GB1215858A - Nitroimidazole derivatives - Google Patents

Nitroimidazole derivatives

Info

Publication number
GB1215858A
GB1215858A GB21125/68A GB2112568A GB1215858A GB 1215858 A GB1215858 A GB 1215858A GB 21125/68 A GB21125/68 A GB 21125/68A GB 2112568 A GB2112568 A GB 2112568A GB 1215858 A GB1215858 A GB 1215858A
Authority
GB
United Kingdom
Prior art keywords
nitroimidazole
indanyl
indenyl
quinolyl
substituent
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
GB21125/68A
Inventor
Lewis H Sarett
Dale R Hoff
David W Henry
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Priority to GB21125/68A priority Critical patent/GB1215858A/en
Publication of GB1215858A publication Critical patent/GB1215858A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/93—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by halogen atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,215,858. Nitroimidazole derivatives. MERCK & CO. Inc. 3 May, 1968, No. 21125/68. Addition to 1,104,412. Heading C2C. The invention comprises compounds of formula wherein one of R 4 and R 5 is NO 2 and the other is H and (with certain provisos), R, R 1 , R 2 and R 3 are each H or a substituent (as defined in the Specification), and Ar is a benzene (C 6 H 2 ) or naphthalene (C 10 H 4 ) residue, or ArRR 2 R 3 is a tetrahydronaphthyl, indanyl, indenyl, quinolyl or quinoxalyl radical; nitration and other standard methods for introducing or modifying substituents are used. The invention further comprises compounds of formula wherein d is 1 or 2, R 4 and R 5 are as defined above, and R 51 and R 52 are each H or a substituent (as defined in the Specification), the compounds being prepared by a multi-stage synthesis in which the final stage is cyclization of a corresponding 2-(halomethyl- or haloethylphenyl)-4-nitroimidazole. Intermediates.-Details are also given for the preparation of 6-indenylcarboxylic acid chloride, amide and nitrile; and and 2-R-imidazoles, wherein R is 3,4,5-trichlorophenyl, 6-indenyl, 5-indanyl, 5-quinolyl or 6-quinoxalyl. Therapeutic compositions, for pharmaceutical and veterinary application against protozoa, helminths, bacteria and pleuro pneumonis like organisms, comprise imidazole derivatives of the above general formulµ. Oral and topical preparations, as well as suppositories, are mentioned.
GB21125/68A 1968-05-03 1968-05-03 Nitroimidazole derivatives Expired GB1215858A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB21125/68A GB1215858A (en) 1968-05-03 1968-05-03 Nitroimidazole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB21125/68A GB1215858A (en) 1968-05-03 1968-05-03 Nitroimidazole derivatives

Publications (1)

Publication Number Publication Date
GB1215858A true GB1215858A (en) 1970-12-16

Family

ID=10157625

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21125/68A Expired GB1215858A (en) 1968-05-03 1968-05-03 Nitroimidazole derivatives

Country Status (1)

Country Link
GB (1) GB1215858A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012414A (en) * 1976-01-29 1977-03-15 Morton-Norwich Products, Inc. 2-(5-Phenyl-2-furyl)imidazoles
US4012415A (en) * 1976-01-29 1977-03-15 Morton-Norwich Products, Inc. 2-[5-(3,4-Dimethoxyphenyl)-2-furyl]imidazole hydrochloride
US4012416A (en) * 1976-01-29 1977-03-15 Morton-Norwich Products, Inc. 2-[5-(3-Trifluoromethylphenyl)2-furyl]imidazole hydrochloride
WO1995030661A1 (en) * 1994-05-04 1995-11-16 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
USRE39263E1 (en) * 1994-05-04 2006-09-05 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
US7297713B2 (en) 2005-07-29 2007-11-20 Wyeth Cyanopyrrole-phenyl amide progesterone receptor modulators and uses thereof
WO2014030142A2 (en) * 2012-08-24 2014-02-27 Auckland Uniservices Limited Nitroimidazole compounds and their use in cancer therapy
EP3010345A4 (en) * 2013-06-21 2017-04-12 The Regents of The University of California Expanded therapeutic potential in nitroheteroaryl antimicrobials

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012414A (en) * 1976-01-29 1977-03-15 Morton-Norwich Products, Inc. 2-(5-Phenyl-2-furyl)imidazoles
US4012415A (en) * 1976-01-29 1977-03-15 Morton-Norwich Products, Inc. 2-[5-(3,4-Dimethoxyphenyl)-2-furyl]imidazole hydrochloride
US4012416A (en) * 1976-01-29 1977-03-15 Morton-Norwich Products, Inc. 2-[5-(3-Trifluoromethylphenyl)2-furyl]imidazole hydrochloride
WO1995030661A1 (en) * 1994-05-04 1995-11-16 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
US6077813A (en) * 1994-05-04 2000-06-20 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
US6331507B1 (en) * 1994-05-04 2001-12-18 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
US6420316B1 (en) 1994-05-04 2002-07-16 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
US6451736B1 (en) 1994-05-04 2002-09-17 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
USRE39263E1 (en) * 1994-05-04 2006-09-05 Bayer Aktiengesellschaft Substituted aromatic thiocarboxylic acid amides and their use as herbicides
US7297713B2 (en) 2005-07-29 2007-11-20 Wyeth Cyanopyrrole-phenyl amide progesterone receptor modulators and uses thereof
US7652062B2 (en) 2005-07-29 2010-01-26 Wyeth Llc Cyanopyrrole-phenyl amide progesterone receptor modulators and uses thereof
WO2014030142A2 (en) * 2012-08-24 2014-02-27 Auckland Uniservices Limited Nitroimidazole compounds and their use in cancer therapy
WO2014030142A3 (en) * 2012-08-24 2014-04-17 Auckland Uniservices Limited Nitroimidazole compounds and their use in cancer therapy
EP3010345A4 (en) * 2013-06-21 2017-04-12 The Regents of The University of California Expanded therapeutic potential in nitroheteroaryl antimicrobials

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