KR830005259A - 안트라사이클린유도체의 신제조법 - Google Patents
안트라사이클린유도체의 신제조법 Download PDFInfo
- Publication number
- KR830005259A KR830005259A KR1019810001101A KR810001101A KR830005259A KR 830005259 A KR830005259 A KR 830005259A KR 1019810001101 A KR1019810001101 A KR 1019810001101A KR 810001101 A KR810001101 A KR 810001101A KR 830005259 A KR830005259 A KR 830005259A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- salt
- halogenodaunomycin
- dihydro
- anthracycline
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 229940045799 anthracyclines and related substance Drugs 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims 13
- -1 dihydrofran Chemical compound 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 229930182470 glycoside Natural products 0.000 claims 4
- 150000002338 glycosides Chemical class 0.000 claims 4
- 239000002994 raw material Substances 0.000 claims 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 claims 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 2
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 claims 1
- SHHYVKSJGBTTLX-UHFFFAOYSA-N 1-ethenoxy-6-methylheptane Chemical compound CC(C)CCCCCOC=C SHHYVKSJGBTTLX-UHFFFAOYSA-N 0.000 claims 1
- XCYWUZHUTJDTGS-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-pyran Chemical class COC1CCC=CO1 XCYWUZHUTJDTGS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- CJTTXGOOWXOTSV-UHFFFAOYSA-N methyl 3,4-dihydro-2h-pyran-2-carboxylate Chemical compound COC(=O)C1CCC=CO1 CJTTXGOOWXOTSV-UHFFFAOYSA-N 0.000 claims 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (4)
- 본문에 상술한 바와 같이 다우노마이신 또는 그 염을, 불활성유기용매의 존재하에서 할로겐화한 다음, 아세톤으로 처리하여 하기 일반식(Ⅰ)로 표시되는 14-할로게노다우노마이신 또는 그 염을 얻어 그것을 사용하거나, 또는 당초부터 직접 14-할로게노다우노마이신 또는 그 염을 사용하든지, 또는 이 14-할로게노다우노마이신, 또는 그 염을 유기용매중에서, 산촉매의 존재하에 있어서, 디히드로피란, 2-아세톡시메틸-3,4-디히드로-2H-피란, 2-메톡시-3,4-디히드로-2-아세톡시메틸-3,4-디히드로-2H-피란, 2-메톡시-3,4-디히드로-2H-피란, 2-카르보메톡시-3,4-디히드로-2H-피란과 같은 디히드로피란유도체, 디히드로프란, 메틸비닐에에테르, 부틸비닐에에테르, 이소부틸비닐에에테르, 6-메틸헵틸비닐에에테르, 시크로 헥실비닐에에테르와 같은 알킬비닐에에테르를 반응시켜서 얻어지는 하기 일반식(Ⅲ)로 표시되는 14-할로게노다우노마이신유도체 또는 그 염을 사용하여, 저급알코올 또는 아세톤수중에서, 알칼리처리하여 탈할로겐화하는 것을 특징으로하는 다음의 일반식(Ⅲ)으로 표시되는 안트라사이클린. 글리코시드 또는 그 산부가염의 제조법.[식중 X는 할로겐원자를 나타낸다.][식중, R2는 테트라히드로피라닐기, 6-아세톡시메틸테트라히드로피라닐기, 6-메톡시테트라히드로피라닐기, 6-카르보메톡시테트라히드로피라닐기와 같은 6-치환테트라히드로피라닐기, 테트라히드로프라닐기, 1-메톡시에틸기, 1-에톡시에틸기, 1-부티록시에틸기, 1-이소부티록시에틸기, 1-(6-메틸헵틸옥시)에틸기 및 시크로헥실옥시에틸기와 같은 알킬옥시에틸기를 나타낸다. X는 할로겐원자를 나타낸다.][식중 R1은 Ⅱ식의 R2와 같거나 또는 수소원자를 나타낸다.]
- 다우노마이신 또는 그 염을 출발원료로 하여, 그것을 할로겐화한 다음, 아세톤으로 처리해서 일반식(Ⅰ)에서 표시되는 14-할로게노다우노마이신을 얻고, 그것을 원료로서 사용하는 특허청구의 범위 1기재의 안트라사이클린, 글리코시드 또는 그 산부가염의 제조법.
- 직접 14-할로게노다우마이신 또는 그 염을 원료로서 사용하는 특허청구의 범위 1기재의 안트라사이클린. 글리코시드 또는 그 산부가염의 제조법.
- 14-할로게노다우노마이신 또는 그 염의 4'-위를 테트라히드로피라닐화, 6-치환테트라히드로피라닐화, 테트라히로프라닐화, 알킬옥시에틸화한 4'-위치환체 또는 그 염을 원료로서 사용하는 특허청구의 범위 1기재의 안트라사이클린. 글리코시드 또는 그 산부가염의 제조법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019810001101A KR840001672B1 (ko) | 1981-04-01 | 1981-04-01 | 안트라사이클린유도체의 신제조법 |
| KR1019840004634A KR850000528B1 (ko) | 1981-04-01 | 1984-10-13 | 안트라사이클린유도체의 신제조법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019810001101A KR840001672B1 (ko) | 1981-04-01 | 1981-04-01 | 안트라사이클린유도체의 신제조법 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004634A Division KR850000528B1 (ko) | 1981-04-01 | 1984-10-13 | 안트라사이클린유도체의 신제조법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830005259A true KR830005259A (ko) | 1983-08-03 |
| KR840001672B1 KR840001672B1 (ko) | 1984-10-13 |
Family
ID=19220595
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810001101A Expired KR840001672B1 (ko) | 1981-04-01 | 1981-04-01 | 안트라사이클린유도체의 신제조법 |
| KR1019840004634A Expired KR850000528B1 (ko) | 1981-04-01 | 1984-10-13 | 안트라사이클린유도체의 신제조법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004634A Expired KR850000528B1 (ko) | 1981-04-01 | 1984-10-13 | 안트라사이클린유도체의 신제조법 |
Country Status (1)
| Country | Link |
|---|---|
| KR (2) | KR840001672B1 (ko) |
-
1981
- 1981-04-01 KR KR1019810001101A patent/KR840001672B1/ko not_active Expired
-
1984
- 1984-10-13 KR KR1019840004634A patent/KR850000528B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR850000528B1 (ko) | 1985-04-17 |
| KR840001672B1 (ko) | 1984-10-13 |
| KR850002017A (ko) | 1985-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19810401 |
|
| PG1501 | Laying open of application | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19840426 Patent event code: PE09021S01D |
|
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19840917 |
|
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19841221 |
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| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19841226 Patent event code: PR07011E01D |
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| PR1002 | Payment of registration fee |
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| PC1801 | Expiration of term |