AR070510A2 - Procesos para la preparacion de derivados de acido ciclopropil carboxilico e intermediarios provistos para estos procesos - Google Patents

Procesos para la preparacion de derivados de acido ciclopropil carboxilico e intermediarios provistos para estos procesos

Info

Publication number
AR070510A2
AR070510A2 ARP080103274A ARP080103274A AR070510A2 AR 070510 A2 AR070510 A2 AR 070510A2 AR P080103274 A ARP080103274 A AR P080103274A AR P080103274 A ARP080103274 A AR P080103274A AR 070510 A2 AR070510 A2 AR 070510A2
Authority
AR
Argentina
Prior art keywords
compound
formula
preparation
prepared
processes
Prior art date
Application number
ARP080103274A
Other languages
English (en)
Original Assignee
Astrazeneca Ab
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GB0013487A external-priority patent/GB0013487D0/en
Priority claimed from SE0002101A external-priority patent/SE0002101D0/xx
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR070510A2 publication Critical patent/AR070510A2/es

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

Un proceso para la preparacion de un compuesto de la formula (1) donde R es fenilo sustituido con uno o más halogenos; Y es OR1, donde R1 es un grupo alquilo de cadena recta, alquilo ramificado, cicloalquilo o un grupo bicicloheptilo sustituido, que comprende contactar un compuesto de la formula (2): R-CH=CH-C(=O)-Y donde R e Y son como se definieron anteriormente, con metiluro de dimetilsulfoxonio ante la presencia de un solvente a una temperatura de -10sC a -90sC. Reivindicacion 4: Un proceso de acuerdo con cualquiera de las reivindicaciones precedentes caracterizado porque el compuesto de la formula (2) se prepara a partir de un compuesto de la formula (3): R-CH=CH-C(=O)-OH donde R es como se definio en la reivindicacion 1, por reaccion con un agente clorante en presencia de un solvente inerte y un catalizador a una temperatura de 0-200sC, y luego haciendo reaccionar la solucion resultante con YH o Y donde Y es como se definio en la reivindicacion 1, a una temperatura elevada. Reivindicacion 7: Un proceso de acuerdo con cualquiera de las reivindicaciones 4 a 6 caracterizado porque un compuesto de la formula (3) se prepara contactando un compuesto de la formula (4): R-C(=O)H, donde R se definio el la reivindicacion 1 con ácido malonico en presencia de piridina y piperidina a temperaturas elevadas. Reivindicacion 8: Un proceso para la preparacion de un compuesto de la formula (5) donde R es como se definio en la reivindicacion 1 caracterizado porque comprende la hidrolisis básica de un compuesto de la formula (1). Reivindicacion 9: Un proceso de acuerdo con la reivindicacion 8, caracterizado porque la hidrolisis básica se logra usando un hidroxido de metal alcalino y un solvente a 10-100sC. Reivindicacion 10: Un proceso para la preparacion de un compuesto de la formula (6) donde R es como se definio en la reivindicacion 1 caracterizado porque se prepara a partir de un compuesto de la formula (5) por reaccion con cloruro de tionilo en presencia de un solvente y un catalizador a 0-200sC. Reivindicacion 11: Un proceso para la preparacion de un compuesto de la formula (7) donde R es como se definio en la reivindicacion 1, caracterizado porque se prepara a partir de un compuesto de la formula (6), por reaccion con una azida de metal alcalino en presencia de un catalizador de transferencia de fase con carbonato de potasio acuoso y un solvente inerte. Reivindicacion 12: Un proceso para la preparacion de un compuesto de la formula (8) donde R es como se definio en la reivindicacion 1 caracterizado porque se prepara a partir de un compuesto de la formula (7) por medio de la disposicion en tolueno a temperaturas elevadas, y la subsiguiente reaccion con ácido clorhídrico a temperaturas elevadas. Reivindicacion 13: Un proceso para la preparacion de un compuesto de la formula (9) donde R es como se definio en la reivindicacion 1 caracterizado porque se prepara ajustando a un pH 10 o más una solucion acuosa de la sal de un compuesto de la formula (8). Reivindicacion 21: Los compuestos intermediarios de las formulas (1), (1a), (2), (3), (5), (5a), (6), (6a), (7), (7a), (8), (8a), (9) y (9a) anteriores.
ARP080103274A 2000-06-02 2008-07-29 Procesos para la preparacion de derivados de acido ciclopropil carboxilico e intermediarios provistos para estos procesos AR070510A2 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0013487A GB0013487D0 (en) 2000-06-02 2000-06-02 Novel process
SE0002101A SE0002101D0 (sv) 2000-06-06 2000-06-06 Novel Process

