JPS5953492A - セフアロスポリン化合物の製造方法 - Google Patents

セフアロスポリン化合物の製造方法

Info

Publication number: JPS5953492A
Authority: JP; Japan
Prior art keywords: compound; solution; methylene chloride; methyl; add
Prior art date: 1982-09-20
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.): Granted

Application number

JP16355682A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0357911B2 (da

Inventor

Kenzo Naito

内藤　建三

Masayasu Kato

加藤　昌靖

Kazuo Tsukamura

塚村　和夫

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.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

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.)

1982-09-20

Filing date

1982-09-20

Publication date

1984-03-28

1982-09-20 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1982-09-20 Priority to JP16355682A priority Critical patent/JPS5953492A/ja

1984-03-28 Publication of JPS5953492A publication Critical patent/JPS5953492A/ja

1991-09-03 Publication of JPH0357911B2 publication Critical patent/JPH0357911B2/ja

Status Granted legal-status Critical Current

Links

-1 cephalosporin compound Chemical class 0.000 title claims abstract description 187
229930186147 Cephalosporin Natural products 0.000 title claims description 10
229940124587 cephalosporin Drugs 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 83
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 66
239000011574 phosphorus Substances 0.000 claims abstract description 63
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 46
230000000269 nucleophilic effect Effects 0.000 claims abstract description 27
125000002252 acyl group Chemical group 0.000 claims abstract description 22
239000003960 organic solvent Substances 0.000 claims abstract description 17
150000002148 esters Chemical group 0.000 claims abstract description 14
150000001782 cephems Chemical group 0.000 claims abstract description 8
239000007795 chemical reaction product Substances 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 abstract description 16
125000003277 amino group Chemical group 0.000 abstract description 5
239000003242 anti bacterial agent Substances 0.000 abstract description 4
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 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 3
125000004122 cyclic group Chemical group 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 405
239000000243 solution Substances 0.000 description 160
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 115
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 97
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 97
238000006243 chemical reaction Methods 0.000 description 77
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
238000003756 stirring Methods 0.000 description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 53
239000010410 layer Substances 0.000 description 51
150000003839 salts Chemical class 0.000 description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 46
229910019142 PO4 Inorganic materials 0.000 description 39
238000001816 cooling Methods 0.000 description 39
239000010452 phosphate Substances 0.000 description 39
239000012044 organic layer Substances 0.000 description 31
239000002253 acid Substances 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
125000000217 alkyl group Chemical group 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000013078 crystal Substances 0.000 description 27
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 25
239000000843 powder Substances 0.000 description 25
239000000047 product Substances 0.000 description 25
238000000034 method Methods 0.000 description 24
125000001424 substituent group Chemical group 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
125000003118 aryl group Chemical group 0.000 description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
239000002904 solvent Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
150000002430 hydrocarbons Chemical group 0.000 description 17
150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
125000000623 heterocyclic group Chemical group 0.000 description 15
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 14
125000003545 alkoxy group Chemical group 0.000 description 14
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
150000001204 N-oxides Chemical class 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 10
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 10
229910052736 halogen Inorganic materials 0.000 description 10
150000002367 halogens Chemical class 0.000 description 10
239000002994 raw material Substances 0.000 description 10
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
238000005406 washing Methods 0.000 description 9
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
125000000753 cycloalkyl group Chemical group 0.000 description 8
229950001902 dimevamide Drugs 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
239000011734 sodium Substances 0.000 description 8
125000004434 sulfur atom Chemical group 0.000 description 8
OWBLFTIPFLNLBN-UHFFFAOYSA-N 2-hydroxy-1,3,2$l^{5}-benzodioxaphosphole 2-oxide Chemical compound C1=CC=C2OP(O)(=O)OC2=C1 OWBLFTIPFLNLBN-UHFFFAOYSA-N 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
125000003710 aryl alkyl group Chemical group 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
OMAZBMROWXOLBQ-UHFFFAOYSA-N 2-methoxy-1,3,2$l^{5}-benzodioxaphosphole 2-oxide Chemical compound C1=CC=C2OP(OC)(=O)OC2=C1 OMAZBMROWXOLBQ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
125000000392 cycloalkenyl group Chemical group 0.000 description 6
238000001035 drying Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
239000000376 reactant Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 4
150000008043 acidic salts Chemical class 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000005042 acyloxymethyl group Chemical group 0.000 description 4
150000001447 alkali salts Chemical class 0.000 description 4
125000005115 alkyl carbamoyl group Chemical group 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
125000004104 aryloxy group Chemical group 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000012046 mixed solvent Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
150000003952 β-lactams Chemical class 0.000 description 4
DTFBPBSAXIOREZ-UHFFFAOYSA-N 3H-dioxaphosphole Chemical compound P1OOC=C1 DTFBPBSAXIOREZ-UHFFFAOYSA-N 0.000 description 3
239000005973 Carvone Substances 0.000 description 3
XWCFYHBHOFBVIV-UHFFFAOYSA-N Deacetylcephalosporin C Natural products S1CC(CO)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C21 XWCFYHBHOFBVIV-UHFFFAOYSA-N 0.000 description 3
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000004450 alkenylene group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
125000004659 aryl alkyl thio group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
XWCFYHBHOFBVIV-JWKOBGCHSA-N deacetylcephalosporin C Chemical compound S1CC(CO)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 XWCFYHBHOFBVIV-JWKOBGCHSA-N 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 3
229940050176 methyl chloride Drugs 0.000 description 3
239000011259 mixed solution Substances 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
229940079877 pyrogallol Drugs 0.000 description 3
125000001453 quaternary ammonium group Chemical group 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000013076 target substance Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 2
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
101710082414 50S ribosomal protein L12, chloroplastic Proteins 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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150000003216 pyrazines Chemical class 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
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PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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VFQXVTODMYMSMJ-UHFFFAOYSA-O pyridin-1-ium-4-carboxamide Chemical compound NC(=O)C1=CC=[NH+]C=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-O 0.000 description 1
KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
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239000010453 quartz Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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238000001953 recrystallisation Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
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238000009958 sewing Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
101150063803 thi4 gene Proteins 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
JJJPTTANZGDADF-UHFFFAOYSA-N thiadiazole-4-thiol Chemical compound SC1=CSN=N1 JJJPTTANZGDADF-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
125000001239 threonyl group Chemical group 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000001425 triazolyl 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002114 valyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

JP16355682A 1982-09-20 1982-09-20 セフアロスポリン化合物の製造方法 Granted JPS5953492A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16355682A JPS5953492A (ja)	1982-09-20	1982-09-20	セフアロスポリン化合物の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16355682A JPS5953492A (ja)	1982-09-20	1982-09-20	セフアロスポリン化合物の製造方法

Publications (2)

Publication Number	Publication Date
JPS5953492A true JPS5953492A (ja)	1984-03-28
JPH0357911B2 JPH0357911B2 (da)	1991-09-03

Family

ID=15776138

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16355682A Granted JPS5953492A (ja)	1982-09-20	1982-09-20	セフアロスポリン化合物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS5953492A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6110591A (ja) *	1984-06-26	1986-01-18	Fujisawa Pharmaceut Co Ltd	７−アミノ−３−（ｎ−含有複素環置換メチル）−３−セフエム−４−カルボキシレ−トまたはその塩類の製造法

1982
- 1982-09-20 JP JP16355682A patent/JPS5953492A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6110591A (ja) *	1984-06-26	1986-01-18	Fujisawa Pharmaceut Co Ltd	７−アミノ−３−（ｎ−含有複素環置換メチル）−３−セフエム−４−カルボキシレ−トまたはその塩類の製造法

Also Published As

Publication number	Publication date
JPH0357911B2 (da)	1991-09-03

Publication	Publication Date	Title
US3843641A (en)	1974-10-22	Process for preparing penicillin and cephalosporin compounds
JPS5946955B2 (ja)	1984-11-15	抗生物質の新規中間体の製造方法
DE2537974A1 (de)	1976-03-11	Thioderivate
DK157138B (da)	1989-11-13	Fremgangsmaade til fremstilling af 7beta-acylamino-7alfa-alkoxycephalosporiner eller 6beta-acylamino-6alfa-alkoxypenicilliner
EP0069373A1 (en)	1983-01-12	(5R, 6R)-Penem compounds, their production and use
US4245088A (en)	1981-01-13	Novel 3-acyloxymethyl-cephem compounds useful as intermediates for preparing cephalosporin antibiotics
JPS5953492A (ja)	1984-03-28	セフアロスポリン化合物の製造方法
US4014873A (en)	1977-03-29	Process for the production of 7-acylamidocephalosporins
EP0164122B1 (en)	1990-09-19	Cephem compounds
EP0074611B1 (en)	1987-07-22	Method for production of cephalosporin compounds
EP0234549B1 (en)	1992-12-16	Method for production of cephalosporin compounds
GB1560532A (en)	1980-02-06	Cepham and penam compounds
WO1989000572A1 (en)	1989-01-26	Process for the preparation of 3-exomethylene cepham derivatives
CA1068258A (en)	1979-12-18	Hydrocarbyl cephem compounds
US4642365A (en)	1987-02-10	Method for production of 1,3,2-dioxaphospholes
CA1260004A (en)	1989-09-26	Method for production of 1,3,2-dioxaphospholes
US4107432A (en)	1978-08-15	7-Diacylimido cephalosporins
JPS5843979A (ja)	1983-03-14	セフアロスポリン化合物の製造方法
US4014872A (en)	1977-03-29	Substituted 3-hydroxy- or 3-oxo-cephams
US4343937A (en)	1982-08-10	3-Substituted-7-methoxy-7-amino-3-cephem-4-carboxylic acids
DE2619243A1 (de)	1976-11-18	Neue 3-acyloxymethyl-cephem-verbindung und verfahren zu ihrer herstellung
US4857521A (en)	1989-08-15	Trialkylsilyl pyridinium cephalosporin antibiotics
JPS61254593A (ja)	1986-11-12	アシルアミノメチル−ペネム化合物、その製法およびそれを含む医薬製剤
CA1072541A (en)	1980-02-26	PROCESS FOR PREPARING 7.beta.-ACYLAMINO-7-ALKOXYCEPHALOSPORINS OR 6.beta.-ACYLAMINO-6-ALKOXYPENICILLINS
US4308381A (en)	1981-12-29	Cephem compounds

JPS5953492A - セフアロスポリン化合物の製造方法 - Google Patents

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