ES2183720A1 - Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-a2-pirazolinas racemicas y enantiomericamente puras. - Google Patents

Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-a2-pirazolinas racemicas y enantiomericamente puras.

Info

Publication number
ES2183720A1
ES2183720A1 ES200101412A ES200101412A ES2183720A1 ES 2183720 A1 ES2183720 A1 ES 2183720A1 ES 200101412 A ES200101412 A ES 200101412A ES 200101412 A ES200101412 A ES 200101412A ES 2183720 A1 ES2183720 A1 ES 2183720A1
Authority
ES
Spain
Prior art keywords
methyl
general formula
trifluoromethyl
enantiomerically pure
reaction
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.)
Granted
Application number
ES200101412A
Other languages
English (en)
Other versions
ES2183720B1 (es
Inventor
Maria Rosa Cuberes-Altisent
Jordi Frigola-Constansa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Esteve Pharmaceuticals SA
Original Assignee
Laboratorios del Dr Esteve SA
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 to ES200101412A priority Critical patent/ES2183720B1/es
Application filed by Laboratorios del Dr Esteve SA filed Critical Laboratorios del Dr Esteve SA
Priority to MXPA03011783A priority patent/MXPA03011783A/es
Priority to DE60208551T priority patent/DE60208551T2/de
Priority to EEP200400016A priority patent/EE200400016A/xx
Priority to US10/312,194 priority patent/US6846935B2/en
Priority to CNB028143280A priority patent/CN1275946C/zh
Priority to RU2004101050/04A priority patent/RU2288915C2/ru
Priority to KR10-2003-7016500A priority patent/KR20040018275A/ko
Priority to PCT/ES2002/000274 priority patent/WO2002102781A1/es
Priority to SI200230277T priority patent/SI1408035T1/sl
Priority to PT02735442T priority patent/PT1408035E/pt
Priority to BR0211009-1A priority patent/BR0211009A/pt
Priority to HU0401715A priority patent/HUP0401715A3/hu
Priority to DK02735442T priority patent/DK1408035T3/da
Priority to SK42-2004A priority patent/SK422004A3/sk
Priority to CZ200481A priority patent/CZ200481A3/cs
Priority to ES02735442T priority patent/ES2256483T3/es
Priority to CA2451132A priority patent/CA2451132C/en
Priority to IL15936702A priority patent/IL159367A0/xx
Priority to EP02735442A priority patent/EP1408035B1/en
Priority to JP2003505323A priority patent/JP2005502604A/ja
Priority to AT02735442T priority patent/ATE315030T1/de
Priority to PL02367773A priority patent/PL367773A1/xx
Priority to ARP020102218A priority patent/AR036050A1/es
Publication of ES2183720A1 publication Critical patent/ES2183720A1/es
Priority to NO20035642A priority patent/NO20035642L/no
Priority to BG108524A priority patent/BG108524A/bg
Application granted granted Critical
Priority to ZA2004/00343A priority patent/ZA200400343B/en
Publication of ES2183720B1 publication Critical patent/ES2183720B1/es
Priority to US11/007,449 priority patent/US6958403B2/en
Priority to US11/006,931 priority patent/US20050096474A1/en
Priority to HK05109018A priority patent/HK1077058A1/xx
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Procedimiento para la preparación de derivados de 1,5-diaril-3-trifluorometil-Delta2-pirazolinas racémicas y enantioméricamente puras. Procedimiento para la obtención de compuestos de fórmula general 1, que incluye las mezclas racémicas (+-)-1, y los compuestos enantioméricamente puros (-)-1 y (+)-l, en la cual R1 y R3, iguales o diferentes, representan un átomo de hidrógeno, cloro, flúor, un grupo metilo, trifluorometilo o metoxi; R2 representa un átomo de hidrógeno, cloro, flúor, un grupo metilo, trifluorometilo, metoxi, trifluorometoxi, metilsulfonilo o aminosulfonilo; R4 representa un átomo de hidrógeno, cloro, flúor, un grupo metilo, trifluorometilo, metoxi, trifluorometoxi, metilsulfonilo o aminosulfonilo, con la condición de que uno de los sustituyentes R2 o R4 es un grupo metilsulfonilo o aminosulfonilo; que comprende la obtención de la mezcla racémica de fórmula general (+-)-1 por reacción de una (E)-1,1,1-trifluoro-4-aril-3-buten-2-ona con una fenilhidrazina, seguido de un tratamiento con ácido clorosulfónico, o bien por reacción con ácido clorosulfónico seguido por reacción con hidróxido sódico y, finalmente, con cloruro de tionilo. El producto obtenido por cualquiera de estos métodos, se hace reaccionar con carbonato amónico o amoniaco, o bien con sulfito sódico y yoduro de metilo o sulfato de metilo. Por otro lado, para obtener los compuestos enantioméricamente puros de fórmula general 1 por resolución de la mezcla racémica de fórmula general (+-)-1, se efectúa una reacción con efedrina ópticamente activa, seguida por la formación de la sal sódica de cada uno de los enantiómeros, reacción con cloruro de tionilo y carbonato amónico o amoniaco, o bien con cloruro de tionilo seguido de sulfito sódico y yoduro de metilo o sulfato de metilo, para obtener así separadamente los compuestos enantioméricamente puros de fórmula general (-)-1 y (+)-1.
ES200101412A 2001-06-18 2001-06-18 Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras. Expired - Fee Related ES2183720B1 (es)

