GB1154290A - Imidazole Derivatives, their preparation and compositions containing them - Google Patents
Imidazole Derivatives, their preparation and compositions containing themInfo
- Publication number
- GB1154290A GB1154290A GB35033/68A GB3503368A GB1154290A GB 1154290 A GB1154290 A GB 1154290A GB 35033/68 A GB35033/68 A GB 35033/68A GB 3503368 A GB3503368 A GB 3503368A GB 1154290 A GB1154290 A GB 1154290A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- nitroimidazole
- imidazole
- prepared
- nitro
- 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
- 150000002460 imidazoles Chemical class 0.000 title abstract 5
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title 1
- -1 aralkanoyloxy Chemical group 0.000 abstract 6
- JLQLFVSTEDRFAD-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbaldehyde Chemical compound CN1C(C=O)=NC=C1[N+]([O-])=O JLQLFVSTEDRFAD-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 abstract 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 2
- 229910052739 hydrogen Chemical group 0.000 abstract 2
- 239000001257 hydrogen Chemical group 0.000 abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 229920002866 paraformaldehyde Polymers 0.000 abstract 2
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 2
- 239000012279 sodium borohydride Substances 0.000 abstract 2
- KNVMOFUTOGRUBR-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)N(C)C(C(=O)C=2C=CC=CC=2)=N1 KNVMOFUTOGRUBR-UHFFFAOYSA-N 0.000 abstract 1
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 abstract 1
- ANSCCMZPJWEICB-UHFFFAOYSA-N 1-(1-methyl-5-nitroimidazol-2-yl)ethanone Chemical compound CC(=O)C1=NC=C([N+]([O-])=O)N1C ANSCCMZPJWEICB-UHFFFAOYSA-N 0.000 abstract 1
- JLZXSFPSJJMRIX-UHFFFAOYSA-N 1-methyl-5-nitroimidazole Chemical compound CN1C=NC=C1[N+]([O-])=O JLZXSFPSJJMRIX-UHFFFAOYSA-N 0.000 abstract 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 abstract 1
- IFELUMYGWLOMEA-UHFFFAOYSA-N 2-benzyl-1-methyl-5-nitroimidazole Chemical compound CN1C(=NC=C1[N+](=O)[O-])CC1=CC=CC=C1 IFELUMYGWLOMEA-UHFFFAOYSA-N 0.000 abstract 1
- NAPDOWNULRULLI-UHFFFAOYSA-N 2-benzyl-1h-imidazole Chemical compound C=1C=CC=CC=1CC1=NC=CN1 NAPDOWNULRULLI-UHFFFAOYSA-N 0.000 abstract 1
- FUCSWGRAIIZMAB-UHFFFAOYSA-N 2-oxoethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=O)C1=CC=CC=C1 FUCSWGRAIIZMAB-UHFFFAOYSA-N 0.000 abstract 1
- DWTFIIXGFKUJFF-UHFFFAOYSA-N 3-(1-methyl-5-nitroimidazol-2-yl)prop-2-enal Chemical compound CN1C(=NC=C1[N+](=O)[O-])C=CC=O DWTFIIXGFKUJFF-UHFFFAOYSA-N 0.000 abstract 1
- 208000004881 Amebiasis Diseases 0.000 abstract 1
- 206010001980 Amoebiasis Diseases 0.000 abstract 1
- 208000014085 Chronic respiratory disease Diseases 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 208000030852 Parasitic disease Diseases 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000005116 aryl carbamoyl group Chemical group 0.000 abstract 1
- 125000000958 aryl methylene group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- HFTNNOZFRQLFQB-UHFFFAOYSA-N ethenoxy(trimethyl)silane Chemical compound C[Si](C)(C)OC=C HFTNNOZFRQLFQB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 229910001641 magnesium iodide Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 201000002311 trypanosomiasis Diseases 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
- C07D233/94—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
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Devices For Checking Fares Or Tickets At Control Points (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47023965A | 1965-07-07 | 1965-07-07 | |
| US55093266A | 1966-05-18 | 1966-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1154290A true GB1154290A (en) | 1969-06-04 |
Family
ID=27043018
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35033/68A Expired GB1154290A (en) | 1965-07-07 | 1966-07-04 | Imidazole Derivatives, their preparation and compositions containing them |
| GB35039/68A Expired GB1155529A (en) | 1965-07-07 | 1966-07-04 | Imidazole derivatives, their Preparation and Compositions containing them |
| GB38884/68A Expired GB1155530A (en) | 1965-07-07 | 1966-07-04 | Imidazole Derivatives, their Preparation and Compositions containing them |
| GB29846/66A Expired GB1153347A (en) | 1965-07-07 | 1966-07-04 | Imidazole Derivatives, their preparation and Compositions containing them. |
| GB32952/68A Expired GB1155528A (en) | 1965-07-07 | 1966-07-04 | Imidazole derivatives, their Preparation and Compositions containing them |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35039/68A Expired GB1155529A (en) | 1965-07-07 | 1966-07-04 | Imidazole derivatives, their Preparation and Compositions containing them |
| GB38884/68A Expired GB1155530A (en) | 1965-07-07 | 1966-07-04 | Imidazole Derivatives, their Preparation and Compositions containing them |
| GB29846/66A Expired GB1153347A (en) | 1965-07-07 | 1966-07-04 | Imidazole Derivatives, their preparation and Compositions containing them. |
| GB32952/68A Expired GB1155528A (en) | 1965-07-07 | 1966-07-04 | Imidazole derivatives, their Preparation and Compositions containing them |
Country Status (18)
| Country | Link |
|---|---|
| JP (3) | JPS5010865B1 (en:Method) |
| AT (5) | AT294487B (en:Method) |
| BE (1) | BE683796A (en:Method) |
| BR (1) | BR6681050D0 (en:Method) |
| CH (3) | CH562806A5 (en:Method) |
| CY (1) | CY565A (en:Method) |
| DE (1) | DE1620018B2 (en:Method) |
| DK (1) | DK141287B (en:Method) |
| ES (1) | ES329085A1 (en:Method) |
| FI (1) | FI46961C (en:Method) |
| FR (2) | FR1502699A (en:Method) |
| GB (5) | GB1154290A (en:Method) |
| IL (2) | IL25931A (en:Method) |
| IT (1) | IT1061026B (en:Method) |
| MY (1) | MY7100055A (en:Method) |
| NL (1) | NL149793B (en:Method) |
| NO (1) | NO122186B (en:Method) |
| SE (1) | SE343578B (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1280355A (en) * | 1969-06-20 | 1972-07-05 | Rech S Et D Applic Scient Et M | Substituted 5-nitro-imidazoles and their preparation |
| BE758145A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Iso-thio-urees et derives |
| US3678066A (en) * | 1970-03-06 | 1972-07-18 | Squibb & Sons Inc | Thiocyanic acid esters |
| US3968228A (en) * | 1973-11-13 | 1976-07-06 | Merck & Co., Inc. | 4-Nitro-5-cyanoimidazoles as coccidiostats |
| JPH02254965A (ja) * | 1989-03-28 | 1990-10-15 | Chiyoudendou Hatsuden Kanren Kiki Zairyo Gijutsu Kenkyu Kumiai | 超電導回転電機の回転子 |
| EA201792151A1 (ru) * | 2015-04-02 | 2018-04-30 | Байер Кропсайенс Акциенгезельшафт | Новые 5-замещенные производные имидазола |
| CR20190165A (es) | 2016-09-29 | 2019-07-09 | Bayer Ag | Novedosos derivados de imidazolilmetilo 5-sustituidos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5149436B2 (en:Method) * | 1971-11-15 | 1976-12-27 |
-
1966
- 1966-06-08 IL IL25931A patent/IL25931A/en unknown
- 1966-07-04 GB GB35033/68A patent/GB1154290A/en not_active Expired
- 1966-07-04 GB GB35039/68A patent/GB1155529A/en not_active Expired
- 1966-07-04 GB GB38884/68A patent/GB1155530A/en not_active Expired
- 1966-07-04 GB GB29846/66A patent/GB1153347A/en not_active Expired
- 1966-07-04 GB GB32952/68A patent/GB1155528A/en not_active Expired
- 1966-07-05 AT AT545669A patent/AT294487B/de not_active IP Right Cessation
- 1966-07-05 ES ES0329085A patent/ES329085A1/es not_active Expired
- 1966-07-05 AT AT643566A patent/AT284114B/de not_active IP Right Cessation
- 1966-07-05 AT AT551669A patent/AT291988B/de not_active IP Right Cessation
- 1966-07-05 AT AT559369A patent/AT291990B/de not_active IP Right Cessation
- 1966-07-05 AT AT559269A patent/AT291989B/de not_active IP Right Cessation
- 1966-07-05 IT IT6615338A patent/IT1061026B/it active
- 1966-07-06 SE SE9274/66A patent/SE343578B/xx unknown
- 1966-07-06 FR FR68482A patent/FR1502699A/fr not_active Expired
- 1966-07-06 NO NO163800A patent/NO122186B/no unknown
- 1966-07-06 DK DK348866AA patent/DK141287B/da unknown
- 1966-07-06 DE DE1966M0070135 patent/DE1620018B2/de active Granted
- 1966-07-06 FI FI661807A patent/FI46961C/fi active
- 1966-07-06 BR BR181050/66A patent/BR6681050D0/pt unknown
- 1966-07-07 JP JP41043868A patent/JPS5010865B1/ja active Pending
- 1966-07-07 NL NL666609552A patent/NL149793B/xx not_active IP Right Cessation
- 1966-07-07 CH CH988566A patent/CH562806A5/xx not_active IP Right Cessation
- 1966-07-07 CH CH988566A patent/CH522651A/de not_active IP Right Cessation
- 1966-07-07 CH CH991771A patent/CH565769A5/xx not_active IP Right Cessation
- 1966-07-07 BE BE683796D patent/BE683796A/xx not_active IP Right Cessation
- 1966-10-05 FR FR78932A patent/FR5890M/fr not_active Expired
-
1970
- 1970-11-09 JP JP45097971A patent/JPS4843909B1/ja active Pending
- 1970-11-09 CY CY56570A patent/CY565A/xx unknown
- 1970-11-27 IL IL35748A patent/IL35748A0/xx unknown
-
1971
- 1971-12-31 MY MY197155A patent/MY7100055A/xx unknown
-
1974
- 1974-11-29 JP JP49136394A patent/JPS5138718B1/ja active Pending
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