DE3014994A1 - Neues nogamycin und analog aufgebaute verbindungen sowie verfahren zu deren herstellung - Google Patents
Neues nogamycin und analog aufgebaute verbindungen sowie verfahren zu deren herstellungInfo
- Publication number
- DE3014994A1 DE3014994A1 DE19803014994 DE3014994A DE3014994A1 DE 3014994 A1 DE3014994 A1 DE 3014994A1 DE 19803014994 DE19803014994 DE 19803014994 DE 3014994 A DE3014994 A DE 3014994A DE 3014994 A1 DE3014994 A1 DE 3014994A1
- Authority
- DE
- Germany
- Prior art keywords
- con
- deoxynogarol
- radical
- formula
- compound according
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 40
- NNEGMXMRXKXKMQ-ZEOBNFASSA-N disnogamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2C[C@@](C)(O)C1 NNEGMXMRXKXKMQ-ZEOBNFASSA-N 0.000 title description 29
- 238000004519 manufacturing process Methods 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 claims description 95
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 38
- 230000000269 nucleophilic effect Effects 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- 239000000376 reactant Substances 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
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- 238000002360 preparation method Methods 0.000 claims description 5
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 4
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- 238000004809 thin layer chromatography Methods 0.000 description 15
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- 125000001424 substituent group Chemical group 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 238000006243 chemical reaction Methods 0.000 description 7
- KGTDRFCXGRULNK-JYOBTZKQSA-N nogalamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2[C@@H](C(=O)OC)[C@@](C)(O)C1 KGTDRFCXGRULNK-JYOBTZKQSA-N 0.000 description 7
- 229950009266 nogalamycin Drugs 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 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 description 4
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 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
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3261479A | 1979-04-23 | 1979-04-23 | |
| US6032679A | 1979-07-25 | 1979-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3014994A1 true DE3014994A1 (de) | 1980-11-06 |
Family
ID=26708664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803014994 Withdrawn DE3014994A1 (de) | 1979-04-23 | 1980-04-18 | Neues nogamycin und analog aufgebaute verbindungen sowie verfahren zu deren herstellung |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH649558A5 (enExample) |
| DE (1) | DE3014994A1 (enExample) |
| FR (1) | FR2455049A1 (enExample) |
| GB (1) | GB2049689B (enExample) |
| NL (1) | NL8002177A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4318790A (en) * | 1980-03-17 | 1982-03-09 | The Upjohn Company | Photochemical process for preparing N-demethyl-derivatives of nogalamycin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4086245A (en) * | 1976-12-09 | 1978-04-25 | The Upjohn Company | Antibiotics 7-O-alkylnogarols |
-
1980
- 1980-04-11 GB GB8012034A patent/GB2049689B/en not_active Expired
- 1980-04-15 NL NL8002177A patent/NL8002177A/nl not_active Application Discontinuation
- 1980-04-16 CH CH294780A patent/CH649558A5/de not_active IP Right Cessation
- 1980-04-18 DE DE19803014994 patent/DE3014994A1/de not_active Withdrawn
- 1980-04-22 FR FR8008989A patent/FR2455049A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL8002177A (nl) | 1980-10-27 |
| FR2455049B1 (enExample) | 1983-07-29 |
| CH649558A5 (de) | 1985-05-31 |
| GB2049689B (en) | 1983-05-18 |
| GB2049689A (en) | 1980-12-31 |
| FR2455049A1 (fr) | 1980-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8141 | Disposal/no request for examination |