JPH0375545B2 - - Google Patents
Info
- Publication number
- JPH0375545B2 JPH0375545B2 JP57103109A JP10310982A JPH0375545B2 JP H0375545 B2 JPH0375545 B2 JP H0375545B2 JP 57103109 A JP57103109 A JP 57103109A JP 10310982 A JP10310982 A JP 10310982A JP H0375545 B2 JPH0375545 B2 JP H0375545B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- general formula
- group
- reaction
- 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 - Lifetime
Links
- -1 methylthiocarbonyl group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 16
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 22
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- ZULMJJCZPOPPGF-UHFFFAOYSA-N 1-bromo-4-chlorobutane-2,3-dione Chemical compound ClCC(=O)C(=O)CBr ZULMJJCZPOPPGF-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- GZCRCGNZLNWBSK-UHFFFAOYSA-N 1-(2-amino-1,3-thiazol-4-yl)-2-chloroethanone Chemical compound NC1=NC(C(=O)CCl)=CS1 GZCRCGNZLNWBSK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- AHPSZWVDPABXPI-UHFFFAOYSA-N 1-chlorobutane-2,3-dione Chemical compound CC(=O)C(=O)CCl AHPSZWVDPABXPI-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- NAPGCGXVYWFSNM-UHFFFAOYSA-N s-methyl 2-(2-amino-1,3-thiazol-4-yl)-2-oxoethanethioate Chemical compound CSC(=O)C(=O)C1=CSC(N)=N1 NAPGCGXVYWFSNM-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
- WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OEZNULIHEQCKJR-UHFFFAOYSA-N ethanol;hydrobromide Chemical compound Br.CCO OEZNULIHEQCKJR-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- UTAIYYASLGUQEM-UHFFFAOYSA-N s-methyl 2-(2-formamido-1,3-thiazol-4-yl)-2-oxoethanethioate Chemical compound CSC(=O)C(=O)C1=CSC(NC=O)=N1 UTAIYYASLGUQEM-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (47)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57103109A JPS58222076A (ja) | 1982-06-17 | 1982-06-17 | 2−アミノチアゾ−ル誘導体 |
GB08315700A GB2122988B (en) | 1982-06-17 | 1983-06-08 | Process for producing 2-(2-aminothiazol-4-yl) glyoxylic acid derivative; intermediates |
AU15500/83A AU542287B2 (en) | 1982-06-17 | 1983-06-08 | Process for producing 2-(2-aminothiazol-4-yl) glyoxylic acid derivative, it:s salt and intermediates therefor |
CA000430079A CA1191512A (en) | 1982-06-17 | 1983-06-09 | Process for producing 2-(2-aminothiazol-4- yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates |
IL68931A IL68931A0 (en) | 1982-06-17 | 1983-06-09 | Novel process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid derivative or a salt thereof,and intermediates therefor and process for producing the intermediates |
DE3348173A DE3348173C2 (nl) | 1982-06-17 | 1983-06-10 | |
DE19833321127 DE3321127A1 (de) | 1982-06-17 | 1983-06-10 | Neues verfahren zur herstellung von 2-(2-aminothiazol-4-yl)-glyoxylsaeure-derivaten oder eines salzes derselben sowie zwischenprodukte derselben und verfahren zur herstellung der zwischenprodukte |
US06/504,317 US4563534A (en) | 1982-06-17 | 1983-06-14 | Process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates |
CH325683A CH659470A5 (en) | 1982-06-17 | 1983-06-14 | Process for preparing 2-(2-aminothiazol-4-yl)glyoxylic acid or a derivative or a salt thereof |
CH544185A CH657613A5 (en) | 1982-06-17 | 1983-06-14 | Novel intermediates for preparing 2-(2-aminothiazol-4-yl)glyoxylic acid derivatives or a salt thereof, and a process for preparing the intermediates |
FI832152A FI85470C (fi) | 1982-06-17 | 1983-06-14 | Foerfarande foer framstaellning av 2- (2- aminotiazol-4-yl)glyoxylsyraderivat eller dess salter. |
AT0219783A AT380877B (de) | 1982-06-17 | 1983-06-14 | Verfahren zur herstellung von tautomeren 2-(2aminothiazol-4-yl)-glyoxylsaeure-derivaten oder salzen oder loesungsmittel-addukten derselben |
IT48504/83A IT1171839B (it) | 1982-06-17 | 1983-06-15 | Procedimento per produrre derivati di acido 2-(2-amminotiazol-4-il)-gliossolico o suoi sali, intermedi per esso e procedimento per produrre gli intermedi |
FR8309863A FR2528839B1 (fr) | 1982-06-17 | 1983-06-15 | Nouveau procede de production de derives de l'acide 2-(2-aminothiazol-4-yl) glyoxylique ou d'un de ses sels, les intermediaires necessaires a la synthese de ces derniers, et le procede de production desdits intermediaires |
NL8302151A NL8302151A (nl) | 1982-06-17 | 1983-06-16 | Werkwijze voor het bereiden van 2-(2-aminothiazool-4-yl)- glyoxylzuur of een zout daarvan, tussenprodukten daarvoor, en werkwijze voor het bereiden van de tussenprodukten. |
NZ204609A NZ204609A (en) | 1982-06-17 | 1983-06-16 | 2-aminothiazole derivatives used as intermediates in production of glyoxylic acid derivatives and precursor compounds therefor |
NO832178A NO161114C (no) | 1982-06-17 | 1983-06-16 | Fremgangsm te for fremstilling av glyoksylsyrederiv |
KR1019830002682A KR860001027B1 (ko) | 1982-06-17 | 1983-06-16 | 2-(2-아미노 티아졸-4-일)글리옥실산 유도체 및 그 중간체의 제조방법 |
BE0/211013A BE897063A (fr) | 1982-06-17 | 1983-06-16 | Nouveau procede de production de derives de l'acide 2-(aminothia-zol-4-yl) glyoxylique ou d'un de ses sels, les intermediaires necessaires a la synthese de ces derniers, et le procede de production desdits intermediaires |
NZ21230483A NZ212304A (en) | 1982-06-17 | 1983-06-16 | 1,4-dihalogenobutane-2,3-diones |
SE8303465A SE452981B (sv) | 1982-06-17 | 1983-06-16 | Nytt forfarande for framstellning av 2-(2-aminotiazol-4-yl)-glyoxylsyraderivat eller ett salt derav |
MX83197676A MX156981A (es) | 1982-06-17 | 1983-06-16 | Procedimiento para preparar un derivado de acido 2-(2-aminotiazol 4-il)glioxilico |
DK278883A DK161073C (da) | 1982-06-17 | 1983-06-16 | Fremgangsmaade til fremstilling af 2-(2-amino-thiazol-4-yl)glyoxylsyrederivater eller salte heraf |
PT76880A PT76880B (en) | 1982-06-17 | 1983-06-16 | Process for preparing 2-(2-aminothiazol-4-yl)-glyoxylic acid derivatives or salts thereof and of intermediates therefor |
ES523348A ES523348A0 (es) | 1982-06-17 | 1983-06-16 | Un procedimiento para la produccion de derivados del acido 2-(2-aminotiazol-4-il) glioxilico |
PH29065A PH18261A (en) | 1982-06-17 | 1983-06-16 | Novel process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid derivative |
FR8400471A FR2540873B1 (fr) | 1982-06-17 | 1984-01-13 | Nouveaux intermediaires pour la production de derives de l'acide 2-(2-aminothiazol-4-yl) glyoxylique ou d'un de ses sels et le procede de production desdits intermediaires |
FR848400472A FR2540860B1 (fr) | 1982-06-17 | 1984-01-13 | Nouveaux intermediaires pour la production de derives de l'acide 2-(2-aminothiazol-4-yl) glyoxylique ou d'un de ses sels et le procede de production desdits intermediaires |
ES530213A ES530213A0 (es) | 1982-06-17 | 1984-03-01 | Un procedimiento para la produccion de una 1, 4-dihalogenobutano-2, 3-diona |
ES530212A ES530212A0 (es) | 1982-06-17 | 1984-03-01 | Un procedimiento para la produccion de un derivado de 2-amino-tiazol. |
PH31191A PH19985A (en) | 1982-06-17 | 1984-09-07 | 2-aminothiazole derivatives and process for producing said compounds |
PH31192A PH20516A (en) | 1982-06-17 | 1984-09-07 | Process for producing a 1,4-dihalogenobutane-3-dione |
AU36370/84A AU567990B2 (en) | 1982-06-17 | 1984-12-06 | Halogenated vicinal diketones |
CA000475356A CA1216310A (en) | 1982-06-17 | 1985-02-27 | Process for producing 2-(2-aminothiazol-4- yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates |
CA000475355A CA1197251A (en) | 1982-06-17 | 1985-02-27 | Process for producing 2-(2-aminothiazol-4- yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates |
AT176785A AT391686B (de) | 1982-06-17 | 1985-06-13 | Verfahren zur herstellung neuer 1,4dihalogenbutan-2,3-dione |
AT176885A AT391469B (de) | 1982-06-17 | 1985-06-13 | Verfahren zur herstellung eines neuen 2-aminothiazol-derivates |
US06/753,068 US4667040A (en) | 1982-06-17 | 1985-07-09 | Novel process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates |
GB08518464A GB2167410B (en) | 1982-06-17 | 1985-07-22 | Dihalobutanones |
NO85854279A NO163366C (no) | 1982-06-17 | 1985-10-25 | Nytt 2-aminotiazolderivat og fremgangsmaate for fremstilling derav. |
NO85854280A NO163616C (no) | 1982-06-17 | 1985-10-25 | Nytt 1,4-dihalogenbutan-2,3-dion. |
IL77921A IL77921A0 (en) | 1982-06-17 | 1986-02-19 | 2-aminothiazol derivatives and process for producing them |
SE8701193A SE8701193L (sv) | 1982-06-17 | 1987-03-23 | Nya mellanprodukter for framstellning av 2-(2-aminotiazol-4-yl)-glyoxylsyraderivat eller ett salt derav samt forfarande for framstellning av mellanprodukterna |
SE8701192A SE8701192D0 (sv) | 1982-06-17 | 1987-03-23 | Nya 2-aminotiazolderivat eller salter derav for framstellning av 2-(2-aminotiazol-4-yl)-glyoxylsyraderivat eller ett salt derav samt forfarande for framstellning av dessa |
FI893076A FI85852C (fi) | 1982-06-17 | 1989-06-22 | 1-brom-4-klorbutan-2,3-dion och ett foerfarande foer framstaellning av det. |
DK229090A DK163582C (da) | 1982-06-17 | 1990-09-21 | Mellemprodukter til brug ved fremstilling af 2-(2-amino-thiazol-4-yl)glyoxylsyrederivater eller salte heraf og fremgangsmaade til fremstilling af mellemprodukterne |
DK229190A DK163816C (da) | 1982-06-17 | 1990-09-21 | 1,4-dihalogenbutan-2,3-dioner til brug som mellemprodukter ved fremstillingen af 2-(2-aminothiazol-4-yl)glyoxylsyrederivater eller salte heraf og fremgangsmaade til fremstilling af mellemprodukterne |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57103109A JPS58222076A (ja) | 1982-06-17 | 1982-06-17 | 2−アミノチアゾ−ル誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58222076A JPS58222076A (ja) | 1983-12-23 |
JPH0375545B2 true JPH0375545B2 (nl) | 1991-12-02 |
Family
ID=14345440
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57103109A Granted JPS58222076A (ja) | 1982-06-17 | 1982-06-17 | 2−アミノチアゾ−ル誘導体 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS58222076A (nl) |
CH (1) | CH657613A5 (nl) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4977264A (en) * | 1988-11-21 | 1990-12-11 | Lonza Ltd. | Process for the production of 4,5-dichloro-6-ethylpyrimidine |
JP4111856B2 (ja) | 2002-04-12 | 2008-07-02 | 昭和電工株式会社 | 安定化されたアスコルビン酸誘導体 |
-
1982
- 1982-06-17 JP JP57103109A patent/JPS58222076A/ja active Granted
-
1983
- 1983-06-14 CH CH544185A patent/CH657613A5/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CH657613A5 (en) | 1986-09-15 |
JPS58222076A (ja) | 1983-12-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1093068A (en) | Cephalosporin antibiotics | |
US4769493A (en) | Process for producing tetrafluorophthalic acid | |
JPH0375545B2 (nl) | ||
US4667040A (en) | Novel process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates | |
JP3078398B2 (ja) | スクアリリウム化合物 | |
JP3196383B2 (ja) | スクアリリウム系化合物 | |
JPH0219810B2 (nl) | ||
JPH0460991B2 (nl) | ||
JPH05255271A (ja) | 3−ヒドロキシメチル−1−プロパルギルイミダゾリジン−2,4−ジオンの製造法 | |
JP3996228B2 (ja) | 3−ピペラジニルベンズイソチアゾール類の製造法 | |
CA1216310A (en) | Process for producing 2-(2-aminothiazol-4- yl)glyoxylic acid derivative or a salt thereof, and intermediates therefor and process for producing the intermediates | |
JP4258590B2 (ja) | ハロゲン置換キノリン誘導体の製造方法 | |
JPS60158137A (ja) | 含フツ素アクリル酸誘導体の製法 | |
JPS6388168A (ja) | 3−ベンゾイルプロピオン酸誘導体 | |
JPH0114917B2 (nl) | ||
NO163366B (no) | Nytt 2-aminotiazolderivat og fremgangsmaate for fremstilling derav. | |
JPH0557259B2 (nl) | ||
JPS5827794B2 (ja) | 4− チカンピペラジン −1− シボウサンルイノセイゾウホウ | |
JPS644510B2 (nl) | ||
JPH07291954A (ja) | 2−アシルイミノチアゾリン誘導体の製造法 | |
CH659470A5 (en) | Process for preparing 2-(2-aminothiazol-4-yl)glyoxylic acid or a derivative or a salt thereof | |
JPS60214767A (ja) | 3,4,5−トリメトキシベンゾニトリルの製造方法 | |
KR960004319A (ko) | 4-아실옥시-2-아제티디논 유도체의 신규 제조방법 | |
JPH08176089A (ja) | 2−置換フェニルヒドラゾノ−プロピオン酸エステル類の製造方法 | |
JPH0892238A (ja) | 5−ハロ−2−(α−アルコキシイミノ)エチルチオフェン及びその製造方法 |