WO2001005354A3 - Procedimiento mejorado para la preparacion de bencensulfonilureas, hipoglucemiantes orales de segunda generacion - Google Patents

Procedimiento mejorado para la preparacion de bencensulfonilureas, hipoglucemiantes orales de segunda generacion Download PDF

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Publication number
WO2001005354A3
WO2001005354A3 PCT/MX2000/000002 MX0000002W WO0105354A3 WO 2001005354 A3 WO2001005354 A3 WO 2001005354A3 MX 0000002 W MX0000002 W MX 0000002W WO 0105354 A3 WO0105354 A3 WO 0105354A3
Authority
WO
WIPO (PCT)
Prior art keywords
benzenesulfonylureas
preparation
generation
improved process
hypoglycemic agents
Prior art date
Application number
PCT/MX2000/000002
Other languages
English (en)
French (fr)
Other versions
WO2001005354A2 (es
Inventor
Ochoa Jose Manuel Francis Lara
La Torre Garcia Juan Antoni De
Andrade Fidencio Franco
Original Assignee
Silanes Sa De Cv Lab
Ochoa Jose Manuel Francis Lara
Torre Garcia Juan Antonio De
Andrade Fidencio Franco
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 MXPA/A/1999/006794A external-priority patent/MXPA99006794A/es
Application filed by Silanes Sa De Cv Lab, Ochoa Jose Manuel Francis Lara, Torre Garcia Juan Antonio De, Andrade Fidencio Franco filed Critical Silanes Sa De Cv Lab
Priority to AU21298/00A priority Critical patent/AU2129800A/en
Publication of WO2001005354A2 publication Critical patent/WO2001005354A2/es
Publication of WO2001005354A3 publication Critical patent/WO2001005354A3/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La presente invención muestra un procedimiento para preparar bencensulfonilureas de fórmula estructural (I). Dependiendo del producto que se deseé preparar el radical R1 puede representar: a) 5-metilpirazinil con X representando hidrógeno, teniéndose así la Glipizida; b) 5-cloro-2-metoxibencil con X representando hidrógeno, teniendose así a la Glibenclamida y c) 3-etil-4-metil-2-oxo-3-pirrolinil con X igual a trans-metilo, representandose así a la Glimepirida; los compuestos de la invención se prepararon por reacción entre las sulfonamidas (II) y los correspondientes 4-nitrofenil-N-ciclohexilcarbamatos (III), de acuerdo con el siguiente esquema de reacción. Las reacciones se llevaron a cabo en un disolvente polar, aprótico como N,N-dimetilformamida (DMF) o dimetilsulfóxido (DMSO), en la presencia de una base tal como hidruro de sodio o metóxido de sodio en condiciones anhidras, desde 50 °C hasta 100 °C.
PCT/MX2000/000002 1999-07-21 2000-01-18 Procedimiento mejorado para la preparacion de bencensulfonilureas, hipoglucemiantes orales de segunda generacion WO2001005354A2 (es)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU21298/00A AU2129800A (en) 1999-07-21 2000-01-18 Improved process for the preparation of benzenesulfonylureas as oral hypoglycemic agents of the second generation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
MXPA/A/1999/006794A MXPA99006794A (es) 1999-07-21 Procedimiento mejorado para la preparacion de bencensulfonilureas hipoglucemiantes orales de segunda generacion
MX996794 1999-07-21

Publications (2)

Publication Number Publication Date
WO2001005354A2 WO2001005354A2 (es) 2001-01-25
WO2001005354A3 true WO2001005354A3 (es) 2001-06-14

Family

ID=19745112

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/MX2000/000002 WO2001005354A2 (es) 1999-07-21 2000-01-18 Procedimiento mejorado para la preparacion de bencensulfonilureas, hipoglucemiantes orales de segunda generacion

Country Status (2)

Country Link
AU (1) AU2129800A (es)
WO (1) WO2001005354A2 (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003235814A1 (en) * 2002-01-07 2003-07-24 Sun Pharmaceutical Industries Limited Novel process for the preparation of trans-3- ethyl-2,5- dihydro-4- methyl-n-(2-( 4-(((((4-methyl cyclohexyl) amino)carbonyl) amino)sulfonyl) phenyl)ethyl) -2-oxo-1h-pyrrole -1-carboxamide
KR100712234B1 (ko) 2003-08-08 2007-04-27 명문제약주식회사 글리메피라이드의 제조방법
CN102993106B (zh) * 2012-12-24 2015-06-17 武汉武药制药有限公司 格列吡嗪的合成新路线
CN107434788B (zh) * 2017-09-11 2018-06-15 威海迪素制药有限公司 一种格列吡嗪的制备方法
GB202111678D0 (en) * 2021-08-13 2021-09-29 Nelson Mandela Univ Flow synthesis process for the production of sulfonylurea compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3454635A (en) * 1965-07-27 1969-07-08 Hoechst Ag Benzenesulfonyl-ureas and process for their manufacture
US4062889A (en) * 1970-05-21 1977-12-13 Lucien Eric Preparation of sulfonylureas

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3454635A (en) * 1965-07-27 1969-07-08 Hoechst Ag Benzenesulfonyl-ureas and process for their manufacture
US4062889A (en) * 1970-05-21 1977-12-13 Lucien Eric Preparation of sulfonylureas

Also Published As

Publication number Publication date
AU2129800A (en) 2001-02-05
WO2001005354A2 (es) 2001-01-25

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