GB1305549A - - Google Patents

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Publication number
GB1305549A
GB1305549A GB1305549DA GB1305549A GB 1305549 A GB1305549 A GB 1305549A GB 1305549D A GB1305549D A GB 1305549DA GB 1305549 A GB1305549 A GB 1305549A
Authority
GB
United Kingdom
Prior art keywords
reaction
formula
imidazole
prepared
benzyl
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
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 filed Critical
Publication of GB1305549A publication Critical patent/GB1305549A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C07D277/28—Radicals substituted by nitrogen atoms
    • 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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1305549 Guanidines SMITH KLINE & FRENCH LABORATORIES Ltd 26 Oct 1970 [29 Oct 1969] 13450/72 Divided out of 1305546 Heading C2C Novel compounds of formula wherein A is such that there is formed with the C and N shown an imidazole, pyrazole, thiazole or 1,2,4-triazole ring which rings may be substituted by a C 1-4 alkyl, a C 1-4 alkylthio, or an amino group, n is 2 to 5, R 1 is H, methyl, aralkyl or amino and R 2 is H, C 1-4 alkyl, aryl aralkyl or imidazolylalkyl or R 1 and R 2 together with the carbon and nitrogen atoms shown may form a five-membered ring provided that R 1 and R 2 are not both H when A is part of an unsubstituted imidazole ring are prepared either (a) by reaction of compounds of Formulµ II and III (b) by reaction of a compound of Formula IV with an appropriate amine, (c) reaction of an isourea with amines of Formula II above, (d) reaction of a cyanamide of formula R 1 HNCN with an amine of Formula II above or reaction of a compound of formula with an amine of Formula II above. Amines of Formula II above are prepared by reduction of either the appropriate nitrile or amide or by introduction or removal of a substituent on the ring nitrogen and also by cyclization for example of 1-chloro-6-phthalimidohex-1-en-3-one with hydrazine hydrate to give 3-(3-aminopropyl)pyrazole. 1 - Benzyl - 2 - (2 carboxamidoethyl)imidazole is obtained by reacting ammonia with 1- benzyl-2-(2-carbethoxyethyl)imidazole. 1 - Benzyl - 2 - (3 - cyanopropyl)imidazole is prepared by action of NaCN on 1-benzyl-2-(3 chloropropyl)imidazole obtained by action of SOCl 2 on the LiAlH 4 reduction product of the 2-(2-carbethoxyethyl compound. 2 - Methyl - 4 (5) - (3 - phthalimidopropyi)- imidazole is prepared by reaction of 1-bromo-5- phthalimidopentan-2-one with a solution of acetamidine and sodium ethoxide in ethanol. 1 - Chloro - 6 - phthalimidohex - 1 - en - 3 - one is obtained by reaction of 4-phthalimidobutyryl chloride with acetylene then ice. 3 - (2 - Thiazolyl)propylphthalimide is prepared by reaction of 3-phthalimidothiobutyramide and bromoacetaldehyde diethyl acetal.
GB1305549D 1969-10-29 1969-10-29 Expired GB1305549A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1345072 1969-10-29

Publications (1)

Publication Number Publication Date
GB1305549A true GB1305549A (en) 1973-02-07

Family

ID=10023212

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1305549D Expired GB1305549A (en) 1969-10-29 1969-10-29

Country Status (1)

