CA1041483A - Procede pour la preparation de nouveaux derives de la cephalosporine - Google Patents

Procede pour la preparation de nouveaux derives de la cephalosporine

Info

Publication number: CA1041483A
Authority: CA; Canada
Prior art keywords: group; mixture; acid; water; phenylacetamido
Prior art date: 1973-06-11
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

CA222,581A

Other languages

English (en)

Other versions

CA222581S (en

Inventor

Masaharu Fujimoto

Tetsuya Maeda

Masuo Murakami

Ichiro Isaka

Masaru Iwanami

Tadao Shibanuma

Norio Kawahara

Yoshinobu Nagano

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.)

Yamanouchi Pharmaceutical Co Ltd

Original Assignee

Yamanouchi Pharmaceutical 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.)

1973-06-11

Filing date

1975-03-19

Publication date

1978-10-31

1973-06-11 Priority claimed from JP6477473A external-priority patent/JPS5321582B2/ja

1974-04-05 Priority claimed from JP49038545A external-priority patent/JPS5953276B2/ja

1974-04-15 Priority claimed from JP4188474A external-priority patent/JPS50140480A/ja

1974-06-04 Priority claimed from JP6312474A external-priority patent/JPS50154282A/ja

1974-10-11 Priority claimed from JP49116976A external-priority patent/JPS5143785A/ja

1974-10-17 Priority claimed from JP11963874A external-priority patent/JPS5148686A/ja

1975-01-31 Priority claimed from JP50013200A external-priority patent/JPS5188988A/ja

1975-03-19 Application filed by Yamanouchi Pharmaceutical Co Ltd filed Critical Yamanouchi Pharmaceutical Co Ltd

