KR830006326A - 이스타마이신(istamycin) B계 화합물의 3-0-데메틸 유도체의 제조방법 - Google Patents
이스타마이신(istamycin) B계 화합물의 3-0-데메틸 유도체의 제조방법 Download PDFInfo
- Publication number
- KR830006326A KR830006326A KR1019810002903A KR810002903A KR830006326A KR 830006326 A KR830006326 A KR 830006326A KR 1019810002903 A KR1019810002903 A KR 1019810002903A KR 810002903 A KR810002903 A KR 810002903A KR 830006326 A KR830006326 A KR 830006326A
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- group
- compound
- general formula
- protecting
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 12
- NEFDRWXEVITQMN-UHFFFAOYSA-N istamycin B Natural products O1C(CNC)CCC(N)C1OC1C(O)C(N(C)C(=O)CN)C(OC)CC1N NEFDRWXEVITQMN-UHFFFAOYSA-N 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000004471 Glycine Substances 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- NEFDRWXEVITQMN-JWYRXTSNSA-N Sannamycin A Chemical compound O1[C@H](CNC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@H](N(C)C(=O)CN)[C@@H](OC)C[C@@H]1N NEFDRWXEVITQMN-JWYRXTSNSA-N 0.000 claims 1
- 125000000320 amidine group Chemical group 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 230000017858 demethylation Effects 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 claims 1
- 229930190043 istamycin Natural products 0.000 claims 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
-
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 다음 일반식(Ⅱ) 또는 그의 산첨가염의 이스타마이신 Bo의 3-메톡시기에서 탈메틸화함을 특징으로 하는 일반식(Ia) 또는 그의 산첨가염의 3-0-데메틸이스타마이신 Bo의 제조방법
- 다음 일반식(Ia), 3-0-데메틸이스타마이신 Bo의 1 및 2´-아미노기와 6´-메틸아미노기를 1가 아미노기로 보호하여 다음 일반식(Ⅲ),3-0-데메틸이스타마이신 Bo의 1-, 2´- 및 6´-N-보호유도체를 얻어 일반식(Ⅲ) 화합물을 아미노보호기가 그 화합물(Ⅲ) 또는 그의 반응성 유도체의 1-2´ 및 6´-위치상의 아미노보호기와 같거나 서로 다른 N-보호글리신과 작용하여 4-메틸아미노기를 아실화하고 다음 일반식(Ⅳ) 화합물은 형성한 다음 일반식(Ⅳ) 화합물의 모든 아미노-보호기를 이탈시켜 일반식(1b)의 3-0-데메틸이스타마이신 B를 얻음을 특징으로 하는 다음 일반식(1b) 또는 그의 산첨가염의 3-0-데메틸이스타마이신 B의 제조방법.식중 R´는 1가 아미노-보호기이고, A는 수소원자를 나타내며, B는 1가 아미노-보호기를 나타내고 동시에 취한 A 및 B는 2가의 아미노-보호기를 형성한다.
- 다음 일반식(Ⅲ), 1-, 2´- 및 6´-트리-N-보호 3-0-데메틸이스타마이신 Bo를 아미노보호기가 일반식(Ⅲ)의 화합물 또는 그의 반응성유도체의 1-, 2´- 및 6´-위치에 있는 아미노기와 다른 N-보호글리신과 작용시켜 4-메틸아미노기를 아실화하여 다음 일반식(Ⅴ) 화합물을 형성하고, 일반식(Ⅴ) 화합물의 글리신성분의 2˝-아미노기에 있는 아미노-보호기를 선택적으로 이탈시키며, 그결과 얻어진 화합물을 아미노에테르와 작용시켜 2˝-아미노기를 아미딘(amidine)기로 전환하여 다음 일반식(Ⅳ) 화합물은 형성한 다음 일반식(Ⅳ) 화합물의 2´- 및 6´-위치상에 있는 잔유아미노-보호기를 이탈시켜 일반식(Ic), 3-0-데메틸-2˝-N-포름아미도일이스타마이신 B를 얻음을 특징으로 하는 일반식(Ic) 또는 그의 산첨가염, 3-0-데메틸-2˝-N-포름이미도일이스타마이신 B의 제조방법.식중, R´은 1가 아미노-보호기, A´는 수소원자, B´는 R´와 다른 1가 아미노-보호기, 또는 동시에 취한 A´및 B´는 2가 아미노-보호기를 형성한다.
- 3-0-데메틸이스타마이신 B 또는 3-0-데메메-2˝-N-포름이미도일이스타마이신 B 또는 그의 의약적으로 수용할 수 있는 산첨가염의 항균유효량을 의약적으로 수용할 수 있는 담체와 병용하여 구성함을 특징으로 하는 의약조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019840004557A KR840001623B1 (ko) | 1980-09-11 | 1984-07-31 | 3-0-데메틸-2"-n-포름이미도일 이스타마이신 b의 제조 방법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP125334 | 1980-09-11 | ||
JP55125334A JPS5750996A (en) | 1980-09-11 | 1980-09-11 | 3-o-demthylistamycin b derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830006326A true KR830006326A (ko) | 1983-09-24 |
KR840001622B1 KR840001622B1 (ko) | 1984-10-12 |
Family
ID=14907532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019810002903A KR840001622B1 (ko) | 1980-09-11 | 1981-08-10 | 3-0-데메틸 이스타마이신 b의 제조방법 |
Country Status (11)
Country | Link |
---|---|
US (1) | US4499083A (ko) |
EP (1) | EP0048549B1 (ko) |
JP (1) | JPS5750996A (ko) |
KR (1) | KR840001622B1 (ko) |
AT (1) | ATE13302T1 (ko) |
AU (1) | AU548292B2 (ko) |
CA (1) | CA1188313A (ko) |
DE (1) | DE3170503D1 (ko) |
ES (2) | ES8302021A1 (ko) |
HU (1) | HU188079B (ko) |
ZA (1) | ZA815449B (ko) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58128395A (ja) * | 1982-01-27 | 1983-07-30 | Microbial Chem Res Found | 3−0−デメチルイスタマイシンbの低毒性誘導体 |
AU1937583A (en) * | 1982-10-08 | 1984-04-12 | Abbott Laboratories | O-demethylation of aminoglycosides |
JPS5984899A (ja) * | 1982-11-05 | 1984-05-16 | Microbial Chem Res Found | 3−デメトキシイスタマイシンb誘導体 |
SI8611592A8 (en) * | 1986-09-12 | 1995-04-30 | Pliva Pharm & Chem Works | Process for preparing complexes of N-methyl-11-aza-10-deoxo-10-dihydroeritromicine A and 11-aza-10-deoxo-10-dihydroeritromicine A with metals |
US5237055A (en) * | 1991-05-30 | 1993-08-17 | Bristol-Myers Squibb Company | Chemical modification of 2"-amino group in elsamicin A |
HU210418B (en) * | 1991-05-30 | 1995-04-28 | Bristol Myers Squibb Co | Process for prepg. 2"-n-acyl derivs of elsamycin a and pharmaceutical compositions containing them |
US9035032B2 (en) * | 2005-12-13 | 2015-05-19 | Solux Corporation | Method for preparing 4-demethyldaunorubicin |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4124756A (en) * | 1976-12-27 | 1978-11-07 | Abbott Laboratories | 3-DE-O-Methylfortimicins |
SE447386B (sv) * | 1978-10-18 | 1986-11-10 | Kowa Co | Aminoglykosider, komposition innehallande dem samt forfarande for framstellning av dem |
US4330673A (en) * | 1979-03-29 | 1982-05-18 | Abbott Laboratories | Process for producing 3-O-demethylaminoglycoside and novel 3-O-demethylfortimicin derivatives |
US4242503A (en) * | 1979-03-29 | 1980-12-30 | Abbott Laboratories | Process for O-demethylating fortimicins |
NL8001842A (nl) * | 1979-05-01 | 1980-11-04 | Microbial Chem Res Found | Nieuwe antibiotica die istamycinen zijn genoemd, werk- wijzen voor de bereiding van deze antibiotica, alsmede farmaceutische preparaten met werkzaamheid tegen bacterien die deze antibiotica bevatten en werkwijze voor het remmen van de groei van bacterien. |
US4283529A (en) * | 1980-03-03 | 1981-08-11 | Abbott Laboratories | 3-O-Demethyl derivatives of Sannamycin C and antibiotic AX-127B-1 |
US4382926A (en) * | 1980-04-01 | 1983-05-10 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Formimidoyl A and B useful as semi-synthetic aminoglycosidic antibiotics |
EP0040764B1 (en) * | 1980-05-22 | 1983-07-20 | Kowa Company, Ltd. | Novel aminoglycosides, and antibiotic use thereof |
-
1980
- 1980-09-11 JP JP55125334A patent/JPS5750996A/ja active Granted
-
1981
- 1981-08-07 ZA ZA815449A patent/ZA815449B/xx unknown
- 1981-08-10 KR KR1019810002903A patent/KR840001622B1/ko active
- 1981-08-18 DE DE8181303758T patent/DE3170503D1/de not_active Expired
- 1981-08-18 AT AT81303758T patent/ATE13302T1/de not_active IP Right Cessation
- 1981-08-18 EP EP81303758A patent/EP0048549B1/en not_active Expired
- 1981-08-20 AU AU74364/81A patent/AU548292B2/en not_active Expired
- 1981-09-03 US US06/298,844 patent/US4499083A/en not_active Expired - Fee Related
- 1981-09-10 CA CA000385579A patent/CA1188313A/en not_active Expired
- 1981-09-10 HU HU812617A patent/HU188079B/hu unknown
- 1981-09-11 ES ES505430A patent/ES8302021A1/es not_active Expired
-
1982
- 1982-08-16 ES ES515015A patent/ES515015A0/es active Granted
Also Published As
Publication number | Publication date |
---|---|
ES8306766A1 (es) | 1983-06-01 |
US4499083A (en) | 1985-02-12 |
EP0048549A1 (en) | 1982-03-31 |
AU548292B2 (en) | 1985-12-05 |
JPS632271B2 (ko) | 1988-01-18 |
EP0048549B1 (en) | 1985-05-15 |
CA1188313A (en) | 1985-06-04 |
AU7436481A (en) | 1982-03-18 |
ES505430A0 (es) | 1983-01-01 |
JPS5750996A (en) | 1982-03-25 |
HU188079B (en) | 1986-03-28 |
ZA815449B (en) | 1982-09-29 |
DE3170503D1 (en) | 1985-06-20 |
ES8302021A1 (es) | 1983-01-01 |
ATE13302T1 (de) | 1985-06-15 |
ES515015A0 (es) | 1983-06-01 |
KR840001622B1 (ko) | 1984-10-12 |
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