Priority Applications (30)

Application Number Priority Date Filing Date Title
ES200101412A ES2183720B1 (es) 2001-06-18 2001-06-18 Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.
IL15936702A IL159367A0 (en) 2001-06-18 2002-06-06 Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl-delta 2 pyrazolines that are racemic and enantiomerically pure
EEP200400016A EE200400016A (et) 2001-06-18 2002-06-06 Protsess 1,5-diarüül-3-trifluorometüül-delta²-pürasoliinide ratseemiliste ja enantiomeerselt puhaste derivaatide valmistamiseks
US10/312,194 US6846935B2 (en) 2001-06-18 2002-06-06 Procedure for the preparation of racemic and enantionmerically pure derivatives of 1,5-diaryl-3-trifluoromethyl-Δ2-pyrazolines
CA2451132A CA2451132C (en) 2001-06-18 2002-06-06 Process for the preparation of racemic and enantiomerically pure derivatives of 1,5-diaryl-3-trifluoromethyl-.delta.2-pyrazolines
RU2004101050/04A RU2288915C2 (ru) 2001-06-18 2002-06-06 Способ получения рацемических и энантиомерно чистых производных 1,5-диарил-3-трифторметил-δ2-пиразолинов
KR10-2003-7016500A KR20040018275A (ko) 2001-06-18 2002-06-06 1,5-디아릴-3-트리플루오르메틸-δ²-피라졸린의 라셈체와거울상이성질에서 순수한 유도체의 제조 공정
DE60208551T DE60208551T2 (de) 2001-06-18 2002-06-06 Verfahren zur herstellung von racemischen und enantiomerenreinen derivaten von 1,5-diaryl-3-trifluormethyl-delta2-pyrazolinen
SI200230277T SI1408035T1 (sl) 2001-06-18 2002-06-06 Postopek za pripravo derivatov 1,5-diaril-3-trifluometil-delta-2-pirazolinov grozdne kisline in enentiomericno cisti
EP02735442A EP1408035B1 (en) 2001-06-18 2002-06-06 Method of preparing derivatives of 1.5-diaryl-3-trifluoromethyl-delta2-pyrazolines that are racemic and enantiomerically pure
BR0211009-1A BR0211009A (pt) 2001-06-18 2002-06-06 Processo para a preparação de derivados racêmicos e enantiomericamente puros de 1,5-diaril-3-trifluormetil-delta2 pirazolinas
HU0401715A HUP0401715A3 (en) 2001-06-18 2002-06-06 Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl-delta2-pyrazolines that are racemic and enantiomerically pure
DK02735442T DK1408035T3 (da) 2001-06-18 2002-06-06 Fremgangsmåde til fremstilling af derivater af 1,5-diaryl-3-trifluormethyl-delta2-pyrazoliner, der er racemiske og enantiomert rene
SK42-2004A SK422004A3 (en) 2001-06-18 2002-06-06 Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl- delta2-pyrazolines that are racemic and enantiomerically pure
CZ200481A CZ200481A3 (cs) 2001-06-18 2002-06-06 Způsob přípravy racemických i enantiomerně čistých derivátů 1,5-diaryl-3-trifluormethyl-delta2-pyrazolinů
