GB1182694A - Benzenesulfonyl Ureas and process for their manufacture - Google Patents

Benzenesulfonyl Ureas and process for their manufacture

Info

Publication number
GB1182694A
GB1182694A GB24852/67A GB2485267A GB1182694A GB 1182694 A GB1182694 A GB 1182694A GB 24852/67 A GB24852/67 A GB 24852/67A GB 2485267 A GB2485267 A GB 2485267A GB 1182694 A GB1182694 A GB 1182694A
Authority
GB
United Kingdom
Prior art keywords
radical
group
benzenesulphonyl
prepared
methyl
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
GB24852/67A
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
Priority claimed from DE1966F0049329 external-priority patent/DE1252201B/en
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1182694A publication Critical patent/GB1182694A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • C07D333/38—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/50—Spiro compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Silicon Compounds (AREA)

Abstract

1,182,694. Benzenesulphonyl-ureas. FARBWERKE HOECHST A.G. 30 May, 1967 [28 May, 1966; 18 April, 1967], No. 24852/67. Heading C2C. Novel benzenesulphonyl-ureas (including salts thereof) of the general formula wherein R is alkyl or phenylalkyl radical or preferably hydrogen, R<SP>1</SP> represents (a) a cyclohexyl radical containing a methyl group and an alkoxy group containing 1 or 2 carbons, (b) a chlorocyclohexyl group, (c) a spiro-(5,5)-undecyl-(3) group, (d) an exo-tricyclo-(3,2,1,0<SP>2,4</SP>) octane group, (e) a 4-methylcyclohexenyl group or (f) a dimethyl- or 4,4-diethylcyclohexyl group; X represents (a) a phenyl radical carrying in any desired positions the substituents Z and Z<SP>1</SP> which may be identical or different in which Z is a hydrogen or halogen atom or an alkyl, alkenyl, alkoxy, alkenoxy, haloalkoxy, alkoxyalkoxy, phenylalkoxy, phenylalkyl, cycloalkoxy, phenyl, phenoxy, acyl, acyloxy, or a benzoyl radical, or a -CF 3 , -OH, -CN or -NO 2 group, Z<SP>1</SP> represents a hydrogen or halogen atom or an alkyl, alkoxy, alkoxyalkoxy or acyloxy radical or a hydroxyl group, (b) a naphthyl radical which may be mono- or di-substituted by a halogen atom or an alkyl or alkoxy radical or a hydroxyl group, (c) a tetrahydronaphthyl radical or an indanyl radical, (d) a thienyl radical which may be mono- or di-substituted by alkyl, phenylalkyl, alkoxy, alkoxyalkoxy, alkenoxy, phenylalkoxy and aryl radicals and halogen atoms or (e) a tetramethylene- or trimethylene-thienyl radical and Y represents a hydrocarbon chain of 1-3 carbon atoms and wherein the phenylene group may be substituted by one or more halogen, alkyl or alkoxy, are prepared utilizing standard methods. 1 - [4 - (# - [2 - Methoxy - 5 - chlorobenzamido]- ethyl) - benzenesulphonyl] - 3 - (4 - chlorocyclohexyl)-parabanic acid is prepared by the interaction of 4-chlorocyclohexyl-parabanic acid and the appropriately substituted benzene-sulphochloride. N - [4 - (# - [2 - Methoxy - 5 - chlorobenzamido] - ethyl) - benzenesulphonyl] - N<SP>1</SP> - (4, 4-dimethylcyclohexyl)-thiourea is obtained by reacting 4,4-dimethylcyclohexylisocyanate with the appropriately substituted benzenesulphonamide. Treatment of this thiourea with HgO/ MeOH yields the corresponding isourea methyl ether and N - [4 - (# - [2 - methoxy - 5 - chlorobenzamido] - ethyl) - benzenesulphonyl] - N<SP>1</SP> - 2- chlorocyclohexyl-isourea methyl ether is similarly prepared from the corresponding thiourea. N,N<SP>1</SP> - Bis - 4 - [# - (benzamido - ethyl) - benzenesulphonyl]-urea is obtained by reacting 4-(#- benzamidoethyl ) -benzenesulphonamide sodium with 4 - (# - benzamidoethyl) - benzenesulphonyl-carbamic acid methyl ester. 4,4-Dimethylcyclohexyl parabanic acid is prepared by the interaction of 4,4-dimethylcyclohexyl-urea and oxalyl chloride. Exo - tricyclo - [3,2,1,0<SP>2,4</SP>] - octane - 3 - antiisocyanate and 4 - methyl - #<SP>3</SP> - cyclohexenylisocyanate are prepared by heating the corresponding acid azides which are in turn prepared from the corresponding acids. 4,4 - Diethyl - cyclohexyl - isocyanate is obtained by reacting 4,4-diethyl-cyclohexylamine with phosgene. 4 - Methyl - 3 - methoxy - (or 3 - ethoxy)- cyclohexylamine (the 3-methoxy compound being isolated as the acetate) are obtained by hydrogenating the corresponding benzene compounds. 4 - Methyl - #<SP>3</SP> - cyclohexenylamine is prepared by treating 4-methyl-#<SP>3</SP>-cyclohexenyl-isocyanate with acetic acid. 4-Chloro-cyclohexylamine is obtained by the interaction of 4-aminocyclohexanol and PCl 5 . Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier, preferably in a form adapted to oral administration, e.g. tablets.
GB24852/67A 1966-05-28 1967-05-30 Benzenesulfonyl Ureas and process for their manufacture Expired GB1182694A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1966F0049329 DE1252201B (en) 1966-05-28 1966-05-28 Process for the preparation of benzenesulfonylureas
DE1967F0052152 DE1618402B2 (en) 1966-05-28 1967-04-18 BENZENE SULFONYL UREA, METHOD OF MANUFACTURING AND PHARMACEUTICAL PREPARATIONS THEREOF

Publications (1)

Publication Number Publication Date
GB1182694A true GB1182694A (en) 1970-03-04

Family

ID=25977218

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24852/67A Expired GB1182694A (en) 1966-05-28 1967-05-30 Benzenesulfonyl Ureas and process for their manufacture

Country Status (22)

Country Link
JP (1) JPS5133903B1 (en)
AR (3) AR192396A1 (en)
AT (2) AT324349B (en)
BE (1) BE699134A (en)
CH (7) CH502318A (en)
CY (1) CY567A (en)
DE (1) DE1618402B2 (en)
DK (1) DK129414B (en)
ES (2) ES340953A1 (en)
FI (1) FI46155C (en)
FR (2) FR1524754A (en)
GB (1) GB1182694A (en)
IL (1) IL28034A (en)
IS (1) IS734B6 (en)
LU (1) LU53740A1 (en)
MC (1) MC654A1 (en)
MY (1) MY7100059A (en)
NL (2) NL157592B (en)
NO (1) NO122921B (en)
OA (1) OA03625A (en)
SE (1) SE336331B (en)
SU (4) SU465783A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11840543B2 (en) 2017-05-24 2023-12-12 The University Of Queensland Compounds and uses

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7200696A (en) * 1971-01-23 1972-07-25

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11840543B2 (en) 2017-05-24 2023-12-12 The University Of Queensland Compounds and uses

Also Published As

Publication number Publication date
BE699134A (en) 1967-11-29
CH533091A (en) 1973-01-31
DK129414C (en) 1975-02-24
AT326682B (en) 1975-12-29
AR192829A1 (en) 1973-03-14
OA03625A (en) 1971-12-25
AR193007A1 (en) 1973-03-21
NL6707340A (en) 1967-11-29
SU465783A3 (en) 1975-03-30
IS734B6 (en) 1970-09-30
CY567A (en) 1970-11-26
DK129414B (en) 1974-10-07
FI46155C (en) 1973-01-10
FR6497M (en) 1968-11-25
AR192396A1 (en) 1973-02-21
NL7801563A (en) 1978-06-30
IL28034A (en) 1971-05-26
MC654A1 (en) 1968-02-13
IS1648A7 (en) 1967-11-29
MY7100059A (en) 1971-12-31
DE1618402A1 (en) 1970-11-05
SU407445A3 (en) 1973-11-21
SU440828A3 (en) 1974-08-25
ES353814A1 (en) 1970-02-01
JPS5133903B1 (en) 1976-09-22
NO122921B (en) 1971-09-06
ES340953A1 (en) 1968-10-01
FR1524754A (en) 1968-05-10
SE336331B (en) 1971-07-05
SU468403A3 (en) 1975-04-25
FI46155B (en) 1972-10-02
LU53740A1 (en) 1969-03-18
CH533090A (en) 1973-01-31
CH502319A (en) 1971-01-31
CH502318A (en) 1971-01-31
CH502998A (en) 1971-02-15
CH502320A (en) 1971-01-31
NL157592B (en) 1978-08-15
CH503709A (en) 1971-02-28
DE1618402B2 (en) 1976-08-19
AT324349B (en) 1975-08-25

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Legal Events

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