GB1364779A - Thiazole derivative - Google Patents

Thiazole derivative

Info

Publication number
GB1364779A
GB1364779A GB2156772A GB2156772A GB1364779A GB 1364779 A GB1364779 A GB 1364779A GB 2156772 A GB2156772 A GB 2156772A GB 2156772 A GB2156772 A GB 2156772A GB 1364779 A GB1364779 A GB 1364779A
Authority
GB
United Kingdom
Prior art keywords
group
lower alkyl
reacting
general formula
phenyl
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
GB2156772A
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.)
Societe dEtudes de Produits Chimiques SA
Original Assignee
Societe dEtudes de Produits Chimiques SA
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 Societe dEtudes de Produits Chimiques SA filed Critical Societe dEtudes de Produits Chimiques SA
Priority to GB2156772A priority Critical patent/GB1364779A/en
Priority to BE130148A priority patent/BE798385A/en
Priority to ZA732677A priority patent/ZA732677B/en
Priority to AU54763/73A priority patent/AU5476373A/en
Priority to JP4581073A priority patent/JPS5314069B2/ja
Priority to NL7306033A priority patent/NL7306033A/xx
Priority to FR7316024A priority patent/FR2183766B3/fr
Priority to FR7316025A priority patent/FR2183767B1/fr
Priority to ES414516A priority patent/ES414516A1/en
Priority to AR247934A priority patent/AR196248A1/en
Priority to DE2323465A priority patent/DE2323465A1/en
Priority to AT408673A priority patent/AT323157B/en
Publication of GB1364779A publication Critical patent/GB1364779A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/673—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/173—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups 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
    • C07D277/20—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
    • C07D277/24—Radicals substituted by oxygen atoms
    • 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
    • C07D277/36—Sulfur atoms

Abstract

1364779 3 - (N,N - Diisopropyl - acetamido)- 4 - methyl - 5 - (beta - hydroxyethyl) - rhiazolium bromide SOC D'ETUDES DE PRODUITS CHIMIQUES 18 April 1973 [9 May 1972] 21567/72 Heading C2C The invention comprises 3-(N,N-diisopropylacetamido) - 4 - methyl - 5 - (beta - hydroxyethyl)-thiazolium bromide having the formula It may be prepared by reacting, in stoichiometric proportions, N,N-diisopropyl-bromacetamide with 4-methyl-5-hydroxyethyl thiazole in boiling butanol. 1364783 Pyrazole derivatives F HOFFMANN-LA ROCHE & CO AG 20 Oct 1972 [22 Oct 1971] 48432/72 Heading C2C Compounds of the general formula wherein R represents a lower alkyl group, which may be substituted with halogen, hydroxy, lower alkoxy, lower alkoxycarbonyl or carboxy or a lower alkenyl group, R 1 represents a hydrogen or halogen atom or a lower alkyl or lower alkoxy group and R 2 represents a grouping of the formula wherein R 3 represents a hydroxyl, lower alkanoyloxy, lower alkoxycarbonyloxy or lower alkoxy group (the alkoxy group being optionally substituted with halogen or lower alkoxy) or a phenylcarbonyloxy, phenyl (lower alkylcarbonyloxy), phenyl-(lower alkenylcarbonyloxy), pyridyl-(lower alkylcarbonyloxy) or pyridyl carbonyloxy group (the phenyl residues and the pyridyl residues being optionally substituted by lower alkyl, lower alkoxy or halogen), R 4 represents a lower alkyl or phenyl group and R 5 represents a hydrogen atom or a lower alkyl group or R 4 and R 5 together with the carbon atom to which they are attached represent a 5-, 6- or 7-membered alicyclic ring and salts thereof are claimed per se. The compounds of the invention may be prepared by a process which comprises (a) reacting a compound of the general formula wherein R and R 1 have the significance given in claim 1 and R 6 represents a lower alkyl group, with hydroxylamine in an inert solvent to give an amidoxime of the general formula or (b) reacting the preceding amidoxime with an appropriate lower acylating agent or a chloroformic acid lower alkyl ester or reacting an alkali metal or alkaline earth metal salt of the above amidoxime with a lower alkylating agent or (c) reacting the above amidoxime with a carbonyl compound of general formula or an acetal thereof and (d) splitting up a racemate obtained into the optical antipodes, if desired, and (e) converting a compound obtained into a salt, if desired. The term "lower" used throughout means having up to 5 carbon atoms.
GB2156772A 1972-05-09 1972-05-09 Thiazole derivative Expired GB1364779A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GB2156772A GB1364779A (en) 1972-05-09 1972-05-09 Thiazole derivative
BE130148A BE798385A (en) 1972-05-09 1973-04-18 THIAZOLE DERIVATIVE AND ITS PREPARATION PROCESS
ZA732677A ZA732677B (en) 1972-05-09 1973-04-18 Thiazole derivative
AU54763/73A AU5476373A (en) 1972-05-09 1973-04-19 Thiazole derivative, its process of preparation and its composition
JP4581073A JPS5314069B2 (en) 1972-05-09 1973-04-24
NL7306033A NL7306033A (en) 1972-05-09 1973-05-01
FR7316024A FR2183766B3 (en) 1972-05-09 1973-05-04
FR7316025A FR2183767B1 (en) 1972-05-09 1973-05-04
ES414516A ES414516A1 (en) 1972-05-09 1973-05-08 Thiazole derivative
AR247934A AR196248A1 (en) 1972-05-09 1973-05-09 PROCEDURE FOR PREPARING 3- (N, N-DIISOPROPYLACETAMIDE) -4-METHYL-5 (BETA-HYDROXYETHYL) -TIAZOLIUM BROMIDE
DE2323465A DE2323465A1 (en) 1972-05-09 1973-05-09 THIAZOLE DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION
AT408673A AT323157B (en) 1972-05-09 1973-05-09 METHOD OF PREPARING THE NEW 3- (DIISOPROPYLCARBAMINOYL-METHYL) -4-METHYL-5- (BETA-HYDROXYETHYL) THIAZOLIUM BROMIDE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2156772A GB1364779A (en) 1972-05-09 1972-05-09 Thiazole derivative

