FI69845C - Foerfarande foer framstaellning av nya antibakteriella penemderivat - Google Patents

Foerfarande foer framstaellning av nya antibakteriella penemderivat Download PDF

Info

Publication number: FI69845C
Authority: FI; Finland
Prior art keywords: mmol; solution; ether; mixture; alk
Prior art date: 1978-12-18

Application number

FI793903A

Other languages

English (en)

Finnish (fi)

Other versions

FI69845B (fi

FI793903A7 (fi

Inventor

Marcel Menard

Alain Martel

Original Assignee

Bristol Myers Co

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.)

1978-12-18

Filing date

1979-12-13

Publication date

1986-05-26

1979-12-13 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1980-06-19 Publication of FI793903A7 publication Critical patent/FI793903A7/fi

1984-10-10 Priority to FI843981A priority Critical patent/FI70717C/fi

1985-12-31 Publication of FI69845B publication Critical patent/FI69845B/fi

1986-05-26 Application granted granted Critical

1986-05-26 Publication of FI69845C publication Critical patent/FI69845C/fi

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 10
230000000844 anti-bacterial effect Effects 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 46
239000002904 solvent Substances 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 22
238000010992 reflux Methods 0.000 claims description 15
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 9
150000002961 penems Chemical class 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
CWZGRMOUEFLYEX-NHXUYEQSSA-N (5R)-3-(2-aminoethoxymethyl)-6-(1-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(C)C1[C@@H]2N(C(=C(S2)COCCN)C(=O)O)C1=O CWZGRMOUEFLYEX-NHXUYEQSSA-N 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 109
239000000243 solution Substances 0.000 description 83
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 74
239000000203 mixture Substances 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
-1 e.g. Chemical class 0.000 description 44
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 25
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
229910052757 nitrogen Inorganic materials 0.000 description 20
238000001914 filtration Methods 0.000 description 19
239000003921 oil Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
239000002585 base Substances 0.000 description 17
238000001704 evaporation Methods 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
235000019439 ethyl acetate Nutrition 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000012267 brine Substances 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
229910052709 silver Inorganic materials 0.000 description 12
239000004332 silver Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
JXBLHBNGWZZSSM-UHFFFAOYSA-N 1-sulfanyl-4-tritylazetidin-2-one Chemical compound C1C(=O)N(S)C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JXBLHBNGWZZSSM-UHFFFAOYSA-N 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 11
238000004458 analytical method Methods 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 10
238000010511 deprotection reaction Methods 0.000 description 10
150000003952 β-lactams Chemical class 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical group 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000003480 eluent Substances 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
238000000746 purification Methods 0.000 description 7
229910001961 silver nitrate Inorganic materials 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FSOUWBZLOHCVTL-UHFFFAOYSA-N 2-(2-azidoethoxy)acetyl chloride Chemical compound ClC(=O)COCCN=[N+]=[N-] FSOUWBZLOHCVTL-UHFFFAOYSA-N 0.000 description 5
230000010933 acylation Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
HVRMNEPIBIGCNZ-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-oxoacetate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)C=O)C=C1 HVRMNEPIBIGCNZ-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
229910004298 SiO 2 Inorganic materials 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
239000006260 foam Substances 0.000 description 4
229910001385 heavy metal Inorganic materials 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000003643 water by type Substances 0.000 description 4
ZCTHWZKWCUEIHN-UHFFFAOYSA-N 4-tritylsulfanylazetidin-2-one Chemical compound N1C(=O)CC1SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZCTHWZKWCUEIHN-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
XLBIHBRARNXONJ-CQSZACIVSA-N N(=[N+]=[N-])CCSCC=1S[C@H]2N(C=1C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(C2)=O Chemical compound N(=[N+]=[N-])CCSCC=1S[C@H]2N(C=1C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C(C2)=O XLBIHBRARNXONJ-CQSZACIVSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
CVYKQPLWSDHSSV-UHFFFAOYSA-N ethyl 2-(2-chloroethoxy)acetate Chemical compound CCOC(=O)COCCCl CVYKQPLWSDHSSV-UHFFFAOYSA-N 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
150000007970 thio esters Chemical class 0.000 description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical compound CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 description 2
POQHWIQIJDBSJL-SSDOTTSWSA-N (5r)-3-(2-aminoethylsulfanylmethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(CSCCN)=C(C(O)=O)N2C(=O)C[C@H]21 POQHWIQIJDBSJL-SSDOTTSWSA-N 0.000 description 2
OSFFNOMIRPFUGK-SSDOTTSWSA-N (5r)-3-(2-aminoethylsulfonylmethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(CS(=O)(=O)CCN)=C(C(O)=O)N2C(=O)C[C@H]21 OSFFNOMIRPFUGK-SSDOTTSWSA-N 0.000 description 2
USTXYASKHZDVMV-UHFFFAOYSA-N 2-(2-azidoethoxy)acetic acid Chemical compound OC(=O)COCCN=[N+]=[N-] USTXYASKHZDVMV-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000606124 Bacteroides fragilis Species 0.000 description 2
229930186147 Cephalosporin Chemical class 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
241000588697 Enterobacter cloacae Species 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
241000606768 Haemophilus influenzae Species 0.000 description 2
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 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
229910006124 SOCl2 Inorganic materials 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001734 carboxylic acid salts Chemical class 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
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238000005406 washing Methods 0.000 description 2
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230000003389 potentiating effect Effects 0.000 description 1
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NYOUQWVIMBQOJL-UHFFFAOYSA-N s-(4-oxoazetidin-2-yl) ethanethioate Chemical compound CC(=O)SC1CC(=O)N1 NYOUQWVIMBQOJL-UHFFFAOYSA-N 0.000 description 1
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238000010561 standard procedure Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
- 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
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- 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
- 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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

FI793903A 1978-12-18 1979-12-13 Foerfarande foer framstaellning av nya antibakteriella penemderivat FI69845C (fi)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
FI843981A FI70717C (fi)	1978-12-18	1984-10-10	2-azetidinonderivat foer anvaendning som mellanprodukter vid framstaellning av terapeutiskt anvaendbara penemderivat

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US96866378A	1978-12-18	1978-12-18
US96866378		1978-12-18

Publications (3)

Publication Number	Publication Date
FI793903A7 FI793903A7 (fi)	1980-06-19
FI69845B FI69845B (fi)	1985-12-31
FI69845C true FI69845C (fi)	1986-05-26

Family

ID=25514601

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
FI793903A FI69845C (fi)	1978-12-18	1979-12-13	Foerfarande foer framstaellning av nya antibakteriella penemderivat
FI793905A FI67853C (fi)	1978-12-18	1979-12-13	Foerfarande foer framstaellning av nya antibakteriella 7-oxo-4-tia-1-aza-bicyklo(3,2,0)hept-2-enderivat

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
FI793905A FI67853C (fi)	1978-12-18	1979-12-13	Foerfarande foer framstaellning av nya antibakteriella 7-oxo-4-tia-1-aza-bicyklo(3,2,0)hept-2-enderivat

Country Status (13)

Country	Link
JP (1)	JPS60222486A (de)
AU (4)	AU541717B2 (de)
CA (2)	CA1286661C (de)
CH (2)	CH643265A5 (de)
DK (5)	DK161520C (de)
ES (1)	ES8101594A1 (de)
FI (2)	FI69845C (de)
GR (2)	GR81420B (de)
IE (3)	IE50597B1 (de)
IL (2)	IL58576A (de)
SE (5)	SE448995B (de)
YU (4)	YU43628B (de)
ZA (2)	ZA796813B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8509180D0 (en) *	1985-04-10	1985-05-15	Erba Farmitalia	Penem derivatives
US4826832A (en) *	1986-05-06	1989-05-02	Ciba-Geigy Corporation	Penen compounds
EP0757051B1 (de) *	1995-02-17	2003-10-29	Daiichi Suntory Pharma Co., Ltd.	Penem-derivate und sie enthaltende anti-mikrobische mittel
WO1999036098A1 (en)	1998-01-13	1999-07-22	Suntory Limited	Antibacterial composition for topical administration containing antibiotics
JP2005239696A (ja)	2004-01-30	2005-09-08	Daiichi Suntory Pharma Co Ltd	無機物質を配合した医薬硬質カプセル剤
CN112746066B (zh) *	2021-01-25	2023-10-31	洛阳华荣生物技术有限公司	一种l-赖氨酸脱羧酶突变体及其应用

1979
- 1979-10-29 IL IL58576A patent/IL58576A/xx unknown
- 1979-11-07 GR GR60450A patent/GR81420B/el unknown
- 1979-11-12 YU YU2760/79A patent/YU43628B/xx unknown
- 1979-11-26 IL IL58804A patent/IL58804A/xx unknown
- 1979-11-29 GR GR60633A patent/GR74491B/el unknown
- 1979-12-10 JP JP79159315D patent/JPS60222486A/ja active Pending
- 1979-12-11 AU AU53710/79A patent/AU541717B2/en not_active Ceased
- 1979-12-13 FI FI793903A patent/FI69845C/fi not_active IP Right Cessation
- 1979-12-13 AU AU53787/79A patent/AU539983B2/en not_active Ceased
- 1979-12-13 FI FI793905A patent/FI67853C/fi not_active IP Right Cessation
- 1979-12-14 ZA ZA00796813A patent/ZA796813B/xx unknown
- 1979-12-14 DK DK533779A patent/DK161520C/da not_active IP Right Cessation
- 1979-12-14 ZA ZA00796812A patent/ZA796812B/xx unknown
- 1979-12-14 DK DK533879A patent/DK533879A/da not_active Application Discontinuation
- 1979-12-17 YU YU3076/79A patent/YU43464B/xx unknown
- 1979-12-17 SE SE7910391A patent/SE448995B/sv not_active IP Right Cessation
- 1979-12-17 SE SE7910390A patent/SE454779B/sv not_active IP Right Cessation
- 1979-12-17 CA CA000342069A patent/CA1286661C/en not_active Expired - Fee Related
- 1979-12-18 ES ES487034A patent/ES8101594A1/es not_active Expired
- 1979-12-18 CH CH1121979A patent/CH643265A5/de not_active IP Right Cessation
- 1979-12-18 IE IE1853/85A patent/IE50597B1/en unknown
- 1979-12-18 CH CH1121879A patent/CH643846A5/de not_active IP Right Cessation
- 1979-12-18 IE IE2462/79A patent/IE49876B1/en unknown
- 1979-12-18 IE IE2246/85A patent/IE49877B1/en unknown
1982
- 1982-09-27 YU YU2153/82A patent/YU43280B/xx unknown
- 1982-09-27 YU YU2157/82A patent/YU42125B/xx unknown
1983
- 1983-03-08 CA CA000423146A patent/CA1268183A/en not_active Expired - Fee Related
1984
- 1984-08-24 AU AU32408/84A patent/AU557545B2/en not_active Ceased
- 1984-09-10 AU AU32884/84A patent/AU563015B2/en not_active Ceased
- 1984-11-14 SE SE8405719A patent/SE461395B/sv not_active IP Right Cessation
- 1984-11-19 SE SE8405812A patent/SE8405812D0/xx not_active Application Discontinuation
- 1984-11-19 SE SE8405813A patent/SE464027B/sv not_active IP Right Cessation
1990
- 1990-10-01 DK DK236590A patent/DK161970C/da not_active IP Right Cessation
- 1990-10-01 DK DK237690A patent/DK237690A/da not_active Application Discontinuation
1991
- 1991-07-15 DK DK135291A patent/DK135291A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA1268183A (en)	1990-04-24
AU563015B2 (en)	1987-06-25
SE8405719D0 (sv)	1984-11-14
FI793905A7 (fi)	1980-06-19
SE8405813L (sv)	1984-11-19
AU557545B2 (en)	1986-12-24
YU43628B (en)	1989-10-31
IL58804A0 (en)	1980-02-29
AU541717B2 (en)	1985-01-17
DK161520B (da)	1991-07-15
CH643265A5 (en)	1984-05-30
AU5371079A (en)	1980-06-26
CA1286661C (en)	1991-07-23
SE448995B (sv)	1987-03-30
DK135291D0 (da)	1991-07-15
SE461395B (sv)	1990-02-12
AU3288484A (en)	1985-03-07
SE8405812L (sv)	1984-11-19
IL58576A0 (en)	1980-01-31
YU276079A (en)	1983-02-28
DK533879A (da)	1980-06-19
CH643846A5 (en)	1984-06-29
FI67853C (fi)	1985-06-10
ES487034A0 (es)	1980-12-16
FI69845B (fi)	1985-12-31
SE8405813D0 (sv)	1984-11-19
DK236590D0 (da)	1990-10-01
ZA796813B (en)	1981-05-27
FI67853B (fi)	1985-02-28
AU5378779A (en)	1980-08-28
SE7910391L (sv)	1981-06-18
DK237690D0 (da)	1990-10-01
YU215782A (en)	1983-06-30
AU3240884A (en)	1984-12-13
YU43464B (en)	1989-08-31
SE8405719L (sv)	1984-11-14
GR81420B (de)	1984-12-11
IL58576A (en)	1985-12-31
AU539983B2 (en)	1984-10-25
IE792462L (en)	1980-06-18
ES8101594A1 (es)	1980-12-16
JPS60222486A (ja)	1985-11-07
IE50597B1 (en)	1986-05-28
DK533779A (da)	1980-06-19
YU43280B (en)	1989-06-30
SE7910390L (sv)	1981-06-18
DK161970C (da)	1992-02-03
GR74491B (de)	1984-06-28
YU215382A (en)	1983-06-30
IL58804A (en)	1986-03-31
IE851853L (en)	1980-06-18
IE852246L (en)	1980-06-18
YU42125B (en)	1988-04-30
YU307679A (en)	1983-02-28
IE49877B1 (en)	1986-01-08
SE464027B (sv)	1991-02-25
DK236590A (da)	1990-10-01
IE49876B1 (en)	1986-01-08
DK135291A (da)	1991-07-15
SE8405812D0 (sv)	1984-11-19
FI793903A7 (fi)	1980-06-19
DK237690A (da)	1990-10-01
DK161520C (da)	1991-12-23
DK161970B (da)	1991-09-02
SE454779B (sv)	1988-05-30
ZA796812B (en)	1981-05-27

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: BRISTOL-MYERS CO

Publication	Publication Date	Title
EP0071908B1 (de)	1989-09-27	1- und 1,1-disubstituierte, 6-substituierte, 2-carbamimidoyl-1-carbadethiapen-2-em-3-carbonsäuren, Verfahren zur Herstellung und diese enthaltende antibiotische Zusammensetzung
GB2042514A (en)	1980-09-24	Antibacterial agents
HU182017B (en)	1983-12-28	Process for preparing 6-substituted thia-aza-derivatives
EP0017992A1 (de)	1980-10-29	2-Substituierte-6-substituierte-1-Carbadethiapen-2-em-3-carbonsäuren, Verfahren zu ihrer Herstellung, sie enthaltende antibiotische pharmazeutische Zusammensetzungen und Verfahren zur Herstellung von Zwischenprodukten
JP4252628B2 (ja)	2009-04-08	三環型カルバペネムのエチリデン誘導体
JPS61207387A (ja)	1986-09-13	抗菌剤
EP0037082B1 (de)	1985-03-20	Verfahren zur Herstellung von 1-Carbapenem-Derivaten und von Zwischenprodukten via silyl-substituierter Dithioacetale
KR880002512B1 (ko)	1988-11-26	페넴 화합물 및 이의 제조방법
KR880001069B1 (ko)	1988-06-20	카르바페넴 유도체및 그의 제조방법
FI69845B (fi)	1985-12-31	Foerfarande foer framstaellning av nya antibakteriella penemderivat
FI85707B (fi)	1992-02-14	Foerfarande foer framstaellning av nya penemfoereningar.
US4675317A (en)	1987-06-23	2-unsaturated alkylthio-pen-2-em-3-carboxylic acids
NL8102736A (nl)	1982-01-04	Penem-3-carbonzuurverbindingen en hun bereiding.
FI77662B (fi)	1988-12-30	Foerfarande foer framstaellning av nya antibakteriella penemderivat.
CA1136617A (en)	1982-11-30	2,6-disubstituted penem compounds
JPH0516433B2 (de)	1993-03-04
EP0235823B1 (de)	1992-05-20	Carbapenem-Antibiotika, ein Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
JPH0532668A (ja)	1993-02-09	置換２−チオキソペナムおよび２−置換チオペネムの製造方法
SE460197B (sv)	1989-09-18	Nya karbapenemderivat och foerfarande foer framstaellning daerav
JPS62270588A (ja)	1987-11-24	ペネム誘導体
US5055463A (en)	1991-10-08	Spirocyclic 6-amido carbapenems
US5183887A (en)	1993-02-02	Spirocyclic 6-amido-carbapenems and azetidinones
US4837215A (en)	1989-06-06	Penem derivatives
FI80702C (fi)	1990-07-10	Foerfarande foer framstaellning av antibakteriella tio-penem-3-karboxylsyror.
JPH045037B2 (de)	1992-01-30