DE2431775A1 - 3-(5-nitro-2-imidazolyl)pyrazole und verfahren zu ihrer herstellung - Google Patents
3-(5-nitro-2-imidazolyl)pyrazole und verfahren zu ihrer herstellungInfo
- Publication number
- DE2431775A1 DE2431775A1 DE2431775A DE2431775A DE2431775A1 DE 2431775 A1 DE2431775 A1 DE 2431775A1 DE 2431775 A DE2431775 A DE 2431775A DE 2431775 A DE2431775 A DE 2431775A DE 2431775 A1 DE2431775 A1 DE 2431775A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- nitro
- imidazolyl
- pyrazole
- amino
- 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.)
- Pending
Links
- -1 5-NITRO-2-IMIDAZOLYL Chemical class 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 68
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 131
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 114
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- 238000002360 preparation method Methods 0.000 claims description 42
- NUGZBVBZIDWZAD-UHFFFAOYSA-N 1h-pyrazole-4-carbonitrile Chemical compound N#CC=1C=NNC=1 NUGZBVBZIDWZAD-UHFFFAOYSA-N 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- FKQVPUMXKPUGBH-UHFFFAOYSA-N 5-amino-1-methyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound N#CC1=C(N)N(C)N=C1C1=NC=C([N+]([O-])=O)N1C FKQVPUMXKPUGBH-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims description 11
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 11
- 241000588724 Escherichia coli Species 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000007857 hydrazones Chemical class 0.000 claims description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 8
- 244000144977 poultry Species 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- ZSBDPRIWBYHIAF-UHFFFAOYSA-N N-acetyl-acetamide Natural products CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 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 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 150000002905 orthoesters Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 claims description 3
- PTTXIGMAOLXWKO-UHFFFAOYSA-N 5-amino-1-(2-chloroethyl)-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NN(CCCl)C(N)=C1C#N PTTXIGMAOLXWKO-UHFFFAOYSA-N 0.000 claims description 3
- SAUUKWGLDNIFRT-UHFFFAOYSA-N 5-amino-1-(2-hydroxyethyl)-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NN(CCO)C(N)=C1C#N SAUUKWGLDNIFRT-UHFFFAOYSA-N 0.000 claims description 3
- CUSFCJZSWTXPSF-UHFFFAOYSA-N 5-amino-1-methyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carboxamide Chemical compound NC(=O)C1=C(N)N(C)N=C1C1=NC=C([N+]([O-])=O)N1C CUSFCJZSWTXPSF-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- GOJDSMIXPMMHPO-UHFFFAOYSA-N n-propanoylpropanamide Chemical compound CCC(=O)NC(=O)CC GOJDSMIXPMMHPO-UHFFFAOYSA-N 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 claims description 2
- RKHRVKJTCSHZCR-UHFFFAOYSA-N 1-[bis(2-chloroethoxy)methoxy]-2-chloroethane Chemical compound ClCCOC(OCCCl)OCCCl RKHRVKJTCSHZCR-UHFFFAOYSA-N 0.000 claims description 2
- IVXPLWROXBUJSE-UHFFFAOYSA-N 1-[bis(2-methylpropoxy)methoxy]-2-methylpropane Chemical compound CC(C)COC(OCC(C)C)OCC(C)C IVXPLWROXBUJSE-UHFFFAOYSA-N 0.000 claims description 2
- DINNDFYYZSTEAI-UHFFFAOYSA-N 1-methyl-3-(1-methyl-5-nitroimidazol-2-yl)-5-(2h-pyridin-3-ylideneamino)pyrazole-4-carbonitrile Chemical compound N#CC1=C(N=C2C=CC=NC2)N(C)N=C1C1=NC=C([N+]([O-])=O)N1C DINNDFYYZSTEAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- HLXQFJWWTNYPFM-UHFFFAOYSA-N 2-methyl-5-(1-methyl-5-nitroimidazol-2-yl)pyrazol-3-amine Chemical compound C1=C(N)N(C)N=C1C1=NC=C([N+]([O-])=O)N1C HLXQFJWWTNYPFM-UHFFFAOYSA-N 0.000 claims description 2
- WUWWRQBTTCHFBU-UHFFFAOYSA-N 3-[bis(2-ethylhexoxy)methoxymethyl]heptane Chemical compound CCCCC(CC)COC(OCC(CC)CCCC)OCC(CC)CCCC WUWWRQBTTCHFBU-UHFFFAOYSA-N 0.000 claims description 2