Publications (1)

Publication Number Publication Date
GB1364779A true GB1364779A (en) 1974-08-29

Family

ID=10165089

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2156772A Expired GB1364779A (en) 1972-05-09 1972-05-09 Thiazole derivative

Country Status (11)

Country Link
JP (1) JPS5314069B2 (en)
AR (1) AR196248A1 (en)
AT (1) AT323157B (en)
AU (1) AU5476373A (en)
BE (1) BE798385A (en)
DE (1) DE2323465A1 (en)
ES (1) ES414516A1 (en)
FR (2) FR2183767B1 (en)
GB (1) GB1364779A (en)
NL (1) NL7306033A (en)
ZA (1) ZA732677B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI119756B (en) * 1995-01-18 2009-03-13 Alteon Inc Use of Thiazolium Compounds to Prevent and Reverse Formation of Long-End Glycosylation
US5656261A (en) 1995-01-18 1997-08-12 The Picower Institute For Medical Research Preventing and reversing advanced glycosylation endproducts
MX9705449A (en) * 1995-01-18 1998-02-28 Alteon Inc Use of thiazolium compounds for preventing and reversing the formation of advanced glycosylation endproducts.
US20050014747A1 (en) 2003-04-18 2005-01-20 Emily Reinhard Dihydrothiazine prodrugs of thiazolium agents

Also Published As

Publication number Publication date
FR2183767B1 (en) 1976-12-03
AU5476373A (en) 1974-10-24
AT323157B (en) 1975-06-25
DE2323465A1 (en) 1973-11-22
BE798385A (en) 1973-10-18
ZA732677B (en) 1974-03-27
ES414516A1 (en) 1976-05-01
JPS4954367A (en) 1974-05-27
AR196248A1 (en) 1973-12-10
FR2183767A1 (en) 1973-12-21
JPS5314069B2 (en) 1978-05-15
NL7306033A (en) 1973-11-13
FR2183766A1 (en) 1973-12-21
FR2183766B3 (en) 1976-04-23

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees