GB1178242A - Novel Biologically Active Bis-Isothioureas - Google Patents

Novel Biologically Active Bis-Isothioureas

Info

Publication number
GB1178242A
GB1178242A GB516866A GB516866A GB1178242A GB 1178242 A GB1178242 A GB 1178242A GB 516866 A GB516866 A GB 516866A GB 516866 A GB516866 A GB 516866A GB 1178242 A GB1178242 A GB 1178242A
Authority
GB
United Kingdom
Prior art keywords
bis
different
group
isothioureas
same
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
GB516866A
Inventor
John Evlyn Warner Billinghurst
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB516866A priority Critical patent/GB1178242A/en
Priority to BE693560D priority patent/BE693560A/xx
Priority to NL6701709A priority patent/NL6701709A/xx
Priority to CH159767A priority patent/CH500177A/en
Priority to DE19671643199 priority patent/DE1643199A1/en
Priority to FR93797A priority patent/FR1538328A/en
Publication of GB1178242A publication Critical patent/GB1178242A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/30—Isothioureas
    • C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,178,242. Medicines comprising bis-isothioureas. WELLCOME FOUNDATION Ltd. 27 Jan., 1967 [5 Feb., 1966], No. 5168/66. Heading A5B. [Also in Division C2] Bis-isothioureas of the general formula wherein either A is a -(CH 2 ) n - group in which n is an integer from 2 to 14, R<SP>1</SP> and R<SP>2</SP>, R<SP>1'</SP> and R<SP>2'</SP>, respectively, are the same or different lower alkyl or different alicyclic groups, or both are the same or different and each is an alkyl-substituted aromatic hydrocarbon group containing a total of up to 10 carbon atoms, or one of them is a lower alkyl group and the other an alkyl-substituted aromatic hydrocarbon group as defined above; or A is a -(CH 2 ) n group in which n is an integer from 15 to 22 or is the N,N'-bis-(1-carbonyldecamethylene) piperazine group, R<SP>1</SP>, R<SP>2</SP>, R<SP>1'</SP> and R<SP>2'</SP> are the same or different, and each is a hydrogen atom or an aliphatic, alicyclic or an optionally alkyl-substituted aromatic hydrocarbon group containing -a total of up to 10 carbon atoms, or R<SP>1</SP> and R<SP>2</SP>, or R<SP>1'</SP> and R<SP>2'</SP>, as aliphatic hydrocarbon groups, may together form a 5- or 6-membered heterocyclic ring with the adjacent -N=C<SP>1</SP>-N- group of the above general formula; and R<SP>3</SP> and R<SP>3'</SP> are the same or different and each is a hydrogen atom or a lower alkyl group containing up to 4 carbon atoms; and therapeutically acceptable acid addition salts thereof may be contained in a vaccine in association with antigenic material, because of their good adjuvant activity, e.g. with diphtheria formol toxoid. The said compounds also show anthelmintic, diuretic, anti-diuretic, hypo- or hyperglycaemic and anti-inflammatory activity and may be employed as the active ingredient in pharmaceutical compositions in combination with a pharmaceutically acceptable carrier. The bis-isothioureas may be in unit dosage form in the said compositions. For oral administration, anthelmintic compositions may contain fine powders or granules of the bis-isothiorurea together with diluents and dispersing and surface-active agents and may be presented in a draft in water or in a syrup; in capsules or cachets in the drystate or in a non-aqueous suspension, when a suspending agent may be included; in tablets, when binders and lubricants may be included; or in a suspension in water, a syrup, an oil, or a water-oil emulsion, when flavouring, preserving, thickening and emulsifying agents may be included. The granules or tablets may be coated.
GB516866A 1966-02-05 1966-02-05 Novel Biologically Active Bis-Isothioureas Expired GB1178242A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB516866A GB1178242A (en) 1966-02-05 1966-02-05 Novel Biologically Active Bis-Isothioureas
BE693560D BE693560A (en) 1966-02-05 1967-02-02
NL6701709A NL6701709A (en) 1966-02-05 1967-02-03
CH159767A CH500177A (en) 1966-02-05 1967-02-03 Bis-isothioureas anthelmintic diuretic anti-diuretic
DE19671643199 DE1643199A1 (en) 1966-02-05 1967-02-03 Process for the production of biologically active sulfur compounds
FR93797A FR1538328A (en) 1966-02-05 1967-02-06 Iso-thioureas and their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB516866A GB1178242A (en) 1966-02-05 1966-02-05 Novel Biologically Active Bis-Isothioureas

