DE2204364A1 - 2-acyl-5-nitrothiazole - Google Patents
2-acyl-5-nitrothiazoleInfo
- Publication number
- DE2204364A1 DE2204364A1 DE2204364A DE2204364A DE2204364A1 DE 2204364 A1 DE2204364 A1 DE 2204364A1 DE 2204364 A DE2204364 A DE 2204364A DE 2204364 A DE2204364 A DE 2204364A DE 2204364 A1 DE2204364 A1 DE 2204364A1
- Authority
- DE
- Germany
- Prior art keywords
- nitrothiazole
- radical
- benzoyl
- general formula
- methyl
- 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 pyrrole radical Chemical class 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 5
- 230000000843 anti-fungal effect Effects 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
- PPYKSXUJXRHLTL-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound ClC=1C=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=CC1C PPYKSXUJXRHLTL-UHFFFAOYSA-N 0.000 claims description 2
- OLQUVEQZDQOKMC-UHFFFAOYSA-N (4-butoxyphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound C(CCC)OC1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 OLQUVEQZDQOKMC-UHFFFAOYSA-N 0.000 claims description 2
- UBEUCJVHCJWINI-UHFFFAOYSA-N (4-fluorophenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=C(F)C=C1 UBEUCJVHCJWINI-UHFFFAOYSA-N 0.000 claims description 2
- KMGHJIANBCQKGH-UHFFFAOYSA-N (4-methoxy-3-methylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound CC=1C=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=CC1OC KMGHJIANBCQKGH-UHFFFAOYSA-N 0.000 claims description 2
- UAXONMKTPVEOLZ-UHFFFAOYSA-N (5-nitro-1,3-thiazol-2-yl)-(4-phenoxyphenyl)methanone Chemical compound O(C1=CC=CC=C1)C1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 UAXONMKTPVEOLZ-UHFFFAOYSA-N 0.000 claims description 2
- GEJHTCFKDKDBIN-UHFFFAOYSA-N (5-nitro-1,3-thiazol-2-yl)-phenylmethanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=CC=C1 GEJHTCFKDKDBIN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- FMYPRMYBSKSMMU-UHFFFAOYSA-N furan-2-yl-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound S1C([N+](=O)[O-])=CN=C1C(=O)C1=CC=CO1 FMYPRMYBSKSMMU-UHFFFAOYSA-N 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims 2
- XADDQIHVHRSTNY-UHFFFAOYSA-N (3,4-dimethylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound C1=C(C)C(C)=CC=C1C(=O)C1=NC=C([N+]([O-])=O)S1 XADDQIHVHRSTNY-UHFFFAOYSA-N 0.000 claims 1
- SHXIJVVHRANJPR-UHFFFAOYSA-N (4-butylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound C(CCC)C1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 SHXIJVVHRANJPR-UHFFFAOYSA-N 0.000 claims 1
- DZOXUSREIVLBID-UHFFFAOYSA-N (4-methylsulfanylphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound CSC1=CC=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=C1 DZOXUSREIVLBID-UHFFFAOYSA-N 0.000 claims 1
- GSRLEXHGKSSJHH-UHFFFAOYSA-N (5-methylfuran-2-yl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound O1C(C)=CC=C1C(=O)C1=NC=C([N+]([O-])=O)S1 GSRLEXHGKSSJHH-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940124350 antibacterial drug Drugs 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 238000003756 stirring Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 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 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 11
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- VVVCJCRUFSIVHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=CS1 VVVCJCRUFSIVHI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OWAGYIWHDIXOMD-UHFFFAOYSA-N [O-][N+]([S+]1C=NC=C1)=O Chemical compound [O-][N+]([S+]1C=NC=C1)=O OWAGYIWHDIXOMD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 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
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- IZGQKBQXQIBSDR-UHFFFAOYSA-N (3-fluoro-4-methoxyphenyl)-(5-nitro-1,3-thiazol-2-yl)methanone Chemical compound FC=1C=C(C(=O)C=2SC(=CN2)[N+](=O)[O-])C=CC1OC IZGQKBQXQIBSDR-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- JIXDOBAQOWOUPA-UHFFFAOYSA-N 1-fluoro-2-methoxybenzene Chemical compound COC1=CC=CC=C1F JIXDOBAQOWOUPA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 229940110432 activated charcoal 300 mg Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 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
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Catalysts (AREA)
- Fodder In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2204364A DE2204364A1 (de) | 1972-01-27 | 1972-01-27 | 2-acyl-5-nitrothiazole |
| CH626872A CH569000A5 (enExample) | 1972-01-27 | 1972-04-27 | |
| DD163353A DD100719A5 (enExample) | 1972-01-27 | 1972-06-01 | |
| AR242556A AR192792A1 (es) | 1972-01-27 | 1972-06-14 | Procedimiento para la produccion de 2-acil-5-nitrotiazoles |
| AT515772A AT315166B (de) | 1972-01-27 | 1972-06-15 | Verfahren zur Herstellung von neuen 2-Acyl-5-nitrothiazolen |
| SE7208197A SE377939B (enExample) | 1972-01-27 | 1972-06-21 | |
| EG274/72A EG10728A (en) | 1972-01-27 | 1972-06-21 | Process for preparation of nitro thiazoles and drugs containing it |
| HUSC400A HU162904B (enExample) | 1972-01-27 | 1972-06-22 | |
| BE785368A BE785368A (fr) | 1972-01-27 | 1972-06-23 | 2-acyl-5-nitrothiazoles et leur procede de preparation |
| FR7222737A FR2169018B1 (enExample) | 1972-01-27 | 1972-06-23 | |
| US00265462A US3830826A (en) | 1972-01-27 | 1972-06-23 | 2-acyl-5-nitrothiazole derivatives |
| GB2983072A GB1400604A (en) | 1972-01-27 | 1972-06-26 | 2-acyl-5-nitrothiazoles |
| NL7208801A NL7208801A (enExample) | 1972-01-27 | 1972-06-26 | |
| IL39838A IL39838A (en) | 1972-01-27 | 1972-07-06 | 2-acyl-5-nitrothiazoles |
| SU1813601A SU432722A3 (enExample) | 1972-01-27 | 1972-07-21 | |
| ES405438A ES405438A1 (es) | 1972-01-27 | 1972-08-02 | Procedimiento para la preparacion de nuevos 2-acil-nitro- tiazoles. |
| ES405437A ES405437A1 (es) | 1972-01-27 | 1972-08-02 | Procedimiento para la preparacion de nuevos 2-acil-nitroti-azoles. |
| CA149,736A CA987326A (en) | 1972-01-27 | 1972-08-18 | Process for producing 2-acyl-5-nitrothiazoles |
| AU45753/72A AU468236B2 (en) | 1972-01-27 | 1972-08-18 | 2-acyl-5-nitrothiazoles |
| JP47083552A JPS4885571A (enExample) | 1972-01-27 | 1972-08-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2204364A DE2204364A1 (de) | 1972-01-27 | 1972-01-27 | 2-acyl-5-nitrothiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2204364A1 true DE2204364A1 (de) | 1973-08-02 |
Family
ID=5834503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2204364A Pending DE2204364A1 (de) | 1972-01-27 | 1972-01-27 | 2-acyl-5-nitrothiazole |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3830826A (enExample) |
| JP (1) | JPS4885571A (enExample) |
| AR (1) | AR192792A1 (enExample) |
| AT (1) | AT315166B (enExample) |
| AU (1) | AU468236B2 (enExample) |
| BE (1) | BE785368A (enExample) |
| CA (1) | CA987326A (enExample) |
| CH (1) | CH569000A5 (enExample) |
| DD (1) | DD100719A5 (enExample) |
| DE (1) | DE2204364A1 (enExample) |
| EG (1) | EG10728A (enExample) |
| ES (2) | ES405437A1 (enExample) |
| FR (1) | FR2169018B1 (enExample) |
| GB (1) | GB1400604A (enExample) |
| HU (1) | HU162904B (enExample) |
| IL (1) | IL39838A (enExample) |
| NL (1) | NL7208801A (enExample) |
| SE (1) | SE377939B (enExample) |
| SU (1) | SU432722A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006241A (en) * | 1972-06-23 | 1977-02-01 | Schering Aktiengesellschaft | Certain halothien-2-yl 5-nitrothiazol-2-yl ketones and fungicidal composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4269985A (en) * | 1980-07-30 | 1981-05-26 | Eastman Kodak Company | Process for the preparation of 2-amino-5-nitrothiazole |
-
1972
- 1972-01-27 DE DE2204364A patent/DE2204364A1/de active Pending
- 1972-04-27 CH CH626872A patent/CH569000A5/xx not_active IP Right Cessation
- 1972-06-01 DD DD163353A patent/DD100719A5/xx unknown
- 1972-06-14 AR AR242556A patent/AR192792A1/es active
- 1972-06-15 AT AT515772A patent/AT315166B/de not_active IP Right Cessation
- 1972-06-21 EG EG274/72A patent/EG10728A/xx active
- 1972-06-21 SE SE7208197A patent/SE377939B/xx unknown
- 1972-06-22 HU HUSC400A patent/HU162904B/hu unknown
- 1972-06-23 FR FR7222737A patent/FR2169018B1/fr not_active Expired
- 1972-06-23 BE BE785368A patent/BE785368A/xx unknown
- 1972-06-23 US US00265462A patent/US3830826A/en not_active Expired - Lifetime
- 1972-06-26 NL NL7208801A patent/NL7208801A/xx unknown
- 1972-06-26 GB GB2983072A patent/GB1400604A/en not_active Expired
- 1972-07-06 IL IL39838A patent/IL39838A/xx unknown
- 1972-07-21 SU SU1813601A patent/SU432722A3/ru active
- 1972-08-02 ES ES405437A patent/ES405437A1/es not_active Expired
- 1972-08-02 ES ES405438A patent/ES405438A1/es not_active Expired
- 1972-08-18 CA CA149,736A patent/CA987326A/en not_active Expired
- 1972-08-18 AU AU45753/72A patent/AU468236B2/en not_active Expired
- 1972-08-21 JP JP47083552A patent/JPS4885571A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006241A (en) * | 1972-06-23 | 1977-02-01 | Schering Aktiengesellschaft | Certain halothien-2-yl 5-nitrothiazol-2-yl ketones and fungicidal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EG10728A (en) | 1976-05-31 |
| JPS4885571A (enExample) | 1973-11-13 |
| AU468236B2 (en) | 1976-01-08 |
| HU162904B (enExample) | 1973-04-28 |
| US3830826A (en) | 1974-08-20 |
| SE377939B (enExample) | 1975-08-04 |
| NL7208801A (enExample) | 1973-07-31 |
| GB1400604A (en) | 1975-07-16 |
| FR2169018B1 (enExample) | 1975-06-20 |
| ES405438A1 (es) | 1975-07-16 |
| IL39838A0 (en) | 1972-09-28 |
| CA987326A (en) | 1976-04-13 |
| FR2169018A1 (enExample) | 1973-09-07 |
| IL39838A (en) | 1975-05-22 |
| AT315166B (de) | 1974-05-10 |
| AU4575372A (en) | 1974-02-21 |
| ES405437A1 (es) | 1975-09-01 |
| BE785368A (fr) | 1972-12-27 |
| SU432722A3 (enExample) | 1974-06-15 |
| CH569000A5 (enExample) | 1975-11-14 |
| AR192792A1 (es) | 1973-03-14 |
| DD100719A5 (enExample) | 1973-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2705446C2 (enExample) | ||
| DE29724281U1 (de) | 4-Phenylpiperidin-Verbindungen | |
| EP0003796B1 (de) | Substituierte Diphenyl-imidazolyl-methane, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel | |
| EP1098891B1 (de) | Polycyclische thiazolidin-2-yliden amine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE2333355C2 (de) | Antimikrobielle Mittel | |
| DE2523103A1 (de) | Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben | |
| DE2633889C2 (de) | Neue Aminobenzocyclohepten-Derivate und deren Salze, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| DE2204364A1 (de) | 2-acyl-5-nitrothiazole | |
| DE1695516A1 (de) | Aromatische Sulfone | |
| DE2007345A1 (de) | Neue substituierte Hexahydroimidazochinoline und deren Säureanlagerungssalze | |
| DE2005959B2 (de) | Nitrochinoline | |
| DE2402705A1 (de) | Tetrahydrofluorensaeuren | |
| DE1695515A1 (de) | Aromatische Sulfoxide und Verfahren zu deren Herstellung | |
| DE2039426C3 (de) | 1-Benzyliden-indenyl-(3)-essigsäuren, deren nicht-toxische, pharmakologisch verträgliche Salze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE2453936A1 (de) | Neue ferrocenderivate und ihre herstellung | |
| DE1695560C3 (de) | Pyrid-2-thione und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2642877A1 (de) | Substituierte 2-nitro-3-phenylbenzofuranverbindungen | |
| DE1914981A1 (de) | Verfahren zur Herstellung heterocyclischer Verbindungen | |
| DE1934392C3 (de) | Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung | |
| DE69901925T2 (de) | 2-(3-Phenyl-2-propenyl)-1,2,3,4-tetrahydro-isochinolin-derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| DE2607570A1 (de) | Triazolobenzocycloalkylthiadiazin- derivate, verfahren zu ihrer herstellung und dieselben enthaltende pharmazeutische praeparate | |
| DE2335080A1 (de) | Neue cyclohexenonester, verfahren zu ihrer herstellung und diese ester enthaltende arzneimittel | |
| DE2217420A1 (de) | N-thienylmethyl-heterocyclen, deren saeureadditionssalze sowie verfahren zu deren herstellung | |
| CH537404A (de) | Verfahren zur Herstellung neuer Thiophenderivate | |
| DE2809183C2 (de) | 3-(1-Carboxy-alkoxy)-pyrazol-Derivate und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |