SE436360B - N,n-dimetylacetamidaddukten av 7-/d(-)-alfa-(4-etyl-2,3-dioxo-1-piperazinkarboxamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-1,2,3,4-tetrazolyl)tiometyl/-delta?723-cefem-4-karboxylsyra - Google Patents
N,n-dimetylacetamidaddukten av 7-/d(-)-alfa-(4-etyl-2,3-dioxo-1-piperazinkarboxamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-1,2,3,4-tetrazolyl)tiometyl/-delta?723-cefem-4-karboxylsyraInfo
- Publication number
- SE436360B SE436360B SE7810106A SE7810106A SE436360B SE 436360 B SE436360 B SE 436360B SE 7810106 A SE7810106 A SE 7810106A SE 7810106 A SE7810106 A SE 7810106A SE 436360 B SE436360 B SE 436360B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- dimethylacetamide
- compound
- methyl
- tetrazolyl
- Prior art date
Links
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical class CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 title claims description 59
- -1 4-ETHYL-2,3-DIOXO-1-PIPERAZINE CARBOXAMIDO Chemical class 0.000 title claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 23
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 15
- 238000005917 acylation reaction Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
- 230000010933 acylation Effects 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000013078 crystal Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000002474 experimental method Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- NCFTXMQPRQZFMZ-WERGMSTESA-M Cefoperazone sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C([O-])=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 NCFTXMQPRQZFMZ-WERGMSTESA-M 0.000 description 11
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000005051 trimethylchlorosilane Substances 0.000 description 5
- IPARGUVYMOMVNU-UHFFFAOYSA-N 2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetic acid Chemical compound O=C1C(=O)N(CC)CCN1C(=O)NC(C(O)=O)C1=CC=C(O)C=C1 IPARGUVYMOMVNU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52115127A JPS6056718B2 (ja) | 1977-09-27 | 1977-09-27 | セフアロスポリンの製法 |
| JP52115126A JPS6056717B2 (ja) | 1977-09-27 | 1977-09-27 | セフアロスポリンのｎ，ｎ−ジメチルアセトアミド付加体及びその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7810106L SE7810106L (sv) | 1979-03-28 |
| SE436360B true SE436360B (sv) | 1984-12-03 |
Family
ID=26453712
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7810106A SE436360B (sv) | 1977-09-27 | 1978-09-26 | N,n-dimetylacetamidaddukten av 7-/d(-)-alfa-(4-etyl-2,3-dioxo-1-piperazinkarboxamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-1,2,3,4-tetrazolyl)tiometyl/-delta?723-cefem-4-karboxylsyra |
| SE8306226A SE447732B (sv) | 1977-09-27 | 1983-11-11 | Nytt forfarande for rening av 7-/d(-)-alfa-(4-etyl-2,3-dioxo-l-piperazinkarboxamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-tetrazolyl)tiometyl/-delta?723-cefem-4-karboxylsyra |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8306226A SE447732B (sv) | 1977-09-27 | 1983-11-11 | Nytt forfarande for rening av 7-/d(-)-alfa-(4-etyl-2,3-dioxo-l-piperazinkarboxamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-tetrazolyl)tiometyl/-delta?723-cefem-4-karboxylsyra |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4237280A (pt) |
| AR (1) | AR223653A1 (pt) |
| AT (1) | AT362502B (pt) |
| AU (1) | AU513336B2 (pt) |
| CA (1) | CA1102309A (pt) |
| CH (1) | CH637967A5 (pt) |
| DD (1) | DD141835A5 (pt) |
| DE (1) | DE2841706C2 (pt) |
| DK (2) | DK164705C (pt) |
| ES (1) | ES473692A1 (pt) |
| FI (1) | FI71743C (pt) |
| FR (1) | FR2409270A1 (pt) |
| GB (1) | GB2005676B (pt) |
| HU (1) | HU177912B (pt) |
| IL (1) | IL55607A (pt) |
| IN (1) | IN149604B (pt) |
| MX (1) | MX5571E (pt) |
| NL (1) | NL7809736A (pt) |
| PT (1) | PT68594A (pt) |
| SE (2) | SE436360B (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100388108B1 (ko) * | 2000-08-11 | 2003-06-18 | 주식회사종근당 | 세팔로스포린계 항생제 중간체 신규 제조방법 |
| CN102532168A (zh) * | 2011-12-27 | 2012-07-04 | 山东鑫泉医药有限公司 | 头孢哌酮酸的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
| US3714157A (en) * | 1970-10-23 | 1973-01-30 | Bristol Myers Co | PROCESS FOR THE DECOLORIZATION OF 7-[ alpha -(4-PYRIDYLTHIO)ACETAMIDO]CEPHALOSPORANIC ACID |
| US3781282A (en) * | 1971-01-20 | 1973-12-25 | W Garbrecht | Cephalosporin process and product |
| US4112090A (en) * | 1974-05-09 | 1978-09-05 | Toyama Chemical Co., Ltd. | Novel penicillins and cephalosporins and process for producing the same |
| US3954745A (en) * | 1974-09-12 | 1976-05-04 | Eli Lilly And Company | Process for preparing cefazolin |
| US4117126A (en) * | 1975-04-03 | 1978-09-26 | Sumitomo Chemical Company, Ltd. | 7-(α-(4-Hydroxy-1,5-naphthyridine-3-carbonamido)-α-phenylacetamido) cephalosporin derivatives |
| US4037922A (en) * | 1975-07-07 | 1977-07-26 | Corning Glass Works | Optical waveguide cable |
| US4064345A (en) * | 1975-12-12 | 1977-12-20 | Bristol-Myers Company | Cephalosporins derivatives 7-cyclized α-amino-3-heterothio |
| US4145418A (en) * | 1976-01-06 | 1979-03-20 | Takeda Chemical Industries, Ltd. | Thienopyridine substituted cephalosporins |
| US4103008A (en) * | 1976-04-07 | 1978-07-25 | Ishimaru Toshiyasu | 7[2(2,3 Dioxopiperazin-1-yl-carbonylamino)substituted 2 phenylacetamido]-3-2'-thiadiazolyl cephalosporanic acid derivatives |
-
1978
- 1978-06-26 AR AR273853A patent/AR223653A1/es active
- 1978-09-18 AU AU39923/78A patent/AU513336B2/en not_active Expired
- 1978-09-18 IN IN1020/CAL/78A patent/IN149604B/en unknown
- 1978-09-20 IL IL55607A patent/IL55607A/xx unknown
- 1978-09-22 FR FR7827249A patent/FR2409270A1/fr active Granted
- 1978-09-25 DE DE2841706A patent/DE2841706C2/de not_active Expired
- 1978-09-25 GB GB7838036A patent/GB2005676B/en not_active Expired
- 1978-09-25 CA CA312,056A patent/CA1102309A/en not_active Expired
- 1978-09-25 FI FI782912A patent/FI71743C/fi not_active IP Right Cessation
- 1978-09-25 US US05/945,346 patent/US4237280A/en not_active Expired - Lifetime
- 1978-09-25 CH CH996678A patent/CH637967A5/fr not_active IP Right Cessation
- 1978-09-25 DD DD78208068A patent/DD141835A5/de not_active IP Right Cessation
- 1978-09-26 AT AT693878A patent/AT362502B/de not_active IP Right Cessation
- 1978-09-26 SE SE7810106A patent/SE436360B/sv not_active IP Right Cessation
- 1978-09-26 DK DK426778A patent/DK164705C/da not_active IP Right Cessation
- 1978-09-26 HU HU78TO1098A patent/HU177912B/hu unknown
- 1978-09-26 ES ES473692A patent/ES473692A1/es not_active Expired
- 1978-09-26 NL NL7809736A patent/NL7809736A/xx active Search and Examination
- 1978-09-26 PT PT68594A patent/PT68594A/pt unknown
- 1978-09-27 MX MX787431U patent/MX5571E/es unknown
-
1979
- 1979-08-24 US US06/069,545 patent/US4304909A/en not_active Expired - Lifetime
-
1983
- 1983-11-11 SE SE8306226A patent/SE447732B/sv not_active IP Right Cessation
-
1991
- 1991-12-06 DK DK197391A patent/DK164405C/da not_active IP Right Cessation
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