PL122698B1 - Process for preparing novel oximes, derivatives of 7-amino-thazolyl-acetamido-cephalosporanic acid - Google Patents
Process for preparing novel oximes, derivatives of 7-amino-thazolyl-acetamido-cephalosporanic acid Download PDFInfo
- Publication number
- PL122698B1 PL122698B1 PL1977195504A PL19550477A PL122698B1 PL 122698 B1 PL122698 B1 PL 122698B1 PL 1977195504 A PL1977195504 A PL 1977195504A PL 19550477 A PL19550477 A PL 19550477A PL 122698 B1 PL122698 B1 PL 122698B1
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- Poland
- Prior art keywords
- formula
- acid
- syn
- hydrogen atom
- isomer
- Prior art date
Links
- 150000002923 oximes Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- -1 amine organic base Chemical class 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 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 claims 1
- 241000353790 Doru Species 0.000 claims 1
- 235000009754 Vitis X bourquina Nutrition 0.000 claims 1
- 235000012333 Vitis X labruscana Nutrition 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 235000014787 Vitis vinifera Nutrition 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 1
- GGWBHVILAJZWKJ-UHFFFAOYSA-N dimethyl-[[5-[2-[[1-(methylamino)-2-nitroethenyl]amino]ethylsulfanylmethyl]furan-2-yl]methyl]azanium;chloride Chemical compound Cl.[O-][N+](=O)C=C(NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-UHFFFAOYSA-N 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 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 claims 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 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis 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
- 239000007858 starting material Substances 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- 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
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia mowycih oksymów, rxchodnych kwasu 7-amino- -tiazoMo^ce(toairriido-oe^ W polskim opisie patentowym or 102 9i25 przed¬ stawiono sposób wytwarzania zwiazków, w których R oznacza irodindik fenyilowy Lub gonupe heterocylkili- ozina, gdzie otircymaino zwiazki zawierajace jedy¬ nie jeden heteroatom.Wyitwairzame zgodnie z tyim pateinteim zwiazki róznia sie wiiec budowa od zwiazków otinzymywa- nyioh zgodnie ze sposobem wedlug wynalazku, któ¬ re zawieraja girupe tiazolo lub aminotiazolu o dwóch heiteattaitomach.Sposród zwiazków hydrctoyijmrino i ailkoksyiimi- no uzyskiwanych wedlug sposobu podanego w pa¬ tencie 102 925 zastosowanie znaJazi tylko 3-kaniba- myiLoksyimetytlo-7-i[/Z/2-^^ acetaimido]-3HCeiemo-4-kadD^^ sodowy., Jed¬ nakze zwiazek ten wykazuje znacznie slabsza ak¬ tywnosc w porównaniu ze zwiazkami wytwairza- nymi sposobem wedlug wynalazku* Obecny wynalazek dotyczy sposobu wytwarzanda nowych oksymów, pochodnych kwasu 7-amdno-itda- zoMo-a<^taimido-(^iailospoaiainowego o ogólnym wizomze 1, w którym Re oznacza a/tom wodoru lub rodnik alkilowy, nasycony lub nienasycony, zawie¬ rajacy od 1 do 4 atomów wegla, A oznacza aitoim wodoru lub równowaznik metalu alkalicznego, zie- mnoaikaiicznego, magnezu lub aminowej zasady organicznej, grupa ORc wystepuje w pozycji syn. 10 15 25 30 2 W zwiazkach wyjsciowych jako gaiupy dajace sie latwo usunac przez hydrolize kwasowa lub pmzez hydirogenoliLze moga wystepowac grupy: trzeciorze¬ dowa butoksykairbonyJlowa. trityiowa, beozyflowa, dwuibeozyiLowa, trójchfloroetylowa liub karbobenzy- loksylowa.Zwiazki o wizonze 1 okreslane jako majace po¬ stac izomeru syn mozna przedstawic schematycz¬ nie za pomoca wzoru 3.Zwiazki o wzorze 2, otaresUone jako