KR840004435A - 페니실란산 1,1-디옥시드 및 그 유도체류의 제조방법 - Google Patents
페니실란산 1,1-디옥시드 및 그 유도체류의 제조방법 Download PDFInfo
- Publication number
- KR840004435A KR840004435A KR1019830001623A KR830001623A KR840004435A KR 840004435 A KR840004435 A KR 840004435A KR 1019830001623 A KR1019830001623 A KR 1019830001623A KR 830001623 A KR830001623 A KR 830001623A KR 840004435 A KR840004435 A KR 840004435A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- carried out
- process according
- dioxide
- hydrogen
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 6
- 238000000034 method Methods 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000007256 debromination reaction Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- -1 acetooxy group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Glass Compositions (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Sink And Installation For Waste Water (AREA)
- Sewage (AREA)
- Steroid Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 6-알파-브로모-및 또는 6,6-디브로모-페니실란 1,1-디옥시드류를 탈브롬화함에 의하여 다음에 기재하는 일반식 Ⅱ로 표시되는 페니실란산 1,1-디옥시드류를 제조함에 있어서, 물 속에서 측정되는 PKa-값이 3.5 보다 적은 산의 존재하에 함수매체 속에서 아연으로 환원함에 의하여 다음에 기재하는 일반석 Ⅲ 및 Ⅳ로 표시되는 물질에 대하여 탈브롬화를 수행한 다음에 필요에 따라 (R=H인 경우) 그 산을 약리학적으로 허용되는 염류 또는 에스테르로 변환시킴을 특징으로 하는 페니실란산 1,1-디옥시드류의 제조방법.(다음)위 일반식 Ⅱ에서,X는 수소이거나 수소원자 또는 할로겐원자 또는 아세토옥시기와 같은 치환분이고, R는 수소 또는 약리학적으로 허용되는 금속 또는 에스테르기이다.
- 불황성 유기용매 속에 함수매체가 함유된 것으로 하여 수행함을 특징으로 하는 철구범위 제1항 기제의 방법.
- 불활성 유기용매로는 아세토니트릴, 메틸아세타트 또는 에틸아세타르로 하고서 수행함을 특징으로 하는 청구범위 제2항 기제의 방법.
- 탈브롬화하는 액체의 pH를 2.5내지 6으로 하고서 수행함을 특징으로 하는 청구범위 제1항 내지 제3항 기재의 방법.
- pH를 3 내지 5로 하고서 수행함을 특징으로 하는 청구범위 제4항 기재의 방법.
- 염화수소산, 브롬화수소산 또는 황산의 존재하에서 아연으로 환원반응을 수행함을 특징으로 하는 청구범위 제1항 내지 제5항 기재의 방법.
- 반응온도를 0 내지 20℃ 바람직한 온도로는 0 내지 10℃로 하고서 반응을 수행함을 특징으로 하는 청구범위 제1항 내지 제6항 기재의방법.
- 출발물질에 존재하는 각개의 브롬원자에 대하여 1.2 내지 2몰비의 분량으로 되는 아년을 사용하여 환원반응을 수행함을 특징으로 하는 청구범위 제1항 내지 제7항 기재의 방법.
- 상술한 각항에 기재된 어느 하나의 방법을 수행하여 얻은 제품인 페니실란산 1,1-디옥시드가 R=H인 경우에는 페니실란산 1,1-디옥시드를 나트륨 또는 칼륨염으로 변환함을 특징으로 하는 상술한 각항중의 어느 하나의 방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8211301 | 1982-04-19 | ||
GB82-11301 | 1982-04-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840004435A true KR840004435A (ko) | 1984-10-15 |
KR870000310B1 KR870000310B1 (ko) | 1987-02-26 |
Family
ID=10529780
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019830001624A KR870000311B1 (ko) | 1982-04-19 | 1983-04-18 | 6-알파-브로모-및 6,6-디브로모-페니실란산 1,1-디옥시드류의 제조방법 |
KR1019830001623A KR870000310B1 (ko) | 1982-04-19 | 1983-04-18 | 페니실란산 1,1-디옥시드 및 염의 제조방법 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019830001624A KR870000311B1 (ko) | 1982-04-19 | 1983-04-18 | 6-알파-브로모-및 6,6-디브로모-페니실란산 1,1-디옥시드류의 제조방법 |
Country Status (14)
Country | Link |
---|---|
US (2) | US4619786A (ko) |
EP (2) | EP0093465B1 (ko) |
JP (3) | JPS58201787A (ko) |
KR (2) | KR870000311B1 (ko) |
AT (2) | ATE26982T1 (ko) |
CA (2) | CA1216842A (ko) |
DE (2) | DE3370799D1 (ko) |
DK (3) | DK165295C (ko) |
ES (3) | ES521426A0 (ko) |
FI (2) | FI80038C (ko) |
GR (2) | GR77456B (ko) |
IE (2) | IE54522B1 (ko) |
NO (2) | NO161565C (ko) |
PT (2) | PT76527B (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4468351A (en) * | 1983-06-06 | 1984-08-28 | Pfizer Inc. | Process for debromination of dibromopenicillanic acid and derivatives |
EP0139047A1 (en) * | 1983-10-18 | 1985-05-02 | Gist-Brocades N.V. | Process for the preparation of 6,6-dibromopenicillanic acid 1,1-dioxide |
EP0139048A1 (en) * | 1983-10-18 | 1985-05-02 | Gist-Brocades N.V. | Process for the dehalogenation of 6,6-dibromopenicillanic acid 1,1-dioxide |
US4760058A (en) * | 1984-08-29 | 1988-07-26 | Farmitalia Carlo Erba S.P.A. | Penam derivatives |
WO1987006230A1 (en) * | 1986-04-10 | 1987-10-22 | Leo Pharmaceutical Products Ltd. A/S | Method for preparing penicillanic acid derivatives |
JPS62249988A (ja) * | 1986-04-22 | 1987-10-30 | Taiho Yakuhin Kogyo Kk | 2β−ハロゲノメチル−2α−メチルペナム−3α−カルボン酸誘導体の製造法 |
AR247212A1 (es) * | 1991-09-13 | 1994-11-30 | Bago Sa Labor | Procedimiento de preparacion de acido 1,1-dioxo penicilanico, sus sales y esteres. |
ES2039299B1 (es) * | 1991-10-04 | 1994-05-16 | Asturpharma S A | Procedimiento de obtencion de esteres de acido 1,1-dioxopenicilanico y sus sales. |
FR2706896B1 (ko) * | 1993-06-23 | 1996-04-12 | Caillot Jean Luc | |
US6160112A (en) * | 1999-03-03 | 2000-12-12 | Alex-Gyogyszer Kutatasi, Fejlesztesi es Tanacsado Korlatot Felelossegu Tarsagag | Procedure for the preparation of dioxopenicillanic acid derivatives |
CN101768035B (zh) * | 2009-01-05 | 2013-11-27 | 浙江华海药业股份有限公司 | 一种制备以及回收芳香甲基联苯化合物的方法 |
CN104910184B (zh) * | 2015-04-27 | 2017-03-29 | 齐鲁天和惠世制药有限公司 | 一种6,6‑二溴青霉烷酸的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4164497A (en) * | 1972-10-20 | 1979-08-14 | Fujisawa Pharmaceutical Co., Ltd. | 2-Substituted penam derivatives |
IN149747B (ko) * | 1977-06-07 | 1982-04-03 | Pfizer | |
DK155942C (da) * | 1977-12-23 | 1989-10-23 | Pfizer | Analogifremgangsmaade til fremstilling af 6-aminopenicillansyre-1,1-dioxid og fysiologisk acceptable syreadditions- og basesalte deraf. |
SE449103B (sv) * | 1979-03-05 | 1987-04-06 | Pfizer | Sett att framstella penicillansyra-1,1-dioxid samt estrar derav |
US4432970A (en) * | 1979-11-23 | 1984-02-21 | Pfizer Inc. | 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
NL7908867A (nl) * | 1979-12-10 | 1981-07-01 | Gist Brocades Nv | Werkwijze voor het bereiden van 6-aminopenicillaanzuur- -1,1-dioxide en zijn zouten. |
US4419284A (en) * | 1981-03-23 | 1983-12-06 | Pfizer Inc. | Preparation of halomethyl esters (and related esters) of penicillanic acid 1,1-dioxide |
US4444687A (en) * | 1981-06-08 | 1984-04-24 | Bristol-Myers Company | 2β-Chloromethyl-2α-methylpenam-3α-carboxylic acid sulfone methylene diol mixed esters |
US4360463A (en) * | 1981-09-02 | 1982-11-23 | Pfizer Inc. | Pure 6,6-diiodopenicillanic acid and process for its preparation |
-
1983
- 1983-04-08 PT PT76527A patent/PT76527B/pt not_active IP Right Cessation
- 1983-04-08 PT PT76526A patent/PT76526B/pt not_active IP Right Cessation
- 1983-04-13 ES ES521426A patent/ES521426A0/es active Granted
- 1983-04-13 ES ES521425A patent/ES521425A0/es active Granted
- 1983-04-15 AT AT83200541T patent/ATE26982T1/de active
- 1983-04-15 DE DE8383200542T patent/DE3370799D1/de not_active Expired
- 1983-04-15 AT AT83200542T patent/ATE26447T1/de not_active IP Right Cessation
- 1983-04-15 EP EP83200541A patent/EP0093465B1/en not_active Expired
- 1983-04-15 DE DE8383200541T patent/DE3371338D1/de not_active Expired
- 1983-04-15 EP EP83200542A patent/EP0092286B1/en not_active Expired
- 1983-04-18 IE IE869/83A patent/IE54522B1/en not_active IP Right Cessation
- 1983-04-18 CA CA000426046A patent/CA1216842A/en not_active Expired
- 1983-04-18 DK DK169183A patent/DK165295C/da not_active IP Right Cessation
- 1983-04-18 FI FI831300A patent/FI80038C/fi not_active IP Right Cessation
- 1983-04-18 KR KR1019830001624A patent/KR870000311B1/ko not_active IP Right Cessation
- 1983-04-18 CA CA000426045A patent/CA1218055A/en not_active Expired
- 1983-04-18 DK DK169083A patent/DK161891C/da active IP Right Grant
- 1983-04-18 GR GR71113A patent/GR77456B/el unknown
- 1983-04-18 FI FI831301A patent/FI78298C/fi not_active IP Right Cessation
- 1983-04-18 IE IE868/83A patent/IE54536B1/en not_active IP Right Cessation
- 1983-04-18 KR KR1019830001623A patent/KR870000310B1/ko not_active IP Right Cessation
- 1983-04-18 GR GR71112A patent/GR79249B/el unknown
- 1983-04-18 NO NO831358A patent/NO161565C/no unknown
- 1983-04-18 NO NO831359A patent/NO159657C/no unknown
- 1983-04-19 US US06/486,981 patent/US4619786A/en not_active Expired - Fee Related
- 1983-04-19 US US06/486,403 patent/US4528135A/en not_active Expired - Fee Related
- 1983-04-19 JP JP58069075A patent/JPS58201787A/ja active Granted
- 1983-04-19 JP JP58069076A patent/JPS58201788A/ja active Granted
-
1984
- 1984-06-29 ES ES533883A patent/ES533883A0/es active Granted
-
1987
- 1987-05-29 JP JP62134809A patent/JPS6354376A/ja active Granted
-
1991
- 1991-11-04 DK DK181691A patent/DK165974C/da not_active IP Right Cessation
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