GB1380136A - Thiadiazoles - Google Patents

Thiadiazoles

Info

Publication number
GB1380136A
GB1380136A GB1125872A GB1125872A GB1380136A GB 1380136 A GB1380136 A GB 1380136A GB 1125872 A GB1125872 A GB 1125872A GB 1125872 A GB1125872 A GB 1125872A GB 1380136 A GB1380136 A GB 1380136A
Authority
GB
United Kingdom
Prior art keywords
general formula
phenylalkanoyl
reacting
formula above
thiosemicarbazide
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
GB1125872A
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 GB1380136A publication Critical patent/GB1380136A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

1380136 2-Amino-5-phenylalkyl-1,3,4-thiadiazoles SANDOZ Ltd 10 March 1972 [15 March 1971] 11258/72 Heading C2C Novel 2-amino-5-phenylalkyl-1,3,4-thiadiazoles of the general formula . wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is a hydrogen fluorine or chlorine atom or a C 1-4 alkyl or C 1-4 alkoxy group and Z is a -(CH 2 ) n -, -CHR 6 -(CH 2 ) m - or -(CH 2 ) m -CHR 6 group in which n is 1-8, m is 0 or 1-7 and R 6 is a C 1-4 alkyl group, with the proviso that when each of R 1 , R 2 , R 3 , R 4 and R 5 is a hydrogen atom and Z is a -(CH 2 ) n - group, then is n other than 1, are prepared (a) by subjecting a 1-phenylalkanoyl-3-thiosemicarbazide of the general formula to strong Lewis acid conditions and (b) by reacting a phenylalkanoyl halide of the general formula wherein X is a chlorine or bromine atom with thiosemicarbazide in a strong Lewis acid medium. 1 - Phenylalkanoyl - 3 - thiosemicarbazides of the second general formula above are prepared (i) by reacting a plenylalkanoyl halide of the third general formula above with thiosemicarbazide in the absence of a Lewis acid and (ii) by reacting a phenylalkanoic acid hydrazide of the general formula with a thioisocyanate. Phenylalkanoic acid hydrazides of the fourth general formula above are prepared by reacting a phenylalkanoyl halide of the third general formula above or a phenylalkanoic acid ester of the general formula wherein R 7 is a C 1-4 alkyl group, with hydrazine. Pharmaceutical compositions having minor tranquillizer - sedative - hypnotic activity comprise, as active ingredient, a 2-amino-5- phenylalkyl-1,3,4-thiadiazole of the first general formula above, in association with a pharmaceutically acceptable diluent or carrier, and may be administered orally or parenterally.
GB1125872A 1971-03-15 1972-03-10 Thiadiazoles Expired GB1380136A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12448971A 1971-03-15 1971-03-15

Publications (1)

Publication Number Publication Date
GB1380136A true GB1380136A (en) 1975-01-08

Family

ID=22415177

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1125872A Expired GB1380136A (en) 1971-03-15 1972-03-10 Thiadiazoles

Country Status (9)

Country Link
AT (1) ATA212072A (en)
AU (1) AU467915B2 (en)
BE (1) BE780618A (en)
DD (1) DD100259A5 (en)
DE (1) DE2212245A1 (en)
FR (1) FR2130233B1 (en)
GB (1) GB1380136A (en)
HU (1) HU163329B (en)
NL (1) NL7203192A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1380977A (en) * 1972-07-18 1975-01-22 May & Baker Ltd Thiadiazole derivatives

Also Published As

Publication number Publication date
HU163329B (en) 1973-07-28
FR2130233A1 (en) 1972-11-03
NL7203192A (en) 1972-09-19
DD100259A5 (en) 1973-09-12
FR2130233B1 (en) 1975-12-26
AU467915B2 (en) 1973-09-20
ATA212072A (en) 1975-05-15
AU4003072A (en) 1973-09-20
BE780618A (en) 1972-09-13
DE2212245A1 (en) 1972-09-28

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Legal Events

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