JPS6322570A - １−メタンスルホニルオキシ−６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−ル及びセファロスポリン誘導体の製造方法 - Google Patents

１−メタンスルホニルオキシ−６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−ル及びセファロスポリン誘導体の製造方法

Info

Publication number: JPS6322570A
Authority: JP; Japan
Prior art keywords: group; general formula; tables; formulas; syn
Prior art date: 1986-06-25
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

Application number

JP62155237A

Other languages

English (en)

Japanese (ja)

Inventor

金　大▲こう▼

李　哲海

金　京淑

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Korea Research Institute of Chemical Technology KRICT

Original Assignee

Korea Research Institute of Chemical Technology KRICT

Priority date (The priority date 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 date listed.)

1986-06-25

Filing date

1987-06-22

Publication date

1988-01-30

1987-06-22 Application filed by Korea Research Institute of Chemical Technology KRICT filed Critical Korea Research Institute of Chemical Technology KRICT

1988-01-30 Publication of JPS6322570A publication Critical patent/JPS6322570A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 10
FKMUKFBHNSAVFW-UHFFFAOYSA-N [6-(trifluoromethyl)benzotriazol-1-yl] methanesulfonate Chemical compound C1=C(C(F)(F)F)C=C2N(OS(=O)(=O)C)N=NC2=C1 FKMUKFBHNSAVFW-UHFFFAOYSA-N 0.000 title description 8
HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 35
-1 acetoxymethyl Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
150000007524 organic acids Chemical class 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
238000000034 method Methods 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
238000001816 cooling Methods 0.000 description 23
239000000243 solution Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 18
238000005917 acylation reaction Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000012964 benzotriazole Substances 0.000 description 13
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 10
238000001035 drying Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
238000001914 filtration Methods 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
241001558496 Talpa caeca Species 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
238000004821 distillation Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000012359 Methanesulfonyl chloride Substances 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
229930186147 Cephalosporin Natural products 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
230000010933 acylation Effects 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000002585 base Substances 0.000 description 5
229940124587 cephalosporin Drugs 0.000 description 5
150000001780 cephalosporins Chemical class 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
150000003951 lactams Chemical class 0.000 description 4
239000010410 layer Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
DGIBHCWBCOAPDN-UHFFFAOYSA-N 1-hydroxy-6-(trifluoromethyl)benzotriazole Chemical compound C1=C(C(F)(F)F)C=C2N(O)N=NC2=C1 DGIBHCWBCOAPDN-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 2
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 2
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 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000588767 Proteus vulgaris Species 0.000 description 2
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000003782 beta lactam antibiotic agent Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
229940007042 proteus vulgaris Drugs 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000009738 saturating Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002132 β-lactam antibiotic Substances 0.000 description 2
229940124586 β-lactam antibiotics Drugs 0.000 description 2
MIHIJWOEDDPOLG-DUXPYHPUSA-N (2e)-2-methoxyiminoacetic acid Chemical compound CO\N=C\C(O)=O MIHIJWOEDDPOLG-DUXPYHPUSA-N 0.000 description 1
XSPUSVIQHBDITA-KXDGEKGBSA-N (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CN1N=NC(C)=N1 XSPUSVIQHBDITA-KXDGEKGBSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
ULLOIGLPCMWRNA-UHFFFAOYSA-N 1-methylsulfonyl-6-(trifluoromethyl)benzotriazole Chemical compound CS(=O)(=O)n1nnc2ccc(cc12)C(F)(F)F ULLOIGLPCMWRNA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
UIYAXIPXULMHAI-JLGRZTKVSA-N Cefteram pivoxil Chemical compound S([C@@H]1[C@@H](C(N1C=1C(=O)OCOC(=O)C(C)(C)C)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CN1N=NC(C)=N1 UIYAXIPXULMHAI-JLGRZTKVSA-N 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000588772 Morganella morganii Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
241000607726 Salmonella enterica subsp. enterica serovar Heidelberg Species 0.000 description 1
241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
241000405965 Scomberomorus brasiliensis Species 0.000 description 1
241000607768 Shigella Species 0.000 description 1
241000607760 Shigella sonnei Species 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229950003588 axetil Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 description 1
HJJDBAOLQAWBMH-YCRCPZNHSA-N cefmenoxime Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NN=NN1C HJJDBAOLQAWBMH-YCRCPZNHSA-N 0.000 description 1
229960003791 cefmenoxime Drugs 0.000 description 1
ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 1
229960000484 ceftazidime Drugs 0.000 description 1
229950000679 cefteram Drugs 0.000 description 1
NNULBSISHYWZJU-LLKWHZGFSA-N ceftizoxime Chemical compound N([C@@H]1C(N2C(=CCS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-LLKWHZGFSA-N 0.000 description 1
229960001991 ceftizoxime Drugs 0.000 description 1
JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 1
229960001668 cefuroxime Drugs 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
101150103001 mEFG1 gene Proteins 0.000 description 1
238000005259 measurement Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

JP62155237A 1986-06-25 1987-06-22 １−メタンスルホニルオキシ−６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−ル及びセファロスポリン誘導体の製造方法 Pending JPS6322570A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
KR1019860005101A KR890002107B1 (ko)	1986-06-25	1986-06-25	세팔로스포린 유도체의 제조방법
KR1986-5101		1986-06-25

Publications (1)

Publication Number	Publication Date
JPS6322570A true JPS6322570A (ja)	1988-01-30

Family

ID=19250716

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62155237A Pending JPS6322570A (ja)	1986-06-25	1987-06-22	１−メタンスルホニルオキシ−６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−ル及びセファロスポリン誘導体の製造方法

Country Status (5)

Country	Link
JP (1)	JPS6322570A (ko)
KR (1)	KR890002107B1 (ko)
DE (2)	DE3720681A1 (ko)
GB (1)	GB2195334A (ko)
IT (1)	IT1205178B (ko)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR890100706A (el) *	1989-10-31	1992-03-20	Han Mi Pharma Ind Co Ltd	Μέ?οδος παρασκευής παραγώγων κεφέμης.
AT398764B (de) *	1992-01-28	1995-01-25	Lek Tovarna Farmacevtskih	Verfahren zur herstellung von ceftriaxondinatrium-salzhemiheptahydrat
AT399877B (de) *	1992-02-20	1995-08-25	Biochemie Gmbh	Neues verfahren zur herstellung von ceftriaxon
WO1996012712A1 (en) *	1994-10-24	1996-05-02	Miwon Co., Ltd.	Reactive phosphate derivatives of thiazolylacetic acid and process for preparing cephalosporin antibiotics using the same
KR100197788B1 (ko) *	1995-06-30	1999-06-15	김충환	세펨 유도체의 제조방법

1986
- 1986-06-25 KR KR1019860005101A patent/KR890002107B1/ko not_active IP Right Cessation
1987
- 1987-06-22 JP JP62155237A patent/JPS6322570A/ja active Pending
- 1987-06-23 DE DE19873720681 patent/DE3720681A1/de not_active Withdrawn
- 1987-06-23 IT IT21014/87A patent/IT1205178B/it active
- 1987-06-23 DE DE19873744772 patent/DE3744772A1/de active Pending
- 1987-06-24 GB GB08714764A patent/GB2195334A/en not_active Withdrawn

Also Published As

Publication number	Publication date
GB2195334A (en)	1988-04-07
DE3720681A1 (de)	1988-01-28
DE3744772A1 (ko)	1989-02-02
KR890002107B1 (ko)	1989-06-19
IT8721014A0 (it)	1987-06-23
GB8714764D0 (en)	1987-07-29
KR880000448A (ko)	1988-03-25
IT1205178B (it)	1989-03-15

Publication	Publication Date	Title
US4264595A (en)	1981-04-28	7-[2-(2-Imino-4-thiazolin-4-yl)-2-(syn)-hydroxy-iminoacetamido]-cephalosporins
JPH0313237B2 (ko)	1991-02-22
JPH05502884A (ja)	1993-05-20	新規３―置換セフェム化合物及びその製造方法
JPS63146863A (ja)	1988-06-18	カルボン酸類
BE897864A (fr)	1984-03-29	Procede de production de composes de 3-vinyl-3-cephem 7-substitues et nouveaux produits ainsi obtenus
CS232735B2 (en)	1985-02-14	Method of making cephalosporine derivatives
JPH0327552B2 (ko)	1991-04-16
HUT53653A (en)	1990-11-28	Process for producing cefalosporin derivatives and pharmaceutical compositions comprising such compounds as active ingredient
EP0392796A3 (en)	1992-02-19	Cephalosporin derivatives
JPS63211288A (ja)	1988-09-02	セフアロスポリン化合物、その製造法および該化合物を含有する殺菌剤
JPS63107989A (ja)	1988-05-12	セファロスポリン化合物
JPH0228185A (ja)	1990-01-30	セファロスポリン化合物及びその合成中間体
JPS6322570A (ja)	1988-01-30	１−メタンスルホニルオキシ−６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−ル及びセファロスポリン誘導体の製造方法
SU1249017A1 (ru)	1986-08-07	Цефалоспорины как промежуточные продукты в синтезе цефалоспоринов,обладающих антибактериальными свойствами
JPS62158290A (ja)	1987-07-14	新規セフアロスポリン誘導体
JPS6310792A (ja)	1988-01-18	新規セフエム化合物
JPS6067483A (ja)	1985-04-17	チアゾリオメチル置換基を有するセフアロスポリン誘導体
JPS61267587A (ja)	1986-11-27	新規セファロスポリン誘導体
LU82979A1 (fr)	1981-03-26	Derives thiazolyle n-substitues de cephalosporines substituees par un groupe oxy-imino
US4137314A (en)	1979-01-30	7-Dithioacetamido cephalosporins and pharmaceutical compositions and methods employing them having antibacterial activity
AU672056B2 (en)	1996-09-19	Cephalosporin salts and process for the preparation thereof
JPH0322392B2 (ko)	1991-03-26
JPH04266889A (ja)	1992-09-22	抗生物質ｃ−３カテコ−ル−置換セファロスボリン化合物、組成物およびその使用法
JPS61251685A (ja)	1986-11-08	新規な１−オキサ−１−デチアセフアロスポリン化合物及びそれを含む抗菌剤
JPS60209589A (ja)	1985-10-22	セフアロスポリン誘導体のエステル