DK155086B - Alfa-beskyttede oxyimino-beta-oxo-gamma-halogensmoersyrederivater til anvendelse som mellemprodukter ved fremstilling af cephemforbindelser - Google Patents
Alfa-beskyttede oxyimino-beta-oxo-gamma-halogensmoersyrederivater til anvendelse som mellemprodukter ved fremstilling af cephemforbindelser Download PDFInfo
- Publication number
- DK155086B DK155086B DK552377AA DK552377A DK155086B DK 155086 B DK155086 B DK 155086B DK 552377A A DK552377A A DK 552377AA DK 552377 A DK552377 A DK 552377A DK 155086 B DK155086 B DK 155086B
- Authority
- DK
- Denmark
- Prior art keywords
- protected
- oxo
- oxyimino
- intermediates
- acid derivatives
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- -1 CEPHEM COMPOUNDS Chemical class 0.000 title description 14
- 239000000543 intermediate Substances 0.000 title description 4
- 239000002253 acid Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 125000000094 2-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
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 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 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DK 155086 B
i
Den foreliggende opfindelse angår hidtil ukendte a-be-skyttede oxyimino-/3-oxo-Y-halogensmørsyrederivater til anvendelse som me11emprodukterved fremstilling af cephem-5 forbindelser med den almene formel h_n s
Yj| : s N--1 -A-CONH- _j/ \ (n)
Cr N'Y^CH2R4
COOH
hvori A betyder -C-, hvor R5 er en med alkyl, der kan NR5 være substitueret, beskyttet hydroxylgruppe, og R4 er hydrogen, en acetoxygruppe, en gruppe -S-R, hvor R er en 10 5- eller 6-leddet heterocyclisk ring, der indeholder 1 ringnitrogenatom og eventuelt 1-3 yderligere ringhete-roatomer valgt blandt oxygen, svovl og nitrogen, og som kan være substitueret med alkyl, alkoxy, halogen, halogenalkyl, amino, mercapto, hydroxyl, carbamoyl eller 15 carboxyl, eller R4 er carbamoyloxy eller en gruppe -N^® \ , \==/ som kan være substitueret med alkyl, halogen, en carbamoylgruppe, carboxyalkyl, hydroxyalkyl eller halogenalkyl, eller farmaceutisk accpetable salte eller 20 estere deraf.
2
DK 155086 B
De «-beskyttede oxyimino-Ø-oxo—y-halogensmørsyrederivater ifølge opfindelsen er ejendommelige ved, at de har den almene formel 5 XCH2 - C - C - COOH (I) il II c O NR5 hvori X betyder et halogenatom, og har den ovenfor angivne betydning, eller er salte eller estere deraf.
Ved anvendelse af de omhandlede forbindelser med formlen I som mellemprodukter ved fremstilling af forbindelser med 10 den almene formel II fremstilles først forbindelser med formlen R1 Sv ΎΪ •ΚΓ 11 .Π - 000H XIV II 5
NR
hvori r! betyder amino, der eventuelt er beskyttet, og r5 har den ovenfor angivne betydning, eller et salt eller en 15 ester deraf, ved omsætning af en forbindelse med formlen I med en forbindelse med formlen
Rl2 Jé- n„2 (XIII) hvori R12 betyder en lavalkoxygruppe eller aminogruppe, der eventuelt er beskyttet, om nødvendigt efterfulgt af 20 fjernelse af beskyttelsesgruppen.
Forbindelserne med den almene formel XIV anvendes derpå til fremstilling af cephemforbindelserne med den almene 3
DK 155086 B
formel II ved omsætning med en forbindelse med den almene formel
H
i Sv --1/ \ 0 J-Ηγ^0Η2 **
COOH
5 hvori R4 har den ovenfor angivne betydning, eller et salt eller en ester deraf.
Carboxylgruppen i forbindelserne med formlen I kan være beskyttet med en beskyttelsesgruppe, der kan fjernes under milde betingelser, såsom ved sure eller alkaliske betin-10 gelser eller ved reduktion. Sådanne beskyttelsesgrupper kan derfor vælges blandt de ved peptidsyntesen almindeligt anvendte for carboxylgrupper og er f.eks. alkalimetaller, såsom natrium og kalium, alkyl, såsom methyl, ethyl, propyl, isopropyl, butyl, sek-butyl, isobutyl og tert-15 butyl, substitueret alkyl, såsom β-methylsuIfonylethyl, trichlorethyl og di-phenylmethyl, aryl, såsom phenyl og toluyl, substitueret aryl, såsom p-tert-butylphenyl og p-nitrophenyl, aralkyl, såsom benzyl, phenethyl og tolu-benzyl, eller substitueret aralkyl, såsom p-methoxybenzyl 20 og p-nitrobenzyl.
Da de omhandlede forbindelser med formlen I teoretisk kan foreligge som syn- og anti-isomerer med hensyn til den beskyttede oxyiminogruppe, kan hver af de to isomere anvendes tilsvarende som nyttigt mellemprodukt.
25 De omhandlede forbindelser med formlen I kan fremstilles 4
DK 155086 B
ved halogenering af de tilsvarende α-beskyttede oxyimini-β-oxo-smørsyrederivater efter i og for sig kendte metoder.
Ved udtrykket "lav" skal der i det ovenstående og efter-5 følgende forstås grupper med fortrinsvis op til 7 carbon-atomer, især indtil 4 carbonatomer.
Ved salte skal eventuelt også forstås syreadditionssalte.
Opfindelsen illustreres nærmere ved hjælp af de efterfølgende eksempler.
10 Eksempel 1.
Til en opløsning af 18,7 g ethyl-or-ethoxyimino-/3-oxo-butyrat i 100 ml chloroform sættes dåbevis en opløsning af 15,9 g brom i 20 ml chloroform under is-køling. Opløsningen omrøres i 30 minutter ved den samme temperatur og 15 yderligere i 1,5 time ved stuetemperatur. Reaktionsblandingen vaskes med vand, vandig natriumhydrogencarbonat-opløsning og derpå med vand i denne rækkefølge, hvorpå det tørres over vandfrit magnesiumsulfat. Fra den tørrede opløsning afdampes opløsningsmidlet. Det opnåede produkt 20 er ethyl-a-ethoxyimino-/3-oxo-7-brom-butyrat, der kan videreomsættes som angivet i dansk patentansøgning nr. 5488/75, eksempel 51-54.
Eksempel 2.
Til en opløsning af 27,3 g ethyl-a-methoxyimino-Ø-oxo-25 butyrat i 120 ml chloroform sættes dråbevis en opløsning af 25,3 g brom i 30 ml chloroform over et tidsrum på 30 minutter. Opløsningen omrøres i 1 time ved stuetemperatur og vaskes med fortyndet vandig natriumhydrogencarbonat-opløsning og vand og tørres. Fra den tørrede opløsning
Claims (3)
- 2. Forbindelser ifølge krav 1, kendetegnet ved, at R1 er en hydroxylgruppe, som er beskyttet med en lavalkyl-gruppe.
- 3. Forbindelser ifølge krav 2, kendetegnet ved, at R1 er en methoxygruppe.
- 4. Forbindelser ifølge krav 2 eller 3, kendetegnet ved, at X betyder brom. Forbindelser ifølge krav 2 eller 3, kendetegnet ved, at X betyder chlor.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14656774 | 1974-12-19 | ||
| JP49146567A JPS5760345B2 (da) | 1974-12-19 | 1974-12-19 | |
| GB24611/75A GB1536281A (en) | 1975-06-09 | 1975-06-09 | Cephem compounds |
| GB2461175 | 1975-06-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK552377A DK552377A (da) | 1977-12-09 |
| DK155086B true DK155086B (da) | 1989-02-06 |
| DK155086C DK155086C (da) | 1989-06-19 |
Family
ID=26257200
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK548875A DK154939C (da) | 1974-12-19 | 1975-12-04 | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| DK552377A DK155086C (da) | 1974-12-19 | 1977-12-09 | Alfa-beskyttede oxyimino-beta-oxo-gamma-halogensmoersyrederivater til anvendelse som mellemprodukter ved fremstilling af cephemforbindelser |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK548875A DK154939C (da) | 1974-12-19 | 1975-12-04 | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
Country Status (18)
| Country | Link |
|---|---|
| US (6) | US4098888A (da) |
| AT (1) | AT357521B (da) |
| AU (1) | AU500104B2 (da) |
| BE (1) | BE836813A (da) |
| BG (1) | BG60437B2 (da) |
| CA (3) | CA1216284A (da) |
| CH (4) | CH624119A5 (da) |
| DE (3) | DE2559942C2 (da) |
| DK (2) | DK154939C (da) |
| ES (4) | ES443627A1 (da) |
| FR (4) | FR2294690A1 (da) |
| GB (1) | GB1536283A (da) |
| HU (1) | HU179798B (da) |
| MX (1) | MX5097E (da) |
| NL (4) | NL183703C (da) |
| NO (1) | NO157933C (da) |
| PH (2) | PH13731A (da) |
| SE (2) | SE442202B (da) |
Families Citing this family (168)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191762A (en) | 1974-03-14 | 1980-03-04 | Fujisawa Pharmaceutical Co., Ltd. | 2-Lower alkyl-7-substituted amino-2 or 3-cephem-4-carboxylic acid compounds |
| US4297489A (en) * | 1974-09-03 | 1981-10-27 | Bristol-Myers Company | 7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids |
| US4182868A (en) * | 1974-10-29 | 1980-01-08 | Takeda Chemical Industries, Ltd. | 7-Methoxycephalosporin derivatives |
| JPS5760345B2 (da) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4196205A (en) * | 1976-01-23 | 1980-04-01 | Roussel Uclaf | 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives |
| SE440655B (sv) | 1976-01-23 | 1985-08-12 | Roussel Uclaf | Sett att framstella nya oximderivat av 7-amino-tiazolyl-acetamido-cefalosporansyra |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| GB1575803A (en) | 1976-03-09 | 1980-10-01 | Fujisawa Pharmaceutical Co | 3,7 disubstituted 3 cephem 4 carboxylic acid compounds andprocesses for the preparation thereof |
| IE44888B1 (en) * | 1976-03-09 | 1982-05-05 | Fujisawa Pharmaceutical Co | 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation theroef |
| US4299829A (en) | 1976-03-12 | 1981-11-10 | Fujisawa Pharmaceutical Co., Ltd. | 2-Lower alkyl-7-substituted-2 or 3-cephem 4-carboxylic acid compounds |
| FR2345153A1 (fr) * | 1976-03-25 | 1977-10-21 | Roussel Uclaf | Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| US4202893A (en) | 1976-03-25 | 1980-05-13 | Roussel Uclaf | Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids |
| JPS5946237B2 (ja) * | 1976-04-02 | 1984-11-10 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| US4166115A (en) * | 1976-04-12 | 1979-08-28 | Fujisawa Pharmaceutical Co., Ltd. | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
| FR2367756B1 (fr) * | 1976-04-12 | 1985-07-05 | Fujisawa Pharmaceutical Co | Derives 2-alcoxyamino-2-(amino-1,3-thiazolyl) acetiques et leur utilisation |
| US4431643A (en) * | 1976-04-12 | 1984-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3-substituted-7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3 |
| US4804752A (en) * | 1976-04-12 | 1989-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
| DK162391C (da) * | 1976-04-12 | 1992-03-09 | Fujisawa Pharmaceutical Co | Analogifremgangsmaade til fremstilling af syn-isomerer af 3,7-disubstituerede 3-cephem-4-carboxylsyreforbindelser |
| US4493833A (en) * | 1976-04-12 | 1985-01-15 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds |
| US4304770A (en) * | 1976-04-12 | 1981-12-08 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
| US4331664A (en) * | 1976-04-12 | 1982-05-25 | Fujisawa Pharmaceutical Co., Ltd. | Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted aminothiazol-4-yl)acetamido]-3-lower alkanoyloxymethyl or heterocyclicthiomethyl-3-cephem-4-carboxylic acid compounds |
| US4364943A (en) * | 1976-04-12 | 1982-12-21 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 7-[2-alkoxyimino-2-(2-amino-alkanoylamino-or haloalkanoylamino-thiazol-4-yl) acetamids]-3-[hexanoyl-, or phenylalkanoyl-oxymethyl or benzothiazolylthiomethyl]-3-cephem-4-carboxylic acid |
| DE2760482C2 (de) * | 1976-04-14 | 1995-02-09 | Takeda Chemical Industries Ltd | Pharmazeutische Zubereitungen, enthaltend ein 7-[2-(2-aminothiazol-4yl)-2-(syn)-methoxyiminoacetamido]cephalosporinderivat |
| DE2760491C2 (de) * | 1976-09-08 | 1995-04-20 | Takeda Chemical Industries Ltd | Pharmazeutische Zubereitungen enthaltend Pivaloyloxymethyl 7- 2-(2-aminothiazol-4-yl)-2-(syn)mehtoxyiminoacetamido desacetoxycephalosporanat und dessen Salze |
| DE2760488C2 (de) * | 1976-04-14 | 1994-04-07 | Takeda Chemical Industries Ltd | Cephalosporinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| DE2715385A1 (de) * | 1976-04-14 | 1977-11-10 | Takeda Chemical Industries Ltd | Cephalosporinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| FI771866A7 (da) * | 1976-06-28 | 1977-12-29 | Fujisawa Pharmaceutical Co | |
| US4963542A (en) * | 1976-09-08 | 1990-10-16 | Takeda Chemical Industries, Ltd. | Cephalosporin derivatives |
| JPS6011713B2 (ja) * | 1976-09-08 | 1985-03-27 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| GB1592149A (en) * | 1976-10-08 | 1981-07-01 | Fujisawa Pharmaceutical Co | 3 7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for preparation thereof |
| JPS53144594A (en) * | 1976-12-27 | 1978-12-15 | Fujisawa Pharmaceut Co Ltd | 3,7-di-substitued-3-cephem-4-carboxylic acid derivatives |
| GB1597848A (en) * | 1976-12-27 | 1981-09-09 | Fujisawa Pharmaceutical Co | Cephalosporin compounds and processes for the preparation thereof |
| JPS6011714B2 (ja) | 1977-02-17 | 1985-03-27 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| JPS53101393A (en) | 1977-02-17 | 1978-09-04 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
| JPS53103493A (en) * | 1977-02-18 | 1978-09-08 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
| FR2381053A1 (fr) * | 1977-02-18 | 1978-09-15 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| DE2710902A1 (de) * | 1977-03-12 | 1978-09-21 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| US4841062A (en) * | 1977-03-14 | 1989-06-20 | Fujisawa Pharmaceutical Company, Limited | New cephem and cepham compounds and processes for preparation thereof |
| PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| SE439312B (sv) | 1977-03-25 | 1985-06-10 | Roussel Uclaf | Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra |
| GB1579533A (en) * | 1977-03-26 | 1980-11-19 | Farmaceutici Italia | Cephalosporins and their preparation |
