GB1293741A - Improvements in or relating to thiazole derivatives - Google Patents

Improvements in or relating to thiazole derivatives

Info

Publication number
GB1293741A
GB1293741A GB71/70A GB7170A GB1293741A GB 1293741 A GB1293741 A GB 1293741A GB 71/70 A GB71/70 A GB 71/70A GB 7170 A GB7170 A GB 7170A GB 1293741 A GB1293741 A GB 1293741A
Authority
GB
United Kingdom
Prior art keywords
general formula
alkyl
alkylimino
phenyl
prepared
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
GB71/70A
Inventor
Robert Everett Manning
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB1293741A publication Critical patent/GB1293741A/en
Expired legal-status Critical Current

Links

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
    • C07D277/32—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 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
    • 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
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/18—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

1293741 2 - Alkylimino - 3 - alkyl - 5 phenyl- 4-thiazoline derivatives SANDOZ Ltd 1 Jan 1970 [13 Jan 1969 19 June 1969] 71/70 Heading C2C Novel 2 - alkylimino - 3 - alkyl - 5 - phenyl - 4- thiazoline derivatives of the general formula wherein R and R o are each a fluorine or chlorine atom or a C 1-3 alkyl or trifluoromethyl group, R 1 and R 2 are each a straight chain C 1-3 alkyl group, R 1 and R 2 are each a straight chain C 1-3 alkyl group or R 1 and R 2 together signify (CH 2 ) n , where n is 2 or 3, A is a hydrogen atom and B is a hydroxyl group or A and B together signify a carbon to carbon bond, and acid addition salts thereof are prepared (a) when A is a hydrogen atom and B is a hydroxyl group, by reaction of an α-halo-phenylacetaldehyde of the general formula with a thiourea of the general formula or (b) when A and B together signify a carbon to carbon bond, by dehydration of the product of (a); followed optionally by salification of the product. α-Halo-phenylacetaldehydes of the second general formula above are prepared by chlorination or bromination of a phenylacetaldehyde of the general formula Phenylacetaldehydes of the fourth general formula above wherein R and R o are not both a halogen atom are prepared by treatment of a phenylacetonitrile of the general formula with aqueous formic acid in the presence of Raney nickel alloy. Pharmaceutical compositions having hypotensive activity comprise, as active ingredient, a 2 - alkylimino - 3 - alkyl - 5 - phenyl - 4 - thiazoline derivative of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutically acceptable carrier, and may be administered orally or parenterally.
GB71/70A 1969-01-13 1970-01-01 Improvements in or relating to thiazole derivatives Expired GB1293741A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US79085369A 1969-01-13 1969-01-13
US84118669A 1969-06-19 1969-06-19

Publications (1)

Publication Number Publication Date
GB1293741A true GB1293741A (en) 1972-10-25

Family

ID=27121087

Family Applications (1)

Application Number Title Priority Date Filing Date
GB71/70A Expired GB1293741A (en) 1969-01-13 1970-01-01 Improvements in or relating to thiazole derivatives

Country Status (10)

Country Link
JP (1) JPS4826009B1 (en)
BE (1) BE744333A (en)
BG (1) BG17616A3 (en)
BR (1) BR7015805D0 (en)
CH (1) CH520703A (en)
DE (1) DE2000788A1 (en)
FR (1) FR2034463B1 (en)
GB (1) GB1293741A (en)
IL (1) IL33687A0 (en)
NL (1) NL7000045A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4489083A (en) * 1981-11-25 1984-12-18 Pfizer Inc. Phenyl imidazole derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB690238A (en) * 1949-08-23 1953-04-15 Knoll Ag Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidine
US2933497A (en) * 1958-01-29 1960-04-19 Searle & Co Bicyclic thiazole derivatives
US2969369A (en) * 1959-10-23 1961-01-24 Searle & Co Derivatives of 3-phenyl-5, 6-dihydroimidazo-[2. 1-b] thiazoles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4489083A (en) * 1981-11-25 1984-12-18 Pfizer Inc. Phenyl imidazole derivatives

Also Published As

Publication number Publication date
BR7015805D0 (en) 1973-01-04
JPS4826009B1 (en) 1973-08-03
FR2034463B1 (en) 1973-01-12
BG17616A3 (en) 1973-11-10
IL33687A0 (en) 1970-03-22
NL7000045A (en) 1970-07-15
BE744333A (en) 1970-07-13
DE2000788A1 (en) 1970-07-23
FR2034463A1 (en) 1970-12-11
CH520703A (en) 1972-03-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees