SU656524A3 - Способ получени 6-метокси- карбоксипенициллинов или их солей - Google Patents

Способ получени 6-метокси- карбоксипенициллинов или их солей

Info

Publication number: SU656524A3
Authority: SU; USSR - Soviet Union
Prior art keywords: proton; acid; benzyl; methoxy; thienyl
Prior art date: 1975-01-17

Application number

SU762314154A

Other languages

English (en)

Russian (ru)

Inventor

Питер Клейтон Джон

Хьюберт Бентли Питер

Original Assignee

Бичам Груп Лимитед (Фирма)

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.)

1975-01-17

Filing date

1976-01-16

Publication date

1979-04-05

1975-01-17 Priority claimed from GB2021/75A external-priority patent/GB1538051A/en

1976-01-16 Application filed by Бичам Груп Лимитед (Фирма) filed Critical Бичам Груп Лимитед (Фирма)

1979-04-05 Application granted granted Critical

1979-04-05 Publication of SU656524A3 publication Critical patent/SU656524A3/ru

Links

238000000034 method Methods 0.000 title description 6
150000003839 salts Chemical class 0.000 title description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
-1 nitro, methyl Chemical group 0.000 description 29
239000000243 solution Substances 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
238000004809 thin layer chromatography Methods 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000002253 acid Substances 0.000 description 19
150000001875 compounds Chemical class 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000003208 petroleum Substances 0.000 description 13
159000000000 sodium salts Chemical class 0.000 description 13
125000001544 thienyl group Chemical group 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000003118 aryl group Chemical group 0.000 description 11
239000000203 mixture Substances 0.000 description 11
230000002378 acidificating effect Effects 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
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 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
230000010933 acylation Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
229910052681 coesite Inorganic materials 0.000 description 5
229910052906 cristobalite Inorganic materials 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
229910052682 stishovite Inorganic materials 0.000 description 5
229910052905 tridymite Inorganic materials 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000012264 purified product Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 1
YJGUVTBNQCVSQB-UHFFFAOYSA-N 2,2-diphenylpropanedioic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(C(=O)O)C1=CC=CC=C1 YJGUVTBNQCVSQB-UHFFFAOYSA-N 0.000 description 1
QXZCJFLPEVHQAQ-UHFFFAOYSA-N 2-[3-(2,3-dihydro-1h-inden-1-yl)phenyl]propanedioic acid Chemical compound OC(=O)C(C(O)=O)C1=CC=CC(C2C3=CC=CC=C3CC2)=C1 QXZCJFLPEVHQAQ-UHFFFAOYSA-N 0.000 description 1
OASFMZFYUHQEFW-UHFFFAOYSA-N 3-(3,4-dimethylphenoxy)-3-oxo-2-phenylpropanoic acid Chemical compound C1=C(C)C(C)=CC=C1OC(=O)C(C(O)=O)C1=CC=CC=C1 OASFMZFYUHQEFW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
101100107555 Mus musculus Aarsd1 gene Proteins 0.000 description 1
101100127288 Mus musculus Kif1a gene Proteins 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002372 labelling Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU762314154A 1975-01-17 1976-01-16 Способ получени 6-метокси- карбоксипенициллинов или их солей SU656524A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2021/75A GB1538051A (en)	1975-01-17	1975-01-17	6-methoxy-6-(alpha-carboxyacetamido)-penicillins

Publications (1)

Publication Number	Publication Date
SU656524A3 true SU656524A3 (ru)	1979-04-05

Family

ID=9732205

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
SU762314154A SU656524A3 (ru)	1975-01-17	1976-01-16	Способ получени 6-метокси- карбоксипенициллинов или их солей
SU762314153A SU623519A3 (ru)	1975-01-17	1976-01-16	Способ получени 6-метокси- -карбоксипенициллиной или их солей
SU762421803A SU703022A3 (ru)	1975-01-17	1976-11-23	Способ получени 6-метокси- -карбоксипенициллинов или их солей

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
SU762314153A SU623519A3 (ru)	1975-01-17	1976-01-16	Способ получени 6-метокси- -карбоксипенициллиной или их солей
SU762421803A SU703022A3 (ru)	1975-01-17	1976-11-23	Способ получени 6-метокси- -карбоксипенициллинов или их солей

Country Status (7)

Country	Link
AT (5)	AT353955B (de)
HU (2)	HU172217B (de)
MY (1)	MY8200281A (de)
PL (3)	PL117562B1 (de)
SU (3)	SU656524A3 (de)
ZA (2)	ZA76145B (de)
ZM (2)	ZM376A1 (de)

1976
- 1976-01-07 ZM ZM376A patent/ZM376A1/xx unknown
- 1976-01-07 ZM ZM476A patent/ZM476A1/xx unknown
- 1976-01-12 ZA ZA00760145A patent/ZA76145B/xx unknown
- 1976-01-12 ZA ZA00760144A patent/ZA76144B/xx unknown
- 1976-01-14 AT AT22176A patent/AT353955B/de not_active IP Right Cessation
- 1976-01-14 AT AT22076A patent/AT351674B/de not_active IP Right Cessation
- 1976-01-16 SU SU762314154A patent/SU656524A3/ru active
- 1976-01-16 HU HU76BE00001254A patent/HU172217B/hu unknown
- 1976-01-16 SU SU762314153A patent/SU623519A3/ru active
- 1976-01-16 HU HU76BE1249A patent/HU175572B/hu not_active IP Right Cessation
- 1976-01-17 PL PL21244176A patent/PL117562B1/pl unknown
- 1976-01-17 PL PL18659876A patent/PL106332B1/pl unknown
- 1976-01-17 PL PL21109976A patent/PL116672B1/pl unknown
- 1976-11-23 SU SU762421803A patent/SU703022A3/ru active
1977
- 1977-09-28 AT AT692977A patent/AT353965B/de not_active IP Right Cessation
1978
- 1978-05-29 AT AT387378A patent/AT354630B/de not_active IP Right Cessation
- 1978-05-29 AT AT387478A patent/AT354631B/de not_active IP Right Cessation
1982
- 1982-12-30 MY MY281/82A patent/MY8200281A/xx unknown

Also Published As

Publication number	Publication date
HU175572B (hu)	1980-09-28
ATA692977A (de)	1979-05-15
SU623519A3 (ru)	1978-09-05
HU172217B (hu)	1978-07-28
PL116672B1 (en)	1981-06-30
AT354630B (de)	1979-01-25
AT353955B (de)	1979-12-10
AT351674B (de)	1979-08-10
SU703022A3 (ru)	1979-12-05
PL117562B1 (en)	1981-08-31
ATA387478A (de)	1979-06-15
ATA22176A (de)	1979-05-15
PL106332B1 (pl)	1979-12-31
ZA76144B (en)	1976-12-29
MY8200281A (en)	1982-12-31
ZM376A1 (en)	1977-08-22
AT353965B (de)	1979-12-10
ZA76145B (en)	1976-12-29
ATA22076A (de)	1979-01-15
AT354631B (de)	1979-01-25
ATA387378A (de)	1979-06-15
ZM476A1 (en)	1977-06-21

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FR1449628A (fr)	1966-08-19	Procédé de préparation d'indoles polynucléaires désacylés, notamment d'esters de la série de la désacétyl-vincaleucoblastine et de la désacétyl-vincristine
US5059596A (en)	1991-10-22	Azabicyclo compounds
CA1131620A (en)	1982-09-14	Penicillins and cephalosporins
CA1055016A (en)	1979-05-22	7.alpha.-LOWER ALKOXY-7.beta.-(2-ARYL-2-HYDROXYIMINOACETAMIDO) CEPH-3-EM-4-CARBOXYLIC ACIDS
JPS6237037B2 (de)	1987-08-10
JP2000109497A (ja)	2000-04-18	スピロ環式ｃ―グリコシド
US3966717A (en)	1976-06-29	7-β-Acylamido-3-carbamoyloxymethylceph-3-em-4-carboxylic acids and salts thereof
US4140698A (en)	1979-02-20	1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles
CA2497632A1 (fr)	2004-03-04	Nouveaux derives de thiophene, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JPS638107B2 (de)	1988-02-19
SU656524A3 (ru)	1979-04-05	Способ получени 6-метокси- карбоксипенициллинов или их солей
FR2676057A1 (fr)	1992-11-06	Derives de 1,2-dithiole-3-thione, procede de preparation de ces derives, ainsi que l'utilisation de ces derives comme intermediaires de synthese ou comme medicaments.
US3976641A (en)	1976-08-24	Cephalosporin intermediates and process therefor
JPH06166681A (ja)	1994-06-14	キナ酸誘導体およびその製造方法
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FR2536075A1 (fr)	1984-05-18	Nouveaux derives de la nitrosouree, leur procede de preparation et les compositions pharmaceutiques les renfermant
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EP0217375B1 (de)	1991-01-16	Verfahren zur Herstellung von optisch aktiven Carbonylverbindungen
Cartwright et al.	1949	334. The chemistry of fungi. Part VII. Syntheses of citrinin and dihydrocitrinin
Aratani et al.	1980	Synthesis of 1-oxa-2-oxocephalosporins
JPS6046116B2 (ja)	1985-10-14	置換セファロスポリン類の製造法
US3936443A (en)	1976-02-03	Penicillin antibiotics
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US3991046A (en)	1976-11-09	Penicillin antibiotics
CA1095077A (en)	1981-02-03	Process for the production of a derivative of phenylacetic acid