Publications (1)

Publication Number Publication Date
AR070510A2 true AR070510A2 (es) 2010-04-14

Family

ID=26244412

Family Applications (2)

Application Number Title Priority Date Filing Date
ARP010102430A AR028110A1 (es) 2000-06-02 2001-05-22 Nuevo proceso
ARP080103274A AR070510A2 (es) 2000-06-02 2008-07-29 Procesos para la preparacion de derivados de acido ciclopropil carboxilico e intermediarios provistos para estos procesos

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ARP010102430A AR028110A1 (es) 2000-06-02 2001-05-22 Nuevo proceso

Country Status (31)

Country Link
US (4) US7122695B2 (es)
EP (4) EP2292591A3 (es)
JP (2) JP4944344B2 (es)
KR (1) KR100755170B1 (es)
CN (2) CN1211344C (es)
AR (2) AR028110A1 (es)
AT (1) ATE386011T1 (es)
AU (2) AU2001262875B2 (es)
BG (4) BG65922B1 (es)
BR (2) BRPI0111329B1 (es)
CA (3) CA2746622C (es)
CY (1) CY1108100T1 (es)
CZ (2) CZ302384B6 (es)
DE (1) DE60132771T2 (es)
DK (1) DK1292561T3 (es)
EE (1) EE05215B1 (es)
ES (1) ES2300331T3 (es)
HK (1) HK1052171B (es)
HU (1) HU230303B1 (es)
IL (4) IL152778A0 (es)
IS (1) IS8828A (es)
MX (1) MXPA02011794A (es)
MY (2) MY140938A (es)
NO (1) NO20025664L (es)
NZ (2) NZ535112A (es)
PL (1) PL205232B1 (es)
PT (1) PT1292561E (es)
SI (1) SI1292561T1 (es)
SK (1) SK287215B6 (es)
TW (1) TWI290549B (es)
WO (1) WO2001092200A1 (es)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
BG66158B1 (bg) 2011-09-30
IL193071A0 (en) 2009-02-11
PL359268A1 (en) 2004-08-23
CN102295555B (zh) 2014-05-28
CA2408591C (en) 2010-06-22
BG110635A (bg) 2010-08-31
HK1052171B (zh) 2008-07-25
SK287215B6 (sk) 2010-03-08
CA2641976A1 (en) 2001-12-06
AU6287501A (en) 2001-12-11
MY140938A (en) 2010-02-12
EP1292561A1 (en) 2003-03-19
EP1760066A3 (en) 2008-09-10
SK16842002A3 (sk) 2003-06-03
CN1431992A (zh) 2003-07-23
DE60132771T2 (de) 2009-02-05
CA2408591A1 (en) 2001-12-06
US20060258879A1 (en) 2006-11-16
BG66157B1 (bg) 2011-09-30
PT1292561E (pt) 2008-04-21
CY1108100T1 (el) 2014-02-12
BG66150B1 (bg) 2011-08-31
US7906662B2 (en) 2011-03-15
MY157627A (en) 2016-06-30
HK1052171A1 (en) 2003-09-05
JP4944344B2 (ja) 2012-05-30
CZ302384B6 (cs) 2011-04-27
ATE386011T1 (de) 2008-03-15
BR0111329A (pt) 2003-06-10
JP2003535072A (ja) 2003-11-25
SI1292561T1 (sl) 2008-06-30
BG107314A (bg) 2003-07-31
EP2292591A3 (en) 2011-11-02
US20120130097A1 (en) 2012-05-24
HU230303B1 (hu) 2015-12-28
EE05215B1 (et) 2009-10-15
KR20030007827A (ko) 2003-01-23
CA2746622C (en) 2014-01-21
BG65922B1 (bg) 2010-05-31
TWI290549B (en) 2007-12-01
US8183412B2 (en) 2012-05-22
CZ301747B6 (cs) 2010-06-09
IL152778A0 (en) 2003-06-24
EP2292582A2 (en) 2011-03-09
BG110454A (bg) 2009-12-31
EE200200666A (et) 2004-06-15
DK1292561T3 (da) 2008-05-26
CA2746622A1 (en) 2001-12-06
EP1292561B1 (en) 2008-02-13
CN1211344C (zh) 2005-07-20
DE60132771D1 (de) 2008-03-27
CA2641976C (en) 2012-03-20
US20110190520A1 (en) 2011-08-04
JP2011236229A (ja) 2011-11-24
US7122695B2 (en) 2006-10-17
CN102295555A (zh) 2011-12-28
BRPI0111329B1 (pt) 2018-05-29
HUP0302287A3 (en) 2008-02-28
IS8828A (is) 2009-06-05
ES2300331T3 (es) 2008-06-16
AU2001262875B2 (en) 2006-08-10
BG110640A (bg) 2010-09-30
PL205232B1 (pl) 2010-03-31
MXPA02011794A (es) 2003-04-10
WO2001092200A1 (en) 2001-12-06
EP1760066A2 (en) 2007-03-07
IL193071A (en) 2011-12-29
NZ535112A (en) 2006-04-28
NZ522639A (en) 2004-10-29
NO20025664D0 (no) 2002-11-25
EP2292591A2 (en) 2011-03-09
CZ20023916A3 (cs) 2003-05-14
EP2292582A3 (en) 2011-11-02
IL214718A0 (en) 2011-09-27
US20030120105A1 (en) 2003-06-26
NO20025664L (no) 2002-11-25
HUP0302287A2 (hu) 2003-10-28
AR028110A1 (es) 2003-04-23
IL152778A (en) 2008-12-29
KR100755170B1 (ko) 2007-09-04

