JPH0352466B2 - - Google Patents

Info

Publication number: JPH0352466B2
Authority: JP; Japan
Prior art keywords: group; protecting group; general formula; nitrobenzyloxycarbonyl; formula
Prior art date: 1983-05-09
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

Application number

JP58081443A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59205379A (ja

Inventor

Jun Sunakawa

Haruki Matsumura

Takaaki Inoe

Masatomo Fukazawa

Masuhiro Kato

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.)

Sumitomo Pharmaceuticals Co Ltd

Original Assignee

Sumitomo Pharmaceuticals Co 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.)

1983-05-09

Filing date

1983-05-09

Publication date

1991-08-12

1983-05-09 Application filed by Sumitomo Pharmaceuticals Co Ltd filed Critical Sumitomo Pharmaceuticals Co Ltd

1983-05-09 Priority to JP58081443A priority Critical patent/JPS59205379A/ja

1984-05-03 Priority to CA000453478A priority patent/CA1283906C/en

1984-05-09 Priority to EP84303128A priority patent/EP0126587B1/en

1984-05-09 Priority to ES532741A priority patent/ES8600305A1/es

1984-05-09 Priority to DE3486382T priority patent/DE3486382T2/de

1984-05-09 Priority to AT84303128T priority patent/ATE121402T1/de

1984-11-20 Publication of JPS59205379A publication Critical patent/JPS59205379A/ja

1987-10-08 Priority to US07/106,036 priority patent/US4943569A/en

1987-10-08 Priority to US07/106,035 priority patent/US4933333A/en

1990-05-21 Priority to US07/525,817 priority patent/US5122604A/en

1991-08-12 Publication of JPH0352466B2 publication Critical patent/JPH0352466B2/ja

1992-06-19 Priority to MX9203063A priority patent/MX9203063A/es

1995-09-12 Priority to NL950019C priority patent/NL950019I2/nl

1995-11-30 Priority to HK183095A priority patent/HK183095A/xx

Status Granted legal-status Critical Current

Links

-1 β-lactam compound Chemical class 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 34
238000000034 method Methods 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
HZAVSJRAODFHGF-UHFFFAOYSA-N 2-methyl-7-oxohept-2-enoic acid Chemical compound OC(=O)C(C)=CCCCC=O HZAVSJRAODFHGF-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
229960002591 hydroxyproline Drugs 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 3
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XYYRIMJKUXHPEM-QWRGUYRKSA-N (4-nitrophenyl)methyl (2s,4s)-2-carbamoyl-4-sulfanylpyrrolidine-1-carboxylate Chemical compound NC(=O)[C@@H]1C[C@H](S)CN1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 XYYRIMJKUXHPEM-QWRGUYRKSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000194017 Streptococcus Species 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002994 raw material Substances 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 2
UHPSFBFTMRQBPR-STQMWFEESA-N (4-nitrophenyl)methyl (2s,4s)-4-acetylsulfanyl-2-carbamoylpyrrolidine-1-carboxylate Chemical compound C1[C@@H](SC(=O)C)C[C@@H](C(N)=O)N1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 UHPSFBFTMRQBPR-STQMWFEESA-N 0.000 description 1
UGFJIHBTZKEQPF-UHFFFAOYSA-N (4-nitrophenyl)methyl (4,6-dimethylpyrimidin-2-yl)sulfanylformate Chemical compound CC1=CC(C)=NC(SC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)=N1 UGFJIHBTZKEQPF-UHFFFAOYSA-N 0.000 description 1
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 1
DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 1
BSIMZHVOQZIAOY-UHFFFAOYSA-N 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCC2CC(=O)N12 BSIMZHVOQZIAOY-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XYNRSEWUNPVMJR-UHFFFAOYSA-N CS(=O)(=O)Cl.O1CCCC1 Chemical compound CS(=O)(=O)Cl.O1CCCC1 XYNRSEWUNPVMJR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
102100020743 Dipeptidase 1 Human genes 0.000 description 1
229940090955 Dipeptidase inhibitor Drugs 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
125000005042 acyloxymethyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
PMMYEEVYMWASQN-QWWZWVQMSA-N cis-4-hydroxy-D-proline Chemical compound O[C@H]1C[NH2+][C@@H](C([O-])=O)C1 PMMYEEVYMWASQN-QWWZWVQMSA-N 0.000 description 1
238000001723 curing Methods 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
125000005633 phthalidyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
AFYIEXRJEABQPF-UHFFFAOYSA-N s-pyrrolidin-3-yl ethanethioate Chemical compound CC(=O)SC1CCNC1 AFYIEXRJEABQPF-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
125000003396 thiol group Chemical group [H]S* 0.000 description 1
PMMYEEVYMWASQN-IUYQGCFVSA-N trans-4-hydroxy-D-proline Chemical compound O[C@@H]1CN[C@@H](C(O)=O)C1 PMMYEEVYMWASQN-IUYQGCFVSA-N 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP58081443A 1983-05-09 1983-05-09 新規なβ−ラクタム化合物及びその製造法 Granted JPS59205379A (ja)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
JP58081443A JPS59205379A (ja)	1983-05-09	1983-05-09	新規なβ−ラクタム化合物及びその製造法
CA000453478A CA1283906C (en)	1983-05-09	1984-05-03	.beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF
EP84303128A EP0126587B1 (en)	1983-05-09	1984-05-09	Carboxylic thio-pyrrolidinyl beta-lactam compounds and production thereof
ES532741A ES8600305A1 (es)	1983-05-09	1984-05-09	Procedimiento de preparar compuestos beta-lactamicos
DE3486382T DE3486382T2 (de)	1983-05-09	1984-05-09	Carboxyl-Thio-Pyrrolidinyl beta-Lactam-Derivate und ihre Herstellung.
AT84303128T ATE121402T1 (de)	1983-05-09	1984-05-09	Carboxyl-thio-pyrrolidinyl beta-lactam-derivate und ihre herstellung.
US07/106,035 US4933333A (en)	1983-05-09	1987-10-08	β-lactam compounds
US07/106,036 US4943569A (en)	1983-05-09	1987-10-08	B-lactam compounds
US07/525,817 US5122604A (en)	1983-05-09	1990-05-21	β-lactam compounds
MX9203063A MX9203063A (es)	1983-05-09	1992-06-19	Compuestos beta-lactamicos y produccion de los mismos.
NL950019C NL950019I2 (nl)	1983-05-09	1995-09-12	Carboxylische thio-pyrrolidinyl-betalactamverbindingen en de bereiding.
HK183095A HK183095A (en)	1983-05-09	1995-11-30	Carboxylic thio-pyrrolidinyl beta-lactam compounds and production thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58081443A JPS59205379A (ja)	1983-05-09	1983-05-09	新規なβ−ラクタム化合物及びその製造法