majace po¬ stac izomeru anty, mozna pmzedstawic schematycz¬ nie za pomoca wzoru 4 lub 5.Pirzedmiotem wynalazku jest w szczególnosci spo¬ sób wytwairzania zwiazków o wzorze w pozycji syn.Sposób wedlug wynalazku obejmuje /równiez wytwarzanie produktów o wzorze 1, w którym Re oznacza atom wodoru, zas A oznacza atom wodo¬ ru, altom sodu lub równowaznik diwuetyloamdny.Sposród zwiazków o wzorze 1 mozna wymienic szczególowo zwiazki opisane nizej w przykladach, a zwlaszcza: Sól sodowa kwasu 3Hacetoksymetylo-7-/2-/2-ami- no-4-tiazoiliio/-2-mj6toksy-iimino-aceitaniido/-ceif-3- -emo-4-fearboksyllowego.Kwas 3Hajcetoksymetylo-7-/B-/E-amto -2-metoksy-imino-aoetar^ ksylowy, izomer syn.Sól sodowa kwasu 3-acetoksymetylo-7-/2-/2-iamd- 122 6983 122 698 4 no-4-tiazolilo/-2-lrnetoksy-iiniino-ao6t(a!mi)do/-icef-3- -emo-4^aribokBy(lowego, izomer syn.Kwas 3-acetoksymetyilo-7-/2^-amiin^ lo/-2Hnetoksy-irniino-ac^ ksyilowy.Sól sodowa kwasu 3-acetylometyio-7-/2-/2-ami- no-4-taazolJiW-2-metofcsyHi^ -emo-4nkariboksyiowego.Krystalizowana sód sodowa kwasu 3nacefoiksyime- tyilo-7-/2Wlaimiino-4-tiazol^^ tamdid PL PL
Claims (3)
1.Zastrzezenia patentowe 1. Sposób wytwarzania nowych oksymów, pocho¬ dnych kwasu 7-amdno-tiazoliilo-acetamiido-oefalo- 5 sporanowego o wzorze 1, w którym Re oznacza atom wodoru lub irodnik alkilowy, nasycony v lulb nienasycony, zawierajajcy od 1 do 4 atomów wegla,
2. A oznacza badz atom wodoru, badz równowaznik metalu alkalicznego, ziemno-alkaldioznego, magnezu 10 lub aminowej zasady organicznej, grupa ORe znaj¬ duje sie w pozycji syn, znamienny tym, ze kwas 7-aimino-cefalosporanowy o wzorze 6 poddaje sie re¬ akcji z kwasem o wzorize 7 izomer syn lulb z po¬ chodna (funkcyjna tego kwasu o wzorze 7, w któ- 15 rym Hd oznacza grupe dajaca sie latwo usunac przez hydrolize kwasowa taka jak grupa III nz. bu- toksykaribonylowa albo triltyloiwa, lufo przez hydro- genolize taka jak grupa trój^Moroetyilowa, benzy¬ lowa, dwuibenzylowa i kairibobenzyloksylowa, zas 20 R'd ma znaczenie podane dla Rd a ponadto oznacza rodnik alkilowy, nasycony lub nienasycony, zawie¬ rajacy od 1 do 4 atomów wegla, w celu otrzyma- nda zwiazku o wzorze 8 izomer syn, w którym Rd i R'd maja wyzej podane znaczenie, który ewentu- 25 ainde hydroldzuje sie w srodowisku kwasnym lub hydrogenoiizuje, otrzymujac zwiazek o wzorze 1, izomer syn, w którym A oznacza atom wodoru, a Re ma wyzej podane znaczenie, który ewentual¬ nie przeprowadza sie w sól. 302. Sposób wytwarzania nowych oksymów, pochod¬ nych kwasu 7-aminoHtiazolillD-acetan^ ramowego o wzorze 1, w którym Re oznacza altom wodoru lub rodnik alkilowy, nasycony luib nienasy¬ cony, zawierajacy od 1 do 4 atomów wegla, A ozna- 35 cza badz atom wodoru, badz równowaznik metalu alkaOtioznego, ziemno^alkalicznego, magnezu lub ami¬ nowej zasady organicznej, grupa ORc znajduje sie w pozycji syn, znamienny tym, ze kwas 7-arnino- -cefalosporanowy o wzorze 6 poddaje sie reakcji 40 z kwasem o wzorze 7 izomer syn lub z pochodna funkcyjna tego kwasu o 'wzorze 7, w którym Rd oznacza grupe dajaca sie latwo usunac przez hy¬ drolize kwasowa taka jak grupa III nz. butoksykar- bonylowa albo tritylowa, R'd ma znaczenie podane 45 dla iRd a ponadto oznacza rodnik alkilowy, nasy¬ cony lub nienasycony, zawierajacy od 1 do 4 ato¬ mów wegla, otrzymujac zwiazek o wzorze 8 izomer syn, w którym Rd i R'd maja wyzej podane zna¬ czenie, który przeprowadza sie w sól a nastepnie 50 hydrolizuje sie w srodowiisku kwasnym otrzymujac zfwdaizek o wzorze 1, izomer syn, w którym A ozna¬ cza altom wodoru, a Re ma wyzej podane znaczenie, który ewentualnie przeprowadza sie w sól.