| DE2716677C2 (de) * | 1977-04-15 | 1985-10-10 | Hoechst Ag, 6230 Frankfurt | Cephemderivate und Verfahren zu ihrer Herstellung |
| US5089490A (en) * | 1977-04-02 | 1992-02-18 | Hoechst Aktiengesellschaft | Cephem derivatives |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| DE2857696C2 (de) * | 1977-07-23 | 1984-08-30 | Toyama Chemical Co. Ltd., Tokio / Tokyo | Cephalosporine |
| JPS609719B2 (ja) * | 1977-08-06 | 1985-03-12 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| FR2400519A1 (fr) * | 1977-08-17 | 1979-03-16 | Roussel Uclaf | Forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino-thiazolyl acetamido cephalosporanique, son procede de preparation et son application comme medicament |
| US4370326A (en) * | 1977-09-13 | 1983-01-25 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds and composition |
| IT1192287B (it) * | 1977-11-14 | 1988-03-31 | Fujisawa Pharmaceutical Co | Derivati di acido cefalosporanico ad azione farmaceutica e relativo procedimento di preparazione |
| FR2410655A1 (fr) * | 1977-12-05 | 1979-06-29 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| JPS5936891B2 (ja) | 1977-12-09 | 1984-09-06 | 武田薬品工業株式会社 | 保護基の脱離方法 |
| DE2758001A1 (de) | 1977-12-24 | 1979-07-12 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| FR2387235A1 (fr) * | 1978-01-23 | 1978-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne |
| JPS54112892A (en) * | 1978-02-23 | 1979-09-04 | Shionogi & Co Ltd | Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acid |
| US4180658A (en) * | 1978-02-24 | 1979-12-25 | Bristol-Myers Company | 7[-2-Alkoxyamino(acetamido)]cephalosporin derivatives |
| JPS54117494A (en) * | 1978-03-03 | 1979-09-12 | Takeda Chem Ind Ltd | Cephalosporin compound and its preparation |
| FR2421907A1 (fr) * | 1978-04-07 | 1979-11-02 | Roussel Uclaf | Nouvelles cephalosporines derivees de l'acide 7-/2-(2-amino 4-thiazolyl)2-(carboxymethoxyimino/acetamido 3-substitue cephalosporanique, leur procede de preparation et leur application comme medicaments |
| SE445350B (sv) * | 1978-04-14 | 1986-06-16 | Roussel Uclaf | Oximderivat av 3-azidometyl-7-amino-tiazolyl-acetamido-cefalosporansyra och dess anvendning som antibiotika |
| DE2818263A1 (de) * | 1978-04-26 | 1979-11-08 | Bayer Ag | Beta-lactamantibiotika |
| AR228726A1 (es) * | 1978-05-26 | 1983-04-15 | Glaxo Group Ltd | Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato |
| CH641468A5 (de) * | 1978-05-30 | 1984-02-29 | Hoffmann La Roche | Cephemderivate. |
| JPS54160392A (en) * | 1978-06-02 | 1979-12-19 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| US4501743A (en) * | 1978-06-16 | 1985-02-26 | E. R. Squibb & Sons, Inc. | Iminothiazolyl ureido cephalosporins |
| US4461767A (en) * | 1978-06-16 | 1984-07-24 | E. R. Squibb & Sons, Inc. | Iminothiazolyl ureido cephalosporins |
| US4268509A (en) * | 1978-07-10 | 1981-05-19 | Fujisawa Pharmaceutical Co., Ltd. | New cephem compounds and processes for preparation thereof |
| US4288435A (en) * | 1978-07-17 | 1981-09-08 | Fujisawa Pharmaceutical Co., Ltd. | 3,7-Disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutical antibacterial compositions containing them |
| JPS6058239B2 (ja) * | 1978-07-20 | 1985-12-19 | 山之内製薬株式会社 | 新規セフアロスポリン誘導体 |
| US4372952A (en) * | 1978-07-31 | 1983-02-08 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4284631A (en) * | 1978-07-31 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them |
| US4305937A (en) * | 1978-08-17 | 1981-12-15 | Fujisawa Pharmaceutical Co., Ltd. | 2-Lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds and antibacterial pharmaceutical compositions containing them |
| US4703046A (en) * | 1978-09-08 | 1987-10-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds and processes for preparation thereof |
| US4341775A (en) * | 1978-09-11 | 1982-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| DE2967053D1 (en) * | 1978-09-12 | 1984-07-19 | Fujisawa Pharmaceutical Co | Starting compounds for preparing cephem compounds and processes for their preparation |
| US4220761A (en) * | 1978-09-12 | 1980-09-02 | Fujisawa Pharmaceutical Co., Ltd. | 7-[Substituted oximinoacetamido]-3-[hydroxy alkyltetrazolo]cephalosporin derivatives |
| US4327093A (en) * | 1978-10-24 | 1982-04-27 | Fujisawa Pharmaceutical Co., Ltd. | 3,7-Disubstituted-2 or 3-cephem-4-carboxylic acid compounds |
| IE49100B1 (en) * | 1978-10-27 | 1985-07-24 | Glaxo Group Ltd | Cephalosporin compounds |
| FI793566A7 (fi) * | 1978-11-15 | 1981-01-01 | Glaxo Group Ltd | Kefalosporiiniantibiootteja. |
| US4313945A (en) * | 1978-11-23 | 1982-02-02 | Ciba-Geigy Corporation | 7-Thiazolyl-acetamido-cephem derivatives with terminal aminocarboxylic acid grouping |
| JPS5579393A (en) * | 1978-12-11 | 1980-06-14 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| US4332798A (en) * | 1978-12-29 | 1982-06-01 | Fujisawa Pharmaceutical Co., Ltd. | 7-Amino-thia-diazole oxyimino derivatives of cephem and cephem compounds |
| AU536842B2 (en) * | 1978-12-29 | 1984-05-24 | Fujisawa Pharmaceutical Co., Ltd. | Cephalosporin antibiotics |
| FR2445830A1 (fr) * | 1979-01-05 | 1980-08-01 | Roussel Uclaf | Nouveaux derives de l'acide (4-thiazolyl) acetique procede de preparation |
| LU82285A1 (fr) * | 1979-03-22 | 1980-10-08 | Glaxo Group Ltd | Antibiotiques du type cephalosporine et procede de preparation |
| US4237128A (en) * | 1979-04-12 | 1980-12-02 | E. R. Squibb & Sons, Inc. | 7-[2-(2-Amino-4-thiazolyl)-2-[(1-carboxy-1,1-dialkyl)alkoxyimino]acetamido]cephem sulfoxides |
| LU82479A1 (fr) * | 1979-05-23 | 1980-12-16 | Rhone Poulenc Ind | Nouvelles thiovinyl-3 cephalosporines,leur preparation et les compositions qui les contiennent |
| FR2457296A1 (fr) * | 1979-05-23 | 1980-12-19 | Rhone Poulenc Ind | Nouveaux derives de vinyl-3 cephalosporines et leur preparation |
| EP0021688B1 (en) * | 1979-06-07 | 1983-07-13 | Yamanouchi Pharmaceutical Co., Ltd. | 7-(thiazolylpropionamido) cephalosporins, their preparation, and pharmaceutical compositions containing them |
| US4275062A (en) * | 1979-09-19 | 1981-06-23 | E. R. Squibb & Sons, Inc. | Aminothiazolyl ureido sulfoxide cephalosporins |
| US4252951A (en) * | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
| US4332800A (en) * | 1979-10-12 | 1982-06-01 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4338313A (en) * | 1979-10-12 | 1982-07-06 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4381299A (en) * | 1980-03-07 | 1983-04-26 | Fujisawa Pharmaceutical Co., Ltd. | 7-Amino-thiadiazole oxyimino derivatives of cephem and cepham compounds |
| US4271157A (en) * | 1980-02-28 | 1981-06-02 | E. R. Squibb & Sons, Inc. | Imidazole derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins |
| US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| US4409215A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
| US5243043A (en) * | 1980-02-18 | 1993-09-07 | Roussel Uclaf | Cephalosporins |
| DE3006888A1 (de) * | 1980-02-23 | 1981-09-10 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DE3007685A1 (de) | 1980-02-29 | 1981-10-01 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue cephylosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4252802A (en) * | 1980-03-13 | 1981-02-24 | E. R. Squibb & Sons, Inc. | Hydroxamic acid derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins |
| IL63207A (en) * | 1980-07-24 | 1985-09-29 | Lonza Ag | Process for the preparation of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyiminoacetic acid esters |
| US4399132A (en) * | 1980-08-11 | 1983-08-16 | American Cyanamid Company | 7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof |
| US4486425A (en) * | 1980-09-30 | 1984-12-04 | Sankyo Company Limited | 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylates |
| US4367228A (en) * | 1980-10-29 | 1983-01-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compound and composition |
| US4431642A (en) * | 1980-12-01 | 1984-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4427677A (en) * | 1980-12-31 | 1984-01-24 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| EP0055465B1 (en) * | 1980-12-31 | 1989-08-23 | Fujisawa Pharmaceutical Co., Ltd. | 7-acylaminocephalosporanic acid derivatives and processes for the preparation thereof |
| JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
| JPS6011917B2 (ja) * | 1981-04-09 | 1985-03-28 | 山之内製薬株式会社 | 新規なセファロスポリン化合物 |
| DE3117438A1 (de) * | 1981-05-02 | 1982-11-18 | Hoechst Ag, 6000 Frankfurt | Cephemderivate und verfahren zu ihrer herstellung |
| DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| US4396620A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin quinolinium betaines |
| US4396619A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin betaines |
| US4400503A (en) * | 1981-10-30 | 1983-08-23 | Eli Lilly And Company | Purification of syn-7-[[(2-amino-4-thiazolyl)(methoxyimino) acetyl]amino]-3-methyl-3-cephem-4-carboxylic acid |
| US4594417A (en) * | 1981-10-30 | 1986-06-10 | Eli Lilly Company | Crystalline antibiotic salt |
| ATE18219T1 (de) * | 1981-11-13 | 1986-03-15 | Glaxo Group Ltd | Thiazol-derivate und ihre verwendung bei der herstellung von beta-lactam-antibiotika. |
| US4426528A (en) | 1982-04-01 | 1984-01-17 | Eli Lilly And Company | Purification of syn-(2-aminothiazol-4-yl)methoxyimino)acetic acid |
| DE3374410D1 (en) | 1982-06-28 | 1987-12-17 | Bristol Myers Co | Cephalosporin derivatives, a process for the manufacture thereof and pharmaceutical compositions containing said derivatives |
| AU1637983A (en) * | 1982-06-30 | 1984-01-05 | Glaxo Group Limited | Cephalosporin antibiotics |
| DE3239365A1 (de) * | 1982-10-23 | 1984-04-26 | Bayer Ag, 5090 Leverkusen | Neue cephalosporine und verfahren zu ihrer herstellung |
| US4480120A (en) * | 1983-03-24 | 1984-10-30 | Eastman Kodak Company | Process for the preparation of alkyl-2-alkoxyimino-3-oxo-4-chlorobutyrates |
| DE150507T1 (de) * | 1983-12-29 | 1987-02-26 | Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo | Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate. |
| US4788185A (en) * | 1984-04-23 | 1988-11-29 | Takeda Chemical Industries, Ltd. | Cephalosporin compounds |
| PH22107A (en) * | 1984-06-07 | 1988-06-01 | Takeda Chemical Industries Ltd | 3-pyrazolo(1,5-a)pyrdinium cephem compounds |
| EP0452987B1 (en) * | 1984-12-27 | 1995-03-01 | Banyu Pharmaceutical Co., Ltd. | Isoindoline derivatives |
| ATE89826T1 (de) * | 1985-03-01 | 1993-06-15 | Takeda Chemical Industries Ltd | Antibakterielle verbindungen, ihre herstellung und verwendung. |
| US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| US4698338A (en) * | 1986-02-19 | 1987-10-06 | Eli Lilly And Company | 7[2-(2-aminothiazol-4-yl)-2-benzyloximino]acetamido-3[4-alkyl-5-oxo-6-hydroxy-3,4-dihydro-1,2,4-triazin-3-yl]thiomethyl cephalosporins |
| US4814328A (en) * | 1986-03-19 | 1989-03-21 | Banyu Pharmaceutical Co., Ltd. | Cephalosporin derivatives, and antibacterial agents |
| JPS6310795A (ja) * | 1986-03-25 | 1988-01-18 | Takeda Chem Ind Ltd | 選択性除草化合物 |
| JPS635091A (ja) * | 1986-06-26 | 1988-01-11 | Senjiyu Seiyaku Kk | 着色防止方法 |
| US5066799A (en) * | 1986-07-28 | 1991-11-19 | American Cyanamid Company | Intermediates for the preparation of aminothiazoloximino cephalosporins |
| US4959495A (en) * | 1986-07-28 | 1990-09-25 | American Cyanamid Company | Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins |
| FR2621589B1 (fr) * | 1987-10-08 | 1990-03-02 | Sanofi Sa | Derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5242913A (en) * | 1987-03-11 | 1993-09-07 | Pfizer Inc. | Substituted 3-cephem compounds as antibacterial agents |
| WO1993013108A1 (en) * | 1987-03-11 | 1993-07-08 | Susumu Nakanishi | Substituted 3-cephem compounds as antibacterial agents |
| US5223496A (en) * | 1987-11-10 | 1993-06-29 | The Upjohn Company | Cephalosporin antibiotics |
| DE3804841A1 (de) * | 1988-02-17 | 1989-08-31 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| EP0333082A3 (en) * | 1988-03-15 | 1991-05-02 | Takeda Chemical Industries, Ltd. | Cephem compounds, their production and use |
| DE3809845A1 (de) * | 1988-03-24 | 1989-10-12 | Hoechst Ag | Verfahren zur herstellung von 4-halo-3-oxo-2-alkoxyiminobuttersaeureestern |
| NZ230921A (en) * | 1988-10-07 | 1990-07-26 | Sankyo Co | 3-phenyloxymethyl-cephalosporin derivatives and medicaments |
| DE3919259A1 (de) * | 1989-06-13 | 1990-12-20 | Hoechst Ag | Kristalline cephem-saeureadditionssalze und verfahren zu ihrer herstellung |
| KR940000112B1 (ko) * | 1990-07-05 | 1994-01-05 | 주식회사 대웅제약 | 신규의 3-치환 세펨화합물 및 그의 제조방법 |
| IL99898A (en) * | 1990-11-09 | 1996-10-31 | Eisai Co Ltd | 7-Acyl-3-substituted carbamoyloxy cephem compounds their preparation and antibacterial compositions containing them |
| YU48484B (sh) * | 1991-05-24 | 1998-09-18 | Hoechst Aktiengesellschaft | Kristalne kiselinske adicione soli diastereomerno čistih 1-(2,2-dimetilpropioniloksi)-etilestara 3-cefem-4-karbonske kiseline |
| US5281589A (en) * | 1991-06-15 | 1994-01-25 | Cheil Foods & Chemicals, Inc. | 3-fused pyridiniummethyl cephalosporins |
| AT396108B (de) * | 1991-08-21 | 1993-06-25 | Biochemie Gmbh | Neues verfahren und neue zwischenprodukte zur herstellung von 7-aminocephalosporansaeurederivaten |
| EP0531875B1 (de) * | 1991-09-07 | 2004-03-24 | Aventis Pharma Deutschland GmbH | Diastereomer des 3-Cephem-4-carbonsäure-1-(-isopropoxycarbonyloxy)ethylesters und Verfahren zu dessen Herstellung |
| TW212181B (da) * | 1992-02-14 | 1993-09-01 | Hoechst Ag | |
| DE59308295D1 (de) * | 1992-05-21 | 1998-04-30 | Hoechst Ag | Verfahren zur Spaltung von Cephalosporin Prodrugestern zu 7-Amino-3-methoxymethylceph-3-em-4-carbonsäure |
| WO1994020505A1 (en) * | 1993-03-12 | 1994-09-15 | The Upjohn Company | Crystalline ceftiofur free acid |
| KR100194994B1 (ko) * | 1993-06-05 | 1999-06-15 | 손경식 | 새로운 세펨 화합물 |
| TW369530B (en) * | 1993-06-10 | 1999-09-11 | Lucky Ltd | Process for preparing cephalosporin compounds from reactive organic acid derivatives |
| US6468995B1 (en) * | 1993-09-09 | 2002-10-22 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| KR100248851B1 (ko) * | 1994-08-16 | 2000-04-01 | 이치로 키타사토 | 신규 세펨 유도체 |
| US5574154A (en) * | 1994-09-29 | 1996-11-12 | Alnejma Bulk Pharmaceutical Co. A.B.P.C. | Process for the preparation of cephalosporanic compounds |
| GB9423459D0 (en) * | 1994-11-21 | 1995-01-11 | Biochemie Gmbh | Silylation process |
| AT402928B (de) * | 1994-12-23 | 1997-09-25 | Biochemie Gmbh | Neues verfahren zur herstellung von cefotaxim |
| KR0164458B1 (ko) * | 1995-04-04 | 1999-01-15 | 김은영 | 암모니오세팔로스포린 계열 항생제 및 그의 제조방법 |
| US5872249A (en) * | 1995-09-01 | 1999-02-16 | Korea Institute Of Science And Technology | 3-ammoniopropenyl cephalosporin compounds as antibacterial agents and process for preparing the same |
| IN184690B (da) * | 1996-03-18 | 2000-09-23 | Ranbaxy Lab Ltd | |
| AU690482B2 (en) * | 1996-03-18 | 1998-04-23 | Ranbaxy Laboratories Limited | Process for producing cephalosporin antibiotics |
| US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
| DE602004028111D1 (de) | 2003-04-16 | 2010-08-26 | Sandoz Ag | Verfahren zur herstellung von cefepim |
| US7847093B2 (en) * | 2003-04-16 | 2010-12-07 | Sandoz Ag | Processes for the preparations of cefepime |
| US20050119244A1 (en) * | 2003-12-02 | 2005-06-02 | Acs Dobfar S.P.A. | Process for preparing cephalosporins with salified intermediate |
| WO2005076694A2 (en) * | 2004-01-16 | 2005-08-25 | Wockhardt Limited | Improved process for the production of cefotaxime sodium |
| CN105153197B (zh) * | 2015-07-28 | 2017-05-31 | 齐鲁安替制药有限公司 | 一种头孢中间体的制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2470083A (en) * | 1946-04-03 | 1949-05-17 | Walter H Hartung | Ethers of oximino acid chlorides |
| US2542812A (en) * | 1946-04-03 | 1951-02-20 | Walter H Hartung | Preparation of aminoacidamides |
| US3038007A (en) * | 1958-05-23 | 1962-06-05 | Reeve Edward Wilkins | Process for the preparation of dl-threonine |
| US3104258A (en) * | 1958-09-25 | 1963-09-17 | Fmc Corp | Novel synthesis of amino acids |
| US3167549A (en) * | 1961-05-18 | 1965-01-26 | Smith Kline French Lab | Derivatives of 7-aminocephalosporanic acid |
| US3360515A (en) * | 1964-07-24 | 1967-12-26 | Fujisawa Pharmaceutical Co | 7-(condensed n-containing heterocyclic carbonamido) cephalosporanic acid and derivatives thereof |
| US3338897A (en) * | 1965-03-10 | 1967-08-29 | Fujisawa Pharmacentical Co Ltd | 7-(alpha-substituted acyl amino) cephalosporanic acid and derivatives thereof |
| US3661977A (en) * | 1968-04-25 | 1972-05-09 | Shionogi & Co | Novel dioximes and processes for preparing the same |
| GB1364453A (en) * | 1970-11-06 | 1974-08-21 | Gist Brocades Nv | Penicillanic and cepholosporanic acid derivatives |
| US3855213A (en) * | 1971-02-18 | 1974-12-17 | Smith Kline French Lab | 3-heterocyclic thiomethyl-cephalosporins |
| US4024134A (en) * | 1971-01-29 | 1977-05-17 | Glaxo Laboratories Limited | Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7 |
| US4024133A (en) * | 1971-05-14 | 1977-05-17 | Glaxo Laboratories Limited | 7β-[2-Etherified oximino-2-(thienyl-,furyl- or pyridylacetamido)]cephalosporins |
| US3971778A (en) * | 1972-05-12 | 1976-07-27 | Glaxo Laboratories Limited | Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position |
| US3974153A (en) * | 1971-05-14 | 1976-08-10 | Glaxo Laboratories Limited | 7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids |
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| US3966717A (en) * | 1971-05-14 | 1976-06-29 | Glaxo Laboratories Limited | 7-β-Acylamido-3-carbamoyloxymethylceph-3-em-4-carboxylic acids and salts thereof |
| US4024137A (en) * | 1971-05-14 | 1977-05-17 | Glaxo Laboratories Limited | 7β-[2-Etherified oximino-2-(phenyl- or naphthylacetamido)] cephalosporins |
| US3821207A (en) * | 1971-06-21 | 1974-06-28 | Smithkline Corp | 7-heterocyclic substituted cephalosporins |
| YU36181B (en) * | 1971-11-29 | 1982-02-25 | Merck & Co Inc | Process for obtaining 7-(2-thienylacetamido)-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylates |
| US4032521A (en) * | 1972-12-29 | 1977-06-28 | Merck & Co., Inc. | Cephalosporin phosphonic acid, sulfonic acid and sulfonamide compounds |
| US4308380A (en) * | 1973-03-15 | 1981-12-29 | Fujisawa Pharmaceutical Co., Ltd. | 2-Lower alkyl-2 or 3-cephem-4-carboxylic acid derivatives |
| DE2512284A1 (de) * | 1974-03-28 | 1975-10-09 | Fujisawa Pharmaceutical Co | Cephalosporansaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| IE41697B1 (en) * | 1974-09-27 | 1980-02-27 | Rhone Poulenc Ind | New cephalosporin derivatives their preparation and compositions containing them |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4668783A (en) * | 1974-12-19 | 1987-05-26 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido cephalosporin compounds |
| GB1536281A (en) * | 1975-06-09 | 1978-12-20 | Takeda Chemical Industries Ltd | Cephem compounds |
| US4011216A (en) * | 1975-04-11 | 1977-03-08 | Bristol-Myers Company | Δ2,3-0-2-Isocephem-4-carboxylic acid and derivatives thereof as antibacterial agents |
-
1975
- 1975-12-04 DK DK548875A patent/DK154939C/da not_active IP Right Cessation
- 1975-12-15 PH PH17868A patent/PH13731A/en unknown
- 1975-12-17 MX MX752873U patent/MX5097E/es unknown
- 1975-12-17 FR FR7538703A patent/FR2294690A1/fr active Granted
- 1975-12-17 HU HU75TA1464A patent/HU179798B/hu unknown
- 1975-12-17 SE SE7514286A patent/SE442202B/xx not_active IP Right Cessation
- 1975-12-17 GB GB28892/78A patent/GB1536283A/en not_active Expired
- 1975-12-17 NO NO754296A patent/NO157933C/no unknown
- 1975-12-17 DE DE2559942A patent/DE2559942C2/de not_active Expired
- 1975-12-17 DE DE2560398A patent/DE2560398C2/de not_active Expired
- 1975-12-17 DE DE2556736A patent/DE2556736C2/de not_active Expired
- 1975-12-18 BE BE162887A patent/BE836813A/xx not_active IP Right Cessation
- 1975-12-18 NL NLAANVRAGE7514811,A patent/NL183703C/xx active Protection Beyond IP Right Term
- 1975-12-18 CA CA000242004A patent/CA1216284A/en not_active Expired
- 1975-12-18 AU AU87667/75A patent/AU500104B2/en not_active Expired
- 1975-12-18 ES ES443627A patent/ES443627A1/es not_active Expired
- 1975-12-19 US US05/642,356 patent/US4098888A/en not_active Expired - Lifetime
- 1975-12-19 CH CH1655675A patent/CH624119A5/de not_active IP Right Cessation
-
1976
- 1976-11-29 FR FR7635966A patent/FR2357552A1/fr not_active Withdrawn
-
1977
- 1977-04-16 ES ES457891A patent/ES457891A1/es not_active Expired
- 1977-07-12 PH PH19987A patent/PH14161A/en unknown
- 1977-07-18 AT AT517277A patent/AT357521B/de not_active IP Right Cessation
- 1977-11-28 CH CH1451477A patent/CH631437A5/de not_active IP Right Cessation
- 1977-12-06 ES ES464772A patent/ES464772A1/es not_active Expired
- 1977-12-06 ES ES464771A patent/ES464771A1/es not_active Expired
- 1977-12-09 DK DK552377A patent/DK155086C/da active
-
1978
- 1978-01-18 US US05/870,932 patent/US4205180A/en not_active Expired - Lifetime
- 1978-01-20 NL NL7800731A patent/NL7800731A/xx not_active Application Discontinuation
- 1978-10-31 CA CA315,025A patent/CA1128957A/en not_active Expired
- 1978-10-31 CA CA000315026A patent/CA1137492A/en not_active Expired
-
1979
- 1979-04-03 SE SE7902954A patent/SE445454B/sv not_active IP Right Cessation
- 1979-05-11 FR FR7912111A patent/FR2434146A1/fr active Granted
- 1979-09-28 FR FR7924297A patent/FR2468599B1/fr not_active Expired
-
1980
- 1980-05-23 CH CH407580A patent/CH628058A5/de not_active IP Right Cessation
- 1980-05-23 CH CH407680A patent/CH633544A5/de not_active IP Right Cessation
- 1980-05-27 NL NL8003054A patent/NL8003054A/nl active Search and Examination
-
1983
- 1983-06-24 US US06/525,663 patent/US4514565A/en not_active Expired - Lifetime
-
1988
- 1988-06-07 US US07/203,409 patent/US4912212A/en not_active Expired - Fee Related
- 1988-06-07 US US07/203,410 patent/US4973684A/en not_active Expired - Fee Related
-
1990
- 1990-01-08 US US07/462,492 patent/US5583216A/en not_active Expired - Lifetime
-
1994
- 1994-02-11 BG BG098461A patent/BG60437B2/bg unknown
-
1995
- 1995-08-22 NL NL950016C patent/NL950016I1/nl unknown
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