DE2337153A1 - 2-acyl-5-nitrothiazole - Google Patents
2-acyl-5-nitrothiazoleInfo
- Publication number
- DE2337153A1 DE2337153A1 DE19732337153 DE2337153A DE2337153A1 DE 2337153 A1 DE2337153 A1 DE 2337153A1 DE 19732337153 DE19732337153 DE 19732337153 DE 2337153 A DE2337153 A DE 2337153A DE 2337153 A1 DE2337153 A1 DE 2337153A1
- Authority
- DE
- Germany
- Prior art keywords
- nitrothiazole
- substituted
- general formula
- benzoyl
- radical
- 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
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 2- (4-methoxy-2,2,6-trimethyl-benzoyl) -5-nitrothiazole Chemical compound 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- 230000000843 anti-fungal effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 3
- PADAVJMJKIGWIP-UHFFFAOYSA-N (2-fluoro-3,4-dimethylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound FC1=C(C)C(C)=CC=C1C(=O)C1=NC=C([N+]([O-])=O)S1 PADAVJMJKIGWIP-UHFFFAOYSA-N 0.000 claims description 2
- RAFZQANEYDBWGG-UHFFFAOYSA-N (5-bromothiophen-2-yl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=C(Br)S1 RAFZQANEYDBWGG-UHFFFAOYSA-N 0.000 claims description 2
- HPABCJUQNSJKCM-UHFFFAOYSA-N (5-iodothiophen-2-yl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=C(I)S1 HPABCJUQNSJKCM-UHFFFAOYSA-N 0.000 claims description 2
- KNAAFBMBMBMZHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole-2-carboxylic acid Chemical class OC(=O)C1=NC=C([N+]([O-])=O)S1 KNAAFBMBMBMZHI-UHFFFAOYSA-N 0.000 claims description 2
- OWAGYIWHDIXOMD-UHFFFAOYSA-N [O-][N+]([S+]1C=NC=C1)=O Chemical class [O-][N+]([S+]1C=NC=C1)=O OWAGYIWHDIXOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- VKTPEVPFLAVBQC-UHFFFAOYSA-N (4-hydroxy-2,3,5-trimethylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound CC1=C(O)C(C)=CC(C(=O)C=2SC(=CN=2)[N+]([O-])=O)=C1C VKTPEVPFLAVBQC-UHFFFAOYSA-N 0.000 claims 1
- 229940124350 antibacterial drug Drugs 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- JNCIUFLBNBFHHF-UHFFFAOYSA-N 5-nitro-1,3-thiazole-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CN=C(C(Cl)=O)S1 JNCIUFLBNBFHHF-UHFFFAOYSA-N 0.000 description 5
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000019169 all-trans-retinol Nutrition 0.000 description 2
- 239000011717 all-trans-retinol Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AWLDSXJCQWTJPC-UHFFFAOYSA-N 1-fluoro-2,3-dimethylbenzene Chemical compound CC1=CC=CC(F)=C1C AWLDSXJCQWTJPC-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- GTPNXFKONRIHRW-UHFFFAOYSA-N 2-iodo-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(I)C(C)=C1 GTPNXFKONRIHRW-UHFFFAOYSA-N 0.000 description 1
- ROIMNSWDOJCBFR-UHFFFAOYSA-N 2-iodothiophene Chemical compound IC1=CC=CS1 ROIMNSWDOJCBFR-UHFFFAOYSA-N 0.000 description 1
- VVVCJCRUFSIVHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=CN=CS1 VVVCJCRUFSIVHI-UHFFFAOYSA-N 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/58—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732337153 DE2337153A1 (de) | 1973-07-18 | 1973-07-18 | 2-acyl-5-nitrothiazole |
| CH959874A CH582165A5 (cs) | 1973-07-18 | 1974-07-11 | |