Publications (1)

Publication Number Publication Date
GB1178242A true GB1178242A (en) 1970-01-21

Family

ID=9790968

Family Applications (1)

Application Number Title Priority Date Filing Date
GB516866A Expired GB1178242A (en) 1966-02-05 1966-02-05 Novel Biologically Active Bis-Isothioureas

Country Status (5)

Country Link
BE (1) BE693560A (en)
CH (1) CH500177A (en)
DE (1) DE1643199A1 (en)
GB (1) GB1178242A (en)
NL (1) NL6701709A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4728656A (en) * 1985-12-12 1988-03-01 Smithkline Beckman Corporation 2,2-alkyldiylbis(thio)bis(imidazoles) useful for inhibition of the 5-lipoxygenase pathway
US4847270A (en) * 1985-12-12 1989-07-11 Smithkline Beckman Corporation Inhibition of the 5-lipoxygenase pathway utilizing certain 2,2'-alkyldiyl bis(thio)bis-imidazoles and derivatives
WO1994012165A2 (en) * 1992-11-27 1994-06-09 The Wellcome Foundation Limited Enzyme inhibitors
WO1995009619A2 (en) * 1993-10-04 1995-04-13 The Wellcome Foundation Limited Substituted urea and isothiourea derivatives as no synthase inhibitors
US5721247A (en) * 1994-09-20 1998-02-24 Astra Aktiebolag Isothiourea derivatives useful in therapy
US5786364A (en) * 1995-02-11 1998-07-28 Astra Aktiebolag Bicyclic isothiourea derivatives useful in therapy
US6090846A (en) * 1994-06-01 2000-07-18 Glaxo Wellcome Inc. Substituted urea and isothiourea derivatives as no synthase inhibitors
US6225305B1 (en) 1993-10-04 2001-05-01 Glaxo Wellcome Inc. Substituted urea and isothiorea derivatives as no synthase inhibitors
US6297276B1 (en) 1993-10-04 2001-10-02 Glaxosmithkline Substituted urea and isothiourea derivatives as no synthase inhibitors
US7358313B2 (en) * 2002-06-12 2008-04-15 Michelin Recherche Et Technique S.A. Thiouronium salt as anti-reversion agent in a vulcanizable rubber composition and tire based on such a composition

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4728656A (en) * 1985-12-12 1988-03-01 Smithkline Beckman Corporation 2,2-alkyldiylbis(thio)bis(imidazoles) useful for inhibition of the 5-lipoxygenase pathway
US4847270A (en) * 1985-12-12 1989-07-11 Smithkline Beckman Corporation Inhibition of the 5-lipoxygenase pathway utilizing certain 2,2'-alkyldiyl bis(thio)bis-imidazoles and derivatives
WO1994012165A2 (en) * 1992-11-27 1994-06-09 The Wellcome Foundation Limited Enzyme inhibitors
WO1994012165A3 (en) * 1992-11-27 1994-12-08 Wellcome Found Enzyme inhibitors
WO1995009619A2 (en) * 1993-10-04 1995-04-13 The Wellcome Foundation Limited Substituted urea and isothiourea derivatives as no synthase inhibitors
WO1995009619A3 (en) * 1993-10-04 1995-06-15 Wellcome Found Substituted urea and isothiourea derivatives as no synthase inhibitors
US6225305B1 (en) 1993-10-04 2001-05-01 Glaxo Wellcome Inc. Substituted urea and isothiorea derivatives as no synthase inhibitors
US6297276B1 (en) 1993-10-04 2001-10-02 Glaxosmithkline Substituted urea and isothiourea derivatives as no synthase inhibitors
US6090846A (en) * 1994-06-01 2000-07-18 Glaxo Wellcome Inc. Substituted urea and isothiourea derivatives as no synthase inhibitors
US5721247A (en) * 1994-09-20 1998-02-24 Astra Aktiebolag Isothiourea derivatives useful in therapy
US5786364A (en) * 1995-02-11 1998-07-28 Astra Aktiebolag Bicyclic isothiourea derivatives useful in therapy
US7358313B2 (en) * 2002-06-12 2008-04-15 Michelin Recherche Et Technique S.A. Thiouronium salt as anti-reversion agent in a vulcanizable rubber composition and tire based on such a composition

Also Published As

Publication number Publication date
DE1643199A1 (en) 1971-06-16
BE693560A (en) 1967-08-02
NL6701709A (en) 1967-08-07
CH500177A (en) 1970-12-15

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