SU520050A3 - Способ получени производных пеницилина или цефалоспорина - Google Patents
Способ получени производных пеницилина или цефалоспоринаInfo
- Publication number
- SU520050A3 SU520050A3 SU1713952A SU1713952A SU520050A3 SU 520050 A3 SU520050 A3 SU 520050A3 SU 1713952 A SU1713952 A SU 1713952A SU 1713952 A SU1713952 A SU 1713952A SU 520050 A3 SU520050 A3 SU 520050A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- acid
- ether
- mixture
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 229930186147 Cephalosporin Natural products 0.000 title claims description 4
- 229940124587 cephalosporin Drugs 0.000 title claims description 4
- 150000001780 cephalosporins Chemical class 0.000 title claims description 4
- 150000002960 penicillins Chemical class 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 148
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 35
- 239000010410 layer Substances 0.000 claims description 34
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- -1 (4-nitro) -phenylisoxazol-5-yl-acetamido Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 21
- 238000004809 thin layer chromatography Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000005457 ice water Substances 0.000 claims description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 17
- 238000001228 spectrum Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 229930182555 Penicillin Natural products 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- 229940049954 penicillin Drugs 0.000 claims description 12
- 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 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 11
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002329 infrared spectrum Methods 0.000 claims description 10
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 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 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- UMJVKPYTXOUBSB-UHFFFAOYSA-N 1-propan-2-ylbenzimidazole Chemical compound C1=CC=C2N(C(C)C)C=NC2=C1 UMJVKPYTXOUBSB-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 2
- 229920001577 copolymer Chemical group 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- RGGFTPMQSOTWJD-UHFFFAOYSA-N 2-[3-(4-nitrophenyl)-1,2-oxazol-5-yl]acetic acid Chemical compound O1C(CC(=O)O)=CC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 RGGFTPMQSOTWJD-UHFFFAOYSA-N 0.000 claims 1
- QHBNLMUCFRLZIA-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-1,2-oxazole Chemical class ClC1=CC=CC(Cl)=C1C1=NOC=C1 QHBNLMUCFRLZIA-UHFFFAOYSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical group ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 101100379079 Emericella variicolor andA gene Proteins 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- JFDZBHWFFUWGJE-KWCOIAHCSA-N benzonitrile Chemical group N#[11C]C1=CC=CC=C1 JFDZBHWFFUWGJE-KWCOIAHCSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000011363 dried mixture Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- YCOFRPYSZKIPBQ-UHFFFAOYSA-N penicillic acid Natural products COC1=CC(=O)OC1(O)C(C)=C YCOFRPYSZKIPBQ-UHFFFAOYSA-N 0.000 claims 1
- VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KVXNKFYSHAUJIA-UHFFFAOYSA-N acetic acid;ethoxyethane Chemical compound CC(O)=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 1
- KXEAZJHCOWBLLF-UHFFFAOYSA-N 3-methyl-3-(3-methylpentan-3-yloxy)pentane Chemical compound CCC(C)(CC)OC(C)(CC)CC KXEAZJHCOWBLLF-UHFFFAOYSA-N 0.000 description 1
- BNMPIJWVMVNSRD-UHFFFAOYSA-N 5-methyl-1,2-oxazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NO1 BNMPIJWVMVNSRD-UHFFFAOYSA-N 0.000 description 1
- NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000427729 Vasum Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- SMDQFHZIWNYSMR-UHFFFAOYSA-N sulfanylidenemagnesium Chemical compound S=[Mg] SMDQFHZIWNYSMR-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5304070A GB1364453A (en) | 1970-11-06 | 1970-11-06 | Penicillanic and cepholosporanic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU520050A3 true SU520050A3 (ru) | 1976-06-30 |
Family
ID=10466394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1713952A SU520050A3 (ru) | 1970-11-06 | 1971-11-05 | Способ получени производных пеницилина или цефалоспорина |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3891635A (de) |
| JP (1) | JPS5212200B1 (de) |
| AU (1) | AU463230B2 (de) |
| BE (1) | BE775012A (de) |
| CA (1) | CA983920A (de) |
| CH (3) | CH572936A5 (de) |
| DE (3) | DE2166467A1 (de) |
| ES (2) | ES396720A1 (de) |
| FR (1) | FR2112504B1 (de) |
| GB (1) | GB1364453A (de) |
| HU (1) | HU162822B (de) |
| NL (1) | NL150117B (de) |
| SU (1) | SU520050A3 (de) |
| ZA (1) | ZA717433B (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1459392A (en) * | 1972-12-22 | 1976-12-22 | Gist Brocades Nv | Heterocyclic compounds |
| AU6620274A (en) * | 1973-03-02 | 1975-09-04 | Gist Brocades Nv | Penicillanic and cephalosporanic acid derivatives |
| 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 |
| JPS5760345B2 (de) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
| CA1088049A (en) * | 1975-06-03 | 1980-10-21 | Takashi Masugi | 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof |
| MD227C2 (ro) * | 1976-01-23 | 1995-11-30 | Roussel Uclaf, Societe Anonyme | Procedeu de obţinere a derivaţilor acidului 7-(2-(2-aminotiazolil-4)-2-oxiiminoacetamido)-3-acetoximetil-3-cefem- 4-carbonic sub formă de sin-izomeri |
| JPS6052713B2 (ja) * | 1978-04-11 | 1985-11-20 | 三共株式会社 | ７−メトキシセフアロスポリン化合物、その製法及びその化合物を主成分とする抗菌剤 |
| CA1128526A (en) * | 1979-10-05 | 1982-07-27 | Cdc Life Sciences Inc. | 3,4-diarylisoxazol-5-acetic acids |
| US4526977A (en) * | 1981-10-07 | 1985-07-02 | American Home Products Corporation | 2-(3-Amino-5-isoxazolyl)-2-oxyimino-acetic acids |
| JPS60141367U (ja) * | 1984-02-29 | 1985-09-19 | タキロン株式会社 | 天窓のロツク装置 |
| US4562187A (en) * | 1985-01-22 | 1985-12-31 | Hoechst-Roussel Pharmaceuticals Inc. | (Isoxazol-3-yl)arylmethanones, compositions and pharmaceutical use |
| US7427680B2 (en) * | 2001-01-12 | 2008-09-23 | The Regents Of The University Of California | Fluorogenic substrates for BETA-lactamase gene expression |
| CA2434679A1 (en) * | 2001-01-12 | 2002-09-06 | Roger Y. Tsien | Beta-lactamase substrates having phenolic ethers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218318A (en) * | 1962-08-31 | 1965-11-16 | Lilly Co Eli | 7-heterocyclic-substituted-acylamido cephalosporins |
| US3459746A (en) * | 1965-10-04 | 1969-08-05 | Lilly Co Eli | 7 - heteromonocyclic-substituted acylamido derivatives of desacetyl cephalosporanic acid |
-
1970
- 1970-11-06 GB GB5304070A patent/GB1364453A/en not_active Expired
-
1971
- 1971-11-03 US US195482A patent/US3891635A/en not_active Expired - Lifetime
- 1971-11-05 DE DE19712166467 patent/DE2166467A1/de active Pending
- 1971-11-05 DE DE2155081A patent/DE2155081B2/de active Granted
- 1971-11-05 NL NL717115231A patent/NL150117B/xx unknown
- 1971-11-05 ES ES396720A patent/ES396720A1/es not_active Expired
- 1971-11-05 CH CH1400375A patent/CH572936A5/xx not_active IP Right Cessation
- 1971-11-05 SU SU1713952A patent/SU520050A3/ru active
- 1971-11-05 BE BE775012A patent/BE775012A/xx unknown
- 1971-11-05 ZA ZA717433A patent/ZA717433B/xx unknown
- 1971-11-05 JP JP46088177A patent/JPS5212200B1/ja active Pending
- 1971-11-05 CH CH1616271A patent/CH573436A5/xx not_active IP Right Cessation
- 1971-11-05 DE DE19712166468 patent/DE2166468A1/de active Pending
- 1971-11-05 FR FR7139822A patent/FR2112504B1/fr not_active Expired
- 1971-11-05 AU AU35431/71A patent/AU463230B2/en not_active Expired
- 1971-11-05 HU HUKO2471A patent/HU162822B/hu unknown
- 1971-11-05 CA CA126,985A patent/CA983920A/en not_active Expired
- 1971-11-05 CH CH1400275A patent/CH572935A5/xx not_active IP Right Cessation
-
1974
- 1974-03-01 ES ES423795A patent/ES423795A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2166468A1 (de) | 1974-02-14 |
| CH572936A5 (de) | 1976-02-27 |
| DE2155081B2 (de) | 1975-05-15 |
| BE775012A (fr) | 1972-05-05 |
| AU3543171A (en) | 1973-05-10 |
| ES423795A1 (es) | 1976-12-16 |
| CH572935A5 (de) | 1976-02-27 |
| AU463230B2 (en) | 1975-07-17 |
| ES396720A1 (es) | 1975-04-16 |
| FR2112504B1 (de) | 1975-10-31 |
| NL150117B (nl) | 1976-07-15 |
| DE2155081A1 (de) | 1972-05-10 |
| JPS5212200B1 (de) | 1977-04-05 |
| NL7115231A (de) | 1972-05-09 |
| CH573436A5 (de) | 1976-03-15 |
| FR2112504A1 (de) | 1972-06-16 |
| DE2155081C3 (de) | 1975-12-18 |
| ZA717433B (en) | 1972-07-26 |
| US3891635A (en) | 1975-06-24 |
| CA983920A (en) | 1976-02-17 |
| DE2166467A1 (de) | 1974-02-14 |
| HU162822B (de) | 1973-04-28 |
| GB1364453A (en) | 1974-08-21 |
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