JPS61501634A - セフアロスポリン類 - Google Patents

セフアロスポリン類

Info

Publication number: JPS61501634A
Authority: JP; Japan
Prior art keywords: formula; tables; formulas; compound; substituted
Prior art date: 1984-03-29
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

JP60501842A

Other languages

English (en)

Japanese (ja)

Inventor

プラガー、ベルンハルト・クリスチヤン

ターラー、ハインリツヒ

シユツルム、フベルト

Original Assignee

ビオヘミ−・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング

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.)

1984-03-29

Filing date

1985-03-23

Publication date

1986-08-07

1985-03-23 Application filed by ビオヘミ−・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング filed Critical ビオヘミ−・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング

1986-08-07 Publication of JPS61501634A publication Critical patent/JPS61501634A/ja

Status Pending legal-status Critical Current

Links

229930186147 Cephalosporin Natural products 0.000 title description 5
229940124587 cephalosporin Drugs 0.000 title description 5
150000001780 cephalosporins Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 42
-1 carbamoyloxy group Chemical group 0.000 claims description 31
238000000034 method Methods 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 10
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000000047 product Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
238000010511 deprotection reaction Methods 0.000 claims description 5
239000012467 final product Substances 0.000 claims description 5
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
150000001768 cations Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
238000003756 stirring Methods 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical group 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 6
OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 description 6
229960003012 cefamandole Drugs 0.000 description 6
239000000203 mixture Substances 0.000 description 6
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical class OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 5
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
241000607768 Shigella Species 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229960002510 mandelic acid Drugs 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000005973 Carvone Substances 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
125000004665 trialkylsilyl group Chemical group 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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
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 2
241000588748 Klebsiella Species 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
241000588767 Proteus vulgaris Species 0.000 description 2
241000607142 Salmonella Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
DYAIAHUQIPBDIP-AXAPSJFSSA-N cefonicid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](O)C=2C=CC=CC=2)CC=1CSC1=NN=NN1CS(O)(=O)=O DYAIAHUQIPBDIP-AXAPSJFSSA-N 0.000 description 2
229960004489 cefonicid Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
230000022244 formylation Effects 0.000 description 2
238000006170 formylation reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012528 membrane Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
229940007042 proteus vulgaris Drugs 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003892 spreading Methods 0.000 description 2
125000003831 tetrazolyl group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
125000001425 triazolyl group Chemical group 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
OGVCUHMGJOJMEE-BAFYGKSASA-N (6r)-4-amino-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound C1=CC(N)S[C@@H]2CC(=O)N21 OGVCUHMGJOJMEE-BAFYGKSASA-N 0.000 description 1
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 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
241000588986 Alcaligenes Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
240000004160 Capsicum annuum Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
241000166344 Dicentria Species 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
241000607726 Salmonella enterica subsp. enterica serovar Heidelberg Species 0.000 description 1
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
150000001218 Thorium Chemical class 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
LISYCWMGWAORRH-UHFFFAOYSA-N [Na].[Th] Chemical compound [Na].[Th] LISYCWMGWAORRH-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QXAITBQSYVNQDR-UHFFFAOYSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)C=NC1=CC=C(C)C=C1C QXAITBQSYVNQDR-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000003796 beauty Effects 0.000 description 1
150000001555 benzenes Chemical group 0.000 description 1
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000003857 carboxamides Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
OJMNTWPPFNMOCJ-CFOLLTDRSA-M cefamandole sodium Chemical compound [Na+].CN1N=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OJMNTWPPFNMOCJ-CFOLLTDRSA-M 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
229940047583 cetamide Drugs 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006198 deformylation Effects 0.000 description 1
238000006344 deformylation reaction Methods 0.000 description 1
125000002720 diazolyl group Chemical group 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
CIJWIJSYZZLMGD-UHFFFAOYSA-N diphenylphosphoryloxybenzene Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)OC1=CC=CC=C1 CIJWIJSYZZLMGD-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
FZYXTYKAZUNHMF-MRVPVSSYSA-N formyl (2r)-2-hydroxy-2-phenylacetate Chemical compound O=COC(=O)[C@H](O)C1=CC=CC=C1 FZYXTYKAZUNHMF-MRVPVSSYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004571 lime Substances 0.000 description 1
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
239000011707 mineral Substances 0.000 description 1
LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

JP60501842A 1984-03-29 1985-03-23 セフアロスポリン類 Pending JPS61501634A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
AT0105584A AT381495B (de)	1984-03-29	1984-03-29	Verfahren zur herstellung von cephalosporinderivaten
AT1055/84		1984-03-29
AT2386/84		1984-07-24
AT2884/84		1984-09-10

Publications (1)

Publication Number	Publication Date
JPS61501634A true JPS61501634A (ja)	1986-08-07

Family

ID=3505605

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60501842A Pending JPS61501634A (ja)	1984-03-29	1985-03-23	セフアロスポリン類

Country Status (4)

Country	Link
JP (1)	JPS61501634A (de)
AT (1)	AT381495B (de)
HU (1)	HU202537B (de)
ZA (1)	ZA852420B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008505169A (ja) *	2004-07-05	2008-02-21	オーキッドケミカルズアンドファーマシューティカルズリミテッド	セファロスポリン抗生物質の製造における新規な塩

1984
- 1984-03-29 AT AT0105584A patent/AT381495B/de not_active IP Right Cessation
1985
- 1985-03-23 HU HU88505A patent/HU202537B/hu not_active IP Right Cessation
- 1985-03-23 JP JP60501842A patent/JPS61501634A/ja active Pending
- 1985-03-29 ZA ZA852420A patent/ZA852420B/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008505169A (ja) *	2004-07-05	2008-02-21	オーキッドケミカルズアンドファーマシューティカルズリミテッド	セファロスポリン抗生物質の製造における新規な塩

Also Published As

Publication number	Publication date
HU202537B (en)	1991-03-28
ATA105584A (de)	1986-03-15
AT381495B (de)	1986-10-27
ZA852420B (en)	1986-11-26

Publication	Publication Date	Title
SU1480763A3 (ru)	1989-05-15	Способ получени производных 1-сульфо-2-оксоазетидинона или их солей, или сложных эфиров
PL172835B1 (pl)	1997-12-31	Chlorowodorek kwasu 7- ß -[(Z)-2-(2-amino-4-tiazolilo)-2-hydroksyiminoacetamido]-3-(1,2,3-triazol-4-ilo)-tiometylotio-3 -cefemo-4-karboksylowego oraz sposób jego wytwarzania, krystaliczny wodzian chlorowodorku kwasu 7- ß -(Z)-2-(2-amino-4-tiazolilo)-2-hydroksyiminoacetamido]-3-(1,2,3-triazol-4-ilo)-tiometylotio-3-ce- femo-4-karboksylowego oraz sposób jego wytwarzania PL PL PL PL PL
US4361557A (en)	1982-11-30	1-Aryl-2-acylamido-3-fluoro-1-propanol acylates, methods for their use as anti-bacterial agents and compositions useful therefor
AU587974B2 (en)	1989-09-07	Process for preparation of cephalosporins
KR920002869B1 (ko)	1992-04-06	7-아미노-3-치환된-메틸-3-세펨-4-카복실산 및 그의 저급 알킬실릴 유도체의 제조방법
JPS63107989A (ja)	1988-05-12	セファロスポリン化合物
JPS61501634A (ja)	1986-08-07	セフアロスポリン類
US3701775A (en)	1972-10-31	Esters of mandeloylaminocephalosporanic acids
CA1048997A (en)	1979-02-20	Cephalosporin derivatives
FI74286C (fi)	1988-01-11	Foerfarande foer framstaellning av saosom antibiotika anvaendbara 7-/2-(2-aminotiazol-4-yl)-2-(karboxialkyloxi- imino)acetamido/-3-uroniumtiometyl)-3-cefem-s-oxid-4- karboxylsyraderivat.
JPS5919114B2 (ja)	1984-05-02	セフアロスポリンの製造法
CS195680B2 (en)	1980-02-29	Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid
Hardy et al.	1984	The chemistry of some 2-aminothiazol-4-ylacetic acid derivatives and the synthesis of derived penicillins
CA1057739A (en)	1979-07-03	Pyridinylthiomethyl derivatives of cyanomethylthioacetyl cephalosporins
US4436904A (en)	1984-03-13	Cephalosporins
Essery et al.	1974	3-Acylthiomethyl cephalosporins
FI82472C (fi)	1991-03-11	Foerfarande foer framstaellning av cefalosporin.
JPS63170384A (ja)	1988-07-14	７α置換セフアロスポリン化合物
HU185685B (en)	1985-03-28	Process for preparing new cefem-carboxylic acid derivatives
JPS59134795A (ja)	1984-08-02	ペネムエステル
KR890002215B1 (ko)	1989-06-23	세펨유도체의 새로운 제조방법
US3225058A (en)	1965-12-21	Substituted n-(4-pyrimidinyl)-6-aminopenicillanic acids
FI72123B (fi)	1986-12-31	7-/d(-)-alfa-(4-etyl-2,3-dioxo-1-piperazinkarboxiamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-1,2,3,4-tetrazolyl)tiometyl/- 3-cefem-4-karboxylsyrans n,n-dimetylacetamidadduktoch foerfarande foer framstaellning av denna
JPH04112865A (ja)	1992-04-14	置換アミド誘導体
Minard et al.	1949	Studies on Antipodes. VI. 1 The Synthesis of Some Derivatives of Enantiomorphs of Valine2

JPS61501634A - セフアロスポリン類 - Google Patents

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Applications Claiming Priority (4)

Publications (1)

Family

ID=3505605

Family Applications (1)

Country Status (4)

Cited By (1)

Cited By (1)

Also Published As

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