JPH0920783A - １，１−ジオキソセフェム−４−ケトンの製造法 - Google Patents

１，１−ジオキソセフェム−４−ケトンの製造法

Info

Publication number: JPH0920783A
Authority: JP; Japan
Prior art keywords: formula; group; compound; alkyl; alkenyl
Prior art date: 1995-07-04
Legal status (The legal status 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 status listed.): Pending

Application number

JP8175061A

Other languages

English (en)

Japanese (ja)

Inventor

Marco Alpegiani

マルコ・アルペジヤーニ

Pierluigi Bissolino

ピエールルイジ・ビツソリーノ

Anello Matteo D

マテオ・ダネロ

Ettore Perrone

エツトル・ペローネ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Pharmacia SpA

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.)

1995-07-04

Filing date

1996-07-04

Publication date

1997-01-21

1996-07-04 Application filed by Pharmacia SpA filed Critical Pharmacia SpA

1997-01-21 Publication of JPH0920783A publication Critical patent/JPH0920783A/ja

Status Pending legal-status Critical Current

Links

-1 methoxy, methylthio Chemical group 0.000 claims abstract description 87
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
150000001875 compounds Chemical class 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
239000003960 organic solvent Substances 0.000 claims abstract description 6
150000003457 sulfones Chemical class 0.000 claims abstract description 6
230000001590 oxidative effect Effects 0.000 claims abstract description 5
230000003647 oxidation Effects 0.000 claims abstract description 4
238000007254 oxidation reaction Methods 0.000 claims abstract description 4
239000000010 aprotic solvent Substances 0.000 claims abstract description 3
150000004967 organic peroxy acids Chemical class 0.000 claims abstract description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 3
150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 19
125000003342 alkenyl group Chemical group 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 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
239000001257 hydrogen Substances 0.000 claims description 4
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims description 2
125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
150000004966 inorganic peroxy acids Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
101150035983 str1 gene Proteins 0.000 claims 1
125000006239 protecting group Chemical group 0.000 abstract description 4
229910052794 bromium Inorganic materials 0.000 abstract description 3
229910052801 chlorine Inorganic materials 0.000 abstract description 3
UDTVQXNZIKQKOI-BAFYGKSASA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid Chemical compound C1=CC(C(=O)O)S[C@@H]2CC(=O)N21 UDTVQXNZIKQKOI-BAFYGKSASA-N 0.000 abstract description 2
229940122055 Serine protease inhibitor Drugs 0.000 abstract description 2
101710102218 Serine protease inhibitor Proteins 0.000 abstract description 2
239000003001 serine protease inhibitor Substances 0.000 abstract description 2
150000002148 esters Chemical group 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
235000019439 ethyl acetate Nutrition 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000243 solution Substances 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000002950 monocyclic group Chemical group 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
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 3
239000000047 product Substances 0.000 description 3
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 2
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
125000003396 thiol group Chemical class [H]S* 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
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 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
RFEPXYRIZIJDQQ-WCBMZHEXSA-N C(C)(=O)C1=C(CS([C@H]2N1C([C@@H]2OC)=O)(=O)=O)C Chemical compound C(C)(=O)C1=C(CS([C@H]2N1C([C@@H]2OC)=O)(=O)=O)C RFEPXYRIZIJDQQ-WCBMZHEXSA-N 0.000 description 1
OBDWBKAJMCRZDF-WCQYABFASA-N C(CCCC)(=O)C1=C(CS([C@H]2N1C([C@@H]2OC)=O)(=O)=O)C Chemical compound C(CCCC)(=O)C1=C(CS([C@H]2N1C([C@@H]2OC)=O)(=O)=O)C OBDWBKAJMCRZDF-WCQYABFASA-N 0.000 description 1
AYZUGWYRGKCMAT-OWJBEEKMSA-N C1(=CC=CC=C1)C1=CC=C(C(=O)C2S([C@H]3N(C=C2C)C([C@@H]3OC)=O)(=O)=O)C=C1 Chemical compound C1(=CC=CC=C1)C1=CC=C(C(=O)C2S([C@H]3N(C=C2C)C([C@@H]3OC)=O)(=O)=O)C=C1 AYZUGWYRGKCMAT-OWJBEEKMSA-N 0.000 description 1
125000005915 C6-C14 aryl group Chemical group 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
125000002252 acyl group Chemical class 0.000 description 1
125000005041 acyloxyalkyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
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
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
QCYIFDAFIXZTQO-UHFFFAOYSA-N lithium;diphenylmethylbenzene Chemical compound [Li+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 QCYIFDAFIXZTQO-UHFFFAOYSA-N 0.000 description 1
150000001247 metal acetylides Chemical class 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 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
125000001624 naphthyl group Chemical group 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
YHOBGCSGTGDMLF-UHFFFAOYSA-N sodium;di(propan-2-yl)azanide Chemical compound [Na+].CC(C)[N-]C(C)C YHOBGCSGTGDMLF-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
WTEHZLSBCPFRHB-UHFFFAOYSA-L sulfonatooxy sulfate;tetrabutylazanium Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC WTEHZLSBCPFRHB-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000005039 triarylmethyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP8175061A 1995-07-04 1996-07-04 １，１−ジオキソセフェム−４−ケトンの製造法 Pending JPH0920783A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9513556.2		1995-07-04
GB9513556A GB2302871B (en)	1995-07-04	1995-07-04	Process for preparing 1,1-dioxo-cephem-4-ketones

Publications (1)

Publication Number	Publication Date
JPH0920783A true JPH0920783A (ja)	1997-01-21

Family

ID=10777076

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8175061A Pending JPH0920783A (ja)	1995-07-04	1996-07-04	１，１−ジオキソセフェム−４−ケトンの製造法

Country Status (4)

Country	Link
JP (1)	JPH0920783A (it)
DE (1)	DE19626616A1 (it)
GB (1)	GB2302871B (it)
IT (1)	IT1284083B1 (it)

1995
- 1995-07-04 GB GB9513556A patent/GB2302871B/en not_active Expired - Fee Related
1996
- 1996-06-27 IT IT96MI001317A patent/IT1284083B1/it active IP Right Grant
- 1996-07-02 DE DE19626616A patent/DE19626616A1/de not_active Withdrawn
- 1996-07-04 JP JP8175061A patent/JPH0920783A/ja active Pending

Also Published As

Publication number	Publication date
GB2302871B (en)	1998-05-13
IT1284083B1 (it)	1998-05-08
GB9513556D0 (en)	1995-09-06
ITMI961317A1 (it)	1997-12-27
DE19626616A1 (de)	1997-01-09
ITMI961317A0 (it)	1996-06-27
GB2302871A (en)	1997-02-05

Publication	Publication Date	Title
US4064343A (en)	1977-12-20	3-Halo cephalosporins
US4366316A (en)	1982-12-28	1-Oxadethiacepham compounds and process for producing said compounds
US4031084A (en)	1977-06-21	Process for cephalosporin antibiotic intermediates
US4699979A (en)	1987-10-13	7-amino-3-propenylcephalosporanic acid and esters thereof
JPH0588715B2 (it)	1993-12-24
JPH0920783A (ja)	1997-01-21	１，１−ジオキソセフェム−４−ケトンの製造法
US4051320A (en)	1977-09-27	Process for preparing alkoxylated derivatives of cephalosporin compounds
US4012380A (en)	1977-03-15	7-Acylamino-3-acyl-2(or 3)cephems
US4939249A (en)	1990-07-03	Process for 1-carba(dethia) cephalosporins
EP0102893B1 (en)	1988-07-06	A novel production of 1-oxacephams
JPH08183789A (ja)	1996-07-16	新規なセフェム化合物の製造法
AU724353B2 (en)	2000-09-21	Process for preparation of 4H-4-oxo-quinolizine-3-carboxylic acid derivatives
JPS61246187A (ja)	1986-11-01	１―オキサデチアセファム化合物の製造方法
JP2602669B2 (ja)	1997-04-23	２β−ハロゲノ置換メチルペニシリン誘導体の製造法
JPH0853441A (ja)	1996-02-27	７−ジアゾ−β−ラクタム誘導体
JPH0587512B2 (it)	1993-12-16
KR920005969B1 (ko)	1992-07-25	세팔로스포린 화합물의 제조방법
US4260746A (en)	1981-04-07	Chemical intermediates useful to prepare cephalosporins
US5037975A (en)	1991-08-06	Cephalosporin free radical compounds
JP2828334B2 (ja)	1998-11-25	ノルボルナン系スルホンアミド誘導体の製造方法
JPH0225914B2 (it)	1990-06-06
JP2959809B2 (ja)	1999-10-06	７―アミノ―３―クロロメチル―△▲上３▼―セフェム―４―カルボン酸エステル類の製造法
KR810000716B1 (ko)	1981-06-25	1-옥사데티아 세팜 화합물의 제조방법
JPH0244474B2 (ja)	1990-10-04	Karubasefuemukagobutsu
JPH0323556B2 (it)	1991-03-29