| DK373774A DK373774A (cs) | 1973-07-18 | 1974-07-11 | |
| ES428224A ES428224A2 (es) | 1973-07-18 | 1974-07-12 | Procedimiento para la preparacion de nuevos 2-acil-5-nitro-tiazoles. |
| AU71249/74A AU7124974A (en) | 1973-07-18 | 1974-07-15 | 2-acyl-5-nitro-thiazole |
| DD17994174A DD112453A6 (cs) | 1973-07-18 | 1974-07-16 | |
| SE7409329A SE7409329L (cs) | 1973-07-18 | 1974-07-17 | |
| US05/489,161 US4006241A (en) | 1972-06-23 | 1974-07-17 | Certain halothien-2-yl 5-nitrothiazol-2-yl ketones and fungicidal composition |
| HUSC000485 HU167674B (cs) | 1973-07-18 | 1974-07-17 | |
| BE146690A BE817807R (fr) | 1973-07-18 | 1974-07-18 | 2-acyl-5-nitrothiazoles et leur procede de preparation |
| NL7409716A NL7409716A (nl) | 1973-07-18 | 1974-07-18 | Werkwijze voor de bereiding van een genees- middel met fungicide werking. |
| JP8267174A JPS5040562A (cs) | 1973-07-18 | 1974-07-18 | |
| FR7424990A FR2237632B2 (cs) | 1973-07-18 | 1974-07-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732337153 DE2337153A1 (de) | 1973-07-18 | 1973-07-18 | 2-acyl-5-nitrothiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2337153A1 true DE2337153A1 (de) | 1975-02-06 |
Family
ID=5887616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732337153 Pending DE2337153A1 (de) | 1972-06-23 | 1973-07-18 | 2-acyl-5-nitrothiazole |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5040562A (cs) |
| AU (1) | AU7124974A (cs) |
| BE (1) | BE817807R (cs) |
| CH (1) | CH582165A5 (cs) |
| DD (1) | DD112453A6 (cs) |
| DE (1) | DE2337153A1 (cs) |
| DK (1) | DK373774A (cs) |
| ES (1) | ES428224A2 (cs) |
| FR (1) | FR2237632B2 (cs) |
| HU (1) | HU167674B (cs) |
| NL (1) | NL7409716A (cs) |
| SE (1) | SE7409329L (cs) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2131888A1 (de) * | 1971-06-24 | 1972-12-28 | Schering Ag | 5-Nitrothiazolderivate und Verfahren zu ihrer Herstellung |
-
1973
- 1973-07-18 DE DE19732337153 patent/DE2337153A1/de active Pending
-
1974
- 1974-07-11 CH CH959874A patent/CH582165A5/xx not_active IP Right Cessation
- 1974-07-11 DK DK373774A patent/DK373774A/da unknown
- 1974-07-12 ES ES428224A patent/ES428224A2/es not_active Expired
- 1974-07-15 AU AU71249/74A patent/AU7124974A/en not_active Expired
- 1974-07-16 DD DD17994174A patent/DD112453A6/xx unknown
- 1974-07-17 SE SE7409329A patent/SE7409329L/xx not_active Application Discontinuation
- 1974-07-17 HU HUSC000485 patent/HU167674B/hu unknown
- 1974-07-18 JP JP8267174A patent/JPS5040562A/ja active Pending
- 1974-07-18 NL NL7409716A patent/NL7409716A/xx unknown
- 1974-07-18 FR FR7424990A patent/FR2237632B2/fr not_active Expired
- 1974-07-18 BE BE146690A patent/BE817807R/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7409716A (nl) | 1975-01-21 |
| AU7124974A (en) | 1976-01-15 |
| HU167674B (cs) | 1975-11-28 |
| FR2237632A2 (cs) | 1975-02-14 |
| DD112453A6 (cs) | 1975-04-05 |
| BE817807R (fr) | 1975-01-20 |
| FR2237632B2 (cs) | 1977-12-02 |
| ES428224A2 (es) | 1976-11-16 |
| CH582165A5 (cs) | 1976-11-30 |
| DK373774A (cs) | 1975-03-03 |
| JPS5040562A (cs) | 1975-04-14 |
| SE7409329L (cs) | 1975-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |