JPS6310709B2 - - Google Patents

Info

Publication number: JPS6310709B2
Authority: JP; Japan
Prior art keywords: general formula; lower alkyl; group; ester; alkyl group
Prior art date: 1979-09-27
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

Application number

JP54123160A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5646885A (en

Inventor

Takashi Tsuruoka

Katsuyoshi Iwamatsu

Kazuko Mizutani

Katsumi Kawarajo

Tadahiro Watanabe

Shigeharu Inoe

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.)

Meiji Seika Kaisha Ltd

Original Assignee

Meiji Seika Kaisha 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.)

1979-09-27

Filing date

1979-09-27

Publication date

1988-03-08

1979-09-27 Application filed by Meiji Seika Kaisha Ltd filed Critical Meiji Seika Kaisha Ltd

1979-09-27 Priority to JP12316079A priority Critical patent/JPS5646885A/ja

1979-12-12 Priority to IL58939A priority patent/IL58939A/xx

1979-12-14 Priority to GB7943159A priority patent/GB2040926B/en

1979-12-14 Priority to AU53869/79A priority patent/AU528886B2/en

1979-12-17 Priority to SE7910387A priority patent/SE446535B/xx

1979-12-17 Priority to PT70602A priority patent/PT70602A/pt

1979-12-17 Priority to IT51101/79A priority patent/IT1162424B/it

1979-12-17 Priority to YU3086/79A priority patent/YU41900B/xx

1979-12-17 Priority to FR7930864A priority patent/FR2444684A1/fr

1979-12-17 Priority to CH1114979A priority patent/CH643851A5/fr

1979-12-17 Priority to SI7913086A priority patent/SI7913086A8/sl

1979-12-18 Priority to ES487040A priority patent/ES487040A0/es

1979-12-18 Priority to DE2950990A priority patent/DE2950990C2/de

1979-12-18 Priority to NLAANVRAGE7909104,A priority patent/NL186161C/xx

1981-04-28 Publication of JPS5646885A publication Critical patent/JPS5646885A/ja

1988-03-08 Publication of JPS6310709B2 publication Critical patent/JPS6310709B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 55
125000000217 alkyl group Chemical group 0.000 claims description 25
150000002148 esters Chemical class 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
-1 1-ethoxyethyl Chemical group 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000000243 solution Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 12
239000000284 extract Substances 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000000844 anti-bacterial effect Effects 0.000 description 8
239000000843 powder Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000003814 drug Substances 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
FBQWMTAAWINZJD-UHFFFAOYSA-N 1-iodoethyl acetate Chemical compound CC(I)OC(C)=O FBQWMTAAWINZJD-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
125000006244 carboxylic acid protecting group Chemical group 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003208 petroleum Substances 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
239000000126 substance Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
IFQSXNOEEPCSLW-HSHFZTNMSA-N (2s)-2-amino-3-sulfanylpropanoic acid;hydron;chloride Chemical compound Cl.SC[C@@H](N)C(O)=O IFQSXNOEEPCSLW-HSHFZTNMSA-N 0.000 description 1
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
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 1
208000035143 Bacterial infection Diseases 0.000 description 1
GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
238000010976 amide bond formation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
229960002682 cefoxitin Drugs 0.000 description 1
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
229940106164 cephalexin Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229960002433 cysteine Drugs 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
JFKJWWJOCJHMGV-UHFFFAOYSA-N ethyl 2-amino-3-sulfanylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(N)CS JFKJWWJOCJHMGV-UHFFFAOYSA-N 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 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
235000019253 formic acid Nutrition 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
150000007529 inorganic bases Chemical class 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
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229960001913 mecysteine Drugs 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
150000003899 tartaric acid esters Chemical class 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
230000001225 therapeutic effect Effects 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
238000005406 washing Methods 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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

Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP12316079A 1978-12-18 1979-09-27 Novel cephamycin ester and its preparation Granted JPS5646885A (en)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
JP12316079A JPS5646885A (en)	1979-09-27	1979-09-27	Novel cephamycin ester and its preparation
IL58939A IL58939A (en)	1978-12-18	1979-12-12	7 alpha-methoxycephalosporin derivatives and their production
GB7943159A GB2040926B (en)	1978-12-18	1979-12-14	7a - methoxysephalosporin derivative and process for producing the same
AU53869/79A AU528886B2 (en)	1978-12-18	1979-12-14	7-alpha-methoxycephalosporin derivatives
SE7910387A SE446535B (sv)	1978-12-18	1979-12-17	7alfa-metoxicefalosporinderivat och forfarande for framstellning derav samt farmaceutisk komposition derav
PT70602A PT70602A (en)	1978-12-18	1979-12-17	Process for preparing 7alpha-methoxycephalosporin derivatives
IT51101/79A IT1162424B (it)	1978-12-18	1979-12-17	Derivati di 7 alfa-metossicefalosporina e procedimento per produrli
YU3086/79A YU41900B (en)	1978-12-18	1979-12-17	Process for obtaining the 7-alpha-methoxy - cephalosporin derivative
FR7930864A FR2444684A1 (fr)	1978-12-18	1979-12-17	Derive de la 7a-methoxycephalosporine, son procede de fabrication et composition pharmaceutique contenant ce derive
CH1114979A CH643851A5 (fr)	1978-12-18	1979-12-17	Derives de la 7alpha-methoxycephalosporine et procedes pour leur preparation.
SI7913086A SI7913086A8 (en)	1978-12-18	1979-12-17	Process for obtaining the 7-alpha-methoxy-cephalosporin derivate
ES487040A ES487040A0 (es)	1978-12-18	1979-12-18	Un derivado de 7x-metoxicefalosporina
DE2950990A DE2950990C2 (de)	1978-12-18	1979-12-18	7α-Methoxycephalosporinderivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
NLAANVRAGE7909104,A NL186161C (nl)	1978-12-18	1979-12-18	Farmaceutisch preparaat met antibacteriele werking, alsmede 7beta-(2-(gesubstitueerd thio)aceetamido)-7alfa-methoxy-3-(gesubstitueerd methyl)-3-cefem-4-carbonzuur derivaat.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP12316079A JPS5646885A (en)	1979-09-27	1979-09-27	Novel cephamycin ester and its preparation

Publications (2)

Publication Number	Publication Date
JPS5646885A JPS5646885A (en)	1981-04-28
JPS6310709B2 true JPS6310709B2 (fi)	1988-03-08

Family

ID=14853661

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP12316079A Granted JPS5646885A (en)	1978-12-18	1979-09-27	Novel cephamycin ester and its preparation

Country Status (1)

Country	Link
JP (1)	JPS5646885A (fi)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5849387A (ja) *	1981-09-17	1983-03-23	Sankyo Co Ltd	７−メトキシセフアロスポリン化合物およびその製法
CN105566213B (zh) *	2009-06-10	2019-11-12	上海泰飞尔生化技术有限公司	具有高穿透性的抗微生物剂和抗微生物剂相关化合物的前药组合物
US9969751B2 (en)	2009-06-10	2018-05-15	Techfields Pharma Co., Ltd.	High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds

1979
- 1979-09-27 JP JP12316079A patent/JPS5646885A/ja active Granted

Also Published As

Publication number	Publication date
JPS5646885A (en)	1981-04-28

Publication	Publication Date	Title
JPH0365350B2 (fi)	1991-10-11
JP2706090B2 (ja)	1998-01-28	３−トリフリルセフェムからの３−不飽和アルキルセフェム
WO1999032497A1 (fr)	1999-07-01	Derives de phosphonocephem, leur procede de preparation et leur utilisation
KR890004132B1 (ko)	1989-10-21	크로모글릭산 유도체의 제조방법
JPH0466230B2 (fi)	1992-10-22
JPH0347187A (ja)	1991-02-28	新規なセファロスポリン誘導体
JP2867192B2 (ja)	1999-03-08	７−アシル−３−置換カルバモイルオキシセフェム化合物及びその製造法
JPS6310709B2 (fi)	1988-03-08
JPH0120156B2 (fi)	1989-04-14
JPH0633281B2 (ja)	1994-05-02	新規セファロスポリン化合物及び抗菌剤
US4138556A (en)	1979-02-06	7-Amino-3-(sulfoalkyl substituted oxadiazolylthiomethyl) cephalosporins
SI8212258A8 (en)	1997-12-31	Process for preparing 7-alpha-methoxy cephalosporin derivatives
JPS58103392A (ja)	1983-06-20	３位においてチオメチルヘテロ環基により置換されたセフアロスポリンの新規な誘導体、これら化合物の製造方法およびこれらを含有する薬学的組成物
JPH0521912B2 (fi)	1993-03-25
JPH0686463B2 (ja)	1994-11-02	新規セフェム化合物、その製造法及び抗菌剤
SI7913086A8 (en)	1997-04-30	Process for obtaining the 7-alpha-methoxy-cephalosporin derivate
EP0212923A2 (en)	1987-03-04	Cephalosporin derivatives
JPS62174086A (ja)	1987-07-30	セフアロスポリン誘導体
US4841044A (en)	1989-06-20	Cephalosporin derivatives
US4761409A (en)	1988-08-02	Cephem derivatives
EP0153418A1 (en)	1985-09-04	Mandelic acid derivatives
JPS638956B2 (fi)	1988-02-25
JPH0613529B2 (ja)	1994-02-23	新規セフアロスポリン誘導体及び抗菌剤
GB1572993A (en)	1980-08-13	Ester derivatives of cefuroxime
JPH0460983B2 (fi)	1992-09-29