HU177581B - Process for producing amides of cyano-acetic acid derivatives of - Google Patents
Process for producing amides of cyano-acetic acid derivatives of Download PDFInfo
- Publication number
- HU177581B HU177581B HU77CI1756A HUCI001756A HU177581B HU 177581 B HU177581 B HU 177581B HU 77CI1756 A HU77CI1756 A HU 77CI1756A HU CI001756 A HUCI001756 A HU CI001756A HU 177581 B HU177581 B HU 177581B
- Authority
- HU
- Hungary
- Prior art keywords
- cyano
- acid
- mol
- ester
- formula
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims description 11
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 title description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 125000006000 trichloroethyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- -1 fluorine ester Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- LVJLBAOLANVTDO-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) 2-cyanoacetate Chemical compound ClC1=C(Cl)C(Cl)=C(OC(=O)CC#N)C(Cl)=C1Cl LVJLBAOLANVTDO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- HDZVSSUKYQMKLY-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) 2-cyano-2-phenylacetate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC(=O)C(C#N)C1=CC=CC=C1 HDZVSSUKYQMKLY-UHFFFAOYSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- VIIFGDKQPSFNOP-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) 2-cyano-3-phenylprop-2-enoate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC(=O)C(C#N)=CC1=CC=CC=C1 VIIFGDKQPSFNOP-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002148 esters Chemical class 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005156 substituted alkylene group Chemical group 0.000 abstract 1
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 150000003951 lactams Chemical class 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- NVIAYEIXYQCDAN-MHTLYPKNSA-N (6r,7s)-7-azaniumyl-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(C)=C(C([O-])=O)N2C(=O)[C@H]([NH3+])[C@@H]12 NVIAYEIXYQCDAN-MHTLYPKNSA-N 0.000 description 6
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 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 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 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 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- NQNQSDYQPRGBSF-YOXFSPIKSA-N (6r)-4-acetamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(C)C(NC(=O)C)S[C@@H]2CC(=O)N21 NQNQSDYQPRGBSF-YOXFSPIKSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- TWAKUJKJKHSKIA-XCGJVMPOSA-N (6r)-3-acetyloxy-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(OC(=O)C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 TWAKUJKJKHSKIA-XCGJVMPOSA-N 0.000 description 1
- RZKUCDISUSRECY-AFYYWNPRSA-N (6r)-3-methyl-8-oxo-4-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@H]1N(C(C1)=O)C(=C1C)C(O)=O)C1NC(=O)CC1=CC=CC=C1 RZKUCDISUSRECY-AFYYWNPRSA-N 0.000 description 1
- UTSDZIDFBMBXNA-BFHBGLAWSA-N (6r)-4-acetamido-3-(acetyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(COC(C)=O)C(NC(=O)C)S[C@@H]2CC(=O)N21 UTSDZIDFBMBXNA-BFHBGLAWSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- GEQZTCMVWVDEDF-UHFFFAOYSA-N 2-cyanoacetyl chloride Chemical compound ClC(=O)CC#N GEQZTCMVWVDEDF-UHFFFAOYSA-N 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
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
- MTEUMURLJRZUKD-UHFFFAOYSA-N acetic acid;butan-1-ol;pyridine;hydrate Chemical compound O.CC(O)=O.CCCCO.C1=CC=NC=C1 MTEUMURLJRZUKD-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1756A HU177581B (en) | 1977-07-14 | 1977-07-14 | Process for producing amides of cyano-acetic acid derivatives of |
| YU01641/78A YU164178A (en) | 1977-07-14 | 1978-07-10 | Process for producing cyanoacetamide derivatives |
| CS784649A CS202015B2 (en) | 1977-07-14 | 1978-07-11 | Process for preparing derivatives of cyanacetamide |
| SE7807744A SE437834B (sv) | 1977-07-14 | 1978-07-11 | Sett att framstella cyanoacetamidderivat av cefalosporinen respektive penicilliner |
| GB7829522A GB2001068B (en) | 1977-07-14 | 1978-07-11 | Process for the preparation of acetamide derivatives |
| CH759878A CH635845A5 (de) | 1977-07-14 | 1978-07-12 | Verfahren zur herstellung von cyanacetamid-derivaten von antibiotika. |
| DE19782830525 DE2830525A1 (de) | 1977-07-14 | 1978-07-12 | Verfahren zur herstellung von cyanacetamidderivaten |
| PL1978208344A PL113906B1 (en) | 1977-07-14 | 1978-07-12 | Process for preparing derivatives of acid amides |
| CA307,252A CA1128931A (en) | 1977-07-14 | 1978-07-12 | Process for the preparation of cyano acetamide derivatives |
| FR7820836A FR2397420A1 (fr) | 1977-07-14 | 1978-07-12 | Procede de preparation de derives de cyano-acetamide utiles en tant qu'antibiotiques |
| AT506078A AT358731B (de) | 1977-07-14 | 1978-07-13 | Verfahren zur herstellung von cyanacetamid- -derivaten und deren salzen |
| NL7807540A NL7807540A (nl) | 1977-07-14 | 1978-07-13 | Werkwijze voor de bereiding van zuuramidederivaten. |
| IT25648/78A IT1112645B (it) | 1977-07-14 | 1978-07-13 | Procedimento per la preparazione di derivati della ciano-acetammide |
| DK783152A DK315278A (da) | 1977-07-14 | 1978-07-13 | Fremgangsmaade til fremstilling af syreamidderivater |
| DD78206707A DD142448A5 (de) | 1977-07-14 | 1978-07-13 | Verfahren zur herstellung von cyanacetamid-derivaten |
| ES471702A ES471702A1 (es) | 1977-07-14 | 1978-07-13 | Procedimiento para la preparacion de derivados de amida de acido |
| JP8462178A JPS5436289A (en) | 1977-07-14 | 1978-07-13 | Preparation of cyanoacetoamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1756A HU177581B (en) | 1977-07-14 | 1977-07-14 | Process for producing amides of cyano-acetic acid derivatives of |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU177581B true HU177581B (en) | 1981-11-28 |
Family
ID=10994660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77CI1756A HU177581B (en) | 1977-07-14 | 1977-07-14 | Process for producing amides of cyano-acetic acid derivatives of |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5436289A (cs) |
| AT (1) | AT358731B (cs) |
| CA (1) | CA1128931A (cs) |
| CH (1) | CH635845A5 (cs) |
| CS (1) | CS202015B2 (cs) |
| DD (1) | DD142448A5 (cs) |
| DE (1) | DE2830525A1 (cs) |
| DK (1) | DK315278A (cs) |
| ES (1) | ES471702A1 (cs) |
| FR (1) | FR2397420A1 (cs) |
| GB (1) | GB2001068B (cs) |
| HU (1) | HU177581B (cs) |
| IT (1) | IT1112645B (cs) |
| NL (1) | NL7807540A (cs) |
| PL (1) | PL113906B1 (cs) |
| SE (1) | SE437834B (cs) |
| YU (1) | YU164178A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU179000B (en) * | 1977-07-13 | 1982-07-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new malonic acid esters |
-
1977
- 1977-07-14 HU HU77CI1756A patent/HU177581B/hu unknown
-
1978
- 1978-07-10 YU YU01641/78A patent/YU164178A/xx unknown
- 1978-07-11 SE SE7807744A patent/SE437834B/sv unknown
- 1978-07-11 GB GB7829522A patent/GB2001068B/en not_active Expired
- 1978-07-11 CS CS784649A patent/CS202015B2/cs unknown
- 1978-07-12 DE DE19782830525 patent/DE2830525A1/de not_active Withdrawn
- 1978-07-12 CA CA307,252A patent/CA1128931A/en not_active Expired
- 1978-07-12 FR FR7820836A patent/FR2397420A1/fr active Granted
- 1978-07-12 CH CH759878A patent/CH635845A5/de not_active IP Right Cessation
- 1978-07-12 PL PL1978208344A patent/PL113906B1/pl unknown
- 1978-07-13 JP JP8462178A patent/JPS5436289A/ja active Pending
- 1978-07-13 IT IT25648/78A patent/IT1112645B/it active
- 1978-07-13 DK DK783152A patent/DK315278A/da not_active Application Discontinuation
- 1978-07-13 DD DD78206707A patent/DD142448A5/de unknown
- 1978-07-13 AT AT506078A patent/AT358731B/de not_active IP Right Cessation
- 1978-07-13 ES ES471702A patent/ES471702A1/es not_active Expired
- 1978-07-13 NL NL7807540A patent/NL7807540A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES471702A1 (es) | 1979-10-01 |
| PL113906B1 (en) | 1981-01-31 |
| JPS5436289A (en) | 1979-03-16 |
| PL208344A1 (pl) | 1979-05-07 |
| CA1128931A (en) | 1982-08-03 |
| YU164178A (en) | 1982-10-31 |
| GB2001068B (en) | 1982-03-10 |
| DE2830525A1 (de) | 1979-01-25 |
| FR2397420B1 (cs) | 1982-12-31 |
| FR2397420A1 (fr) | 1979-02-09 |
| ATA506078A (de) | 1980-02-15 |
| AT358731B (de) | 1980-09-25 |
| SE437834B (sv) | 1985-03-18 |
| GB2001068A (en) | 1979-01-24 |
| IT7825648A0 (it) | 1978-07-13 |
| SE7807744L (sv) | 1979-01-15 |
| CH635845A5 (de) | 1983-04-29 |
| CS202015B2 (en) | 1980-12-31 |
| DD142448A5 (de) | 1980-06-25 |
| NL7807540A (nl) | 1979-01-16 |
| DK315278A (da) | 1979-01-15 |
| IT1112645B (it) | 1986-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |