KR840002413A - 거대 분자 항생제의 합성법 - Google Patents
거대 분자 항생제의 합성법 Download PDFInfo
- Publication number
- KR840002413A KR840002413A KR1019820005343A KR820005343A KR840002413A KR 840002413 A KR840002413 A KR 840002413A KR 1019820005343 A KR1019820005343 A KR 1019820005343A KR 820005343 A KR820005343 A KR 820005343A KR 840002413 A KR840002413 A KR 840002413A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- carried out
- reaction
- reduction reaction
- hydrogenation
- Prior art date
Links
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 238000006722 reduction reaction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000007810 chemical reaction solvent Substances 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 230000011987 methylation Effects 0.000 claims 3
- 238000007069 methylation reaction Methods 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical group FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DGQBNDRZRZYTER-UHFFFAOYSA-N (pentafluoro-$l^{6}-sulfanyl) hypofluorite Chemical compound FOS(F)(F)(F)(F)F DGQBNDRZRZYTER-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- YVNRFQCFZVYDRO-UHFFFAOYSA-N 4-hydroxy-5-methoxybenzene-1,3-dicarbaldehyde Chemical compound COC1=CC(C=O)=CC(C=O)=C1O YVNRFQCFZVYDRO-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 1
- 239000000292 calcium oxide Substances 0.000 claims 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 claims 1
- QWLICVXJMVMDDQ-UHFFFAOYSA-N fluoro acetate Chemical compound CC(=O)OF QWLICVXJMVMDDQ-UHFFFAOYSA-N 0.000 claims 1
- XOEUHCONYHZURQ-HNUBZJOYSA-N flurithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@@](C)(F)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 XOEUHCONYHZURQ-HNUBZJOYSA-N 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 1
- 229940029284 trichlorofluoromethane Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- (a) 다음 일반식(I) 또는 (III)의 화합물을 친전자성 불소를 발생할 수 있는 화합물과 반응시켜서 다음 일반식(II) 또는 (IV)를 얻는 공정과 (b) 위에서 얻은 일반식(II) 또는 (IV)의 화합물을 x=0일 때에는 메틸화를 수반하여 환원시키는 공정으로 이루어진 것이 특징인 다음 일반식(V)의 (8S)-8-플루오로에리스로마이신의 합성법.상기 각 일반식에서,X는 D 또는 1, R3는 X=1일 때 CH3, X=0일 때 수소원자.
- 제1항에 있어서, 친전자성 불소를 생성할 수 있는 화합물이 퍼클로릴 플루오라이드, 플루오록시-퍼플루오로-알칸류, 플루오록시-술퍼-펜타플루오라이드, 불소 분자, 사초산 납-불화 수소 및 트리플루오로 아세틸하이포플루오릿트로 구성된 군에서 선택됨을 특징으로 하는 방법.
- 제2항에 있어서, 친전자성 불소를 생성할 수 있는 화합물이 플루오록시트리플루오로 메탄임을 특징으로 하는 방법.
- 제2항에 있어서, 친전자성 불소 생성 화합물이 퍼클로릴플루오라이드임을 특징으로 하는 방법.
- 제1항에 있어서, 반응 용매가 물, 피리딘으로 희석한 할로겐화 탄화수소, 테트라히드로푸란, 디옥산 및 그들의 혼합물 중에서 선택된 것임을 특징으로 하는 방법.
- 제5항에 있어서, 반응 용매가 트리클로로플루오로메탄, 클로로포름, 염화메틸렌 또는 테트라히드로푸란 및 물에서 선택됨을 특징으로 하는 방법.
- 제1항에 있어서, 반응 온도가 -75℃와 -85℃ 사이 또는 -10℃와 +10℃ 범위에 있음을 특징으로 하는 방법.
- 제1항에 있어서, 상기 플루오르화반응이 산화칼슘, 피리딘 또는 초산칼꿈과 같은 염기 존재하에서 수행됨을 특징으로 하는 방법.
- 제1항에 있어서, 상기 반응이 수소화반응의 촉매 존재하에서 수소화반응에 의해 수행됨을 특징으로 하는 방법.
- 제9항에 있어서, 수소화반응의 촉매가 탄소지지체상의 팔라듐임을 특징으로 하는 방법.
- 제9항에 있어서, 반응용매가 에탄올, 메탄올, 테트라히드로푸란 및 초산에틸 중에서 선택됨을 특징으로 하는 방법.
- 제10항에 있어서, 환원 반응이 실온에서 수행됨을 특징으로 하는 방법.
- 제10항에 있어서, 환원반응이 1기압의 수소압력에서 수행됨을 특징으로 하는 방법.
- 제1항에 있어서, 환원반응이 메틸화시약의 존재하에서 수행됨을 특징으로 하는 방법.
- 제14항에 있어서, 메틸화 시약이 포름알데히드임을 특징으로 하는 방법.
- 제15항에 있어서, 환원반응이 제9항 또는 13항에 따르는 조건에서 유기용매 존재하에 수행됨을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25345A/81 | 1981-11-27 | ||
| IT25345/81A IT1195299B (it) | 1981-11-27 | 1981-11-27 | Procedimento chimico di sintesi per la preparazione di antibiotici macrolidici |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002413A true KR840002413A (ko) | 1984-07-02 |
| KR880001566B1 KR880001566B1 (ko) | 1988-08-22 |
Family
ID=11216419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205343A KR880001566B1 (ko) | 1981-11-27 | 1982-11-26 | 마크로리드 항생물질의 화학적 합성법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4514562A (ko) |
| EP (1) | EP0080763B1 (ko) |
| JP (1) | JPS58109496A (ko) |
| KR (1) | KR880001566B1 (ko) |
| AT (1) | ATE15805T1 (ko) |
| BE (1) | BE895155A (ko) |
| CA (1) | CA1209987A (ko) |
| CH (1) | CH660596A5 (ko) |
| DE (1) | DE3266578D1 (ko) |
| FI (1) | FI75835C (ko) |
| FR (1) | FR2517311B1 (ko) |
| IT (1) | IT1195299B (ko) |
| PH (1) | PH18391A (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1163796B (it) * | 1983-07-18 | 1987-04-08 | Pierrel Spa | Procedimento per la preparazione di (8s)-8-fluoroeritromicina |
| IT1196041B (it) * | 1984-03-08 | 1988-11-10 | Pierrel Spa | Emichetali di (8s)-8-fluoroeritromicine,il procedimento per la loro preparazione e le formulazioni adatte alla somministrazione orale che contengono i prodotti |
| DE3424525A1 (de) * | 1984-07-04 | 1986-01-16 | Kernforschungsanlage Jülich GmbH, 5170 Jülich | Verfahren zur herstellung von (pfeil hoch)1(pfeil hoch)(pfeil hoch)8(pfeil hoch)f-alkyl- und arylverbindungen durch halogenaustausch |
| JPS6185378A (ja) * | 1984-10-02 | 1986-04-30 | Daikin Ind Ltd | ８−フルオロエリスロノライド誘導体の製法 |
| US4876245A (en) * | 1986-12-22 | 1989-10-24 | Daikin Industries Ltd. | Fluorine-containing macrolide compounds and their use |
| PE5591A1 (es) * | 1988-12-19 | 1991-02-15 | Lilly Co Eli | Un nuevo grupo de compuestos de macrolida |
| US5591606A (en) * | 1992-11-06 | 1997-01-07 | Dowelanco | Process for the production of A83543 compounds with Saccharopolyspora spinosa |
| BR9406587A (pt) * | 1993-03-12 | 1996-01-02 | Dowelanco | Novos compostos a83543 e processo para a produção dos mesmos |
| US5393743A (en) * | 1993-07-06 | 1995-02-28 | Abbott Laboratories | Erythromycin derivatives |
| US5552533A (en) * | 1994-09-14 | 1996-09-03 | Alliedsignal Inc. | Preparation of (8S)-8-fluoroerythromycins with N-F fluorinating agents |
| US6001981A (en) * | 1996-06-13 | 1999-12-14 | Dow Agrosciences Llc | Synthetic modification of Spinosyn compounds |
| KR20070012643A (ko) * | 2004-02-24 | 2007-01-26 | 아르끄마 프랑스 | 삼블록 연속 공중합체를 포함하는 가교 조성물, 그의 제조방법 및 그의 용도 |
| WO2011080739A2 (en) | 2009-12-29 | 2011-07-07 | Yeda Research And Development Co. Ltd. | Synergistic antibiotic combinations and derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2812323A (en) * | 1954-11-03 | 1957-11-05 | Lilly Co Eli | Des-n-methyl erythromycin |
| US3674773A (en) * | 1970-10-06 | 1972-07-04 | Abbott Lab | Erythromycin derivatives |
| DE3268339D1 (en) * | 1981-01-09 | 1986-02-20 | Pierrel Spa | Novel semisynthetic macrolidic antibiotics, microbiological processes for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing them |
-
1981
- 1981-11-27 IT IT25345/81A patent/IT1195299B/it active
-
1982
- 1982-11-19 AT AT82201476T patent/ATE15805T1/de not_active IP Right Cessation
- 1982-11-19 DE DE8282201476T patent/DE3266578D1/de not_active Expired
- 1982-11-19 EP EP82201476A patent/EP0080763B1/en not_active Expired
- 1982-11-22 US US06/443,580 patent/US4514562A/en not_active Expired - Lifetime
- 1982-11-26 CA CA000416447A patent/CA1209987A/en not_active Expired
- 1982-11-26 FI FI824084A patent/FI75835C/fi not_active IP Right Cessation
- 1982-11-26 FR FR8219865A patent/FR2517311B1/fr not_active Expired
- 1982-11-26 KR KR8205343A patent/KR880001566B1/ko active
- 1982-11-26 PH PH28203A patent/PH18391A/en unknown
- 1982-11-26 BE BE0/209580A patent/BE895155A/fr unknown
- 1982-11-26 CH CH6889/82A patent/CH660596A5/it not_active IP Right Cessation
- 1982-11-27 JP JP57208363A patent/JPS58109496A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4514562A (en) | 1985-04-30 |
| KR880001566B1 (ko) | 1988-08-22 |
| EP0080763B1 (en) | 1985-09-25 |
| JPH0312077B2 (ko) | 1991-02-19 |
| JPS58109496A (ja) | 1983-06-29 |
| FI75835B (fi) | 1988-04-29 |
| CH660596A5 (it) | 1987-05-15 |
| FI824084L (fi) | 1983-05-28 |
| IT8125345A0 (it) | 1981-11-27 |
| ATE15805T1 (de) | 1985-10-15 |
| PH18391A (en) | 1985-06-21 |
| FI824084A0 (fi) | 1982-11-26 |
| CA1209987A (en) | 1986-08-19 |
| EP0080763A1 (en) | 1983-06-08 |
| FR2517311A1 (fr) | 1983-06-03 |
| IT1195299B (it) | 1988-10-12 |
| BE895155A (fr) | 1983-03-16 |
| FR2517311B1 (fr) | 1987-12-24 |
| FI75835C (fi) | 1988-08-08 |
| DE3266578D1 (en) | 1985-10-31 |
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