3. Sposób wytwarzania nowych oksymów, pochod- 55 nych kwasu 7^aimtiino-itiaizoMoHac^^ ranowego o wzorze 1, w którym Re oznacza atom wodoru lub rodnik alkilowy, nasycony lub niena¬ sycony, zawierajacy od 1 do 4 atomów wegla, A oznacza badz atom wodoru, badz równowaznik me- 60 talu alkalicznego, ziemno-alkalicznego, magnezu luib amonowej zasady oirganiesznej, grupa ORc znaj¬ duje sie w pozycji syn, znamienny tym, ze kwas 7-aniino-cefalosporanowy o wzorze 6 poddaje sie reakcji z kwasem o wzorze 7 izomer syn, lub z «5 pochodna funkcyjna tego kwasu o wzorze 7, w któ-122 698 33 rym Rd oznacza grape chloroacetylowa, a R'd ma znaczenie podane dla Rd a ponadto oznacza rod¬ nik aillkillowy, nasycony lub nienasycony, zawiera¬ jacy od 1 do 4 atomów wegla, otrzymujac zwiazek o wzorze 8 izomer syn, w którym Rd i R'd maja wyzej podane znaczenie, który ewentualnie przepro¬ wadza sie w sól a nastepnie traktuje tiomocznd- 34 kiem, otrzymujac zwiazek o wzorze 1, izomer syn, w którym A oznacza badz atom wodoru badz rów¬ nowaznik metalu alkalicznego, ziemno-alkalicznego, magnezu iiub aminowej zasady organicznej, a Re ma wyzej podane znaczenie, który ewentualnie przeprowadza sie w sól, gdy A oznacza atom wo¬ doru. VH2 0 SAN Jl fi NHVS1 N 0^NYVrO-C-CH, 1 CO A " 3 ORc UU2A 0 WZÓR 1 NH-R II 0 N 0 T^CH9-0- OR" ~°2 WZÓR 2 ¦" '2 w n~CH3 0 NH N \_-^S\| ^ ^ 2 8 3 WZÓR 3 tf O^Y^CH2-OC-CH3 C02A l Wzór A I n o o^NY^cH2-g-c-cH3 OR' C°2A 0 Wzór 5 h2Nyys"i 0-NY^CH2-0-Cj-CH3 C02H 0 Wzór 6122 698 NH-Rd S^N C-C02H N I OR'd WZÓR 7 NH-Rd ^M O S SN I O Y CH9-0-C0-CHo 0R'd C02H 2 3 WZÓR 8 NH2 X„ o "N NH^^S^ i o y ch2-o-co-ch3 0Rc C02H WZÓR 9 Drukarnia Narodowa, Zaklad Nr 6, 519/83 Cena 100 zl PL PL PL
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7601834A FR2346014A1 (fr) | 1976-01-23 | 1976-01-23 | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| FR7617743A FR2361893A2 (fr) | 1976-01-23 | 1976-06-11 | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| FR7625051A FR2361894A2 (fr) | 1976-01-23 | 1976-08-18 | Nouvelles oximes derivees de l'acide 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL195504A1 PL195504A1 (pl) | 1978-03-13 |
| PL122698B1 true PL122698B1 (en) | 1982-08-31 |
Family
ID=27250574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977195504A PL122698B1 (en) | 1976-01-23 | 1977-01-22 | Process for preparing novel oximes, derivatives of 7-amino-thazolyl-acetamido-cephalosporanic acid |
Country Status (31)
| Country | Link |
|---|---|
| JP (3) | JPS52102293A (pl) |
| AR (1) | AR231985A1 (pl) |
| AT (2) | AT355205B (pl) |
| AU (1) | AU511680B2 (pl) |
| BE (1) | BE850662A (pl) |
| CA (1) | CA1319682C (pl) |
| CH (1) | CH622264A5 (pl) |
| CY (1) | CY1123A (pl) |
| DD (2) | DD128594A5 (pl) |
| DE (3) | DE2760287C2 (pl) |
| DK (1) | DK161082C (pl) |
| ES (2) | ES455089A1 (pl) |
| GB (2) | GB1580623A (pl) |
| GE (1) | GEP19970783B (pl) |
| GR (1) | GR70302B (pl) |
| HK (1) | HK50381A (pl) |
| HU (1) | HU173110B (pl) |
| IE (1) | IE45015B1 (pl) |
| IL (2) | IL51192A (pl) |
| IT (1) | IT1104601B (pl) |
| KE (1) | KE3365A (pl) |
| LU (1) | LU76624A1 (pl) |
| MX (1) | MX4407E (pl) |
| MY (1) | MY8500417A (pl) |
| NL (1) | NL7700706A (pl) |
| NZ (1) | NZ183150A (pl) |
| PL (1) | PL122698B1 (pl) |
| PT (1) | PT66099B (pl) |
| SE (2) | SE440655B (pl) |
| SU (1) | SU822754A3 (pl) |
| YU (3) | YU41060B (pl) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2408613A2 (fr) * | 1977-07-19 | 1979-06-08 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| GB1576625A (en) * | 1976-04-12 | 1980-10-08 | Fujisawa Pharmaceutical Co | Syn isomer 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 |
| GR63088B (en) * | 1976-04-14 | 1979-08-09 | Takeda Chemical Industries Ltd | Preparation process of novel cephalosporins |
| PH17188A (en) | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| ZA781502B (en) * | 1977-03-14 | 1979-09-26 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and processes for preparation thereof |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| 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 |
| JPS5444695A (en) * | 1977-09-13 | 1979-04-09 | Fujisawa Pharmaceut Co Ltd | 3,7-disubstituted-3-cephem-4-carboxylic acid and its salt and their preparation |
| 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 |
| JPS5498795A (en) * | 1978-01-13 | 1979-08-03 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| 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 |
| FR2432521A1 (fr) * | 1978-03-31 | 1980-02-29 | Roussel Uclaf | Nouvelles oximes o-substituees derivees de l'acide 7-amino thiazolyl acetamido 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 |
| US4284631A (en) * | 1978-07-31 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them |
| FR2448543A1 (fr) * | 1979-02-09 | 1980-09-05 | Roussel Uclaf | Nouvelles oximes o-substituees par un radical comportant un ammonium quaternaire et derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| FR2461713A1 (fr) * | 1979-07-19 | 1981-02-06 | Roussel Uclaf | Nouvelles alcoyloximes substituees derivees de l'acide 7-(2-amino 4-thiazolyl) acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| FR2461712A1 (fr) * | 1979-07-23 | 1981-02-06 | Hoechst Ag | Procede de preparation de derives de cepheme |
| JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
| FR2506307A1 (fr) * | 1981-05-22 | 1982-11-26 | Roussel Uclaf | Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation |
| JPS57163386A (en) * | 1981-08-13 | 1982-10-07 | Takeda Chem Ind Ltd | Cephalosporin derivative and its production |
| CA1296012C (en) | 1986-03-19 | 1992-02-18 | Susumu Nakagawa | 6,7-dihydroxy-isoquinoline derivatives |
| HUT53892A (en) * | 1989-04-07 | 1990-12-28 | Technologishen Kom Za Promy Mi | Process for producing synaminothiazolyl and synaminooxazolyl derivatives |
| CN112457271A (zh) * | 2020-11-18 | 2021-03-09 | 河北合佳医药科技集团股份有限公司 | 一种氨噻肟酸中间体的连续流合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| 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 |
| GB1536281A (en) * | 1975-06-09 | 1978-12-20 | Takeda Chemical Industries Ltd | Cephem compounds |
