GB855017A - Biguanide derivatives - Google Patents

Biguanide derivatives

Info

Publication number
GB855017A
GB855017A GB348358A GB348358A GB855017A GB 855017 A GB855017 A GB 855017A GB 348358 A GB348358 A GB 348358A GB 348358 A GB348358 A GB 348358A GB 855017 A GB855017 A GB 855017A
Authority
GB
United Kingdom
Prior art keywords
formula
oxygen
biguanides
under reflux
organic liquid
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
GB348358A
Inventor
John William James
Leslie Frederick Wiggins
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.)
Aspro Nicholas Ltd
Original Assignee
Aspro Nicholas Ltd
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 Aspro Nicholas Ltd filed Critical Aspro Nicholas Ltd
Priority to GB348358A priority Critical patent/GB855017A/en
Priority to US789522A priority patent/US3101336A/en
Priority to CH6905859A priority patent/CH401065A/en
Priority to DEA31262A priority patent/DE1292656B/en
Priority to DE19591795443 priority patent/DE1795443A1/en
Publication of GB855017A publication Critical patent/GB855017A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises biguanides of the formula: <FORM:0855017/IV(b)/1> and non-toxic acid addition salts thereof, wherein R represents an aryl group optionally substituted by one or more of any combination of alkyl, aryl, aralkyl, alkaryl, alkoxy and nitro groups and halogen atoms (e.g. chlorine), X is oxygen, R5-N < or <FORM:0855017/IV(b)/2> R1, R2, R3 and R4 are independently hydrogen or C1-4 alkyl groups, R5 is a C1-4 alkyl group, n is an integer of from 2 to 6 and the polymethylene chain may be interrupted by an oxygen atom, and p and q, which may be the same or different, are 0 or 1. Biguanides of the above formula, in which X is oxygen or R5-N <, are prepared by heating under reflux in an inert organic liquid a salt of dicyanimide with a heterocyclic amine of the formula: <FORM:0855017/IV(b)/3> wherein X is oxygen or R5-N < and Y is hydrogen or -(CH2)n-NH2, to form a cyanoamidine compound of the formula: <FORM:0855017/IV(b)/4> wherein q is 0 or 1, and thereafter heating such cyanoamidine compound under reflux in an inert organic liquid with an amine of the formula RNH2. Biguanides of the above formula, in which X is: <FORM:0855017/IV(b)/5> are prepared by heating under reflux in an inert organic liquid one molecular proportion of a piperazine derivative of the formula: <FORM:0855017/IV(b)/6> wherein Y1 and Y2 are independently hydrogen or -(CH2)n-NH2, with at least two molecular proportions of a salt of dicyanimide to form a cyanoamidine compound of the formula: <FORM:0855017/IV(b)/7> wherein p and q are each 0 or 1, and thereafter heating one molecular proportion of such cyanoamidine compound with at least two molecular proportions of an amine of the formula R NH2.
GB348358A 1958-02-03 1958-02-03 Biguanide derivatives Expired GB855017A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB348358A GB855017A (en) 1958-02-03 1958-02-03 Biguanide derivatives
US789522A US3101336A (en) 1958-02-03 1959-01-28 Heterocyclic substituted biguanides and cyanoguanidines
CH6905859A CH401065A (en) 1958-02-03 1959-02-02 Process for the preparation of biguanides
DEA31262A DE1292656B (en) 1958-02-03 1959-02-03 Piperazine derivatives and a process for their preparation
DE19591795443 DE1795443A1 (en) 1958-02-03 1959-02-03 Process for the preparation of piperazine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB348358A GB855017A (en) 1958-02-03 1958-02-03 Biguanide derivatives

Publications (1)

Publication Number Publication Date
GB855017A true GB855017A (en) 1960-11-30

Family

ID=9759174

Family Applications (1)

Application Number Title Priority Date Filing Date
GB348358A Expired GB855017A (en) 1958-02-03 1958-02-03 Biguanide derivatives

Country Status (1)

Country Link
GB (1) GB855017A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5620831A (en) * 1994-04-05 1997-04-15 Taiyo Ink Manufacturing Co., Ltd. Cyanoguanidine derivatives, and thermosetting or photocurable, thermosetting resin composition using the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5620831A (en) * 1994-04-05 1997-04-15 Taiyo Ink Manufacturing Co., Ltd. Cyanoguanidine derivatives, and thermosetting or photocurable, thermosetting resin composition using the same

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