GB1274521A - Dithiocarbazinic ester derivatives - Google Patents

Dithiocarbazinic ester derivatives

Info

Publication number
GB1274521A
GB1274521A GB31122/69A GB3112269A GB1274521A GB 1274521 A GB1274521 A GB 1274521A GB 31122/69 A GB31122/69 A GB 31122/69A GB 3112269 A GB3112269 A GB 3112269A GB 1274521 A GB1274521 A GB 1274521A
Authority
GB
United Kingdom
Prior art keywords
substituted
chlorobenzyl
dimethoxy
aralkyl
oxo
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
GB31122/69A
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.)
Egyesult Gyogyszer es Tapszergyar
Egyt Gyogyszervegyeszeti Gyar
Original Assignee
Egyesult Gyogyszer es Tapszergyar
Egyt Gyogyszervegyeszeti Gyar
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 Egyesult Gyogyszer es Tapszergyar, Egyt Gyogyszervegyeszeti Gyar filed Critical Egyesult Gyogyszer es Tapszergyar
Publication of GB1274521A publication Critical patent/GB1274521A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/14—Dithiocarbamic acids; Derivatives thereof
    • C07C333/18—Esters of dithiocarbamic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • 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
    • 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
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,274,521. Compounds containing hydrazono and dithiocarboxylic ester groups. EGYESULT GYOGYSZER ES TAPSZERGYAR. 19 June, 1969 [24 July, 1968], No. 31122/69. Heading C2C. Novel compounds I (including salts and hydrates thereof) wherein R<SP>1</SP> is H, straight or branched chain alkyl, alkenyl, aralkyl or aralkenyl (the aryl moiety embraces heteroaryl) which may be substituted by alkoxy, carboalkoxy, CO 2 H, amino, alkylamino, dialkylamino or trialkylammonium, or R<SP>1</SP> is phenyl, pyridyl, indolyl, quinolyl, thienyl or furyl which may be mono- or poly-substituted with halogen, alkyl, alkoxy, acyl, OH, SO 3 H, carboalkoxy or CO 2 H, R<SP>2</SP> is H, straight or branched chain alkyl or aralkyl which may be substituted as stated for R<SP>1</SP>, CO 2 H or R<SP>1</SP> and R<SP>2</SP> comprise together with the attached carbon a mono- or poly-cyclic radical having at least one of the ring carbons substituted by = O or = NÀNHCSSR<SP>3</SP>, and R<SP>3</SP> is straight or branched chain alkyl, alkenyl or aralkyl which may be mono- or poly-substituted by halogen and straight or branched alkyl, are obtained by reacting: (a) R<SP>1</SP>COR<SP>2</SP> (may be formed in situ) with NH 2 ÀNHÀCSSR<SP>3</SP>; (b) R<SP>1</SP>COR<SP>2</SP> with NH 2 NHÀCSSZ (one or both of the reactants may be formed in situ; Z is alkali or alkaline earth metal, ammonium or hydrazinium cation) and the intermediate compound so obtained is subsequently converted into 1 by standard methods; (c) R<SP>1</SP>R<SP>2</SP>C: NNH 2 with sodium, potassium, sodium amide or sodium hydride to afford R<SP>1</SP>R<SP>2</SP>ÀC: NNHZ 1 (Z 1 is sodium or potassium) which is in turn treated with carbon disulphide to give (converted to I by standard methods); (d) R<SP>1</SP>R<SP>2</SP>C = NNHZ 1 with ClCSSR<SP>3</SP>; (e) R<SP>1</SP>R<SP>2</SP>C = NNHZ 1 with thiophosgene to afford R<SP>1</SP>R<SP>2</SP>C: NNHCSCl which, in turn, is reacted with R<SP>3</SP>SZ to afford I; or (f) R<SP>1</SP>R<SP>2</SP>C: NNH 2 with R<SP>4</SP>SCSSR<SP>4</SP> at below 150‹ C. (R<SP>4</SP> is alkyl or aralkyl). The invention also encompasses exemplified novel compounds of the structure I but which are not covered by the preceding definitions of R 1 and R 2 . They are made from the following oxo-compounds (R 3 is given in parenthesis): chloral (Me, benzyl or p-chlorobenzyl), acetylacetone (Me), acetobutyrolactone (Me), pnitrobenzaldehyde (Me), piperonal (Me), pnitroacetophenone (Me or Et), p-nitro-α- acetamido - acetophenone (Me), 2 - hydroxy- 1 - naphthaldehyde (Me), 2 - methoxy - 3,4- methylenedioxy - 6 - vinyl - benzaldehyde (Me), α - formyl- or α - methoxymethylene - 3,4 - dimethoxyphenyl - acetonitrile (Me), DL - pnitro - α - acetamido - # hydroxy - propiophenone (Me and benzyl), 2-benzoylpyridine (Me), 2 - acetyl - 1 - naphthol (Me), 1- and 2- acetyl - naphthalenes (Me), 2,3 - dichloro - 4- butyryl - phenoxyacetic acid (Me), benzoylacetone (Me), benzophenone (Me), m-nitrobenzaldehyde (p - chlorobenzyl, 2,3 - dichloro- 4 - (2<SP>1 </SP>- methylenebutyryl) phenoxyacetic acid (Me), benzil (Me), benzoin (Me), #-piperidinopropiophenone (Me), 2-oxo-9,10-dimethoxy-, 2 - oxo - 3 - ethyl - 9,10 dimethoxy and 2-oxo - 4,4 - dimethyl - 9,10 - dimethoxy - 1,2,3,4,6,7- hexahydro - 11b - benzo[a]quinolizines (Me), dibenzal - acetone (Me), α - formyl - 3,4 - dimethoxy - phenyl - acetonitrile (p - chlorobenzyl), dibenzoylmethane (Me) and dibenzalacetone (p-chlorobenzyl). Dithiocarbazinic esters, NH 2 NHÀCSSR<SP>3</SP>, are obtained by reacting hydrazine hydrate with carbon disulphide in the presence of potassium hydroxide, ammonia or excess hydrazine hydrate and converting the dithiocarbazinic acid salt so obtained into the ester utilizing standard methods. Methyl - p - nitrophenyl - ketazin is obtained by the interaction of p-nitroacetophenone and NH 2 NHCSSEt. Pharmaceutical preparations, in particular, showing anthelmintic and tuberculostatic effects contain I as active ingredient; administration is, e.g. topically, orally and parenterally.
GB31122/69A 1968-07-24 1969-06-19 Dithiocarbazinic ester derivatives Expired GB1274521A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUEE001547 1968-07-24

