DE2348473A1 - Verfahren zur herstellung von substituierten malonsaeure-monoestern und ihre verwendung zur herstellung von alphacarboxypenicillinen oder cephalosporinen - Google Patents
Verfahren zur herstellung von substituierten malonsaeure-monoestern und ihre verwendung zur herstellung von alphacarboxypenicillinen oder cephalosporinenInfo
- Publication number
- DE2348473A1 DE2348473A1 DE19732348473 DE2348473A DE2348473A1 DE 2348473 A1 DE2348473 A1 DE 2348473A1 DE 19732348473 DE19732348473 DE 19732348473 DE 2348473 A DE2348473 A DE 2348473A DE 2348473 A1 DE2348473 A1 DE 2348473A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- radical
- ester
- substituted
- formula
- Prior art date
- 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
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229930186147 Cephalosporin Natural products 0.000 title claims description 7
- 229940124587 cephalosporin Drugs 0.000 title claims description 7
- 150000001780 cephalosporins Chemical class 0.000 title description 5
- -1 alicyclic radical Chemical class 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 22
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 21
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000002168 ethanoic acid esters Chemical class 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 8
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 8
- 229940043279 diisopropylamine Drugs 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- SIJUFSMIUVCHDT-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-thiophen-2-ylpropanoic acid Chemical compound CCOC(=O)C(C(O)=O)C1=CC=CS1 SIJUFSMIUVCHDT-UHFFFAOYSA-N 0.000 description 2
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 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 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- JQIYZCAQCVWAQF-UHFFFAOYSA-N 2-(furan-2-yl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)C1=CC=CO1 JQIYZCAQCVWAQF-UHFFFAOYSA-N 0.000 description 1
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 1
- ANTBOPDCAHZIHT-UHFFFAOYSA-N 2-sulfinylacetic acid Chemical compound OC(=O)C=S=O ANTBOPDCAHZIHT-UHFFFAOYSA-N 0.000 description 1
- GCOOGCQWQFRJEK-UHFFFAOYSA-N 2-thiophen-3-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)C=1C=CSC=1 GCOOGCQWQFRJEK-UHFFFAOYSA-N 0.000 description 1
- XDOMMHKHICBYDF-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-thiophen-3-ylpropanoic acid Chemical compound CCOC(=O)C(C1=CSC=C1)C(=O)O XDOMMHKHICBYDF-UHFFFAOYSA-N 0.000 description 1
- IZCKKYIBCWNRNP-UHFFFAOYSA-N 3-oxo-3-phenylmethoxy-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C(=O)O)C(=O)OCC1=CC=CC=C1 IZCKKYIBCWNRNP-UHFFFAOYSA-N 0.000 description 1
- BCYTTWDACSKYHU-UHFFFAOYSA-N 3-oxo-3-phenylmethoxy-2-thiophen-3-ylpropanoic acid Chemical compound C1=CSC=C1C(C(=O)O)C(=O)OCC1=CC=CC=C1 BCYTTWDACSKYHU-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- AFYCAIBLAZNEIZ-UHFFFAOYSA-N benzyl 2-thiophen-3-ylacetate Chemical compound C=1C=CC=CC=1COC(=O)CC=1C=CSC=1 AFYCAIBLAZNEIZ-UHFFFAOYSA-N 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HZCXBPTUYRYPPT-UHFFFAOYSA-N ethyl 2-(furan-2-yl)acetate Chemical compound CCOC(=O)CC1=CC=CO1 HZCXBPTUYRYPPT-UHFFFAOYSA-N 0.000 description 1
- QSUANHXENVRFDN-UHFFFAOYSA-N ethyl 2-thiophen-2-ylacetate Chemical compound CCOC(=O)CC1=CC=CS1 QSUANHXENVRFDN-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 125000001181 organosilyl group Chemical class [SiH3]* 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- UHMOHYVZZQBQIB-UHFFFAOYSA-N propan-2-yl 2-thiophen-3-ylacetate Chemical compound CC(C)OC(=O)CC=1C=CSC=1 UHMOHYVZZQBQIB-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 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 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4593672A GB1426557A (en) | 1972-10-05 | 1972-10-05 | Production of substituted monomalonate esters and their use in the production of alpha-carboxy penicillins and cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2348473A1 true DE2348473A1 (de) | 1974-04-18 |
Family
ID=10439170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732348473 Pending DE2348473A1 (de) | 1972-10-05 | 1973-09-26 | Verfahren zur herstellung von substituierten malonsaeure-monoestern und ihre verwendung zur herstellung von alphacarboxypenicillinen oder cephalosporinen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5745226B2 (enrdf_load_stackoverflow) |
| BE (1) | BE805298A (enrdf_load_stackoverflow) |
| CH (1) | CH587275A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2348473A1 (enrdf_load_stackoverflow) |
| DK (1) | DK132409C (enrdf_load_stackoverflow) |
| FR (1) | FR2202093B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1426557A (enrdf_load_stackoverflow) |
| NL (1) | NL7313636A (enrdf_load_stackoverflow) |
| SE (1) | SE402774B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002846A1 (en) * | 1977-12-06 | 1979-07-11 | Océ-Andeno B.V. | 3-Thienylmalonic acids, the corresponding diesters and their preparation |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334079A (en) * | 1980-11-03 | 1982-06-08 | Eli Lilly And Company | Synthesis of substituted benzyl esters |
| JPH02142917U (enrdf_load_stackoverflow) * | 1989-05-01 | 1990-12-04 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3651050A (en) * | 1969-01-23 | 1972-03-21 | Pfizer | Acylation of 6-aminopenicillanic acid and 7-aminocephalosporanic acid |
-
1972
- 1972-10-05 GB GB4593672A patent/GB1426557A/en not_active Expired
-
1973
- 1973-09-25 BE BE136034A patent/BE805298A/xx not_active IP Right Cessation
- 1973-09-26 DE DE19732348473 patent/DE2348473A1/de active Pending
- 1973-09-26 FR FR7334471A patent/FR2202093B1/fr not_active Expired
- 1973-10-03 SE SE7313478A patent/SE402774B/xx unknown
- 1973-10-04 JP JP11109173A patent/JPS5745226B2/ja not_active Expired
- 1973-10-04 DK DK540573A patent/DK132409C/da active
- 1973-10-04 NL NL7313636A patent/NL7313636A/xx unknown
- 1973-10-04 CH CH1418173A patent/CH587275A5/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002846A1 (en) * | 1977-12-06 | 1979-07-11 | Océ-Andeno B.V. | 3-Thienylmalonic acids, the corresponding diesters and their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DK132409B (da) | 1975-12-01 |
| FR2202093B1 (enrdf_load_stackoverflow) | 1979-04-13 |
| CH587275A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| DK132409C (da) | 1976-05-03 |
| JPS4992061A (enrdf_load_stackoverflow) | 1974-09-03 |
| JPS5745226B2 (enrdf_load_stackoverflow) | 1982-09-27 |
| BE805298A (fr) | 1974-03-25 |
| NL7313636A (enrdf_load_stackoverflow) | 1974-04-09 |
| FR2202093A1 (enrdf_load_stackoverflow) | 1974-05-03 |
| GB1426557A (en) | 1976-03-03 |
| SE402774B (sv) | 1978-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3001328A1 (de) | Neue nortropan-derivate, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel | |
| DE2708219A1 (de) | Verfahren zur herstellung von 7-oxocephalosporansaeure- und 6-oxopenicillansaeure-verbindungen | |
| DE2147023A1 (de) | Verfahren zur herstellung von 1htetrazol-verbindungen | |
| DE2540374C2 (de) | Verfahren zur Herstellung von Cefazolin | |
| DE2348473A1 (de) | Verfahren zur herstellung von substituierten malonsaeure-monoestern und ihre verwendung zur herstellung von alphacarboxypenicillinen oder cephalosporinen | |
| DE2822876A1 (de) | Verfahren zur herstellung von hydroxy- alpha-aminobenzylpenicillin | |
| DE2534926A1 (de) | Sauerstoffanaloge von cephalosporinen | |
| DE2249085A1 (de) | Neue penicilline und verfahren zu ihrer herstellung | |
| EP0722946A1 (de) | Verfahren zur Herstellung von 3-Formyl-Cephem-Derivaten | |
| CH625805A5 (enrdf_load_stackoverflow) | ||
| DE1924117A1 (de) | Verfahren zur Herstellung von Phosphonsaeuren | |
| DE1445685A1 (de) | Antibiotisch wirksame Cephalospransaeurederivate und Verfahren zu ihrer Herstellung | |
| DE2520647A1 (de) | Verfahren zur herstellung von penicillinverbindungen | |
| DE1901918A1 (de) | Penicilline und Verfahren zu ihrer Herstellung | |
| DE2334343C2 (de) | Verfahren zur Herstellung von Pivaloyloxymethyl-6-[ α-(carboxy)phenylacetamido]-penicillanat | |
| DE2243242A1 (de) | Verfahren zur herstellung von 7-amino3-cephem-4-carbonsaeurederivaten | |
| DE2550151A1 (de) | Neue cephalosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE940828C (de) | Verfahren zur Herstellung von Estern des Penicillins mit Phenolen und Thiophenolen | |
| DE2302037A1 (de) | Chromon-3-carbonsaeuren bzw. deren ester, verfahren zu ihrer herstellung und verwendung derselben | |
| AT341092B (de) | Verfahren zur herstellung von derivaten von 7-aminocephalosporansaure und 7-aminodesacetoxycephalosporansaure | |
| DE935128C (de) | Verfahren zur Herstellung von neuen therapeutisch wirksamen Estern der Penicillin-Reihe und deren Metallkomplex-Verbindungen | |
| AT229489B (de) | Verfahren zur Herstellung von neuen Derivaten der 6-Aminopenicillansäure | |
| AT306236B (de) | Verfahren zur Herstellung von Alkali- oder Erdalkalisalzen einen β-Lactamring enthaltender Carbonsäuren | |
| DE2500919C3 (de) | 5-(l-Allyl-2-pyrrolidinylmethylaminocarbonyl)-6-methoxy-benzotriazol sowie seine pharmazeutisch verträglichen Additionssalze mit Säuren | |
| DE2813287A1 (de) | Verfahren zur herstellung von 2-benzoyl- 3,3-dimethyl-7-oxo-alpha-(4-benzyloxyphenyl) -4-thia-2,6-diazabicyclo-eckige klammer auf 3.2.0 eckige klammer zu heptan-6-essigsaeurebenzylester |