CA1058206A - Les acides amines, leur production et leur utilisation - Google Patents

Les acides amines, leur production et leur utilisation

Info

Publication number: CA1058206A
Authority: CA; Canada
Prior art keywords: formula; glycine; compound; mesylaminophenyl; reacting
Prior art date: 1973-07-06
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

CA289,462A

Other languages

English (en)

Inventor

Kunihiko Tanaka

Yoshiharu Nakai

Teiji Kishimoto

Keiji Takai

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.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa 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.)

1973-07-06

Filing date

1977-10-25

Publication date

1979-07-10

1973-07-06 Priority claimed from JP48076785A external-priority patent/JPS5934715B2/ja

1973-08-13 Priority claimed from JP9114073A external-priority patent/JPS5629662B2/ja

1977-10-25 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1977-10-25 Priority to CA289,462A priority Critical patent/CA1058206A/fr

1979-07-10 Application granted granted Critical

1979-07-10 Publication of CA1058206A publication Critical patent/CA1058206A/fr

Status Expired legal-status Critical Current

Links

150000001413 amino acids Chemical class 0.000 title description 20
238000004519 manufacturing process Methods 0.000 title description 4
-1 cephalosporin compounds Chemical class 0.000 claims abstract description 136
150000001875 compounds Chemical class 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 42
239000002253 acid Substances 0.000 claims abstract description 39
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 25
239000000047 product Substances 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 21
150000001408 amides Chemical class 0.000 claims abstract description 18
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 16
125000006239 protecting group Chemical group 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 12
125000005907 alkyl ester group Chemical group 0.000 claims abstract description 11
229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 8
239000007795 chemical reaction product Substances 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
239000004471 Glycine Substances 0.000 claims description 15
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 12
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
NYCSZUOGZQGPTJ-MRVPVSSYSA-N (2r)-2-amino-2-[3-(methanesulfonamido)phenyl]acetic acid Chemical compound CS(=O)(=O)NC1=CC=CC([C@@H](N)C(O)=O)=C1 NYCSZUOGZQGPTJ-MRVPVSSYSA-N 0.000 claims description 9
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 8
PCTNHJKMUWYKHK-SNVBAGLBSA-N (2r)-2-(3-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)C1=CC=CC(N)=C1 PCTNHJKMUWYKHK-SNVBAGLBSA-N 0.000 claims description 3
UCGZNHXYVJOCMV-SSDOTTSWSA-N (2r)-2-amino-2-(3-aminophenyl)acetic acid Chemical compound OC(=O)[C@H](N)C1=CC=CC(N)=C1 UCGZNHXYVJOCMV-SSDOTTSWSA-N 0.000 claims description 3
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 claims description 2
238000007344 nucleophilic reaction Methods 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
230000001681 protective effect Effects 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
UGYAXZLBVOGLLY-SECBINFHSA-N (2R)-2-amino-2-[3-(ethylsulfonylamino)phenyl]acetic acid Chemical compound C(C)S(=O)(=O)NC=1C=C([C@@H](N)C(=O)O)C=CC=1 UGYAXZLBVOGLLY-SECBINFHSA-N 0.000 claims 2
HXLIBDVOCZWRIU-MRVPVSSYSA-N (2R)-2-amino-2-[4-(methanesulfonamido)phenyl]acetic acid Chemical compound CS(=O)(=O)NC1=CC=C(C=C1)[C@@H](N)C(O)=O HXLIBDVOCZWRIU-MRVPVSSYSA-N 0.000 claims 2
HAKACKSZUHLWQM-SNVBAGLBSA-N (2r)-2-(4-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)C1=CC=C(N)C=C1 HAKACKSZUHLWQM-SNVBAGLBSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
229930186147 Cephalosporin Natural products 0.000 abstract description 21
229940124587 cephalosporin Drugs 0.000 abstract description 21
229910052739 hydrogen Inorganic materials 0.000 abstract description 11
239000001257 hydrogen Substances 0.000 abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 9
125000004442 acylamino group Chemical group 0.000 abstract description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 79
239000000243 solution Substances 0.000 description 72
229940093499 ethyl acetate Drugs 0.000 description 63
235000019439 ethyl acetate Nutrition 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
230000002829 reductive effect Effects 0.000 description 47
239000000203 mixture Substances 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
229960000443 hydrochloric acid Drugs 0.000 description 37
235000011167 hydrochloric acid Nutrition 0.000 description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
229940073584 methylene chloride Drugs 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
238000001816 cooling Methods 0.000 description 29
239000010410 layer Substances 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 26
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000007864 aqueous solution Substances 0.000 description 20
239000013078 crystal Substances 0.000 description 20
229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000001914 filtration Methods 0.000 description 18
235000017557 sodium bicarbonate Nutrition 0.000 description 18
238000003756 stirring Methods 0.000 description 18
239000011369 resultant mixture Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 15
239000012047 saturated solution Substances 0.000 description 15
239000011780 sodium chloride Substances 0.000 description 15
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
229960000583 acetic acid Drugs 0.000 description 13
239000000284 extract Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
229940086542 triethylamine Drugs 0.000 description 12
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 11
235000011054 acetic acid Nutrition 0.000 description 11
230000008030 elimination Effects 0.000 description 11
238000003379 elimination reaction Methods 0.000 description 11
235000019253 formic acid Nutrition 0.000 description 11
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
238000011282 treatment Methods 0.000 description 10
125000003277 amino group Chemical group 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
229960003390 magnesium sulfate Drugs 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
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 7
229940106164 cephalexin Drugs 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000002024 ethyl acetate extract Substances 0.000 description 7
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
SDMNLZJVXWONEY-LLVKDONJSA-N (2r)-2-[3-(methanesulfonamido)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)C1=CC=CC(NS(C)(=O)=O)=C1 SDMNLZJVXWONEY-LLVKDONJSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
239000002585 base Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
239000002198 insoluble material Substances 0.000 description 6
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
150000008065 acid anhydrides Chemical class 0.000 description 5
229940023032 activated charcoal Drugs 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
229940088710 antibiotic agent Drugs 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
239000003456 ion exchange resin Substances 0.000 description 5
229920003303 ion-exchange polymer Polymers 0.000 description 5
238000005406 washing Methods 0.000 description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
230000000845 anti-microbial effect Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
150000001780 cephalosporins Chemical group 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
VVROHPDPNYEIKD-JLHJGDBNSA-N 2,2,2-trichloroethyl (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.S1CC(C)=C(C(=O)OCC(Cl)(Cl)Cl)N2C(=O)C(N)[C@@H]12 VVROHPDPNYEIKD-JLHJGDBNSA-N 0.000 description 3
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 3
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000002262 Schiff base Substances 0.000 description 3
150000004753 Schiff bases Chemical class 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
125000001118 alkylidene group Chemical group 0.000 description 3
229960001040 ammonium chloride Drugs 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000002736 metal compounds Chemical class 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
125000004665 trialkylsilyl group Chemical group 0.000 description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
PVUUUZGQAPDABO-XCGJVMPOSA-N 2,2,2-trichloroethyl (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(C)=C(C(=O)OCC(Cl)(Cl)Cl)N2C(=O)C(N)[C@@H]12 PVUUUZGQAPDABO-XCGJVMPOSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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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 1
230000009920 chelation Effects 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 1
RSJOBNMOMQFPKQ-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate Chemical compound [Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O RSJOBNMOMQFPKQ-UHFFFAOYSA-L 0.000 description 1
CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 description 1
HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
LZJJVTQGPPWQFS-UHFFFAOYSA-L copper;propanoate Chemical compound [Cu+2].CCC([O-])=O.CCC([O-])=O LZJJVTQGPPWQFS-UHFFFAOYSA-L 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
FWBOFUGDKHMVPI-UHFFFAOYSA-K dicopper;2-oxidopropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O FWBOFUGDKHMVPI-UHFFFAOYSA-K 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
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
239000002609 medium Substances 0.000 description 1
OBGCGAGMPORYOY-OGFXRTJISA-N methyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride Chemical compound Cl.COC(=O)C1=CCS[C@H]2N1C(C2)=O OBGCGAGMPORYOY-OGFXRTJISA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
VTACLVUOTMPORB-UHFFFAOYSA-N n,n-bis(trimethylsilyl)acetamide Chemical compound CC(=O)N([Si](C)(C)C)[Si](C)(C)C VTACLVUOTMPORB-UHFFFAOYSA-N 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
IOSIHTQSEBJGDT-UHFFFAOYSA-N n-[3-[amino(cyano)methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(N)C#N)=C1 IOSIHTQSEBJGDT-UHFFFAOYSA-N 0.000 description 1
JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 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
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-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
238000000746 purification Methods 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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

Cephalosporin Compounds (AREA)

CA289,462A 1973-07-06 1977-10-25 Les acides amines, leur production et leur utilisation Expired CA1058206A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA289,462A CA1058206A (fr)	1973-07-06	1977-10-25	Les acides amines, leur production et leur utilisation

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP48076785A JPS5934715B2 (ja)	1973-07-06	1973-07-06	７−置換アシルアミノ−３−置換−３−セフエム−４−カルボン酸類の製造法
JP9114073A JPS5629662B2 (fr)	1973-08-13	1973-08-13
CA289,462A CA1058206A (fr)	1973-07-06	1977-10-25	Les acides amines, leur production et leur utilisation

Publications (1)

Publication Number	Publication Date
CA1058206A true CA1058206A (fr)	1979-07-10

Family

ID=27165344

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,462A Expired CA1058206A (fr)	1973-07-06	1977-10-25	Les acides amines, leur production et leur utilisation

Country Status (1)

Country	Link
CA (1)	CA1058206A (fr)

1977
- 1977-10-25 CA CA289,462A patent/CA1058206A/fr not_active Expired

Publication	Publication Date	Title
US4680390A (en)	1987-07-14	Esters of 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methyl-ceph-3-em-4-carboxylic acid
US4008246A (en)	1977-02-15	Aminothiazole derivatives
EP0189287B1 (fr)	1992-12-16	Bêta-lactames antibiotiques
CA1289555C (fr)	1991-09-24	Composes de cephem
JPH03135973A (ja)	1991-06-10	アミノチアゾリル酢酸類
CA1132538A (fr)	1982-09-28	Cephalosporine
SE450384B (sv)	1987-06-22	Nya cefemforeningar och forfarande for deras framstellning
US4252952A (en)	1981-02-24	7-(α-Substituted glycinamido)-3-substituted methyl-3-cephem-4-carboxylic acids and their derivatives
EP0045937A2 (fr)	1982-02-17	Dérivés de céphalosporine et procédés pour leur préparation
EP0082498A2 (fr)	1983-06-29	Dérivés bêta-lactame et procédé pour leur préparation
CA1102307A (fr)	1981-06-02	Traduction non-disponible
IE49100B1 (en)	1985-07-24	Cephalosporin compounds
IE51486B1 (en)	1987-01-07	7-beta-(alpha-syn-methoxyimino-alpha-(2-amino-thiazol-4-yl)acetamido)-3-((1,2,3-thiadiazol-5-ylthio)methyl)-3-cephem-4-carboxylic acid and c1-c6 alkyl derivatives thereof
CA1058206A (fr)	1979-07-10	Les acides amines, leur production et leur utilisation
US4576938A (en)	1986-03-18	Cephalosporin compound and process for preparing the same
CA1131618A (fr)	1982-09-14	Composes de cephalosporine
US4000133A (en)	1976-12-28	Substituted 7-styryl-carbonyloxy-acetamido cephalosporanic
US4160830A (en)	1979-07-10	Cephalosporins
CA1049503A (fr)	1979-02-27	Acides amines
US4311842A (en)	1982-01-19	Cephalosporin compounds
CA1306994C (fr)	1992-09-01	Derives cephalosporine, procede pour leur preparation et agents antibacteriens
GB2103205A (en)	1983-02-16	New cephem compounds
CA1215355A (fr)	1986-12-16	Esters de cephalosporine, leur production et leur emploi
US4085277A (en)	1978-04-18	7(2-Phenyl or thienyl-2-isonicotinoyloxyacetamido)-3-(1-methyl-1-H tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid
US4178445A (en)	1979-12-11	7-(α-Substituted glycinamido)-3-substituted methyl-3-cephem-4-carboxylic acids and their derivatives