Publications (1)

Publication Number Publication Date
GB1274521A true GB1274521A (en) 1972-05-17

Family

ID=10995263

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31122/69A Expired GB1274521A (en) 1968-07-24 1969-06-19 Dithiocarbazinic ester derivatives

Country Status (8)

Country Link
AT (1) AT293432B (en)
AU (1) AU502845B2 (en)
CH (1) CH532556A (en)
DE (1) DE1934809A1 (en)
FR (1) FR2013568A1 (en)
GB (1) GB1274521A (en)
NL (1) NL6911272A (en)
PL (1) PL88879B1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985004333A1 (en) * 1984-03-23 1985-10-10 A/S Cheminova A biocidal, particularly fungicidal and/or bactericidal, composition
EP0841324A2 (en) * 1996-11-07 1998-05-13 Bayer Corporation A proces for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base
US5861526A (en) * 1996-11-07 1999-01-19 Bayer Corporation Process for reducing dithiocarbazinate buildup in the preparation of methyl dithiocarbazinate
US5877339A (en) * 1996-11-07 1999-03-02 Bayer Corporation Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide and hydrazine in an aqueous medium
US6025514A (en) * 1996-11-07 2000-02-15 Bayer Corporation Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base
EP2530073A1 (en) * 2010-01-27 2012-12-05 Mitsubishi Rayon Co., Ltd. Novel chain transfer agent and emulsion polymerization using same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4602099A (en) * 1973-04-02 1986-07-22 Merrell Dow Pharmaceuticals Inc. Antirhinovirus agents
DE3709414C1 (en) * 1987-03-21 1988-02-18 Bayer Ag Process for the preparation of methyl dithiocarbazate
CH686642A5 (en) * 1993-07-27 1996-05-15 Sylvia Hover Spectacle lens.

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985004333A1 (en) * 1984-03-23 1985-10-10 A/S Cheminova A biocidal, particularly fungicidal and/or bactericidal, composition
EP0841324A2 (en) * 1996-11-07 1998-05-13 Bayer Corporation A proces for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base
US5861526A (en) * 1996-11-07 1999-01-19 Bayer Corporation Process for reducing dithiocarbazinate buildup in the preparation of methyl dithiocarbazinate
US5877339A (en) * 1996-11-07 1999-03-02 Bayer Corporation Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide and hydrazine in an aqueous medium
US6025514A (en) * 1996-11-07 2000-02-15 Bayer Corporation Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base
EP0841324A3 (en) * 1996-11-07 2001-09-19 Bayer Corporation A proces for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base
EP2530073A1 (en) * 2010-01-27 2012-12-05 Mitsubishi Rayon Co., Ltd. Novel chain transfer agent and emulsion polymerization using same
EP2530073A4 (en) * 2010-01-27 2014-10-08 Mitsubishi Rayon Co Novel chain transfer agent and emulsion polymerization using same
US9452978B2 (en) 2010-01-27 2016-09-27 Mitsubishi Rayon Co., Ltd. Chain transfer agent and emulsion polymerization using the same
US9676888B2 (en) 2010-01-27 2017-06-13 Mitsubishi Chemical Corporation Chain transfer agent and emulsion polymerization using the same

Also Published As

Publication number Publication date
AU8444475A (en) 1977-03-10
NL6911272A (en) 1970-01-27
DE1934809A1 (en) 1970-01-29
FR2013568A1 (en) 1970-04-03
AT293432B (en) 1971-10-11
PL88879B1 (en) 1976-10-30
AU502845B2 (en) 1979-08-09
CH532556A (en) 1973-01-15

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee