KR850000452A - 디브로모페니실란 및 그의 유도체의 탈브롬화방법 - Google Patents
디브로모페니실란 및 그의 유도체의 탈브롬화방법 Download PDFInfo
- Publication number
- KR850000452A KR850000452A KR1019840003124A KR840003124A KR850000452A KR 850000452 A KR850000452 A KR 850000452A KR 1019840003124 A KR1019840003124 A KR 1019840003124A KR 840003124 A KR840003124 A KR 840003124A KR 850000452 A KR850000452 A KR 850000452A
- Authority
- KR
- South Korea
- Prior art keywords
- reaction
- hydrogen
- formula
- compound
- bisulfite
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- 238000007256 debromination reaction Methods 0.000 title 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 8
- -1 dibromo compound Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 4
- 239000003125 aqueous solvent Substances 0.000 claims 3
- 239000000872 buffer Substances 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000004962 physiological condition Effects 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cephalosporin Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 일반식(II)의 디브로모 화합물을 반응-불활성 수성 용매중, 0 내지 100℃에서 대략 1몰 당량의 비설파이트 염으로 처리함을 특징으로 하여, 일반식(I)의 모노브로모 화합물을 제조하는 방법.상기식에서, n은 0,1 또는 2이고; R8은 수소, 가수소분해에 의해 제거될 수 있는 통상적인 카복시 보호 그룹 또는 생리적 조건하에서 가수분해될 수 있는 통상적인 에스테르 형성 라디칼이다.
- 제1항에 있어서, R8은 수소 또는 가수소분해로 제거될 수 있는 그룹, 즉 벤질, 벤즈히드릴 또는 2-나프틸메틸이며, 반응은 완충제로 1 내지 3당량의 중탄산 나트륨 존재하에 0 내지 40℃에서 비설파이트염으로 나트륨 비설파이트를 사용하여 수행하는 방법.
- 제3항에 있어서, R8은 수소이고 n이 0 또는 2이거나, R8이 벤질이고 n이 2인 방법.
- 제1항에 있어서, 0 내지 40℃에서 비설파이트염으로는 나트륨 비설파이트를 사용하며, R8은 가수분해될 수 있는 에스테르 라디칼 즉, γ-부티로락톤-4-일, -CHR20COR3또는-CHR20COOR3(여기서 R2는 수소 또는 메틸이고 R3는(C1-C6)-알킬이다)인 방법.
- 제4항에 있어서, R8이 피발로일옥시메틸인 방법.
- 반응-불활성 수성용매중, 50 내지 100℃에서, 일반식(IV)의 α-또는 β-브로모 화합물을 적어도 1몰 당량의 비설파이트 염으로 처리하거나, 일반식(V)의 디브로모 화합물을 적어도 2몰당량의 비설파이트염으로 처리함을 특징으로 하여, 일반식(II)의 데스브로모 화합물을 제조하는 방법.상기식에서, n은 0, 1 또는 2 이고; R6은 수소 또는 가수소분해에 의해 제거될 수 있는 통상적인 카복시 보호그룹이다.
- 제6항에 있어서, 반응을 완충제로 1 내지 3당량의 중탄산나트륨 존재하에 비설파이트 염으로는 나트륨 비설파이트를 사용하여 수행하며, 가수소분해에 의해 제거될 수 있는 그룹 R6가 벤질, 벤즈히드릴 또는 2-나프틸메틸인 방법.
- 제7항에 있어서, 처리되는 화합물이 디브로모화합이고 n이 2이며 R6는 수소인 방법.
- 일반식(VII)의 브로모 화합물을 반응-불활성 수성용매중, 50 내지 100℃에서 적어도 1몰 당량의 비설파이트염으로 처리함을 특징으로 하여, 일반식(VI)의 6-α 및 6-β 화합물의 혼합물을 제조하는 방법.상기식에서, R은(C1-C4) 알킬 또는 벤질이고; R6은 수소 또는 가수소분해에 의해 제거될 수 있는 통상적인 카복시 보호그룹이다.
- 제9항에 있어서, 반응을 완충제로 1 내지 3당량의 중탄산나트륨 존재하에 비설파이트염으로 나트륨 비설파이트를 사용하기 수행하며, 가수소분해에 의해 제거될 수 있는 그룹 R6가 벤질, 벤즈히드릴 또는 2-나프틸 메틸인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US501,731 | 1983-06-06 | ||
| US06/501,731 US4468351A (en) | 1983-06-06 | 1983-06-06 | Process for debromination of dibromopenicillanic acid and derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850000452A true KR850000452A (ko) | 1985-02-27 |
| KR870000324B1 KR870000324B1 (ko) | 1987-02-27 |
Family
ID=23994800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840003124A KR870000324B1 (ko) | 1983-06-06 | 1984-06-05 | 디브로모페니실란산 및 그의 유도체의 탈브롬화방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4468351A (ko) |
| EP (1) | EP0129360B1 (ko) |
| JP (1) | JPS608293A (ko) |
| KR (1) | KR870000324B1 (ko) |
| AT (1) | ATE29722T1 (ko) |
| AU (1) | AU551236B2 (ko) |
| CA (1) | CA1210388A (ko) |
| DE (1) | DE3466220D1 (ko) |
| DK (1) | DK275684A (ko) |
| ES (1) | ES8602807A1 (ko) |
| FI (1) | FI82938C (ko) |
| GR (1) | GR81625B (ko) |
| HU (1) | HU193931B (ko) |
| IE (1) | IE57561B1 (ko) |
| IL (1) | IL72004A (ko) |
| NO (1) | NO162722C (ko) |
| NZ (1) | NZ208379A (ko) |
| PH (1) | PH20990A (ko) |
| PL (1) | PL143370B1 (ko) |
| PT (1) | PT78691A (ko) |
| YU (1) | YU44872B (ko) |
| ZA (1) | ZA844185B (ko) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4588527A (en) * | 1983-06-06 | 1986-05-13 | Pfizer Inc. | Process for preparing penicillanic acid 1,1-dioxide derivatives |
| EP0139048A1 (en) * | 1983-10-18 | 1985-05-02 | Gist-Brocades N.V. | Process for the dehalogenation of 6,6-dibromopenicillanic acid 1,1-dioxide |
| US4596677A (en) * | 1984-04-06 | 1986-06-24 | Bristol-Myers Company | Anhydropenicillin intermediates |
| US4816580A (en) * | 1986-04-10 | 1989-03-28 | Leo Pharmaceutical Products Ltd. A/S | Improved method for preparing penicillanic acid derivatives |
| US4885370A (en) * | 1987-03-11 | 1989-12-05 | Pfizer Inc. | Synthetic method for indol-2(3H)-ones |
| GB8808701D0 (en) * | 1988-04-13 | 1988-05-18 | Erba Carlo Spa | Beta-lactam derivatives |
| GB2343676A (en) | 1998-11-12 | 2000-05-17 | Merck & Co Inc | Selective mono-debromination of polybromoalkyl aryl ketones |
| CA2537406C (en) * | 2003-09-03 | 2010-09-14 | Otsuka Chemical Co., Ltd. | Process for producing penicillanic acid compound |
| CN102702228A (zh) * | 2012-06-26 | 2012-10-03 | 齐鲁天和惠世制药有限公司 | 一种舒巴坦制备方法 |
| 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 (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4180506A (en) * | 1978-01-18 | 1979-12-25 | Rex Pratt | 6β-Bromo penicillanic acid |
| DE3068390D1 (en) * | 1979-01-10 | 1984-08-09 | Beecham Group Plc | Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds |
| US4420426A (en) * | 1979-03-05 | 1983-12-13 | Pfizer Inc. | 6-Alpha-halopenicillanic acid 1,1-dioxides |
| GB2051046B (en) * | 1979-05-21 | 1984-03-28 | Leo Pharm Prod Ltd | Penicillanic acid derivatives |
| US4432970A (en) * | 1979-11-23 | 1984-02-21 | Pfizer Inc. | 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
| US4427678A (en) * | 1982-01-11 | 1984-01-24 | Pfizer Inc. | 6-Aminomethylpenicillanic acid 1,1-dioxide derivatives as beta-lactamase inhibitors |
| PT76527B (en) * | 1982-04-19 | 1985-12-09 | Gist Brocades Nv | A process for the preparation of penicillanic acid 1,1-dioxide and derivatives thereof |
-
1983
- 1983-06-06 US US06/501,731 patent/US4468351A/en not_active Expired - Fee Related
-
1984
- 1984-06-04 AT AT84303735T patent/ATE29722T1/de not_active IP Right Cessation
- 1984-06-04 PT PT78691A patent/PT78691A/pt not_active IP Right Cessation
- 1984-06-04 GR GR74908A patent/GR81625B/el unknown
- 1984-06-04 DE DE8484303735T patent/DE3466220D1/de not_active Expired
- 1984-06-04 PH PH30764A patent/PH20990A/en unknown
- 1984-06-04 IL IL72004A patent/IL72004A/xx unknown
- 1984-06-04 DK DK275684A patent/DK275684A/da not_active Application Discontinuation
- 1984-06-04 PL PL1984248046A patent/PL143370B1/pl unknown
- 1984-06-04 EP EP84303735A patent/EP0129360B1/en not_active Expired
- 1984-06-04 CA CA000455814A patent/CA1210388A/en not_active Expired
- 1984-06-05 ES ES533149A patent/ES8602807A1/es not_active Expired
- 1984-06-05 YU YU972/84A patent/YU44872B/xx unknown
- 1984-06-05 KR KR1019840003124A patent/KR870000324B1/ko not_active IP Right Cessation
- 1984-06-05 IE IE1392/84A patent/IE57561B1/en not_active IP Right Cessation
- 1984-06-05 HU HU842179A patent/HU193931B/hu not_active IP Right Cessation
- 1984-06-05 NO NO842250A patent/NO162722C/no unknown
- 1984-06-05 FI FI842253A patent/FI82938C/fi not_active IP Right Cessation
- 1984-06-05 NZ NZ208379A patent/NZ208379A/en unknown
- 1984-06-05 AU AU29079/84A patent/AU551236B2/en not_active Ceased
- 1984-06-05 ZA ZA844185A patent/ZA844185B/xx unknown
- 1984-06-06 JP JP59116338A patent/JPS608293A/ja active Granted
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