Similar Documents

Publication Publication Date Title
AR070510A2 (es) Procesos para la preparacion de derivados de acido ciclopropil carboxilico e intermediarios provistos para estos procesos
ES2625106T3 (es) Métodos de producción de compuestos de sulfilimina
BR0313341A (pt) Método para a preparação de uma oxazinona fundida e método para a preparação de um composto de fórmula iii
PE20060018A1 (es) Proceso para la preparacion de haluros de aril y hetoaril-alquilsulfonilo
Okada et al. An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl· 5H 2 O) crystals
BRPI0922087B1 (pt) Processos para fabricar um composto e para preparar um composto
AR058210A1 (es) Procedimiento para preparar 5-amino-3h-tiazolo[4,5-d]pirimidin-2-ona, un intermediario util para la preparacion de ciertos nucleosidos de tiazolo[4,5-d]pirimidina que actuan como inmunomoduladores.
CN107337663B (zh) 一种可见光诱导3-硫代螺环三烯酮化合物的制备方法
ES2024515B3 (es) Procedimiento para preparar cloruros de retinoilo.
US5629426A (en) Carbonate-mediated hydrogen peroxide oxidations of 4-hydroxy-2,2,6,6-tetramethylpiperidine
ES2670677T3 (es) Procedimiento de fabricación de anhídrido 5-clorometil-2,3-dicarboxílico
PT1026148E (pt) Processo para a sintese de esteres malonicos
RU2018130160A (ru) Способ получения 4-алкокси-3-гидроксипиколиновых кислот
ES2545477T3 (es) Procedimiento de preparación de derivados de la 2-cianopiridina
CN105017232A (zh) 一种三唑类杀菌剂的合成方法
DE602004018592D1 (de) Magnesiumthiosulfatlösung und deren Herstellungsverfahren
UA73329C2 (uk) N-(4,5-бісметансульфоніл-2-метилбензоїл)гуанідину гідрохлорид та спосіб його одержання
AR073278A1 (es) Procedimiento para sintetizar isoquinolinas sustituidas
BR9912561A (pt) Processo aperfeiçoado para o preparo de n-óxido 2-halopiridina
CN104262278A (zh) 一种异噁唑草酮的制备方法
ES2348257T3 (es) Procedimiento para la produccion de eteres de dicloro hidroquinona.
BRPI0713347A2 (pt) Processo para produção de composto de álcool
KR880002591B1 (ko) 술폰아미드기를 함유하는 페녹시벤조산 유도체의 제조방법
JPH04282337A (ja) ２−アリールオキシ−１−クロルプロパンの製造方法
JP4641624B2 (ja) トリブロモメチルスルホニルピリジンの製造方法

Legal Events

Date Code Title Description
FG Grant, registration