1978-10-31 Application granted granted Critical

1978-10-31 Publication of CA1041483A publication Critical patent/CA1041483A/fr

Status Expired legal-status Critical Current

Links

229930186147 Cephalosporin Natural products 0.000 title claims abstract description 9
229940124587 cephalosporin Drugs 0.000 title claims abstract description 9
150000001780 cephalosporins Chemical class 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 41
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 42
-1 hetero-cyclic ring compound Chemical class 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
QMDFJHAAWUGVKQ-UHFFFAOYSA-N 2h-thiopyran Chemical group C1SC=CC=C1 QMDFJHAAWUGVKQ-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
241000589516 Pseudomonas Species 0.000 abstract description 4
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
241000588769 Proteus <enterobacteria> Species 0.000 abstract description 2
150000001782 cephems Chemical group 0.000 abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 81
239000000243 solution Substances 0.000 description 81
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
239000000203 mixture Substances 0.000 description 75
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 65
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 63
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
239000002244 precipitate Substances 0.000 description 58
238000000862 absorption spectrum Methods 0.000 description 49
239000011541 reaction mixture Substances 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 44
238000001914 filtration Methods 0.000 description 44
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 42
229960000443 hydrochloric acid Drugs 0.000 description 39
235000011167 hydrochloric acid Nutrition 0.000 description 39
239000011734 sodium Substances 0.000 description 38
229910052708 sodium Inorganic materials 0.000 description 37
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 36
238000001816 cooling Methods 0.000 description 35
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 33
239000011369 resultant mixture Substances 0.000 description 33
229910000030 sodium bicarbonate Inorganic materials 0.000 description 32
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 32
235000017557 sodium bicarbonate Nutrition 0.000 description 31
239000000706 filtrate Substances 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
229940086542 triethylamine Drugs 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
150000001408 amides Chemical class 0.000 description 17
238000002844 melting Methods 0.000 description 16
239000000725 suspension Substances 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
230000008018 melting Effects 0.000 description 15
229950004030 cefaloglycin Drugs 0.000 description 12
239000000047 product Substances 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000001228 spectrum Methods 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 10
239000000843 powder Substances 0.000 description 10
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 9
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 8
229960000603 cefalotin Drugs 0.000 description 8
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
241000894006 Bacteria Species 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
150000008065 acid anhydrides Chemical class 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
235000001055 magnesium Nutrition 0.000 description 5
229940091250 magnesium supplement Drugs 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 4
229960001139 cefazolin Drugs 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
FFOHOZBDRVVZIM-PFBPGKLMSA-N (6r,7r)-3-(acetyloxymethyl)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FFOHOZBDRVVZIM-PFBPGKLMSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
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 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000523 sample Substances 0.000 description 3
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 3
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
DZXGDEPWZLFUEA-UHFFFAOYSA-N 2-(1,3,4-thiadiazol-2-ylsulfanyl)acetic acid Chemical compound OC(=O)CSC1=NN=CS1 DZXGDEPWZLFUEA-UHFFFAOYSA-N 0.000 description 2
DZIQDBROLFSEQQ-UHFFFAOYSA-N 2-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)ethanethioic s-acid Chemical compound OC(=S)CC1=NN=C(S)S1 DZIQDBROLFSEQQ-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical compound SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229940007042 proteus vulgaris Drugs 0.000 description 2
125000003373 pyrazinyl group Chemical group 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000012898 sample dilution Substances 0.000 description 2
FNEDHAVUXWEPMP-UHFFFAOYSA-M sodium;2-methylhexanoate Chemical compound [Na+].CCCCC(C)C([O-])=O FNEDHAVUXWEPMP-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
150000003536 tetrazoles Chemical group 0.000 description 2
150000004867 thiadiazoles Chemical group 0.000 description 2
210000001835 viscera Anatomy 0.000 description 2
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical group C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
DERHNSJVDWFDKZ-UHFFFAOYSA-N 1,3,4-thiadiazole-2-carboxylic acid Chemical compound OC(=O)C1=NN=CS1 DERHNSJVDWFDKZ-UHFFFAOYSA-N 0.000 description 1
UCMPRUFAFLOKGI-UHFFFAOYSA-N 2,4-dioxo-1h-pyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=CNC(=O)NC1=O UCMPRUFAFLOKGI-UHFFFAOYSA-N 0.000 description 1
KJUCPVIVNLPLEE-UHFFFAOYSA-N 2,6-difluoro-n-[2-fluoro-5-[5-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]-2-propan-2-yl-1,3-thiazol-4-yl]phenyl]benzenesulfonamide Chemical compound S1C(C(C)C)=NC(C=2C=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C(F)=CC=2)=C1C(N=1)=CC=NC=1NC(C=N1)=CC=C1N1CCOCC1 KJUCPVIVNLPLEE-UHFFFAOYSA-N 0.000 description 1
MYTWYPWDKHLWED-UHFFFAOYSA-N 2-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)acetic acid Chemical compound OC(=O)CC1=NN=C(S)S1 MYTWYPWDKHLWED-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
KYBOCQHDFLVQIB-UHFFFAOYSA-N 2-(4-methyl-2-sulfanylidene-3h-1,3-thiazol-5-yl)acetic acid Chemical compound CC=1N=C(S)SC=1CC(O)=O KYBOCQHDFLVQIB-UHFFFAOYSA-N 0.000 description 1
OYLWNIRWHSRRDC-UHFFFAOYSA-N 2-(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)acetic acid Chemical compound OC(=O)CC1=NN=C(S)N1 OYLWNIRWHSRRDC-UHFFFAOYSA-N 0.000 description 1
HRQWRDVVMBXGDS-UHFFFAOYSA-N 2-[(2-methyl-6-sulfanylidene-1h-pyrimidin-4-yl)sulfanyl]acetic acid Chemical compound CC1=NC(S)=CC(SCC(O)=O)=N1 HRQWRDVVMBXGDS-UHFFFAOYSA-N 0.000 description 1
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UJBXVTJYSIDCIE-UHFFFAOYSA-N 2-[(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)sulfanyl]acetic acid Chemical compound OC(=O)CSC1=NNC(=S)S1 UJBXVTJYSIDCIE-UHFFFAOYSA-N 0.000 description 1
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239000002585 base Substances 0.000 description 1
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 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
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ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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150000003951 lactams Chemical class 0.000 description 1
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230000000144 pharmacologic effect Effects 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
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BYRWCXYBQUYZNW-UHFFFAOYSA-M sodium;2-[(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)sulfanyl]ethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCSC1=NNC(=S)S1 BYRWCXYBQUYZNW-UHFFFAOYSA-M 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
VNXUJPCYZSNXDG-UHFFFAOYSA-N thiopyran-4-one Chemical compound O=C1C=CSC=C1 VNXUJPCYZSNXDG-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA222,581A 1973-06-11 1975-03-19 Procede pour la preparation de nouveaux derives de la cephalosporine Expired CA1041483A (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
JP6477473A JPS5321582B2 (fr)	1973-06-11	1973-06-11
JP49038545A JPS5953276B2 (ja)	1974-04-05	1974-04-05	新セフアロスポリン誘導体の製造方法
JP4188474A JPS50140480A (fr)	1974-04-15	1974-04-15
JP6312474A JPS50154282A (fr)	1974-06-04	1974-06-04
JP49116976A JPS5143785A (en)	1974-10-11	1974-10-11	Shinsefuarosuhorinkanrenkagobutsuno goseiho
JP11963874A JPS5148686A (ja)	1974-10-17	1974-10-17	Shinsefuarosuhorinkanrenkagobutsuno goseihoho
JP50013200A JPS5188988A (fr)	1975-01-31	1975-01-31

Publications (1)

Publication Number	Publication Date
CA1041483A true CA1041483A (fr)	1978-10-31

Family

ID=27563644

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA222,581A Expired CA1041483A (fr)	1973-06-11	1975-03-19	Procede pour la preparation de nouveaux derives de la cephalosporine

Country Status (1)

Country	Link
CA (1)	CA1041483A (fr)

1975
- 1975-03-19 CA CA222,581A patent/CA1041483A/fr not_active Expired

Publication	Publication Date	Title
CA1316171C (fr)	1993-04-13	Derives de cephalosporine
CA1178271A (fr)	1984-11-20	Derives de cephalosporine, et methode de preparation connexe
US4421912A (en)	1983-12-20	Cephalosporin derivatives
HU184145B (en)	1984-07-30	Process for preparing cef-3-em-4-carboxylic acid derivatives
DK165060B (da)	1992-10-05	Analogifremgangsmaade til fremstilling af cephalosporiner, som er substitueret med en aminothiazolyl-oximino-acetamidosidekaede
GB1601328A (en)	1981-10-28	7-(2-(2-amino-4-thiazolyl)-2-oxo-acetamide)-cephalosporins and analogues thereof
EP0150507A2 (fr)	1985-08-07	Dérivés de céphalosporine, procédés pour leur péparation et compositions pharmaceutiques
US3865819A (en)	1975-02-11	Substituted sulfonylacetamido cephalosporins
US4068074A (en)	1978-01-10	Cephalosporin derivatives having at the 3-position of the cephem ring a heterocyclic thiomethyl group with a carboxy or sulfo group and at the 7-position of the cephem ring an α-heterocylic acylaminophenyl-acetamide group
CA1074784A (fr)	1980-04-01	N-ACYLAMINO-.alpha.-ARYLACETAMIDOCEPHALOSPORINES
CS199714B2 (en)	1980-07-31	Process for preparing heteromonocyclic and heterobicyclic derivatives of unsaturated 7-acylamido-3-cephem-4-carboxylic acids
SU1005664A3 (ru)	1983-03-15	Способ получени производных цефалоспорина или их солей с щелочными металлами
GB2071654A (en)	1981-09-23	Hydroxamic acid derivatives of 7-(2-amino-4-thiazolyl)oximino cephalosporins
CA1041483A (fr)	1978-10-31	Procede pour la preparation de nouveaux derives de la cephalosporine
US4888332A (en)	1989-12-19	Cephalosporin derivatives
US5028601A (en)	1991-07-02	Cephalosporin compounds and antibacterial agents
US4091211A (en)	1978-05-23	Cephalosporins
CA1072949A (fr)	1980-03-04	Composes a base de cephem
CA1114808A (fr)	1981-12-22	Derives d'oxyiminoacetamidocephalosporines substituees en 7
US4197298A (en)	1980-04-08	[3-Heterocyclic-7-(2-methoxyimino-2-aminothiazolyl) acetamido]cephalosporins
CS205006B2 (cs)	1981-04-30	Způsob přípravy N-acylamniG-a-arylacetamidocefalospopiiiii
CA1177064A (fr)	1984-10-30	Derives de cephalosporine, leur production et leurs emplois
US4239758A (en)	1980-12-16	Cephalosporins
US5262410A (en)	1993-11-16	3-heterocyclic thiomethyl cephalosporins
US4229573A (en)	1980-10-21	7α-Methoxycephalosporin derivatives