SU452100A3 - Способ получени - карбоксибензилпенициллина - Google Patents

Способ получени - карбоксибензилпенициллина

Info

Publication number: SU452100A3
Authority: SU; USSR - Soviet Union
Prior art keywords: carboxybenzylpenicillin; sodium; solution; general formula; acid
Prior art date: 1971-05-05

Application number

SU1781077A

Other languages

English (en)

Russian (ru)

Inventor

Ежи Цесьляк

Ежи Миколайчик

Мацей Домарадски

Original Assignee

Институт Прзэмыслу Фармацевтичнего (Инопредприятие)

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.)

1971-05-05

Filing date

1972-05-04

Publication date

1974-11-30

1972-05-04 Application filed by Институт Прзэмыслу Фармацевтичнего (Инопредприятие) filed Critical Институт Прзэмыслу Фармацевтичнего (Инопредприятие)

1974-11-30 Application granted granted Critical

1974-11-30 Publication of SU452100A3 publication Critical patent/SU452100A3/ru

Links

238000000034 method Methods 0.000 title description 14
229960003669 carbenicillin Drugs 0.000 title description 9
238000004519 manufacturing process Methods 0.000 title description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 8
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 7
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
KKSXPIZEAGEAMG-UHFFFAOYSA-N 3-amino-3-oxo-2-phenylpropanoic acid Chemical class NC(=O)C(C(O)=O)C1=CC=CC=C1 KKSXPIZEAGEAMG-UHFFFAOYSA-N 0.000 description 5
-1 monocarbonyl-substituted phenylmalonic acid Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229910021538 borax Inorganic materials 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012047 saturated solution Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000004328 sodium tetraborate Substances 0.000 description 4
235000010339 sodium tetraborate Nutrition 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
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 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
FDSDBAPKHOYUHU-UHFFFAOYSA-N butan-1-ol ethanol propan-2-one hydrate Chemical compound O.CCO.CC(C)=O.CCCCO FDSDBAPKHOYUHU-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1

Classifications

- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1781077A 1971-05-05 1972-05-04 Способ получени - карбоксибензилпенициллина SU452100A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL14795871A PL76934B1 (2)	1971-05-05	1971-05-05

Publications (1)

Publication Number	Publication Date
SU452100A3 true SU452100A3 (ru)	1974-11-30

Family

ID=19954271

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1781077A SU452100A3 (ru)	1971-05-05	1972-05-04	Способ получени - карбоксибензилпенициллина

Country Status (8)

Country	Link
JP (1)	JPS5243838B1 (2)
CS (1)	CS186762B2 (2)
DD (1)	DD97657A5 (2)
GB (1)	GB1347208A (2)
HU (1)	HU164262B (2)
PL (1)	PL76934B1 (2)
SE (1)	SE385373B (2)
SU (1)	SU452100A3 (2)

1971
- 1971-05-05 PL PL14795871A patent/PL76934B1/xx unknown
1972
- 1972-04-25 GB GB1912272A patent/GB1347208A/en not_active Expired
- 1972-05-03 DD DD16271672A patent/DD97657A5/xx unknown
- 1972-05-04 SE SE589072A patent/SE385373B/xx unknown
- 1972-05-04 JP JP7243766A patent/JPS5243838B1/ja active Pending
- 1972-05-04 CS CS303072A patent/CS186762B2/cs unknown
- 1972-05-04 SU SU1781077A patent/SU452100A3/ru active
- 1972-05-05 HU HUII000095 patent/HU164262B/hu unknown

Also Published As

Publication number	Publication date
JPS5243838B1 (2)	1977-11-02
DD97657A5 (2)	1973-05-12
CS186762B2 (en)	1978-12-29
HU164262B (2)	1974-01-28
SE385373B (sv)	1976-06-28
PL76934B1 (2)	1975-02-28
GB1347208A (en)	1974-02-27

Publication	Publication Date	Title
US3976680A (en)	1976-08-24	Production of an ester of one enantiomer of an α-amino acid in the form of a salt with an optically active acid
RU2081121C1 (ru)	1997-06-10	Способ получения клавулановой кислоты или ее фармацевтически приемлемых солей или эфиров, соль клавулановой кислоты с амином
US5380934A (en)	1995-01-10	Process for producing alanylgutamine
JPH03246253A (ja)	1991-11-01	分割媒体
JPH0655757B2 (ja)	1994-07-27	Ｎ−アルキル化ジペプチドおよびそれらのエステルの製造法
JPH03176495A (ja)	1991-07-31	ドーパミン及びドーパミン誘導体の４―０―リン酸エステルの製造方法
JPS6339869A (ja)	1988-02-20	アミノチアゾリル酢酸の新規なオキシム誘導体及びその製造法
SU452100A3 (ru)	1974-11-30	Способ получени - карбоксибензилпенициллина
US4520205A (en)	1985-05-28	Chemical resolution of (+)-2,3-dihydroindole-2-carboxylic acid
JP3088777B2 (ja)	2000-09-18	新規光学分割剤及びそれを用いる光学活性アミンの製造方法
EP0132373B1 (en)	1988-10-05	A neutral amino acid complex and a method for optical resolution of a dl-amino acid
US3983109A (en)	1976-09-28	Process for recovering cephalosporin C from A fermentation broth as the N-(p-nitrobenzoyl) derivative
US2794025A (en)	1957-05-28	Process of resolving amino acids of the proline type
RU2130449C1 (ru)	1999-05-20	Способ получения 3,4-дигидрокси-5-нитробензальдегида
DK167319B1 (da)	1993-10-11	Stabilt hydrat af et penicillinderivat og fremgangsmaade til fremstilling deraf
US3933801A (en)	1976-01-20	Process for preparing rifamycin S by hydrolysis of rifamycin O
US4446069A (en)	1984-05-01	Process for the preparation of β-lactam antibiotics
JPH023628A (ja)	1990-01-09	光学活性１−メチル−３−フェニルプロピルアミンの製法
US3362959A (en)	1968-01-09	Production of (-)-2-dehydroemetine and intermediates employed therein
JP3679231B2 (ja)	2005-08-03	光学活性α−アミノアジピン酸−γ−セミアルデヒドエチレンアセタール
US4416828A (en)	1983-11-22	Process for the resolution of the racemate S-(carboxymethyl)-(RS)-cysteine (A)
JPS58177933A (ja)	1983-10-18	Ｄｌ−マンデル酸の光学分割方法
JPH023627A (ja)	1990-01-09	光学活性１−メチル−３−フェニルプロピルアミンの製造法
JP2576598B2 (ja)	1997-01-29	光学活性１−メチル−３−フェニルプロピルアミンの製法
KR820001179B1 (ko)	1982-06-29	6-메톡시-α-메틸-2-나프탈렌초산 라세미체를 그의 대장체로 분할하는 방법.