Publications (2)

Publication Number	Publication Date
JPS59205379A JPS59205379A (ja)	1984-11-20
JPH0352466B2 true JPH0352466B2 (ko)	1991-08-12

Family

ID=13746537

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58081443A Granted JPS59205379A (ja)	1983-05-09	1983-05-09	新規なβ−ラクタム化合物及びその製造法

Country Status (1)

Country	Link
JP (1)	JPS59205379A (ko)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6019787A (ja) *	1983-07-12	1985-01-31	Sumitomo Chem Co Ltd	新規なβ−ラクタム化合物及びその製造法
FI81576C (fi) *	1984-12-25	1990-11-12	Sankyo Co	Foerfarande foer framstaellning av derivat av 6-(1-hydroxietyl)-2-(1,2-disubstituerade-4-pyrrolidinyltio)-2- karbapenem-3-karboxylsyra, vilka aer anvaendbara som laekemedel.
JPH0780883B2 (ja) *	1986-03-27	1995-08-30	住友製薬株式会社	新規なβ−ラクタム化合物

1983
- 1983-05-09 JP JP58081443A patent/JPS59205379A/ja active Granted

Also Published As

Publication number	Publication date
JPS59205379A (ja)	1984-11-20

Publication	Publication Date	Title
EP0126587B1 (en)	1995-04-19	Carboxylic thio-pyrrolidinyl beta-lactam compounds and production thereof
JP2542773B2 (ja)	1996-10-09	ピロリジルチオカルバペネム誘導体
DE68925223T2 (de)	1996-06-13	3-Alkenyl-1-azabicyclo(3.2.0)hept-2-en-2-carbonsäure-Verbindungen
DE3785163T2 (de)	1993-07-29	3-pyrrolidinylthio-1-azabicyclo(3.2.0)hept-2-en-2-carbonsaeurederivate und verfahren zu deren herstellung.
JPH0463878B2 (ko)	1992-10-13
JPH0367068B2 (ko)	1991-10-21
JP2559949B2 (ja)	1996-12-04	１−メチルカルバペネム誘導体
JPS6355514B2 (ko)	1988-11-02
JPH0352466B2 (ko)	1991-08-12
JPH03120280A (ja)	1991-05-22	ハロメチルカルバペネム化合物の製法
JP4213958B2 (ja)	2009-01-28	新規なβ−ラクタム化合物およびその製造法
US20200339582A1 (en)	2020-10-29	Atypical Carbapenem Antibiotics with Improved Activity Against Carbapenemase-Producing Acinetobacter baumannii
JPH0463076B2 (ko)	1992-10-08
US4772597A (en)	1988-09-20	2-azacycloalkylthiopenem derivatives
CA2194399C (en)	2007-02-13	Novel carbapenem derivative
EP0641795B1 (en)	2002-09-25	Carbapenem derivative
KR20010029454A (ko)	2001-04-06	신규한 β-락탐 화합물 및 이의 제조 방법
JPH0551594B2 (ko)	1993-08-03
JPH0529229B2 (ko)	1993-04-28
JP3344662B2 (ja)	2002-11-11	カルバペネム−３−カルボン酸誘導体
JPH0466872B2 (ko)	1992-10-26
JP3242677B2 (ja)	2001-12-25	新規なβ−ラクタム化合物及びその製造法
JPH05105681A (ja)	1993-04-27	２−（９−フルオレノニル）−カルバペネム
JPH05310740A (ja)	1993-11-22	カルバペネム誘導体
JPH0328434B2 (ko)	1991-04-19