ES02735442T ES2256483T3 (es) 2001-06-18 2002-06-06 Procedimiento para la obtencion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.
MXPA03011783A MXPA03011783A (es) 2001-06-18 2002-06-06 Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-?¦-pirazolinas racemicas y enantiomericamente puras.
PCT/ES2002/000274 WO2002102781A1 (es) 2001-06-18 2002-06-06 Procedimiento para la preparación de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racémicas y enantioméricamente puras
PT02735442T PT1408035E (pt) 2001-06-18 2002-06-06 Metodo de preparacao de derivativos de 1.5-diaril-3-trifluorometilo-delta2-pirazolinas que sejam racemicos e enanciomericamente puros
JP2003505323A JP2005502604A (ja) 2001-06-18 2002-06-06 １，５−ジアリル−３−トリフルオロメチル−δ２−ピラゾリンのラセミ誘導体及びエナンチオマーとして純粋な誘導体の調製方法
AT02735442T ATE315030T1 (de) 2001-06-18 2002-06-06 Verfahren zur herstellung von racemischen und enantiomerenreinen derivaten von 1,5-diaryl-3- trifluormethyl-delta2-pyrazolinen
PL02367773A PL367773A1 (en) 2001-06-18 2002-06-06 Method of preparing derivatives of 1.5-diaryl-3-trifluoromethyl-delta2-pyrazolines that are racemic and enantiomerically pure
CNB028143280A CN1275946C (zh) 2001-06-18 2002-06-06 制备外消旋与对映异构纯的1,5－二芳基－3－三氟甲基－△2－吡唑啉衍生物的方法
ARP020102218A AR036050A1 (es) 2001-06-18 2002-06-12 Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2- pirazolinas racemicas y enantiomericamente puras
NO20035642A NO20035642L (no) 2001-06-18 2003-12-17 Fremgangsmate for fremstilling av derivater av 1,5-diaryl-3-trifluormetyl-delta2-pyrazoliner som er racemisk og enantiomerisk rene
BG108524A BG108524A (bg) 2001-06-18 2004-01-13 М...'од за пол"-аван... на ра-...ми-ни и ...нан'иом...рно -и''и производни на 1,5-диарил-3-'ри"л"ором...'ил-д...л'а2 пиразолини
ZA2004/00343A ZA200400343B (en) 2001-06-18 2004-01-16 Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl-del ta2-pyrazolines that are racemic and enantiomerically pure
US11/007,449 US6958403B2 (en) 2001-06-18 2004-12-08 Procedure for the preparation of racemic and enantiomerically pure derivatives of 1,5 diaryl-3-trifluorromethyl-Δ2-pyrazolines
US11/006,931 US20050096474A1 (en) 2001-06-18 2004-12-08 Procedure for the preparation of racemic derivatives of 1,5-diaryl-3-trifluoromethyl-delta2-pyrazolines
HK05109018A HK1077058A1 (en) 2001-06-18 2005-10-13 Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl-delta2-pyrazolnes that are racemic and enantiomerically pure

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200101412A ES2183720B1 (es) 2001-06-18 2001-06-18 Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.

Publications (2)

Publication Number Publication Date
ES2183720A1 true ES2183720A1 (es) 2003-03-16
ES2183720B1 ES2183720B1 (es) 2004-01-16

Family

ID=8498105

Family Applications (2)

Application Number Title Priority Date Filing Date
ES200101412A Expired - Fee Related ES2183720B1 (es) 2001-06-18 2001-06-18 Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.
ES02735442T Expired - Lifetime ES2256483T3 (es) 2001-06-18 2002-06-06 Procedimiento para la obtencion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES02735442T Expired - Lifetime ES2256483T3 (es) 2001-06-18 2002-06-06 Procedimiento para la obtencion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.

Country Status (27)

Country Link
US (3) US6846935B2 (es)
EP (1) EP1408035B1 (es)
JP (1) JP2005502604A (es)
KR (1) KR20040018275A (es)
CN (1) CN1275946C (es)
AR (1) AR036050A1 (es)
AT (1) ATE315030T1 (es)
BG (1) BG108524A (es)
BR (1) BR0211009A (es)
CA (1) CA2451132C (es)
CZ (1) CZ200481A3 (es)
DE (1) DE60208551T2 (es)
DK (1) DK1408035T3 (es)
EE (1) EE200400016A (es)
ES (2) ES2183720B1 (es)
HK (1) HK1077058A1 (es)
HU (1) HUP0401715A3 (es)
IL (1) IL159367A0 (es)
MX (1) MXPA03011783A (es)
NO (1) NO20035642L (es)
PL (1) PL367773A1 (es)
PT (1) PT1408035E (es)
RU (1) RU2288915C2 (es)
SI (1) SI1408035T1 (es)
SK (1) SK422004A3 (es)
WO (1) WO2002102781A1 (es)
ZA (1) ZA200400343B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2183720B1 (es) * 2001-06-18 2004-01-16 Esteve Labor Dr Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.
US20080138282A1 (en) * 2004-06-03 2008-06-12 The Trustees Of Columbia University In The City Of New York Radiolabeled Arylsulfonyl Compounds and Uses Thereof
DE102004057303A1 (de) * 2004-11-26 2006-06-01 Merck Patent Gmbh Stabile Kristallmodifikationen von DOTAP Chlorid
EP1757587A1 (en) * 2005-07-15 2007-02-28 Laboratorios Del Dr. Esteve, S.A. Substituted pyrazoline compounds, their preparation and use as medicaments
US9376420B2 (en) * 2012-10-25 2016-06-28 Yuhan Corporation 4,5-dihydro-1H-pyrazole derivative or salts thereof, and pharmaceutical composition comprising same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999062884A1 (es) * 1998-05-29 1999-12-09 Laboratorios Del Dr. Esteve, S.A. Derivados de pirazolinas, su preparacion y su aplicacion como medicamentos
WO2000076503A1 (en) * 1999-06-16 2000-12-21 Temple University - Of The Commonwealth System Of Higher Education 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines as inhibitors of cyclooxygenase-2

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE788658R (fr) * 1971-09-09 1973-03-12 Hoechst Ag Derives de 3-(3', 4'-dichloro-6'-alkylphenyl) -delta2-pyrazolines, leurpreparation et leur utilisation comme agents d'azurage
ES2183720B1 (es) * 2001-06-18 2004-01-16 Esteve Labor Dr Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999062884A1 (es) * 1998-05-29 1999-12-09 Laboratorios Del Dr. Esteve, S.A. Derivados de pirazolinas, su preparacion y su aplicacion como medicamentos
WO2000076503A1 (en) * 1999-06-16 2000-12-21 Temple University - Of The Commonwealth System Of Higher Education 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines as inhibitors of cyclooxygenase-2

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BASE DE DATOS CA en STN, AN 90:186855 & Canadian Journal Chemistry, Vol. 57, pßginas 360-366, 1979. MUKAI et al. "On the synthesis and the optical properties of optically active 2-pyrazoline compounds". Resumen. *
J. JACQUES et al. "Enantiomers, Racemates and Resolutions", 1991, Krieger Publishing Company, Florida (USA), pßginas 258-259. *

Also Published As

Publication number Publication date
US20040019222A1 (en) 2004-01-29
CA2451132A1 (en) 2002-12-27
RU2004101050A (ru) 2005-06-27
HUP0401715A3 (en) 2005-06-28
NO20035642L (no) 2004-02-12
CZ200481A3 (cs) 2004-07-14
HK1077058A1 (en) 2006-02-03
US6958403B2 (en) 2005-10-25
ATE315030T1 (de) 2006-02-15
DE60208551T2 (de) 2006-10-19
SK422004A3 (en) 2004-07-07
JP2005502604A (ja) 2005-01-27
KR20040018275A (ko) 2004-03-02
RU2288915C2 (ru) 2006-12-10
DK1408035T3 (da) 2006-05-08
BG108524A (bg) 2004-08-31
NO20035642D0 (no) 2003-12-17
EP1408035B1 (en) 2006-01-04
PT1408035E (pt) 2006-05-31
DE60208551D1 (de) 2006-03-30
EP1408035A1 (en) 2004-04-14
CN1275946C (zh) 2006-09-20
WO2002102781A1 (es) 2002-12-27
ES2256483T3 (es) 2006-07-16
ES2183720B1 (es) 2004-01-16
US6846935B2 (en) 2005-01-25
AR036050A1 (es) 2004-08-04
CA2451132C (en) 2010-10-12
IL159367A0 (en) 2004-06-01
HUP0401715A2 (hu) 2005-01-28
BR0211009A (pt) 2004-11-03
PL367773A1 (en) 2005-03-07
CN1610672A (zh) 2005-04-27
SI1408035T1 (sl) 2006-04-30
US20050096474A1 (en) 2005-05-05
ZA200400343B (en) 2005-03-30
EE200400016A (et) 2004-04-15
US20050096373A1 (en) 2005-05-05
MXPA03011783A (es) 2004-04-02

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