SE438679B - Nytt sett for framstellning av 7-amino-tiazolyl-acetamido-cefalosporansyraderivat - Google Patents

Nytt sett for framstellning av 7-amino-tiazolyl-acetamido-cefalosporansyraderivat

Info

Publication number: SE438679B
Authority: SE; Sweden
Prior art keywords: formula; group; compound; preparation; base
Prior art date: 1978-10-23

Application number

SE7906605A

Other languages

English (en)

Swedish (sv)

Other versions

SE7906605L (sv

Inventor

J Warnant

J Jolly

Original Assignee

Roussel Uclaf

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.)

1978-10-23

Filing date

1979-08-06

Publication date

1985-04-29

1979-08-06 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1980-04-24 Publication of SE7906605L publication Critical patent/SE7906605L/

1985-04-29 Publication of SE438679B publication Critical patent/SE438679B/sv

Links

238000002360 preparation method Methods 0.000 title claims description 25
-1 acetoxymethyl group Chemical group 0.000 claims description 81
150000001875 compounds Chemical class 0.000 claims description 73
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 37
239000002585 base Substances 0.000 claims description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 17
238000000034 method Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
125000004185 ester group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
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 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
239000003125 aqueous solvent Substances 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
239000011736 potassium bicarbonate Substances 0.000 claims description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
235000011181 potassium carbonates Nutrition 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 claims description 2
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
235000015424 sodium Nutrition 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
238000003756 stirring Methods 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
239000008367 deionised water Substances 0.000 description 15
229910021641 deionized water Inorganic materials 0.000 description 15
229940086542 triethylamine Drugs 0.000 description 14
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
PKPGSMOHYWOGJR-UHFFFAOYSA-N 2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 PKPGSMOHYWOGJR-UHFFFAOYSA-N 0.000 description 5
229910002092 carbon dioxide Inorganic materials 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000725 suspension Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
AGPORCHKBPLKKN-UHFFFAOYSA-M 4-methylbenzenesulfonate tris(dimethylamino)-[2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]oxyphosphanium Chemical compound S(=O)(=O)([O-])C1=CC=C(C)C=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)C(C(=O)O[P+](N(C)C)(N(C)C)N(C)C)=NOC AGPORCHKBPLKKN-UHFFFAOYSA-M 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 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
125000005270 trialkylamine group Chemical group 0.000 description 2
230000007306 turnover Effects 0.000 description 2
IHFZSFMOJYFAHV-VCHQGTEKSA-N (6R)-3-(acetyloxymethyl)-7-[[2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C)(=O)OCC=1CS[C@H]2N(C=1C(=O)O)C(C2NC(C(=NOC)C=1N=C(SC=1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O IHFZSFMOJYFAHV-VCHQGTEKSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 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
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000002102 aryl alkyloxo group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SE7906605A 1978-10-23 1979-08-06 Nytt sett for framstellning av 7-amino-tiazolyl-acetamido-cefalosporansyraderivat SE438679B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7830053A FR2439785A1 (fr)	1978-10-23	1978-10-23	Nouveau procede de preparation des produits derives de l'acide 7-amino-thiazolyl acetamido cephalosporanique

Publications (2)

Publication Number	Publication Date
SE7906605L SE7906605L (sv)	1980-04-24
SE438679B true SE438679B (sv)	1985-04-29

Family

ID=9214034

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7906605A SE438679B (sv)	1978-10-23	1979-08-06	Nytt sett for framstellning av 7-amino-tiazolyl-acetamido-cefalosporansyraderivat

Country Status (14)

Country	Link
JP (1)	JPS5557593A (de)
AT (1)	AT370418B (de)
CA (1)	CA1124232A (de)
CH (1)	CH643847A5 (de)
DE (1)	DE2942797A1 (de)
DK (1)	DK160312C (de)
ES (1)	ES484639A1 (de)
FR (1)	FR2439785A1 (de)
GB (1)	GB2033390B (de)
HU (1)	HU182572B (de)
IT (1)	IT1188860B (de)
NL (1)	NL7907789A (de)
PT (1)	PT70316A (de)
SE (1)	SE438679B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2945248A1 (de) *	1978-11-13	1980-05-22	Fujisawa Pharmaceutical Co	Cephem-verbindungen, verfahren zu ihrer herstellung und sie enthaltende antibakterielle pharmazeutische mittel
FR2462439A1 (fr) *	1979-07-26	1981-02-13	Roussel Uclaf	Nouveau procede de preparation de produits derives de l'acide 7-/(2-aryl) 2-hydroxyimino acetamido/cephalosporanique
US4252802A (en) *	1980-03-13	1981-02-24	E. R. Squibb & Sons, Inc.	Hydroxamic acid derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins
EP0377987A3 (de) *	1988-12-27	1991-08-28	Eli Lilly And Company	Acylierungsverfahren zur Herstellung von Cephalosporinderivaten
KR950013578B1 (ko) *	1993-04-10	1995-11-09	주식회사럭키	신규 티아(디아)졸 초산의 반응성 티오포스페이트 유도체 및 그의 제조방법
TW369530B (en) *	1993-06-10	1999-09-11	Lucky Ltd	Process for preparing cephalosporin compounds from reactive organic acid derivatives
US5883247A (en) *	1996-06-10	1999-03-16	Hoffmann-La Roche Inc.	Preparation of cephem and isooxacephem derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5175091A (en) *	1974-12-24	1976-06-29	Teikoku Hormone Mfg Co Ltd	Sefuarosuhorinkei koseibutsushitsunoseizoho

1978
- 1978-10-23 FR FR7830053A patent/FR2439785A1/fr active Granted
1979
- 1979-08-06 SE SE7906605A patent/SE438679B/sv not_active IP Right Cessation
- 1979-10-02 ES ES484639A patent/ES484639A1/es not_active Expired
- 1979-10-15 PT PT70316A patent/PT70316A/pt unknown
- 1979-10-15 IT IT50568/79A patent/IT1188860B/it active
- 1979-10-16 GB GB7935808A patent/GB2033390B/en not_active Expired
- 1979-10-22 AT AT0687879A patent/AT370418B/de not_active IP Right Cessation
- 1979-10-22 DK DK443879A patent/DK160312C/da not_active IP Right Cessation
- 1979-10-22 CA CA338,145A patent/CA1124232A/fr not_active Expired
- 1979-10-22 CH CH946579A patent/CH643847A5/fr not_active IP Right Cessation
- 1979-10-22 HU HU79RO1038A patent/HU182572B/hu not_active IP Right Cessation
- 1979-10-23 DE DE19792942797 patent/DE2942797A1/de not_active Withdrawn
- 1979-10-23 NL NL7907789A patent/NL7907789A/nl not_active Application Discontinuation
- 1979-10-23 JP JP13600879A patent/JPS5557593A/ja active Pending

Also Published As

Publication number	Publication date
JPS5557593A (en)	1980-04-28
CH643847A5 (fr)	1984-06-29
DK443879A (da)	1980-04-24
IT7950568A0 (it)	1979-10-15
DK160312B (da)	1991-02-25
FR2439785B1 (de)	1981-07-10
IT1188860B (it)	1988-01-28
NL7907789A (nl)	1980-04-25
HU182572B (en)	1984-02-28
CA1124232A (fr)	1982-05-25
ATA687879A (de)	1982-08-15
SE7906605L (sv)	1980-04-24
DE2942797A1 (de)	1980-04-30
FR2439785A1 (fr)	1980-05-23
GB2033390A (en)	1980-05-21
AT370418B (de)	1983-03-25
DK160312C (da)	1991-07-29
ES484639A1 (es)	1980-06-16
PT70316A (fr)	1979-11-01
GB2033390B (en)	1982-12-08

Publication	Publication Date	Title
DK167680B1 (da)	1993-12-06	Syn-isomere 2-pyridyl- og 2-benzothiazolylthioestere samt fremgangsmaade til fremstilling deraf
SE453086B (sv)	1988-01-11	2-(2kloracetamidotiazol-4-yl)-2-oximinoettiksyraderivat till anvendning som mellanprodukt for framstellning av motsvarande cefalosporinderivat
EP0023453B1 (de)	1983-11-16	Verfahren zur Herstellung derivierter Produkte der 7-(2-Aryl)-2-hydroxyimino-acetamido-cephalosporansäure
EP0914322A1 (de)	1999-05-12	Neue indolyl und benzofuranylcarboxamide als inhibitoren der stickoxidproduktion
SE455307B (sv)	1988-07-04	2-amino-4-tiazolyl-oxiimino-ettiksyraderivat till anvendning som mellanprodukt till motsvarande cefalosporinderivat samt forfarande for framstellning derav
JP2556722B2 (ja)	1996-11-20	新規なスルホンアミド化合物
JPH04234844A (ja)	1992-08-24	新規化合物の３−アミノ−２−オキソアゼチジン誘導体及びそれらの製造法
EP0036510B1 (de)	1984-11-21	Synisomer von Cephalosporinverbindungen und Verfahren zu ihrer Herstellung
US20050227914A1 (en)	2005-10-13	New process
SE438679B (sv)	1985-04-29	Nytt sett for framstellning av 7-amino-tiazolyl-acetamido-cefalosporansyraderivat
US4845211A (en)	1989-07-04	Amino-3-substituted-methyl-3-cephem-4-carboxylic acid and lower alkylsilyl derivatives thereof
AU690482B2 (en)	1998-04-23	Process for producing cephalosporin antibiotics
US5869649A (en)	1999-02-09	Process for producing cephalosporin antibiotics
SE458609B (sv)	1989-04-17	7-acyl-3-karbamoyloxi-3-metyl-cefam-foereningar samt foerfarande foer framstaellning daerav
JPS6178791A (ja)	1986-04-22	セフエム誘導体の製造法
EP0347777A2 (de)	1989-12-27	Verfahren zur Herstellung von Cephalosporin und Zwischenverbindungen
JPS5932475B2 (ja)	1984-08-09	２−アルキル−７−置換−２もしくは３−セフエム−４−カルボン酸化合物類およびその塩類およびそれらの製造法
GB2159817A (en)	1985-12-11	Preparation of amidohydroxycephams, novel aminoacyloxycephams and derivatives thereof
US5580865A (en)	1996-12-03	2,2-disubstituted cephem sulphones
JPS6097983A (ja)	1985-05-31	セフアロスポリン誘導体、その製法および医薬組成物
US4665166A (en)	1987-05-12	Process for preparing cephalosporin compounds
US4118563A (en)	1978-10-03	Production of 7-(2-aminomethylphenylacetamido-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
JP2572382B2 (ja)	1997-01-16	セフアロスポリン誘導体の新規製造方法
JPH0358351B2 (de)	1991-09-05
FI72521C (fi)	1987-06-08	Foerfarande foer framstaellning av cefalosporinderivat.

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