GB776118A - New heterocyclic compounds and their production - Google Patents

New heterocyclic compounds and their production

Info

Publication number
GB776118A
GB776118A GB29198/55A GB2919855A GB776118A GB 776118 A GB776118 A GB 776118A GB 29198/55 A GB29198/55 A GB 29198/55A GB 2919855 A GB2919855 A GB 2919855A GB 776118 A GB776118 A GB 776118A
Authority
GB
United Kingdom
Prior art keywords
isonicotinic acid
general formula
heating
thiosemicarbazide
triazoline
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
GB29198/55A
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.)
WOLFGANG WILDE
Original Assignee
WOLFGANG WILDE
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 WOLFGANG WILDE filed Critical WOLFGANG WILDE
Publication of GB776118A publication Critical patent/GB776118A/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
    • C07D285/13—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

Landscapes

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

Abstract

The invention comprises substituted 1,2,4-triazoline-5-thiones of the general formula <FORM:0776118/IV(b)/1> wherein R1 and R2 represent hydrogen atoms or methyl radicals, the triazoline-5-thiones may be in the tautomeric form indicated by the following general formul <FORM:0776118/IV(b)/2> and salts thereof derived from acids and bases, and the preparation thereof by heating an isonicotinic acid thiosemicarbazide of the general formula <FORM:0776118/IV(b)/3> wherein R1 and R2 have the above significance, or by reacting isonicotinic acid hydrazide with a thiocyanate to form an isonicotinic acid thiosemicarbazide of the above general formula which is then heated. The heating step may be carried out in the absence of or in the presence of a high-boiling solvent such as tetrahydronaphthalene or cumene. The ring closure may also be brought about by means of an alkaline condensing agent such as an alkali metal alcoholate in an alcohol. Bases which may be used for salt formation with the thionones of the above general formula are alkalis such as sodium carbonate and bicarbonate, and organic bases such as isonicotinic acid hydrazide, p-aminosalicylic acid, ethanolamine and diethanolamine. The isonicotinic acid thiosemicarbazide intermediate of the above general formula may also be isolated in the form of salts with acids or bases-suitable acids being hydrochloric, hydrobromic and thiocyanic acid. In the examples, 3-g -pyridyl-D 2-1,2,4-triazoline-5-thione is prepared by heating isonicotinic acid thiosemicarbazide which is obtainable by heating isonicotinic acid and ammonium thiocyanate, and 3-(21-methyl-pyridyl-4)-D 2-1,2,4-triazoline-5-thione is prepared by heating 2-methyl-isonicotinic acid thiosemicarbazide.
GB29198/55A 1954-10-13 1955-10-13 New heterocyclic compounds and their production Expired GB776118A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE337538X 1954-10-13

Publications (1)

Publication Number Publication Date
GB776118A true GB776118A (en) 1957-06-05

Family

ID=6221570

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29198/55A Expired GB776118A (en) 1954-10-13 1955-10-13 New heterocyclic compounds and their production

Country Status (4)

Country Link
CH (1) CH337538A (en)
DE (1) DE1066200B (en)
FR (1) FR1171968A (en)
GB (1) GB776118A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3625951A (en) * 1970-12-23 1971-12-07 Air Prod & Chem Preparation of 3,4-disubstituted-delta-2-1,2,-triazoline-5-thiones
US4952593A (en) * 1985-10-29 1990-08-28 Merrell Dow Pharmaceuticals Inc. 5-heterocyclic-2,4-dialkyl-3H-1,2,4-triazole-3-thiones and their use as antidepressants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3173289D1 (en) 1980-06-21 1986-02-06 Beecham Wuelfing Gmbh & Co Kg Xanthine derivatives, pharmaceutical compositions containing them and a process for their preparation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3625951A (en) * 1970-12-23 1971-12-07 Air Prod & Chem Preparation of 3,4-disubstituted-delta-2-1,2,-triazoline-5-thiones
US4952593A (en) * 1985-10-29 1990-08-28 Merrell Dow Pharmaceuticals Inc. 5-heterocyclic-2,4-dialkyl-3H-1,2,4-triazole-3-thiones and their use as antidepressants

Also Published As

Publication number Publication date
DE1066200B (en) 1959-10-01
FR1171968A (en) 1959-02-04
CH337538A (en) 1959-04-15

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