DD251751A5 - Verfahren zur herstellung von beta-lactamverbindungen - Google Patents

Verfahren zur herstellung von beta-lactamverbindungen Download PDF

Info

Publication number: DD251751A5
Authority: DD; German Democratic Republic
Prior art keywords: optionally substituted; amino; yield; mol; formula
Prior art date: 1985-03-08

Application number

DD86287635A

Other languages

German (de)

English (en)

Inventor

Gunter Schmidt

Hans-Joachim Zeiler

Karl G Metzger

Original Assignee

��@��k��

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.)

1985-03-08

Filing date

1986-03-06

Publication date

1987-11-25

1986-03-06 Application filed by ��@��k�� filed Critical ��@��k��

1987-11-25 Publication of DD251751A5 publication Critical patent/DD251751A5/de

Links

-1 BETA-LACTAM COMPOUNDS Chemical class 0.000 title claims description 50
238000004519 manufacturing process Methods 0.000 title 1
238000002360 preparation method Methods 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 16
230000008569 process Effects 0.000 claims abstract description 5
239000000460 chlorine Chemical group 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 39
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
125000004432 carbon atom Chemical group C* 0.000 claims description 24
150000001780 cephalosporins Chemical class 0.000 claims description 21
229930186147 Cephalosporin Natural products 0.000 claims description 20
229940124587 cephalosporin Drugs 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
229910052731 fluorine Inorganic materials 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 13
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 10
125000003107 substituted aryl group Chemical group 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
150000008064 anhydrides Chemical class 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
230000004913 activation Effects 0.000 claims description 8
150000001413 amino acids Chemical class 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
229930182555 Penicillin Natural products 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
229940049954 penicillin Drugs 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 5
239000003242 anti bacterial agent Substances 0.000 abstract description 2
229940088710 antibiotic agent Drugs 0.000 abstract description 2
239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 138
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 130
239000000243 solution Substances 0.000 description 77
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
BDAGIHXWWSANSR-PFUFQJKNSA-N formic acid-d2 Chemical compound [2H]OC([2H])=O BDAGIHXWWSANSR-PFUFQJKNSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
229960000583 acetic acid Drugs 0.000 description 20
239000003480 eluent Substances 0.000 description 19
239000000706 filtrate Substances 0.000 description 18
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 18
239000003208 petroleum Substances 0.000 description 18
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
229910000041 hydrogen chloride Inorganic materials 0.000 description 17
239000011734 sodium Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical class CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 16
NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
239000000047 product Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000001816 cooling Methods 0.000 description 13
238000004128 high performance liquid chromatography Methods 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 11
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 11
239000012267 brine Substances 0.000 description 11
239000012071 phase Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
239000000126 substance Substances 0.000 description 11
229920001429 chelating resin Polymers 0.000 description 10
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
239000013543 active substance Substances 0.000 description 9
239000001099 ammonium carbonate Substances 0.000 description 9
235000012501 ammonium carbonate Nutrition 0.000 description 9
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 8
239000012043 crude product Substances 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
230000014759 maintenance of location Effects 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
238000002953 preparative HPLC Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
229960003237 betaine Drugs 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 description 4
229960005361 cefaclor Drugs 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000008298 dragée Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000006187 pill Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 4
239000003826 tablet Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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 4
LPMULTSCZSOABY-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl)methanol Chemical compound C1=C(CO)C=C2SC(N)=NC2=C1 LPMULTSCZSOABY-UHFFFAOYSA-N 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
KGOXEOVTUNSMPR-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=C(C(F)(F)F)NC2=C1 KGOXEOVTUNSMPR-UHFFFAOYSA-N 0.000 description 3
DCNYZCPMDDDDLR-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbaldehyde Chemical compound C1=C(C=O)C=C2SC(N)=NC2=C1 DCNYZCPMDDDDLR-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
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 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
235000010419 agar Nutrition 0.000 description 3
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
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239000002585 base Substances 0.000 description 3
235000012216 bentonite Nutrition 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
125000004663 dialkyl amino group Chemical group 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
150000002960 penicillins Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
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235000012222 talc Nutrition 0.000 description 3
238000005406 washing Methods 0.000 description 3
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235000012239 silicon dioxide Nutrition 0.000 description 1
229960005456 sisomicin Drugs 0.000 description 1
URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
230000009885 systemic effect Effects 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
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
229960000707 tobramycin Drugs 0.000 description 1
NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
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 1
235000019871 vegetable fat Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- 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
- C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Animal Husbandry (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)
Fodder In General (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD86287635A 1985-03-08 1986-03-06 Verfahren zur herstellung von beta-lactamverbindungen DD251751A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853508258 DE3508258A1 (de)	1985-03-08	1985-03-08	Ss-lactamantibiotika, verfahren zur herstellung und ihre verwendung als und in arzneimitteln

Publications (1)

Publication Number	Publication Date
DD251751A5 true DD251751A5 (de)	1987-11-25

Family

ID=6264592

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD86287635A DD251751A5 (de)	1985-03-08	1986-03-06	Verfahren zur herstellung von beta-lactamverbindungen
DD86311493A DD266502A5 (de)	1985-03-08	1986-03-06	Verwendung von beta-lactamverbindungen

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD86311493A DD266502A5 (de)	1985-03-08	1986-03-06	Verwendung von beta-lactamverbindungen

Country Status (20)

Country	Link
US (2)	US4748163A (pt)
EP (1)	EP0195947B1 (pt)
JP (1)	JPH0649708B2 (pt)
KR (1)	KR930007420B1 (pt)
AT (1)	ATE137238T1 (pt)
AU (1)	AU594941B2 (pt)
CA (1)	CA1281315C (pt)
DD (2)	DD251751A5 (pt)
DE (2)	DE3508258A1 (pt)
DK (1)	DK105286A (pt)
ES (1)	ES8800234A1 (pt)
FI (1)	FI85708C (pt)
GR (1)	GR860626B (pt)
HU (1)	HU200183B (pt)
IE (1)	IE860598L (pt)
IL (1)	IL78042A0 (pt)
NO (1)	NO165108C (pt)
PH (1)	PH24000A (pt)
PT (1)	PT82143B (pt)
ZA (1)	ZA861713B (pt)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3509618A1 (de) *	1985-03-16	1986-09-18	Bayer Ag, 5090 Leverkusen	Ss-lactam-antibiotika, verfahren zur herstellung und ihre verwendung als arzneimittel
DE3734005A1 (de) *	1987-05-26	1988-12-15	Bayer Ag	Substituierte vinylcephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
AU637400B2 (en) *	1987-05-26	1993-05-27	Bayer Aktiengesellschaft	Substituted vinylcephalosporins, processes for their preparation and their use as medicaments
DE3734004A1 (de) *	1987-05-26	1988-12-15	Bayer Ag	Substituierte vinylcephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5171854A (en) *	1987-05-26	1992-12-15	Bayer Aktiengesellschaft	Substituted vinylcephalosporins
DE3733626A1 (de) *	1987-10-05	1989-04-13	Bayer Ag	Heteroanellierte phenylglycin-(beta)-lactam-antibiotika, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3803169A1 (de) *	1988-02-03	1989-08-17	Bayer Ag	Ss-lactam-antibiotika, verfahren zu ihrer herstellung und ihre verwendung als und in arzneimitteln
EP0630899B1 (en) *	1992-09-18	2002-02-13	Otsuka Kagaku Kabushiki Kaisha	Cephem compound, process for producing the same, and medicine containing the same
US5604222A (en) *	1993-12-27	1997-02-18	Lupin Laboratories, Ltd.	Method for the preparation of 2-chloro sulfinyl azetidinones
US5578721A (en) *	1994-07-11	1996-11-26	Lupin Laboratories Limited	Process for preparation of 3-exomethylene cepham sulfoxide esters
DE4443892A1 (de) *	1994-12-09	1996-06-13	Bayer Ag	4-(Chinolin-2-yl-methoxy)-phenyl-essigsäurederivate
WO2004019943A1 (en)	2002-08-30	2004-03-11	Memory Pharmaceuticals Corporation	Anabaseine derivatives useful in the treatment of neurodegenerative diseases
MY147152A (en) *	2006-05-31	2012-11-14	Toyama Chemical Co Ltd	Anti-foot-and-mouth disease virus agent for animal belonging to family suidae or sheep, and method for prevention or treatment of foot-and-mouth disease in animal belonging to family suidae or sheep
US9271978B2 (en)	2012-12-21	2016-03-01	Zenith Epigenetics Corp.	Heterocyclic compounds as bromodomain inhibitors
WO2015004533A2 (en)	2013-06-21	2015-01-15	Zenith Epigenetics Corp.	Novel substituted bicyclic compounds as bromodomain inhibitors
SG11201510409QA (en)	2013-06-21	2016-01-28	Zenith Epigenetics Corp	Novel bicyclic bromodomain inhibitors
AU2014298051B2 (en)	2013-07-31	2018-11-15	Zenith Epigenetics Ltd.	Novel quinazolinones as bromodomain inhibitors
WO2016087936A1 (en)	2014-12-01	2016-06-09	Zenith Epigenetics Corp.	Substituted pyridinones as bromodomain inhibitors
WO2016087942A1 (en)	2014-12-01	2016-06-09	Zenith Epigenetics Corp.	Substituted pyridines as bromodomain inhibitors
CN107207474B (zh)	2014-12-11	2021-05-07	恒翼生物医药科技(上海)有限公司	被取代的杂环作为溴结构域抑制剂
CA2966450A1 (en)	2014-12-17	2016-06-23	Olesya KHARENKO	Inhibitors of bromodomains

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3080356A (en) *	1960-06-15	1963-03-05	Beecham Res Lab	Process for the production of synthetic penicillins
SE302125B (pt) *	1961-03-23	1968-07-08	Bristol Myers Co
GB1174335A (en) *	1967-03-07	1969-12-17	Lilly Co Eli	7-Alpha-Amino-3-Methyl Cephalosporin Analogues, Pharmaceutical Compositions comprising the same and processes for preparing the same
YU36970B (en) *	1973-02-23	1984-08-31	Lilly Co Eli	Process for obtaining 7-(amino)-acylamido-3-halocephalosporins
IL52144A (en) *	1976-07-01	1979-10-31	Lilly Co Eli	De-esterification process for -lactam antibiotic esters
DE2857696C2 (de) *	1977-07-23	1984-08-30	Toyama Chemical Co. Ltd., Tokio / Tokyo	Cephalosporine
US4229575A (en) *	1978-02-27	1980-10-21	Richardson-Merrell Inc.	7-(2,3-Dihydrobenzo-5-furanyl)-acetamido cephalosporin derivatives
US4138397A (en) *	1978-02-27	1979-02-06	Richardson-Merrell Inc.	6-(2,3-Dihydro-5-benzofuranyl)acetamido penicillin derivatives
US4219648A (en) *	1978-03-06	1980-08-26	Richardson-Merrell Inc.	7-[[Amino(1,3-dihydrobenzo[c]thienyl)acetyl]amino]cephalosporin derivatives
US4461767A (en) *	1978-06-16	1984-07-24	E. R. Squibb & Sons, Inc.	Iminothiazolyl ureido cephalosporins
US4317775A (en) *	1980-01-07	1982-03-02	Hoffmann-La Roche Inc.	Amoxicillin derivatives
FR2511375A1 (fr) *	1981-08-17	1983-02-18	Rhone Poulenc Sante	Nouveaux derives de la cephalosporine, leur preparation et les medicaments qui les contiennent
US4537886A (en) *	1982-03-31	1985-08-27	Beecham Group P.L.C.	β-lactam antibacterial agents and compositions containing them
US4501741A (en) *	1983-04-12	1985-02-26	Eli Lilly And Company	Cephalosporin antibiotics

1985
- 1985-03-08 DE DE19853508258 patent/DE3508258A1/de not_active Withdrawn
1986
- 1986-02-21 US US06/832,483 patent/US4748163A/en not_active Ceased
- 1986-02-24 NO NO860679A patent/NO165108C/no unknown
- 1986-02-26 EP EP86102491A patent/EP0195947B1/de not_active Expired - Lifetime
- 1986-02-26 DE DE3650518T patent/DE3650518D1/de not_active Expired - Fee Related
- 1986-02-26 AT AT86102491T patent/ATE137238T1/de not_active IP Right Cessation
- 1986-03-04 PH PH33474A patent/PH24000A/en unknown
- 1986-03-05 IL IL78042A patent/IL78042A0/xx not_active IP Right Cessation
- 1986-03-05 ES ES552683A patent/ES8800234A1/es not_active Expired
- 1986-03-05 PT PT82143A patent/PT82143B/pt not_active IP Right Cessation
- 1986-03-06 DD DD86287635A patent/DD251751A5/de not_active IP Right Cessation
- 1986-03-06 DD DD86311493A patent/DD266502A5/de not_active IP Right Cessation
- 1986-03-06 CA CA000503441A patent/CA1281315C/en not_active Expired - Lifetime
- 1986-03-06 GR GR860626A patent/GR860626B/el unknown
- 1986-03-06 FI FI860945A patent/FI85708C/fi not_active IP Right Cessation
- 1986-03-07 ZA ZA861713A patent/ZA861713B/xx unknown
- 1986-03-07 HU HU86986A patent/HU200183B/hu not_active IP Right Cessation
- 1986-03-07 IE IE860598A patent/IE860598L/xx unknown
- 1986-03-07 DK DK105286A patent/DK105286A/da unknown
- 1986-03-07 JP JP61048721A patent/JPH0649708B2/ja not_active Expired - Lifetime
- 1986-03-07 AU AU54430/86A patent/AU594941B2/en not_active Ceased
- 1986-03-08 KR KR1019860001646A patent/KR930007420B1/ko not_active Expired - Lifetime
1989
- 1989-08-29 US US07/400,200 patent/USRE33948E/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0195947A3 (en)	1988-05-04
FI85708C (fi)	1992-05-25
ES552683A0 (es)	1987-11-01
AU5443086A (en)	1986-09-11
JPH0649708B2 (ja)	1994-06-29
USRE33948E (en)	1992-06-02
PT82143B (pt)	1988-07-29
NO165108C (no)	1990-12-27
EP0195947A2 (de)	1986-10-01
KR930007420B1 (ko)	1993-08-10
HU200183B (en)	1990-04-28
NO165108B (no)	1990-09-17
FI85708B (fi)	1992-02-14
JPS61207388A (ja)	1986-09-13
ZA861713B (en)	1986-11-26
PT82143A (en)	1986-04-01
DE3508258A1 (de)	1986-09-18
ATE137238T1 (de)	1996-05-15
DK105286A (da)	1986-09-09
GR860626B (en)	1986-07-07
ES8800234A1 (es)	1987-11-01
IE860598L (en)	1986-09-08
EP0195947B1 (de)	1996-04-24
DD266502A5 (de)	1989-04-05
FI860945A0 (fi)	1986-03-06
NO860679L (no)	1986-09-09
DE3650518D1 (de)	1996-05-30
DK105286D0 (da)	1986-03-07
US4748163A (en)	1988-05-31
FI860945A7 (fi)	1986-09-09
CA1281315C (en)	1991-03-12
PH24000A (en)	1990-02-09
KR860007265A (ko)	1986-10-10
HUT41031A (en)	1987-03-30
AU594941B2 (en)	1990-03-22
IL78042A0 (en)	1986-07-31

Legal Events

Date	Code	Title	Description
1995-11-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0195947B1 (de)	1996-04-24	Beta-Lactamantibiotika, Verfahren zur Herstellung und ihre Verwendung als und in Arzneimitteln
DE3137854A1 (de)	1982-04-15	Neue cephalosporine, verfahren zur herstellung derselben, zwischenstufen derselben und verfahren zur herstellung der zwischenstufen
AT391137B (de)	1990-08-27	Neue cephalosporinderivate und diese enthaltende pharmazeutische praeparate
CH632513A5 (de)	1982-10-15	Verfahren zur herstellung von ungesaettigten derivaten der 7-acylamido-3-cephem-4-carbonsaeure.
EP0163190A2 (de)	1985-12-04	Beta-Lactamantibiotika, Verfahren zu deren Herstellung sowie ihre Verwendung als Arzneimittel oder Wachstumsförderer in der Tieraufzucht oder als Antioxidantien
EP0197294B1 (de)	1991-04-03	Beta-Lactam-Antibiotika, Verfahren zur Herstellung und ihre Verwendung als Arzneimittel
EP0000392B1 (de)	1982-04-28	Cephalosporin und Penicillin-derivate, Verfahren zu deren Herstellung, und deren pharmazeutische Präparate
DE69622801T2 (de)	2003-03-27	Neue carbapenemderivate
EP0292808B1 (de)	1994-03-02	Substituierte Vinylcephalosporine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE69030502T2 (de)	1997-07-24	Cephalosporinverbindungen und deren herstellung
EP0144032A2 (de)	1985-06-12	Cephalosporine und Verfahren zu ihrer Herstellung
EP0292806B1 (de)	1994-11-02	Substituierte Vinylcephalosporine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0223184A2 (de)	1987-05-27	Neue Cephalosporine, Verfahren zu deren Herstellung sowie ihre Verwendung als Arzneimittel
DE3920743A1 (de)	1991-01-10	2-isocepheme und 2-oxa-isocepheme, verfahren zu ihrer herstellung und ihre verwendung als und in arzneimitteln
DD283329A5 (de)	1990-10-10	Verfahren zur herstellung von heteroanellierten phenylglycin-beta-lactam-antibiotika
DE2539214C2 (de)	1984-03-29	7-Methoxythienyl-ureido-cephalosporin und dieses enthaltendes Arzneimittel
DE3711343A1 (de)	1988-10-20	Cephalosporinderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DD282915A5 (de)	1990-09-26	Verfahren zur herstellung von heteroanellierte phenylglycin-beta-lactam-antibiotika
CH640241A5 (de)	1983-12-30	Cephalosporinverbindungen, verfahren zur herstellung derselben und solche wirksubstanzen enthaltende therapeutische praeparate.
CH660364A5 (de)	1987-04-15	Cephalosporine und verfahren zu ihrer herstellung.
AT367061B (de)	1982-05-25	Verfahren zur herstellung von neuen antibiotischen verbindungen
DE3342929A1 (de)	1985-06-05	Ss-lactamantibiotika, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel
DD281601A5 (de)	1990-08-15	Verfahren zur herstellung von beta-lactam-verbindungen
DE3939533A1 (de)	1991-06-06	Neue cephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DD274422A5 (de)	1989-12-20	Verfahren zur herstellung von beta-lactam-verbindungen