- MHWJFZBIEQEJHB-UHFFFAOYSA-N 5-amino-1-ethyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound N#CC1=C(N)N(CC)N=C1C1=NC=C([N+]([O-])=O)N1C MHWJFZBIEQEJHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002262 Schiff base Substances 0.000 claims description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical group C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
Classifications
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38513673A | 1973-08-02 | 1973-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2431775A1 true DE2431775A1 (de) | 1975-02-20 |
Family
ID=23520163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2431775A Pending DE2431775A1 (de) | 1973-08-02 | 1974-07-02 | 3-(5-nitro-2-imidazolyl)pyrazole und verfahren zu ihrer herstellung |
Country Status (18)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014268700B2 (en) * | 2013-05-20 | 2018-07-05 | University Of Washington Through Its Center For Commercialization | 5-aminopyrazole-4-carboxamide inhibitors of CDPK1 from T. gondii and C. parvum |
-
1974
- 1974-06-18 ZA ZA00743887A patent/ZA743887B/xx unknown
- 1974-06-20 IL IL45073A patent/IL45073A/en unknown
- 1974-07-02 DE DE2431775A patent/DE2431775A1/de active Pending
- 1974-07-24 RO RO7400079581A patent/RO63973A/ro unknown
- 1974-07-25 NL NL7410033A patent/NL7410033A/xx unknown
- 1974-07-29 AR AR254925A patent/AR203854A1/es active
- 1974-07-29 DD DD180187A patent/DD112759A5/xx unknown
- 1974-07-31 AT AT627474A patent/AT337691B/de not_active IP Right Cessation
- 1974-08-01 BR BR6317/74A patent/BR7406317D0/pt unknown
- 1974-08-01 JP JP49088635A patent/JPS5047978A/ja active Pending
- 1974-08-01 SE SE7409957A patent/SE7409957L/xx unknown
- 1974-08-01 IT IT25881/74A patent/IT1049204B/it active
- 1974-08-01 DK DK410874A patent/DK410874A/da unknown
- 1974-08-02 BE BE1006105A patent/BE818417A/xx unknown
- 1974-08-02 ES ES428914A patent/ES428914A0/es active Pending
- 1974-08-02 PL PL1974192766A patent/PL96805B1/pl unknown
- 1974-08-02 PL PL1974173196A patent/PL91696B1/pl unknown
- 1974-08-02 PL PL1974192765A patent/PL96804B1/pl unknown
- 1974-08-02 FR FR7427017A patent/FR2240009A1/fr active Granted
- 1974-08-02 PL PL1974184214A patent/PL94238B1/pl unknown
- 1974-08-02 PL PL1974184215A patent/PL92429B1/pl unknown
-
1975
- 1975-01-01 AR AR257999A patent/AR205814A1/es active
- 1975-01-01 AR AR258000A patent/AR204130A1/es active
- 1975-09-04 SU SU7502170651A patent/SU565630A3/ru active
- 1975-09-12 SU SU7502171154A patent/SU582758A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BE818417A (fr) | 1975-02-03 |
| AR205814A1 (es) | 1976-06-07 |
| ES428914A0 (es) | 1977-02-01 |
| SU565630A3 (ru) | 1977-07-15 |
| PL92429B1 (enrdf_load_stackoverflow) | 1977-04-30 |
| RO63973A (fr) | 1978-09-15 |
| JPS5047978A (enrdf_load_stackoverflow) | 1975-04-28 |
| AT337691B (de) | 1977-07-11 |
| AR204130A1 (es) | 1975-11-20 |
| DD112759A5 (enrdf_load_stackoverflow) | 1975-05-05 |
| AU7052874A (en) | 1976-01-08 |
| BR7406317D0 (pt) | 1975-05-20 |
| ATA627474A (de) | 1976-11-15 |
| ZA743887B (en) | 1975-06-25 |
| IL45073A (en) | 1977-07-31 |
| IL45073A0 (en) | 1974-09-10 |
| PL96804B1 (pl) | 1978-01-31 |
| DK410874A (enrdf_load_stackoverflow) | 1975-04-01 |
| SE7409957L (enrdf_load_stackoverflow) | 1975-02-03 |
| PL91696B1 (enrdf_load_stackoverflow) | 1977-03-31 |
| IT1049204B (it) | 1981-01-20 |
| PL94238B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| FR2240009A1 (en) | 1975-03-07 |
| AR203854A1 (es) | 1975-10-31 |
| PL96805B1 (pl) | 1978-01-31 |
| SU582758A3 (ru) | 1977-11-30 |
| FR2240009B1 (enrdf_load_stackoverflow) | 1978-07-28 |
| NL7410033A (nl) | 1975-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |