SE448995B - 2-substituerade och 2,6-disubstituerade penem-foreningar samt forfarande for framstellning derav - Google Patents

2-substituerade och 2,6-disubstituerade penem-foreningar samt forfarande for framstellning derav

Info

Publication number: SE448995B
Authority: SE; Sweden
Prior art keywords: mmol; solution; azetidinone; isomer; mixture
Prior art date: 1978-12-18

Application number

SE7910391A

Other languages

English (en)

Swedish (sv)

Other versions

SE7910391L (sv

Inventor

M Menard

A 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

1979-12-17

Publication date

1987-03-30

1979-12-17 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1981-06-18 Publication of SE7910391L publication Critical patent/SE7910391L/xx

1987-03-30 Publication of SE448995B publication Critical patent/SE448995B/sv

Links

238000000034 method Methods 0.000 title claims description 52
150000002961 penems Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 126
238000002360 preparation method Methods 0.000 claims description 53
239000002904 solvent Substances 0.000 claims description 44
150000002148 esters Chemical class 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 10
239000012039 electrophile Substances 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 3
238000007796 conventional method Methods 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000000844 anti-bacterial effect Effects 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 224
239000000243 solution Substances 0.000 description 198
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 142
239000000203 mixture Substances 0.000 description 141
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 125
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 114
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 112
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 112
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
-1 1-ephenamine Chemical compound 0.000 description 84
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 59
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 54
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical group C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 46
239000012267 brine Substances 0.000 description 45
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
239000000047 product Substances 0.000 description 43
238000006243 chemical reaction Methods 0.000 description 41
239000003921 oil Substances 0.000 description 40
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
235000019439 ethyl acetate Nutrition 0.000 description 38
239000000741 silica gel Substances 0.000 description 36
229910002027 silica gel Inorganic materials 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 35
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 32
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 32
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
239000000460 chlorine Substances 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
238000002844 melting Methods 0.000 description 28
230000008018 melting Effects 0.000 description 28
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 27
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 26
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 25
229910052943 magnesium sulfate Inorganic materials 0.000 description 24
235000019341 magnesium sulphate Nutrition 0.000 description 24
239000007864 aqueous solution Substances 0.000 description 23
238000001704 evaporation Methods 0.000 description 23
230000008020 evaporation Effects 0.000 description 23
238000003756 stirring Methods 0.000 description 23
239000012043 crude product Substances 0.000 description 22
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 22
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
238000001914 filtration Methods 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
239000002253 acid Substances 0.000 description 20
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 20
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 17
229910052709 silver Inorganic materials 0.000 description 17
239000002585 base Substances 0.000 description 16
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
239000004332 silver Substances 0.000 description 16
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000004440 column chromatography Methods 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 14
238000000746 purification Methods 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
239000000543 intermediate Substances 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 12
239000002808 molecular sieve Substances 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
239000003480 eluent Substances 0.000 description 11
239000006260 foam Substances 0.000 description 11
229910001961 silver nitrate Inorganic materials 0.000 description 11
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
239000003610 charcoal Substances 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
JXQGXEUVZKGSDW-UHFFFAOYSA-N O=C1C[ClH]N1 Chemical compound O=C1C[ClH]N1 JXQGXEUVZKGSDW-UHFFFAOYSA-N 0.000 description 9
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
229940043279 diisopropylamine Drugs 0.000 description 9
239000000284 extract Substances 0.000 description 9
229910052698 phosphorus Inorganic materials 0.000 description 9
239000011574 phosphorus Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
239000000725 suspension Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
230000010933 acylation Effects 0.000 description 7
238000005917 acylation reaction Methods 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000012259 ether extract Substances 0.000 description 7
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
FSOUWBZLOHCVTL-UHFFFAOYSA-N 2-(2-azidoethoxy)acetyl chloride Chemical compound ClC(=O)COCCN=[N+]=[N-] FSOUWBZLOHCVTL-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
150000001450 anions Chemical class 0.000 description 6
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
229930182555 Penicillin Natural products 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
238000001665 trituration Methods 0.000 description 5
238000005406 washing Methods 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
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 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
229930186147 Cephalosporin Chemical class 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
229940124587 cephalosporin Drugs 0.000 description 4
150000001780 cephalosporins Chemical class 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 4
229910001385 heavy metal Inorganic materials 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
150000003952 β-lactams Chemical class 0.000 description 4
OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical compound CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 description 3
USTXYASKHZDVMV-UHFFFAOYSA-N 2-(2-azidoethoxy)acetic acid Chemical compound OC(=O)COCCN=[N+]=[N-] USTXYASKHZDVMV-UHFFFAOYSA-N 0.000 description 3
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 3
101710134784 Agnoprotein Proteins 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229910004298 SiO 2 Inorganic materials 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
230000021736 acetylation Effects 0.000 description 3
238000006640 acetylation reaction Methods 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
ZMQQDISIMRVKLC-UHFFFAOYSA-N ethyl 2-(2-azidoethoxy)acetate Chemical compound CCOC(=O)COCCN=[N+]=[N-] ZMQQDISIMRVKLC-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
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
239000010410 layer Substances 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
150000002960 penicillins Chemical class 0.000 description 3
229910000073 phosphorus hydride Inorganic materials 0.000 description 3
125000005633 phthalidyl group Chemical group 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
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239000012345 acetylating agent Substances 0.000 description 1
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150000008065 acid anhydrides Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
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125000005042 acyloxymethyl group Chemical group 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
GRDITWOBURDWBB-UHACKZLKSA-N af-o Chemical compound OC=1C(C(O)=C2C)=C3C(=O)\C(=C/NO)C=1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O GRDITWOBURDWBB-UHACKZLKSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
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BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
IMNRJGSQCGFPHL-UHFFFAOYSA-N benzene;oxolane Chemical compound C1CCOC1.C1=CC=CC=C1 IMNRJGSQCGFPHL-UHFFFAOYSA-N 0.000 description 1
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239000003782 beta lactam antibiotic agent Substances 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
UXNMZEXWIDRFTD-UHFFFAOYSA-N bromomethoxy(bromomethoxymethoxy)methane Chemical compound BrCOCOCOCBr UXNMZEXWIDRFTD-UHFFFAOYSA-N 0.000 description 1
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KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
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238000003113 dilution method Methods 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
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SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
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NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
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238000000338 in vitro Methods 0.000 description 1
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150000007529 inorganic bases Chemical class 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical compound [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 description 1
244000144972 livestock Species 0.000 description 1
239000011777 magnesium Chemical class 0.000 description 1
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OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
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208000004396 mastitis Diseases 0.000 description 1
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
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239000002184 metal Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
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MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
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229940116315 oxalic acid Drugs 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
230000037361 pathway Effects 0.000 description 1
HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
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238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
NYOUQWVIMBQOJL-UHFFFAOYSA-N s-(4-oxoazetidin-2-yl) ethanethioate Chemical compound CC(=O)SC1CC(=O)N1 NYOUQWVIMBQOJL-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000017105 transposition Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
- 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
- C07F7/18—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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- 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)

SE7910391A 1978-12-18 1979-12-17 2-substituerade och 2,6-disubstituerade penem-foreningar samt forfarande for framstellning derav SE448995B (sv)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
SE7910391L SE7910391L (sv)	1981-06-18
SE448995B true SE448995B (sv)	1987-03-30

Family

ID=25514601

Family Applications (5)

Application Number	Title	Priority Date	Filing Date
SE7910391A SE448995B (sv)	1978-12-18	1979-12-17	2-substituerade och 2,6-disubstituerade penem-foreningar samt forfarande for framstellning derav
SE7910390A SE454779B (sv)	1978-12-18	1979-12-17	2,6-disubstituerade penemforeningar, forfarande for framstellning derav samt farmaceutisk komposition derav med antibakteriell verkan
SE8405719A SE461395B (sv)	1978-12-18	1984-11-14	4-(2'-azidoetoxiacetyltio)-1-(2"-trifenylfosforanyliden-2"-acetat)-2-azetidinoner
SE8405812A SE8405812D0 (sv)	1978-12-18	1984-11-19	Mellanprodukter for framstellning av nya 2-substituerade och 2,6-disubstituerade penem-foreningar
SE8405813A SE464027B (sv)	1978-12-18	1984-11-19	Mellanprodukter foer framstaellning av nya 2-substituerade och 2,6-disubstituerade penem-foereningar

Family Applications After (4)

Application Number	Title	Priority Date	Filing Date
SE7910390A SE454779B (sv)	1978-12-18	1979-12-17	2,6-disubstituerade penemforeningar, forfarande for framstellning derav samt farmaceutisk komposition derav med antibakteriell verkan
SE8405719A SE461395B (sv)	1978-12-18	1984-11-14	4-(2'-azidoetoxiacetyltio)-1-(2"-trifenylfosforanyliden-2"-acetat)-2-azetidinoner
SE8405812A SE8405812D0 (sv)	1978-12-18	1984-11-19	Mellanprodukter for framstellning av nya 2-substituerade och 2,6-disubstituerade penem-foreningar
SE8405813A SE464027B (sv)	1978-12-18	1984-11-19	Mellanprodukter foer framstaellning av nya 2-substituerade och 2,6-disubstituerade penem-foereningar

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
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
FI69845C (fi)	1986-05-26
DK161970B (da)	1991-09-02
SE454779B (sv)	1988-05-30
ZA796812B (en)	1981-05-27

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1995-01-31

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Publication	Publication Date	Title
GB2042515A (en)	1980-09-24	Antibacterial agents
SE436130B (sv)	1984-11-12	Sett att framstella 1-karba-2-penem-3-karboxylsyror
JPS62129264A (ja)	1987-06-11	β―ラクタム化合物
DE3321864C2 (de)	1992-03-26
CH638209A5 (de)	1983-09-15	N-acylderivate von thienamycin.
GB2119371A (en)	1983-11-16	Carbapenem antibiotics
DE3122523C2 (de)	1990-10-18
SE461734B (sv)	1990-03-19	Nya karbapenem-antibiotika samt foerfarande foer framstaellning daerav
CA1136617A (en)	1982-11-30	2,6-disubstituted penem compounds
DE3408347A1 (de)	1984-09-13	Verfahren zur herstellung von carbapenem-derivaten, dabei eingesetzte zwischenprodukte und verfahren zu deren herstellung
FI67853C (fi)	1985-06-10	Foerfarande foer framstaellning av nya antibakteriella 7-oxo-4-tia-1-aza-bicyklo(3,2,0)hept-2-enderivat
SE454590B (sv)	1988-05-16	Forfarande for framstellning av 2-tiacefemderivat
JPS63310888A (ja)	1988-12-19	新規化合物、その製法及びそれを含む医薬組成物
SE460197B (sv)	1989-09-18	Nya karbapenemderivat och foerfarande foer framstaellning daerav
CA1268183C (en)	1990-04-25	Phosphorane intermediates for use in preparing penem antibiotics
EP0392681B1 (de)	1994-01-12	Antibakteriell wirkende 2-Carbapenem-Derivate
US4374065A (en)	1983-02-15	Antibacterial agents of the β-lactam type
US4461727A (en)	1984-07-24	4-Acylthioazetidinone intermediates for antibacterial agents
US4406834A (en)	1983-09-27	2,6 Disubstituted penems and intermediates therefor
IE50596B1 (en)	1986-05-28	Penem compounds
EP0082113A1 (de)	1983-06-22	2-Aminobutyl-2-penem Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
CS250658B2 (cs)	1987-05-14	Způsob výroby karbapenemových derivátů