GB783706A - New pyrazole compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents

New pyrazole compounds, a process for their preparation and pharmaceutical compositions containing them

Info

Publication number
GB783706A
GB783706A GB3010054A GB3010054A GB783706A GB 783706 A GB783706 A GB 783706A GB 3010054 A GB3010054 A GB 3010054A GB 3010054 A GB3010054 A GB 3010054A GB 783706 A GB783706 A GB 783706A
Authority
GB
United Kingdom
Prior art keywords
nitroso
methyl
benzyl
phenylpyrazole
pharmaceutical compositions
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
GB3010054A
Inventor
Wilfred Arthur Freeman
Ronald Slack
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.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
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 May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB3010054A priority Critical patent/GB783706A/en
Publication of GB783706A publication Critical patent/GB783706A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • C07D231/14—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 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
    • C07D231/16—Halogen atoms or nitro radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises nitrosopyrazoles of the formula <FORM:0783706/IV (a)/1> wherein R1 and R2 are different and represent either methyl or benzyl groups, a process for their preparation by nitrosating 1-phenylpentane-2 : 4-dione and condensing the resulting isonitrosoketone with phenylhydrazine, and, if desired, separating the isomeric pyrazoles produced (preferably by fractional crystallization from light petroleum), and pharmaceutic preparations (see Group VI) containing the products, which are useful for combatting fungi and bacteria (especially Mycobacterium tuberculosis). In an example, aqueous sodium nitrite is added to an ice-cooled solution of 1-phenylpentane-2 : 4-dione in dilute hydrochloric acid, and, after stirring for an hour, a solution of phenylhydrazine in aqueous acetic acid is added, the stirring continued, and the product separated by decantation, dissolved in benzene, chromatographed on a charcoal column and the mixture of nitroso pyrazoles separated by fractional crystallization from petrol ether (60-80 DEG ), giving 3 - benzyl - 5 - methyl - 4 - nitroso - 1 - phenylpyrazole and 5 - benzyl - 3 - methyl-4-nitroso-1-phenylpyrazole.ALSO:Pharmaceutical compositions for combatting fungi and bacteria, particularly Mycobacterium tuberculosis, comprise 3 - benzyl - 5 - methyl-4 - nitroso - 1 - phenylpyrazole or 5 - benzyl-3 - methyl - 4 - nitroso - 1 - phenylpyrazole or mixtures thereof together with a suitable solid or liquid carrier, e.g. starch, lactose, talc, stearic acid, magnesium stearate, gelatine or water. The compositions may be administered in the form of elixirs, tablets, capsules, powders, ointments or by injection.
GB3010054A 1954-10-19 1954-10-19 New pyrazole compounds, a process for their preparation and pharmaceutical compositions containing them Expired GB783706A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3010054A GB783706A (en) 1954-10-19 1954-10-19 New pyrazole compounds, a process for their preparation and pharmaceutical compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3010054A GB783706A (en) 1954-10-19 1954-10-19 New pyrazole compounds, a process for their preparation and pharmaceutical compositions containing them

Publications (1)

Publication Number Publication Date
GB783706A true GB783706A (en) 1957-09-25

Family

ID=10302267

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3010054A Expired GB783706A (en) 1954-10-19 1954-10-19 New pyrazole compounds, a process for their preparation and pharmaceutical compositions containing them

Country Status (1)

Country Link
GB (1) GB783706A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1151804B (en) * 1958-12-03 1963-07-25 May & Baker Ltd Process for the preparation of pyrazole derivatives
DE1162376B (en) * 1959-10-26 1964-02-06 May &. Baker Limited, Dagenham, Essex (Großbritannien) Process for the preparation of 4-nitro-pyrazole derivatives.
EP2829536A1 (en) * 2013-07-26 2015-01-28 LIONEX Diagnostics and Therapeutics GmbH 4-Nitro-5-dichloromethylpyrazol derivatives for the treatment of infectious diseases

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1151804B (en) * 1958-12-03 1963-07-25 May & Baker Ltd Process for the preparation of pyrazole derivatives
DE1162376B (en) * 1959-10-26 1964-02-06 May &. Baker Limited, Dagenham, Essex (Großbritannien) Process for the preparation of 4-nitro-pyrazole derivatives.
EP2829536A1 (en) * 2013-07-26 2015-01-28 LIONEX Diagnostics and Therapeutics GmbH 4-Nitro-5-dichloromethylpyrazol derivatives for the treatment of infectious diseases

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