DD266502A5 - Verwendung von beta-lactamverbindungen - Google Patents

Verwendung von beta-lactamverbindungen Download PDF

Info

Publication number: DD266502A5
Authority: DD; German Democratic Republic
Prior art keywords: mol; yield; optionally substituted; mmol; amino
Prior art date: 1985-03-08

Application number

DD86311493A

Other languages

German (de)

English (en)

Inventor

Gunter Schmidt

Hans-Joachim Zeitler

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

1989-04-05

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

1989-04-05 Publication of DD266502A5 publication Critical patent/DD266502A5/de

Links

-1 BETA LACTAM COMPOUNDS Chemical class 0.000 title claims abstract description 55
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 28
125000006239 protecting group Chemical group 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
125000003107 substituted aryl group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
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
150000002431 hydrogen Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910006069 SO3H Inorganic materials 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
150000002357 guanidines Chemical class 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 2
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 135
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
239000000243 solution Substances 0.000 description 69
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 49
239000000460 chlorine Substances 0.000 description 44
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
150000001875 compounds Chemical class 0.000 description 35
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 30
BDAGIHXWWSANSR-PFUFQJKNSA-N formic acid-d2 Chemical compound [2H]OC([2H])=O BDAGIHXWWSANSR-PFUFQJKNSA-N 0.000 description 29
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
229960000583 acetic acid Drugs 0.000 description 25
239000000203 mixture Substances 0.000 description 22
239000003480 eluent Substances 0.000 description 21
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
229910000041 hydrogen chloride Inorganic materials 0.000 description 21
239000000706 filtrate Substances 0.000 description 19
239000003208 petroleum Substances 0.000 description 18
239000002904 solvent Substances 0.000 description 18
239000002253 acid Substances 0.000 description 17
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 16
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
239000011734 sodium Substances 0.000 description 16
229930186147 Cephalosporin Chemical class 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 15
229940124587 cephalosporin Drugs 0.000 description 15
150000001780 cephalosporins Chemical class 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
229910052731 fluorine Inorganic materials 0.000 description 15
239000011737 fluorine Substances 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 14
239000012071 phase Substances 0.000 description 14
238000004128 high performance liquid chromatography Methods 0.000 description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 12
238000001816 cooling Methods 0.000 description 12
239000000126 substance Substances 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
239000013543 active substance Substances 0.000 description 11
239000012267 brine Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 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 9
239000012362 glacial acetic acid Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
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 9
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
239000000825 pharmaceutical preparation Substances 0.000 description 8
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
229930182555 Penicillin Natural products 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000001099 ammonium carbonate Substances 0.000 description 7
235000012501 ammonium carbonate Nutrition 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
230000014759 maintenance of location Effects 0.000 description 7
238000000034 method Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000000725 suspension Substances 0.000 description 7
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
150000001413 amino acids Chemical class 0.000 description 6
238000002953 preparative HPLC Methods 0.000 description 6
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 6
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 5
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 5
230000004913 activation Effects 0.000 description 5
229960003237 betaine Drugs 0.000 description 5
229920001429 chelating resin Polymers 0.000 description 5
238000004587 chromatography analysis Methods 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
229910052763 palladium Inorganic materials 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000007858 starting material Substances 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
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 description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000013078 crystal Substances 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
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229940049954 penicillin Drugs 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000006187 pill Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229940068917 polyethylene glycols Drugs 0.000 description 4
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
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
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
BPBGTPDKBXLWRX-UHFFFAOYSA-N 5-(2-amino-1,3-benzothiazol-6-yl)imidazolidine-2,4-dione Chemical compound C1=C2SC(N)=NC2=CC=C1C1NC(=O)NC1=O BPBGTPDKBXLWRX-UHFFFAOYSA-N 0.000 description 3
XQMVBICWFFHDNN-UHFFFAOYSA-N 5-amino-4-chloro-2-phenylpyridazin-3-one;(2-ethoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) methanesulfonate Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1.C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 XQMVBICWFFHDNN-UHFFFAOYSA-N 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
241000588724 Escherichia coli Species 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 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
230000000844 anti-bacterial effect Effects 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
229910001863 barium hydroxide Inorganic materials 0.000 description 3
235000012216 bentonite Nutrition 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 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
125000001153 fluoro group Chemical group F* 0.000 description 3
239000000499 gel Substances 0.000 description 3
235000011187 glycerol Nutrition 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
150000002960 penicillins Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 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
238000005406 washing Methods 0.000 description 3
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 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
MDTNTKLGRUURFT-RXMQYKEDSA-N (6r)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(Cl)CS[C@@H]2CC(=O)N12 MDTNTKLGRUURFT-RXMQYKEDSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
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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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Fodder In General (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD86311493A 1985-03-08 1986-03-06 Verwendung von beta-lactamverbindungen DD266502A5 (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
DD266502A5 true DD266502A5 (de)	1989-04-05

Family

ID=6264592

Family Applications (2)

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

Family Applications After (1)

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

Country Status (20)

Country	Link
US (2)	US4748163A (fr)
EP (1)	EP0195947B1 (fr)
JP (1)	JPH0649708B2 (fr)
KR (1)	KR930007420B1 (fr)
AT (1)	ATE137238T1 (fr)
AU (1)	AU594941B2 (fr)
CA (1)	CA1281315C (fr)
DD (2)	DD266502A5 (fr)
DE (2)	DE3508258A1 (fr)
DK (1)	DK105286A (fr)
ES (1)	ES8800234A1 (fr)
FI (1)	FI85708C (fr)
GR (1)	GR860626B (fr)
HU (1)	HU200183B (fr)
IE (1)	IE860598L (fr)
IL (1)	IL78042A0 (fr)
NO (1)	NO165108C (fr)
PH (1)	PH24000A (fr)
PT (1)	PT82143B (fr)
ZA (1)	ZA861713B (fr)

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* Cited by examiner, † Cited by third party
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DE3509618A1 (de) *	1985-03-16	1986-09-18	Bayer Ag, 5090 Leverkusen	Ss-lactam-antibiotika, verfahren zur herstellung und ihre verwendung als arzneimittel
DE3734004A1 (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
US5171854A (en) *	1987-05-26	1992-12-15	Bayer Aktiengesellschaft	Substituted vinylcephalosporins
DE3734005A1 (de) *	1987-05-26	1988-12-15	Bayer Ag	Substituierte vinylcephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
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 (fr) *	1992-09-18	2002-02-13	Otsuka Kagaku Kabushiki Kaisha	Compose de cepheme, son procede de production et medicament le contenant
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
AU2003265842A1 (en)	2002-08-30	2004-03-19	Memory Pharmaceuticals Corporation	Anabaseine derivatives useful in the treatment of neurodegenerative diseases
KR101388061B1 (ko) *	2006-05-31	2014-04-22	토야마 케미칼 컴퍼니 리미티드	멧돼지과 동물 또는 양(羊)용 항 구제역 바이러스제 및 멧돼지과 동물 또는 양의 구제역의 예방 또는 치료방법
KR20150096794A (ko)	2012-12-21	2015-08-25	제니쓰 에피제네틱스 코포레이션	브로모도메인 저해제로서의 신규한 헤테로사이클릭 화합물
SG10201710705UA (en)	2013-06-21	2018-02-27	Zenith Epigenetics Ltd	Novel bicyclic bromodomain inhibitors
ES2661437T3 (es) *	2013-06-21	2018-04-02	Zenith Epigenetics Corp.	Nuevos compuestos bicíclicos sustituidos como inhibidores de bromodominio
EA201690087A1 (ru)	2013-07-31	2016-08-31	Зенит Эпидженетикс Корп.	Новые квиназолиноны как ингибиторы бромодомена
WO2016087942A1 (fr)	2014-12-01	2016-06-09	Zenith Epigenetics Corp.	Pyridines substituées comme inhibiteurs de bromodomaine
WO2016087936A1 (fr)	2014-12-01	2016-06-09	Zenith Epigenetics Corp.	Pyridinones substituées utilisées comme inhibiteurs de bromodomaines
US10292968B2 (en)	2014-12-11	2019-05-21	Zenith Epigenetics Ltd.	Substituted heterocycles as bromodomain inhibitors
CN107406438B (zh)	2014-12-17	2021-05-14	恒翼生物医药科技(上海)有限公司	溴结构域的抑制剂

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US3080356A (en) *	1960-06-15	1963-03-05	Beecham Res Lab	Process for the production of synthetic penicillins
SE302125B (fr) *	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
DE2831568C2 (de) *	1977-07-23	1985-01-10	Toyama Chemical Co. Ltd., Tokio / Tokyo	7α-Methoxycephalosporine und Verfahren zur Herstellung derselben
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
NZ203734A (en) *	1982-03-31	1986-03-14	Beecham Group Plc	Beta-lactam derivatives and pharmaceutical compositions
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/fr 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 DD86311493A patent/DD266502A5/de not_active IP Right Cessation
- 1986-03-06 GR GR860626A patent/GR860626B/el unknown
- 1986-03-06 CA CA000503441A patent/CA1281315C/fr not_active Expired - Lifetime
- 1986-03-06 FI FI860945A patent/FI85708C/fi not_active IP Right Cessation
- 1986-03-06 DD DD86287635A patent/DD251751A5/de not_active IP Right Cessation
- 1986-03-07 ZA ZA861713A patent/ZA861713B/xx unknown
- 1986-03-07 DK DK105286A patent/DK105286A/da unknown
- 1986-03-07 IE IE860598A patent/IE860598L/xx unknown
- 1986-03-07 HU HU86986A patent/HU200183B/hu not_active IP Right Cessation
- 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 active IP Right Grant
1989
- 1989-08-29 US US07/400,200 patent/USRE33948E/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ATE137238T1 (de)	1996-05-15
CA1281315C (fr)	1991-03-12
DE3508258A1 (de)	1986-09-18
FI860945A (fi)	1986-09-09
PT82143B (pt)	1988-07-29
DD251751A5 (de)	1987-11-25
NO860679L (no)	1986-09-09
DE3650518D1 (de)	1996-05-30
NO165108B (no)	1990-09-17
ES8800234A1 (es)	1987-11-01
HUT41031A (en)	1987-03-30
US4748163A (en)	1988-05-31
DK105286D0 (da)	1986-03-07
ES552683A0 (es)	1987-11-01
PH24000A (en)	1990-02-09
PT82143A (en)	1986-04-01
DK105286A (da)	1986-09-09
AU594941B2 (en)	1990-03-22
IE860598L (en)	1986-09-08
NO165108C (no)	1990-12-27
EP0195947A2 (fr)	1986-10-01
IL78042A0 (en)	1986-07-31
KR930007420B1 (ko)	1993-08-10
ZA861713B (en)	1986-11-26
USRE33948E (en)	1992-06-02
KR860007265A (ko)	1986-10-10
GR860626B (en)	1986-07-07
EP0195947B1 (fr)	1996-04-24
JPS61207388A (ja)	1986-09-13
FI85708B (fi)	1992-02-14
HU200183B (en)	1990-04-28
FI85708C (fi)	1992-05-25
JPH0649708B2 (ja)	1994-06-29
EP0195947A3 (en)	1988-05-04
AU5443086A (en)	1986-09-11
FI860945A0 (fi)	1986-03-06

Publication	Publication Date	Title
DD266502A5 (de)	1989-04-05	Verwendung von beta-lactamverbindungen
EP0163190A2 (fr)	1985-12-04	Bêta-lactam antibiotiques, procédé pour leur préparation et leur utilisation comme médicaments ou comme stimulants de la croissance dans l'élevage d'animaux ou comme anti-oxydants
EP0197294B1 (fr)	1991-04-03	Bêta-lactame antibiotiques, leur procédé de préparation et leur application comme médicaments
EP0000392B1 (fr)	1982-04-28	Céphalosporines et pénicillines, procédés pour leur préparation et leurs compositions pharmaceutiques
EP0292808B1 (fr)	1994-03-02	Vinylcéphalosporines substituées, procédé pour leur préparation et leur utilisation comme médicaments
CH636879A5 (de)	1983-06-30	Verfahren zur herstellung 7-substituierter aminoacetamido-oxadethia-cephalosporine.
DE69030502T2 (de)	1997-07-24	Cephalosporinverbindungen und deren herstellung
US3865820A (en)	1975-02-11	Acylamino-cephalosporanic acids
DE2521063A1 (de)	1975-11-27	Phenylacetamidocephalosporin- derivate
EP0292806B1 (fr)	1994-11-02	Vinylcéphalosporines substituées, leur procédé de préparation et leur utilisation comme médicaments
DE3215085A1 (de)	1983-10-27	Ss-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2539214C2 (de)	1984-03-29	7-Methoxythienyl-ureido-cephalosporin und dieses enthaltendes Arzneimittel
DE3920743A1 (de)	1991-01-10	2-isocepheme und 2-oxa-isocepheme, verfahren zu ihrer herstellung und ihre verwendung als und in arzneimitteln
US4046904A (en)	1977-09-06	Novel penicillin, and its preparation and use
DD283329A5 (de)	1990-10-10	Verfahren zur herstellung von heteroanellierten phenylglycin-beta-lactam-antibiotika
DE2525541C2 (de)	1984-01-12	&beta;-Lactam-Antibiotica, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel
DD201142A5 (de)	1983-07-06	Verfahren zur herstellung von bistetrazolyl-methylsubstituierten cephalosporiantibiotika
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.
DD282915A5 (de)	1990-09-26	Verfahren zur herstellung von heteroanellierte phenylglycin-beta-lactam-antibiotika
AT343283B (de)	1978-05-26	Verfahren zur herstellung der neuen 6- (d-2- (3-hydroxypyridazin-4-carbonamido)-2- (p-hydroxyphenyl)-acetamido)-penicillansaure und ihrer salze
DE3211034A1 (de)	1983-09-29	7-(alpha)-aminoacyl-3-chlorcephalosporine, verfahren zu ihrer herstellung sowie ihrer verwendung als arzneimittel
DE3342929A1 (de)	1985-06-05	Ss-lactamantibiotika, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel
DE3711343A1 (de)	1988-10-20	Cephalosporinderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE2309135A1 (de)	1973-09-06	Antibakterielle mittel und verfahren zu deren herstellung

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Date	Code	Title	Description
1995-07-20	ENJ	Ceased due to non-payment of renewal fee