SU425402A3 - Способ получения производных 7-аминоцефалоспорановой кислоты - Google Patents

Способ получения производных 7-аминоцефалоспорановой кислоты

Info

Publication number: SU425402A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; solution; group; methylene chloride; substituted
Prior art date: 1968-01-02

Application number

SU1295124A

Other languages

English (en)

Russian (ru)

Original Assignee

Ганс Бикель, Рольф Боссгард, Бруно Фехтиг, Енрико Менард, Иоганнес Мюллер , Гейнрих Петер

Иностранна фирма

Циба Гейги

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-01-02

Filing date

1969-01-02

Publication date

1974-04-25

1969-01-02 Application filed by Ганс Бикель, Рольф Боссгард, Бруно Фехтиг, Енрико Менард, Иоганнес Мюллер , Гейнрих Петер, Иностранна фирма, Циба Гейги filed Critical Ганс Бикель, Рольф Боссгард, Бруно Фехтиг, Енрико Менард, Иоганнес Мюллер , Гейнрих Петер

1974-04-25 Application granted granted Critical

1974-04-25 Publication of SU425402A3 publication Critical patent/SU425402A3/ru

Links

238000000034 method Methods 0.000 title claims description 14
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title description 3
-1 mercaptoacetyl group Chemical group 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 8
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
150000003566 thiocarboxylic acids Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 35
235000019439 ethyl acetate Nutrition 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000008346 aqueous phase Substances 0.000 description 14
159000000000 sodium salts Chemical class 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000012071 phase Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000008363 phosphate buffer Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000012047 saturated solution Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
239000005909 Kieselgur Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
235000019796 monopotassium phosphate Nutrition 0.000 description 3
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
KKHBRTFQIYIHEI-UHFFFAOYSA-N 4,5-dimethyl-3h-1,3-thiazole-2-thione Chemical compound CC=1N=C(S)SC=1C KKHBRTFQIYIHEI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
108010013043 Acetylesterase Proteins 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
102100036617 Monoacylglycerol lipase ABHD2 Human genes 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
HSAJRDKFYZAGLU-UHFFFAOYSA-M perchloryloxymercury Chemical compound [Hg+].[O-]Cl(=O)(=O)=O HSAJRDKFYZAGLU-UHFFFAOYSA-M 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
STUWXYZZZISNAM-UHFFFAOYSA-M sodium;hydrogen carbonate;propan-2-one Chemical compound [Na+].CC(C)=O.OC([O-])=O STUWXYZZZISNAM-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Husbandry (AREA)
Zoology (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Cephalosporin Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SU1295124A 1968-01-02 1969-01-02 Способ получения производных 7-аминоцефалоспорановой кислоты SU425402A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH168A CH511890A (de)	1968-01-02	1968-01-02	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure

Publications (1)

Publication Number	Publication Date
SU425402A3 true SU425402A3 (ru)	1974-04-25

Family

ID=4177159

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1295124A SU425402A3 (ru)	1968-01-02	1969-01-02	Способ получения производных 7-аминоцефалоспорановой кислоты

Country Status (4)

Country	Link
AT (2)	AT297925B (de)
CH (2)	CH511890A (de)
ES (1)	ES361988A1 (de)
SU (1)	SU425402A3 (de)

1968
- 1968-01-02 CH CH168A patent/CH511890A/de not_active IP Right Cessation
- 1968-01-02 CH CH1220070A patent/CH505146A/de not_active IP Right Cessation
- 1968-12-30 AT AT00145/70A patent/AT297925B/de not_active IP Right Cessation
- 1968-12-30 AT AT1268468A patent/AT283595B/de not_active IP Right Cessation
- 1968-12-30 ES ES361988A patent/ES361988A1/es not_active Expired
1969
- 1969-01-02 SU SU1295124A patent/SU425402A3/ru active

Also Published As

Publication number	Publication date
CH505146A (de)	1971-03-31
CH511890A (de)	1971-08-31
SU402222A3 (de)	1973-10-12
ES361988A1 (es)	1970-11-01
AT297925B (de)	1972-03-15
AT283595B (de)	1970-08-10

Publication	Publication Date	Title
US5386032A (en)	1995-01-31	Method of synthesis of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl-1H-benzimidazole (omeprazole)
EP0126709A1 (de)	1984-11-28	Verfahren zur Herstellung von optisch aktiven Azetidinonen
US4613666A (en)	1986-09-23	Neplanocin A derivatives
SU425402A3 (ru)	1974-04-25	Способ получения производных 7-аминоцефалоспорановой кислоты
FI77459B (fi)	1988-11-30	Foerfarande foer framstaellning av (5r)-penemderivat.
DE2431484C2 (de)	1982-10-21	Verfahren zur Herstellung von 7 beta- Amino-7 alpha-methoxy-3-cephemestern
EP0226093B1 (de)	1993-06-16	Verfahren zur Herstellung von Cefodizim
FI75168C (fi)	1988-05-09	Foerfarande foer framstaellning av natriumcefuroxim eller ett solvat daerav och natriumcefuroximtetrahydrofuransolvat anvaendbart som mellanprodukt vid foerfarandet.
FR2565590A1 (fr)	1985-12-13	Procede de preparation d'aminohydroxycephamcarboxylates
US4051129A (en)	1977-09-27	Process for preparing 7-methoxycephalosporin compounds
SE505050C2 (sv)	1997-06-16	Process för framställning av cephemderivat
HK52487A (en)	1987-07-17	Process and intermediates for production of 1,1-dioxopenicillanoyloxymethyl 6-(2-amino-2-phenylacetamido)penicillanates
KR910006983B1 (ko)	1991-09-14	피리딘 유도체의 제조방법
US4183850A (en)	1980-01-15	Process for preparing 2-acyloxymethylpenams and 3-acyloxycephams
SU410590A3 (de)	1974-01-05
DE1816824A1 (de)	1969-07-31	Verfahren zur Herstellung von Acylaminoverbindungen
EP0098478B1 (de)	1985-11-06	Verfahren zur Herstellung von 7-Amino-1-dethia-1-oxa-3-hydroymethyl-cephem-4-carbonsäuren
SU419040A3 (ru)	1974-03-05	Способ получения производных7-ациламиноцефалоспоранобой кислоты
US4058660A (en)	1977-11-15	Process for the conversion of 6-aminopenicillanic acid (6-APA) in 7-aminodesacetoxycephalosporanic acid (7-ADCA)
US4352935A (en)	1982-10-05	Process for obtaining P-acetamido phenol α-methyl-4(2'thienyl-carbonyl) phenyl acetate
US4148995A (en)	1979-04-10	Process for preparing cephem lactones for cephalosporin-type antibiotics
CS196272B2 (en)	1980-03-31	Method of producing delta up 3-cephalosporin esters
Allan et al.	1974	Transformations of penicillins. Part VI. Preparation and reactions of thiosulphonate S-esters derived from penicillin S-oxides
Sheehan et al.	1977	Synthesis and reactions of 7-hydrazonocephalosporanates
SU432723A3 (ru)	1974-06-15	Способ получения производных 7-аминоцефалоспорановой кислоты