Country Link
GB (1) GB1305549A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4098898A (en) * 1975-05-21 1978-07-04 Smith Kline & French Laboratories Limited Imidazolyl alkylguanidine compounds
US4165378A (en) 1977-04-20 1979-08-21 Ici Americas Inc. Guanidine derivatives of imidazoles and thiazoles
US4165377A (en) 1977-04-20 1979-08-21 Ici Americas Inc. Guanidino imidazoles and thiazoles
US4166856A (en) * 1975-05-21 1979-09-04 Smith Kline & French Laboratories Limited Thiazole and isothiazole derivative as blockers of histamine H2 -receptors
US4192879A (en) * 1975-05-21 1980-03-11 Smith Kline & French Laboratories Limited Imidazolyl alkylamino nitroethylene compounds
US4212875A (en) * 1977-05-05 1980-07-15 Smith Kline & French Laboratories Limited Imidazolyl alkyl bisamidines
EP0020173A1 (en) * 1979-06-04 1980-12-10 Merck & Co. Inc. Imidazole guanidines, their preparation and compositions containing them
US4242350A (en) 1978-05-24 1980-12-30 Imperial Chemical Industries Limited Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them
EP0397364A1 (en) * 1989-05-09 1990-11-14 Pfizer Inc. Heterocyclic guanidines AS 5HT 3 Antagonists
FR2686084A1 (en) * 1992-01-10 1993-07-16 Bioprojet Soc Civ NEW IMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATIONS
USRE37303E1 (en) * 1992-01-10 2001-07-31 Institut National Del La Sante Et De La Recherche Medicale Imidazole compounds and their therapeutic applications

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4166856A (en) * 1975-05-21 1979-09-04 Smith Kline & French Laboratories Limited Thiazole and isothiazole derivative as blockers of histamine H2 -receptors
US4192879A (en) * 1975-05-21 1980-03-11 Smith Kline & French Laboratories Limited Imidazolyl alkylamino nitroethylene compounds
US4098898A (en) * 1975-05-21 1978-07-04 Smith Kline & French Laboratories Limited Imidazolyl alkylguanidine compounds
US4440775A (en) * 1975-05-21 1984-04-03 Smith Kline & French Laboratories Limited Azolyl alkylthioureas and guanidines alkylaminonitroethylene compounds
US4333946A (en) 1975-05-21 1982-06-08 Smith Kline & French Laboratories Limited Blocking histamine H2 -receptors with imidazolylalkyl guanidine derivatives
US4262126A (en) 1977-04-20 1981-04-14 Imperial Chemical Industries Limited Guanidine derivatives of imidazoles and thiazoles
US4165378A (en) 1977-04-20 1979-08-21 Ici Americas Inc. Guanidine derivatives of imidazoles and thiazoles
US4165377A (en) 1977-04-20 1979-08-21 Ici Americas Inc. Guanidino imidazoles and thiazoles
US4234735A (en) 1977-04-20 1980-11-18 Imperial Chemical Industries Limited Guanidino imidazoles and thiazoles
US4212875A (en) * 1977-05-05 1980-07-15 Smith Kline & French Laboratories Limited Imidazolyl alkyl bisamidines
US4372963A (en) 1977-05-05 1983-02-08 Smith Kline & French Laboratories Limited Oxazolyl, isoxazolyl, triazolyl and thiadiazolyl alkyl bisamidines
US4242350A (en) 1978-05-24 1980-12-30 Imperial Chemical Industries Limited Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them
EP0020173A1 (en) * 1979-06-04 1980-12-10 Merck & Co. Inc. Imidazole guanidines, their preparation and compositions containing them
EP0397364A1 (en) * 1989-05-09 1990-11-14 Pfizer Inc. Heterocyclic guanidines AS 5HT 3 Antagonists
FR2686084A1 (en) * 1992-01-10 1993-07-16 Bioprojet Soc Civ NEW IMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATIONS
WO1993014070A2 (en) * 1992-01-10 1993-07-22 Institut National De La Sante Et De La Recherche Medicale Novel imidazole derivatives, their preparation and therapeutic applications
WO1993014070A3 (en) * 1992-01-10 1993-08-19 Inst Nat Sante Rech Med Novel imidazole derivatives, their preparation and therapeutic applications
US5559113A (en) * 1992-01-10 1996-09-24 Institut National De La Sante Et De La Recherche Medicale Imidazole compounds and their therapeutic applications
US5708171A (en) * 1992-01-10 1998-01-13 Institut National De La Sante Et De La Recherche Medicale Imidazole derivatives for pharmaceutical use
USRE37303E1 (en) * 1992-01-10 2001-07-31 Institut National Del La Sante Et De La Recherche Medicale Imidazole compounds and their therapeutic applications

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Legal Events

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