GB1204699A - 0-substituted-5-nitro-2-imidazolyl compounds and the preparation thereof - Google Patents
0-substituted-5-nitro-2-imidazolyl compounds and the preparation thereofInfo
- Publication number
- GB1204699A GB1204699A GB54654/67A GB5465467A GB1204699A GB 1204699 A GB1204699 A GB 1204699A GB 54654/67 A GB54654/67 A GB 54654/67A GB 5465467 A GB5465467 A GB 5465467A GB 1204699 A GB1204699 A GB 1204699A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- methyl
- alkyl
- amino
- substituted
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 4
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 3
- 125000001589 carboacyl group Chemical group 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- -1 1-substituted-5-nitro- 2-imidazole carboxaldehyde semicarbazone Chemical class 0.000 abstract 2
- WJRXMOFXMJZTJG-UHFFFAOYSA-N 5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-amine Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2SN(N)NC=2)=N1 WJRXMOFXMJZTJG-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 abstract 2
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 2
- YJRCDSXLKPERNV-UHFFFAOYSA-N 1-(2-nitrophenyl)piperazine Chemical compound [O-][N+](=O)C1=CC=CC=C1N1CCNCC1 YJRCDSXLKPERNV-UHFFFAOYSA-N 0.000 abstract 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 abstract 1
- XOSGGYZKBFPVBJ-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbohydrazide Chemical compound CN1C(C(=O)NN)=NC=C1[N+]([O-])=O XOSGGYZKBFPVBJ-UHFFFAOYSA-N 0.000 abstract 1
- VDZJVXFACHQYKK-UHFFFAOYSA-N 2-(2-formyl-5-nitroimidazol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1C(C=O)=NC=C1[N+]([O-])=O VDZJVXFACHQYKK-UHFFFAOYSA-N 0.000 abstract 1
- XAKKAVOLKNKDQV-UHFFFAOYSA-N 2-chloro-5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2SN(Cl)NC=2)=N1 XAKKAVOLKNKDQV-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- MKDHCSQJKHOFAH-UHFFFAOYSA-N 5-(1-methyl-5-nitroimidazol-2-yl)-3h-oxadiazol-2-amine Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2ON(N)NC=2)=N1 MKDHCSQJKHOFAH-UHFFFAOYSA-N 0.000 abstract 1
- 150000004958 5-nitroimidazoles Chemical class 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 1
- XVEWCEUNSHFUOH-UHFFFAOYSA-N ethyl 4-(aminocarbamothioyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(C(=S)NN)CC1 XVEWCEUNSHFUOH-UHFFFAOYSA-N 0.000 abstract 1
- YYBPYVOWKWKFFE-UHFFFAOYSA-N ethyl 4-[5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1N1SC(C=2N(C(=CN=2)[N+]([O-])=O)C)=CN1 YYBPYVOWKWKFFE-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 abstract 1
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010344 sodium nitrate Nutrition 0.000 abstract 1
- 239000004317 sodium nitrate Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- 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
- C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60415866A | 1966-12-23 | 1966-12-23 | |
| US65959667A | 1967-08-10 | 1967-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1204699A true GB1204699A (en) | 1970-09-09 |
Family
ID=27084600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54654/67A Expired GB1204699A (en) | 1966-12-23 | 1967-11-30 | 0-substituted-5-nitro-2-imidazolyl compounds and the preparation thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3452035A (https=) |
| BE (1) | BE708528A (https=) |
| DE (1) | DE1670018A1 (https=) |
| ES (2) | ES348599A1 (https=) |
| FR (1) | FR7528M (https=) |
| GB (1) | GB1204699A (https=) |
| GR (1) | GR35178B (https=) |
| IL (1) | IL29034A (https=) |
| NL (1) | NL6717685A (https=) |
| NO (1) | NO120369B (https=) |
| SE (1) | SE328894B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065567A (en) * | 1966-12-23 | 1977-12-27 | American Cyanamid Company | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3991200A (en) * | 1974-04-25 | 1976-11-09 | American Cyanamid Company | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3904756A (en) * | 1966-12-23 | 1975-09-09 | American Cyanamid Co | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3711495A (en) * | 1970-01-07 | 1973-01-16 | Merck & Co Inc | Isoxazalin-3-yl-substituted-5-nitroimidazoles |
| US4058617A (en) * | 1972-10-04 | 1977-11-15 | Ciba-Geigy Corporation | Imidazoles and pharmaceutical composition |
| US3980794A (en) * | 1974-05-13 | 1976-09-14 | Eli Lilly And Company | Method for promoting growth of poultry with 3-(5-nitro-2-imidazolyl)pyrazoles |
| EP0000452B1 (fr) * | 1977-07-12 | 1981-05-06 | Synthelabo | Dérivés d'oxadiazole-1,2,4, leur préparation et leur application en thérapeutique. |
| EP1809282B1 (en) * | 2004-10-18 | 2013-01-09 | Amgen, Inc | Thiadiazole compounds and methods of use |
| EP2173728A2 (en) | 2007-07-17 | 2010-04-14 | Amgen Inc. | Heterocyclic modulators of pkb |
| US7919504B2 (en) * | 2007-07-17 | 2011-04-05 | Amgen Inc. | Thiadiazole modulators of PKB |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025303A (en) * | 1957-09-30 | 1962-03-13 | Pharmacia Ab | Certain nitrofuryl, thiadiazolyl amines |
-
1967
- 1967-08-10 US US659596A patent/US3452035A/en not_active Expired - Lifetime
- 1967-11-22 NO NO170661A patent/NO120369B/no unknown
- 1967-11-23 GR GR670135178A patent/GR35178B/el unknown
- 1967-11-29 IL IL29034A patent/IL29034A/en unknown
- 1967-11-30 GB GB54654/67A patent/GB1204699A/en not_active Expired
- 1967-12-20 FR FR133070A patent/FR7528M/fr not_active Expired
- 1967-12-21 SE SE17613/67A patent/SE328894B/xx unknown
- 1967-12-23 DE DE19671670018 patent/DE1670018A1/de active Pending
- 1967-12-23 ES ES348599A patent/ES348599A1/es not_active Expired
- 1967-12-27 NL NL6717685A patent/NL6717685A/xx unknown
- 1967-12-27 BE BE708528D patent/BE708528A/xx unknown
-
1968
- 1968-10-30 ES ES359720A patent/ES359720A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3452035A (en) | 1969-06-24 |
| SE328894B (https=) | 1970-09-28 |
| GR35178B (el) | 1968-08-22 |
| FR7528M (https=) | 1969-12-22 |
| IL29034A (en) | 1972-05-30 |
| DE1670018A1 (de) | 1971-01-21 |
| ES348599A1 (es) | 1969-06-16 |
| ES359720A1 (es) | 1970-09-16 |
| BE708528A (https=) | 1968-06-27 |
| NL6717685A (https=) | 1968-06-24 |
| NO120369B (https=) | 1970-10-12 |
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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 |