン酸誘導体の製造法 |
GB8429932D0 (en) * | 1984-11-27 | 1985-01-03 | Pfizer Ltd | Triazole antifungal agents |
JPH0296571A (ja) * | 1988-09-30 | 1990-04-09 | Morishita Pharmaceut Co Ltd | 1−(2−フェニルエチル)−1h−1,2,4−トリアゾール誘導体 |
DE3834437A1 (de) * | 1988-10-10 | 1990-04-12 | Basf Ag | Azolylmethylcyclopropane und ihre verwendung als pflanzenschutzmittel |
JPH02289535A (ja) * | 1989-02-16 | 1990-11-29 | Sagami Chem Res Center | 含フッ素α,ω―二官能性化合物 |
US5286736A (en) * | 1990-11-22 | 1994-02-15 | Dr. Karl Thomae Gmbh | Pyridyl compounds and pharmaceutical compositions containing these compounds |
DE4037112A1 (de) * | 1990-11-22 | 1992-05-27 | Thomae Gmbh Dr K | Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
US5283736A (en) * | 1990-11-29 | 1994-02-01 | Konica Corporation | Radiographic image processing apparatus |
IL99759A (en) * | 1991-10-16 | 1997-06-10 | Teva Pharma | Mono-fluorinated derivatives of n-propargyl-1-aminoindan, their preparation and pharmaceutical compositions containing them |
JPH06179360A (ja) * | 1992-12-14 | 1994-06-28 | Toyota Motor Corp | ブレーキブースタ装置 |
JPH07304710A (ja) * | 1994-05-16 | 1995-11-21 | Fuji Photo Film Co Ltd | トリフエニレン誘導体の混合物 |
JP3542165B2 (ja) * | 1994-05-19 | 2004-07-14 | 富山化学工業株式会社 | 新規なキノロンカルボン酸誘導体またはその塩 |
JP3716460B2 (ja) * | 1995-09-01 | 2005-11-16 | 日産化学工業株式会社 | 不斉シクロプロパン化反応 |
EP0785212A1 (en) * | 1996-01-22 | 1997-07-23 | Laboratoire Theramex | New 19-nor-pregnene derivatives |
ES2222859T3 (es) * | 1996-04-09 | 2005-02-16 | Givaudan Sa | Derivados de ciclopentenbutanol. |
CA2294346A1 (en) * | 1997-06-18 | 1998-12-23 | Merck & Co., Inc. | Alpha 1a adrenergic receptor antagonists |
TW530058B (en) * | 1997-07-22 | 2003-05-01 | Astra Pharma Prod | Triazolo [4,5-d]pyrimidine compounos and their use and process for preparation |
JPH1160543A (ja) * | 1997-08-19 | 1999-03-02 | Ichikawa Gosei Kagaku Kk | 1−アミノテトラリン−2−オールの光学分割方法と分割の過程で生じるジアステレオマー塩 |
TR200002380T2 (tr) * | 1998-02-17 | 2001-03-21 | Astrazeneca Uk Limited | Yeni triazolo (4,5-d) pirimidin bileşikleri |
FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
WO2000027827A1 (en) * | 1998-11-10 | 2000-05-18 | Merck & Co., Inc. | Oxazolidinones useful as alpha 1a adrenoceptor antagonists |
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 |
AR028110A1 (es) * | 2000-06-02 | 2003-04-23 | Astrazeneca Ab | Nuevo proceso |
-
2001
- 2001-05-22 AR ARP010102430A patent/AR028110A1/es active IP Right Grant
- 2001-05-22 TW TW090112266A patent/TWI290549B/zh not_active IP Right Cessation
- 2001-05-31 PT PT01937110T patent/PT1292561E/pt unknown
- 2001-05-31 CA CA2746622A patent/CA2746622C/en not_active Expired - Lifetime
- 2001-05-31 CA CA2408591A patent/CA2408591C/en not_active Expired - Fee Related
- 2001-05-31 ES ES01937110T patent/ES2300331T3/es not_active Expired - Lifetime
- 2001-05-31 CZ CZ20090623A patent/CZ302384B6/cs not_active IP Right Cessation
- 2001-05-31 CN CNB018105637A patent/CN1211344C/zh not_active Expired - Fee Related
- 2001-05-31 DK DK01937110T patent/DK1292561T3/da active
- 2001-05-31 SK SK1684-2002A patent/SK287215B6/sk not_active IP Right Cessation
- 2001-05-31 MX MXPA02011794A patent/MXPA02011794A/es active IP Right Grant
- 2001-05-31 PL PL359268A patent/PL205232B1/pl not_active IP Right Cessation
- 2001-05-31 BR BRPI0111329-1A patent/BRPI0111329B1/pt unknown
- 2001-05-31 JP JP2002500816A patent/JP4944344B2/ja not_active Expired - Lifetime
- 2001-05-31 MY MYPI20012579A patent/MY140938A/en unknown
- 2001-05-31 AU AU2001262875A patent/AU2001262875B2/en not_active Ceased
- 2001-05-31 MY MYPI20093489A patent/MY157627A/en unknown
- 2001-05-31 HU HU0302287A patent/HU230303B1/hu not_active IP Right Cessation
- 2001-05-31 EP EP10183117A patent/EP2292591A3/en not_active Withdrawn
- 2001-05-31 CN CN201110096573.5A patent/CN102295555B/zh not_active Expired - Lifetime
- 2001-05-31 WO PCT/SE2001/001240 patent/WO2001092200A1/en active Application Filing
- 2001-05-31 BR BR0111329-1A patent/BR0111329A/pt active IP Right Grant
- 2001-05-31 EP EP06014147A patent/EP1760066A3/en not_active Withdrawn
- 2001-05-31 IL IL15277801A patent/IL152778A0/xx unknown
- 2001-05-31 EE EEP200200666A patent/EE05215B1/xx not_active IP Right Cessation
- 2001-05-31 AT AT01937110T patent/ATE386011T1/de active
- 2001-05-31 AU AU6287501A patent/AU6287501A/xx active Pending
- 2001-05-31 NZ NZ535112A patent/NZ535112A/en unknown
- 2001-05-31 US US10/275,547 patent/US7122695B2/en not_active Expired - Fee Related
- 2001-05-31 DE DE60132771T patent/DE60132771T2/de not_active Expired - Lifetime
- 2001-05-31 CZ CZ20023916A patent/CZ301747B6/cs not_active IP Right Cessation
- 2001-05-31 CA CA2641976A patent/CA2641976C/en not_active Expired - Lifetime
- 2001-05-31 SI SI200130822T patent/SI1292561T1/sl unknown
- 2001-05-31 NZ NZ522639A patent/NZ522639A/en unknown
- 2001-05-31 EP EP01937110A patent/EP1292561B1/en not_active Expired - Lifetime
- 2001-05-31 EP EP10183120A patent/EP2292582A3/en not_active Withdrawn
- 2001-05-31 KR KR1020027016377A patent/KR100755170B1/ko active IP Right Grant
-
2002
- 2002-11-11 IL IL152778A patent/IL152778A/en not_active IP Right Cessation
- 2002-11-25 NO NO20025664A patent/NO20025664L/no not_active Application Discontinuation
- 2002-11-25 BG BG107314A patent/BG65922B1/bg unknown
-
2003
- 2003-06-23 HK HK03104491.3A patent/HK1052171B/zh not_active IP Right Cessation
-
2006
- 2006-07-17 US US11/487,457 patent/US7906662B2/en active Active
-
2008
- 2008-04-15 CY CY20081100409T patent/CY1108100T1/el unknown
- 2008-07-24 IL IL193071A patent/IL193071A/en active IP Right Grant
- 2008-07-29 AR ARP080103274A patent/AR070510A2/es active IP Right Grant
-
2009
- 2009-06-05 IS IS8828A patent/IS8828A/is unknown
- 2009-08-31 BG BG10110454A patent/BG66150B1/bg unknown
-
2010
- 2010-04-19 BG BG10110635A patent/BG66157B1/bg unknown
- 2010-04-28 BG BG10110640A patent/BG66158B1/bg unknown
-
2011
- 2011-02-08 US US12/929,687 patent/US8183412B2/en not_active Expired - Fee Related
- 2011-06-30 JP JP2011145213A patent/JP2011236229A/ja active Pending
- 2011-08-18 IL IL214718A patent/IL214718A0/en unknown
-
2012
- 2012-01-30 US US13/361,214 patent/US20120130097A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100755170B1 (ko) | 시클로프로필 카르복실산 에스테르 및 그의 유도체의 제조방법 | |
AU2001262875A1 (en) | Process for the preparation of cyclopropyl carboxylic acid esters and derivatives | |
EP0438314B1 (en) | Process for the production of 3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl) indole | |
RU2296116C2 (ru) | Способ получения эфиров и производных циклопропилкарбоновой кислоты | |
AU774567B2 (en) | Method for preparing cyclohexane carboxylic acids |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
G170 | Re-publication after modification of scope of protection [patent] | ||
FPAY | Annual fee payment |
Payment date: 20120802 Year of fee payment: 6 |
|
FPAY | Annual fee payment |
Payment date: 20130801 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20150729 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20160727 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20170804 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20180730 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20190729 Year of fee payment: 13 |