GB1215858A - Nitroimidazole derivatives - Google Patents
Nitroimidazole derivativesInfo
- 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
Links
- 229940058965 antiprotozoal agent against amoebiasis and other protozoal diseases nitroimidazole derivative Drugs 0.000 title abstract 2
- 150000004957 nitroimidazoles Chemical class 0.000 title abstract 2
- -1 6-indenyl Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 1
- SKTRBKNAHBPVFM-UHFFFAOYSA-N 3h-indene-5-carbonyl chloride Chemical compound ClC(=O)C1=CC=C2C=CCC2=C1 SKTRBKNAHBPVFM-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 244000000013 helminth Species 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
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.
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)
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 |
US4012416A (en) * | 1976-01-29 | 1977-03-15 | Morton-Norwich Products, Inc. | 2-[5-(3-Trifluoromethylphenyl)2-furyl]imidazole hydrochloride |
US4012415A (en) * | 1976-01-29 | 1977-03-15 | Morton-Norwich Products, Inc. | 2-[5-(3,4-Dimethoxyphenyl)-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 |
-
1968
- 1968-05-03 GB GB21125/68A patent/GB1215858A/en not_active Expired
Cited By (14)
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 |
US4012416A (en) * | 1976-01-29 | 1977-03-15 | Morton-Norwich Products, Inc. | 2-[5-(3-Trifluoromethylphenyl)2-furyl]imidazole hydrochloride |
US4012415A (en) * | 1976-01-29 | 1977-03-15 | Morton-Norwich Products, Inc. | 2-[5-(3,4-Dimethoxyphenyl)-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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