IE38123B1 - Heterocyclic substituted guanidines - Google Patents

Heterocyclic substituted guanidines

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Publication number
IE38123B1
IE38123B1 IE1467/73A IE146773A IE38123B1 IE 38123 B1 IE38123 B1 IE 38123B1 IE 1467/73 A IE1467/73 A IE 1467/73A IE 146773 A IE146773 A IE 146773A IE 38123 B1 IE38123 B1 IE 38123B1
Authority
IE
Ireland
Prior art keywords
formula
compound
alkyl
prepared
methylthio
Prior art date
Application number
IE1467/73A
Other versions
IE38123L (en
Original Assignee
Smith Kline French Lab
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 Smith Kline French Lab filed Critical Smith Kline French Lab
Publication of IE38123L publication Critical patent/IE38123L/en
Publication of IE38123B1 publication Critical patent/IE38123B1/en

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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
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
    • C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
    • C07C337/08—Compounds containing any of the groups, e.g. thiosemicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. thiosemicarbazones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • C07D241/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/26—Radicals substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1398426 Heterocyclic substituted guanidines SMITH KLINE & FRENCH LABORATORIES Ltd 21 Aug 1973 [5 Sept 1972] 41161/72 Addition to 1338169 Heading C2C The novel guanidines of general Formula I wherein R 1 is H or C 1-4 alkyl; R 2 is a group of Formula II in which Het is an imidazole, pyridine, thiazole, isothiazole, oxazole, isoxazole, pyrazole, triazole, thiadiazole, pyrimidine, pyrazine or pyridazine ring which is optionally substituted by C 1-4 alkyl, CF 3 , OH, halogen or amino, Z is S, O, NH or CH 2 , m and n are integers 0-4 such that m+n is 2-4; X is COR 3 , CSR 3 , SO 2 R 4 , N=CHR 5 or, when Z is CH 2 X is NO 2 ; R 3 is C 1-4 alkyl or alkoxy, or amino; R 4 is C 1-4 alkyl, optionally substituted aryl, CF 3 or amino and R 5 is optionally substituted aryl may be prepared by (i) reacting an amine of formula with (a) a compound of Formula III wherein R 1 , R 2 and X are as defined above, Y is S or O and A is C 1-4 alkyl, or (b) a compound of Formula IV wherein A, Y and X are as defined above, the product of Formula V then being reacted with an amine R 1 NH 2 in which R 1 is H or C 1-4 alkyl to produce the desired compound of Formula I, (ii) reacting a guanidine of Formula VI with a diaminosulphonyl compound of Formula VII in which W is derived from a secondary amine of formula W=NH, e.g. piperidine to produce a compound of Formula I in which X is amino sulphonyl, (iii) mild acid hydrolysis of a cyanoguanidine of Formula VIII to obtain a compound of Formula I in which X is aminocarbonyl, or by (iv) reaction of a compound of Formula VIII with H 2 S in the presence of a strong base to produce compounds of Formula I in which x is aminothiocarbonyl. N,S - dimethyl - N<SP>1</SP> - trifluoromethanesulphonylisothiourea is prepared by reacting trifluoromethanesulphonamide with bis-5- methylthio-N-methylformimine. N - (4 - chlorobenzenesulphonyl) - N<SP>1</SP>,S- dimethylisothiourea is prepared by reaction of 4 - chlorobenzenesulphonamide with bis - S- methylthio-N-methylformimine. N - (3,4 - dichlorobenzenesulphonyl) - N<SP>1</SP>,S- dimethylisothiourea is prepared by reaction of 3,4 - dichlorobenzenesulphonamide and bis - S- methylthio-N-methylformimine. N - ethylsulphonyl-, N - propylsulphonyl- and N - 4 - aminobenzenesulphonyl - iminodithiocarbonic acid dimethyl esters are prepared by reaction of the corresponding sulphonamides with CS Z and methyliodide in the presence of hydroxide. N - methyl - N<SP>11</SP> - [2 - ((4 - methyl - 5 - imidazolyl)metltylthio)ethyl]guanidine dihydrochloride is prepared by hydrolysis N-cyano-N<SP>1</SP>-methyl- N<SP>11</SP> - [2 - ((4 - methyl - 5 - imidazolyl) - methylthio)ethyl]guanidine in hydrochloric acid. Pharmaceutical compositions having antihistamine activity for oral or parenteral administration comprise a compound of Formula I together with a pharmaceutically acceptable carrier. [GB1398426A]
IE1467/73A 1972-09-05 1973-08-22 Heterocyclic substituted guanidines IE38123B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4116172A GB1398426A (en) 1972-09-05 1972-09-05 Heterocyclic substituted guanidines

Publications (2)

Publication Number Publication Date
IE38123L IE38123L (en) 1974-03-05
IE38123B1 true IE38123B1 (en) 1978-01-04

Family

ID=10418396

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1467/73A IE38123B1 (en) 1972-09-05 1973-08-22 Heterocyclic substituted guanidines

Country Status (11)

Country Link
JP (1) JPS5732062B2 (en)
AU (1) AU473158B2 (en)
BE (1) BE804145A (en)
CA (1) CA1053242A (en)
DE (1) DE2344833C2 (en)
FR (1) FR2199466B2 (en)
GB (1) GB1398426A (en)
HU (1) HU166637B (en)
IE (1) IE38123B1 (en)
IL (1) IL42879A (en)
NL (1) NL7310836A (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1554153A (en) * 1975-05-15 1979-10-17 Smith Kline French Lab Process for making 2-amino-2-alkylthionitroethylenes
US4165378A (en) 1977-04-20 1979-08-21 Ici Americas Inc. Guanidine derivatives of imidazoles and thiazoles
NZ186965A (en) 1977-04-20 1980-02-21 Ici Ltd Guanidino derivatives and pharmaceutical compositions
DE2817078C2 (en) * 1977-04-20 1995-06-14 Zeneca Ltd Guanidine derivatives
DE2835695A1 (en) 1977-08-29 1979-03-15 Yamanouchi Pharma Co Ltd NEW HETEROCYCLIC COMPOUNDS, METHODS OF MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEM
EP0006679B1 (en) 1978-05-24 1982-07-21 Imperial Chemical Industries Plc Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them
JPS5610175A (en) * 1979-07-06 1981-02-02 Fujisawa Pharmaceut Co Ltd Preparation of imidazole derivative
AU7474881A (en) * 1980-08-27 1982-03-04 Glaxo Group Limited 1,2,4-triazole derivatives
DE3108753A1 (en) * 1981-03-07 1982-09-16 Degussa Ag, 6000 Frankfurt Substituted alkylphenylsulphonylguanidines with a heterocyclic radical
DE3213509A1 (en) * 1982-04-10 1983-10-20 Basf Ag, 6700 Ludwigshafen N-SUBSTITUTED IMIDAZOLE DERIVATIVES, THEIR PRODUCTION, THE MEDICINES CONTAINING THEM AND THEIR USE
PT77623B (en) * 1982-11-25 1986-03-19 Smith Kline French Lab Process for the preparation of a small class of histamine h2-antagonists
NL8303965A (en) * 1982-12-08 1984-07-02 Degussa NEW FOOD DIAMINE AND GUANIDINE DERIVATIVES; METHOD FOR PREPARING THEREOF MEDICINES CONTAINING THEM; METHOD FOR PREPARING SUCH MEDICINES; APPLICATION OF THE COMPOUNDS FOR THE PREPARATION OF MEDICINAL PRODUCTS AND IN MEDICINE.
GB8419223D0 (en) * 1984-07-27 1984-08-30 Hoechst Uk Ltd Sulphamoylguanidine derivatives
KR100935925B1 (en) * 2003-05-28 2010-01-11 엘지전자 주식회사 Capacitor holder of washer
JP6006634B2 (en) * 2011-12-28 2016-10-12 東和薬品株式会社 Method for producing epinastine using isourea compound

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE758146A (en) * 1969-10-29 1971-04-28 Smith Kline French Lab AMIDINE DERIVATIVES
IE36050B1 (en) * 1971-03-09 1976-08-04 Smith Kline French Lab Ureas thioureas and guanidines

Also Published As

Publication number Publication date
CA1053242A (en) 1979-04-24
DE2344833A1 (en) 1974-03-14
FR2199466A2 (en) 1974-04-12
JPS5732062B2 (en) 1982-07-08
HU166637B (en) 1975-04-28
DE2344833C2 (en) 1981-10-29
AU5890673A (en) 1975-02-06
IL42879A0 (en) 1973-11-28
FR2199466B2 (en) 1977-01-28
JPS4975575A (en) 1974-07-20
IL42879A (en) 1976-10-31
IE38123L (en) 1974-03-05
NL7310836A (en) 1974-03-07
GB1398426A (en) 1975-06-18
AU473158B2 (en) 1976-06-17
BE804145A (en) 1974-02-28

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