| DE2760123C2 (de) | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| 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 |
-
1976
- 1976-12-29 SE SE7614678A patent/SE440655B/xx not_active IP Right Cessation
- 1976-12-31 IL IL51192A patent/IL51192A/xx unknown
-
1977
- 1977-01-15 ES ES455089A patent/ES455089A1/es not_active Expired
- 1977-01-18 SU SU772439818A patent/SU822754A3/ru active
- 1977-01-19 AR AR266241A patent/AR231985A1/es active
- 1977-01-19 YU YU137/77A patent/YU41060B/xx unknown
- 1977-01-20 IT IT47727/77A patent/IT1104601B/it active Protection Beyond IP Right Term
- 1977-01-20 MX MX775372U patent/MX4407E/es unknown
- 1977-01-21 CY CY1123A patent/CY1123A/xx unknown
- 1977-01-21 GB GB15561/79A patent/GB1580623A/en not_active Expired
- 1977-01-21 DE DE2760287A patent/DE2760287C2/de not_active Expired
- 1977-01-21 PT PT66099A patent/PT66099B/pt unknown
- 1977-01-21 DE DE2759895A patent/DE2759895C2/de not_active Expired
- 1977-01-21 DD DD7700197036A patent/DD128594A5/xx unknown
- 1977-01-21 DK DK023677A patent/DK161082C/da active
- 1977-01-21 NZ NZ183150A patent/NZ183150A/xx unknown
- 1977-01-21 LU LU76624A patent/LU76624A1/xx unknown
- 1977-01-21 GB GB2640/77A patent/GB1580621A/en not_active Expired
- 1977-01-21 CH CH78777A patent/CH622264A5/fr not_active IP Right Cessation
- 1977-01-21 HU HU77RO909A patent/HU173110B/hu unknown
- 1977-01-21 DD DD7700200629A patent/DD132869A5/xx unknown
- 1977-01-21 JP JP504977A patent/JPS52102293A/ja active Granted
- 1977-01-21 DE DE2702501A patent/DE2702501C2/de not_active Expired
- 1977-01-21 BE BE174311A patent/BE850662A/xx not_active IP Right Cessation
- 1977-01-21 CA CA000270375A patent/CA1319682C/fr not_active Expired - Lifetime
- 1977-01-22 PL PL1977195504A patent/PL122698B1/pl unknown
- 1977-01-22 GR GR52630A patent/GR70302B/el unknown
- 1977-01-24 AU AU21579/77A patent/AU511680B2/en not_active Expired
- 1977-01-24 IE IE148/77A patent/IE45015B1/en not_active IP Right Cessation
- 1977-01-24 AT AT41277A patent/AT355205B/de not_active IP Right Cessation
- 1977-01-24 NL NL7700706A patent/NL7700706A/xx not_active Application Discontinuation
-
1978
- 1978-02-01 ES ES466539A patent/ES466539A1/es not_active Expired
-
1979
- 1979-03-20 AT AT0209479A patent/AT373592B/de not_active IP Right Cessation
- 1979-05-31 IL IL57445A patent/IL57445A0/xx not_active IP Right Cessation
-
1981
- 1981-10-22 HK HK503/81A patent/HK50381A/xx unknown
-
1982
- 1982-08-26 SE SE8204893A patent/SE455307B/sv not_active IP Right Cessation
-
1983
- 1983-01-04 YU YU11/83A patent/YU43143B/xx unknown
- 1983-01-04 YU YU00012/83A patent/YU1283A/xx unknown
-
1984
- 1984-01-11 KE KE3365A patent/KE3365A/xx unknown
-
1985
- 1985-12-30 MY MY417/85A patent/MY8500417A/xx unknown
-
1990
- 1990-04-19 JP JP2101872A patent/JPH03204868A/ja active Pending
-
1993
- 1993-01-20 JP JP5023427A patent/JPH05247013A/ja active Pending
- 1993-09-09 GE GEAP19931537A patent/GEP19970783B/en unknown
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