GB1322980A - Thiophen-sulphonyl ureas and process for preparing them - Google Patents

Thiophen-sulphonyl ureas and process for preparing them

Info

Publication number
GB1322980A
GB1322980A GB3825570A GB3825570A GB1322980A GB 1322980 A GB1322980 A GB 1322980A GB 3825570 A GB3825570 A GB 3825570A GB 3825570 A GB3825570 A GB 3825570A GB 1322980 A GB1322980 A GB 1322980A
Authority
GB
United Kingdom
Prior art keywords
sulphonyl
thiophen
urea
acid
substituted
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
Application number
GB3825570A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1322980A publication Critical patent/GB1322980A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms

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)

Abstract

1322980 Thiophen - sulphonyl - ureas FARBWERKE HOECHST AG 7 Aug 1970 [7 Aug 1969] 38255/70 Heading C2C Novel thiophen-2-sulphonyl-ureas of the general Formula I or a salt thereof, wherein X is in the 4 or 5 position and is hydrogen, fluorine, chlorine, bromine or methyl; Y is CH 2 , CH 2 CH 2 , or CH 2 CH(CH 3 ); and R is a C 4-6 alkyl, C 5-8 cycloalkyl or 3-methylcyclopentyl, 4-methyl cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 4 - chlorocyclohexyl, 4,4 - dimethylcyclohexyl, 3 - methyl - cyclopentenyl, methylcyclohexenyl, endo - alkylene - cyclohexyl, endoalkylene - cyclohexenyl, endoalkylene cyclohexyl methyl or endoalkylene - cyclohexenylmethyl may be prepared by (a) reacting an amine RNH 2 with an appropriately substituted sulphonyl-isocyanate, sulphonyl-carbamate, sulphonyl thiocarbamate, sulphonyl urea, semicarbazide or semicarbazone; (b) reacting a sulphonamide II with an R-substituted isocyanate, carbamate, thiocarbamate, carbamoyl halide or urea; (c) hydrolysing the corresponding sulphonyl isourea ether, sulphonyl isothiourea ether, sulphonyl parabanic acid or sulphonyl halo formic acid amidine; (d) adding water to the corresponding carbodiimide; (e) replacement of sulphur by oxygen in the thiourea radical of a corresponding sulphonyl thiourea; (f) oxidizing the corresponding sulphinyl or sulphenyl to sulphonyl; (g) acylating the thiophen sulphonyl urea III (h) reacting an R substituted urea with a corresponding sulphonyl halide; (i) replacement of sulphur in a thioamide group by oxygen; (j) saponification of a compound IV or V or a parabanic acid derivative of IV, wherein U is C 1-4 alkoxy or thioalkyl or halogen; or (k) reaction of an N-R-N<SP>1</SP> hydroxy urea with a corresponding sulphinic acid halide or, in the presence of an acid condensation agent, the free sulphinic acid or alkali metal salt thereof. The intermediate thiophen sulphonamide II may be formed by chlorosulphonation followed by treatment of ammonia of the corresponding thiophen or condensation of an amino substituted thiophen sulphonamide with a substituted benzoyl chloride to form the amide group. The intermediate thiophen sutphonyl carbamic acid esters may be formed by condensation of the corresponding thiophen sulphonamide with a chloroformic ester. Pharmaceutical compositions of the compound I with the usual excipients show hypoglycemic activity when administered orally.
GB3825570A 1969-08-07 1970-08-07 Thiophen-sulphonyl ureas and process for preparing them Expired GB1322980A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691940131 DE1940131A1 (en) 1969-08-07 1969-08-07 Thiophenesulfonylureas and process for their preparation

Publications (1)

Publication Number Publication Date
GB1322980A true GB1322980A (en) 1973-07-11

Family

ID=5742128

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3825570A Expired GB1322980A (en) 1969-08-07 1970-08-07 Thiophen-sulphonyl ureas and process for preparing them

Country Status (7)

Country Link
BE (1) BE754588A (en)
BR (1) BR6915286D0 (en)
DE (1) DE1940131A1 (en)
FR (1) FR2068472B1 (en)
GB (1) GB1322980A (en)
NL (1) NL7011219A (en)
ZA (1) ZA704949B (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62116575A (en) * 1985-10-09 1987-05-28 メルク　エンド　カムパニ−　インコ−ポレ−テツド Anti-glaucoma substituted thiophene-2-sulfonamide
US5792788A (en) * 1995-02-01 1998-08-11 Hoechst Aktiengesellschaft Substituted thiophenesulfonylureas and -thioureas, processes for their preparation, their use as a medicament or diagnostic, and medicament containing them
WO2019034688A1 (en) * 2017-08-15 2019-02-21 Inflazome Limited Novel sulfonamide carboxamide compounds
US10538487B2 (en) 2015-02-16 2020-01-21 The University Of Queensland Sulfonylureas and related compounds and use of same
US11465992B2 (en) 2017-07-07 2022-10-11 Inflazome Limited Sulfonamide carboxamide compounds
US11542255B2 (en) 2017-08-15 2023-01-03 Inflazome Limited Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors
US11613542B2 (en) 2017-08-15 2023-03-28 Inflazome Limited Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors
US11840543B2 (en) 2017-05-24 2023-12-12 The University Of Queensland Compounds and uses
US11905252B2 (en) 2018-03-02 2024-02-20 Inflazome Limited Compounds
US11926600B2 (en) 2017-08-15 2024-03-12 Inflazome Limited Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors
US12012392B2 (en) 2017-11-09 2024-06-18 Inflazome Limited Sulfonamide carboxamide compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH391730A (en) * 1961-08-10 1965-05-15 Geigy Ag J R Process for the preparation of N'-substituted N-thiophenesulfonylureas

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62116575A (en) * 1985-10-09 1987-05-28 メルク　エンド　カムパニ−　インコ−ポレ−テツド Anti-glaucoma substituted thiophene-2-sulfonamide
US5792788A (en) * 1995-02-01 1998-08-11 Hoechst Aktiengesellschaft Substituted thiophenesulfonylureas and -thioureas, processes for their preparation, their use as a medicament or diagnostic, and medicament containing them
CN1071752C (en) * 1995-02-01 2001-09-26 赫彻斯特股份公司 Substituted thiophenesulfonylureas and-thioureas, processes for their preparation, their use as medicament or diagnostic, and medicament containing them
US10538487B2 (en) 2015-02-16 2020-01-21 The University Of Queensland Sulfonylureas and related compounds and use of same
US11130731B2 (en) 2015-02-16 2021-09-28 The Provost, Fellows, Foundation Scholars, And The Other Members Of Board, Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth Near Dublin Sulfonylureas and related compounds and use of same
US11840543B2 (en) 2017-05-24 2023-12-12 The University Of Queensland Compounds and uses
US11465992B2 (en) 2017-07-07 2022-10-11 Inflazome Limited Sulfonamide carboxamide compounds
US11981667B2 (en) 2017-07-07 2024-05-14 Inflazome Limited Sulfonamide carboxamide compounds
US11542255B2 (en) 2017-08-15 2023-01-03 Inflazome Limited Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors
US11613542B2 (en) 2017-08-15 2023-03-28 Inflazome Limited Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors
WO2019034688A1 (en) * 2017-08-15 2019-02-21 Inflazome Limited Novel sulfonamide carboxamide compounds
US11926600B2 (en) 2017-08-15 2024-03-12 Inflazome Limited Sulfonylureas and sulfonylthioureas as NLRP3 inhibitors
US12012392B2 (en) 2017-11-09 2024-06-18 Inflazome Limited Sulfonamide carboxamide compounds
US11905252B2 (en) 2018-03-02 2024-02-20 Inflazome Limited Compounds

Also Published As

Publication number Publication date
BE754588A (en) 1971-02-08
FR2068472A1 (en) 1971-08-27
NL7011219A (en) 1971-02-09
BR6915286D0 (en) 1973-04-19
DE1940131A1 (en) 1971-02-18
FR2068472B1 (en) 1974-02-01
ZA704949B (en) 1971-04-28

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee