KR830007704A - 빈블라스틴 옥사졸리딘 디온 디설파이드 화합물의 제조방법 - Google Patents
빈블라스틴 옥사졸리딘 디온 디설파이드 화합물의 제조방법 Download PDFInfo
- Publication number
- KR830007704A KR830007704A KR1019810005165A KR810005165A KR830007704A KR 830007704 A KR830007704 A KR 830007704A KR 1019810005165 A KR1019810005165 A KR 1019810005165A KR 810005165 A KR810005165 A KR 810005165A KR 830007704 A KR830007704 A KR 830007704A
- Authority
- KR
- South Korea
- Prior art keywords
- nco
- prepare
- vinblastine
- compound
- dione
- 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.)
- Ceased
Links
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 title claims 7
- 229960003048 vinblastine Drugs 0.000 title claims 7
- 238000000034 method Methods 0.000 title claims 3
- -1 vinblastine oxazolidine dione disulfide compound Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 8
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims 6
- 239000000543 intermediate Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 3
- 239000012948 isocyanate Substances 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000000908 ammonium hydroxide Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/220,472 US4362664A (en) | 1980-12-29 | 1980-12-29 | Vinblastine oxazolidinedione disulfides and related compounds |
| US220472 | 2005-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830007704A true KR830007704A (ko) | 1983-11-04 |
Family
ID=22823667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810005165A Ceased KR830007704A (ko) | 1980-12-29 | 1981-12-28 | 빈블라스틴 옥사졸리딘 디온 디설파이드 화합물의 제조방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4362664A (ref) |
| EP (1) | EP0055602A3 (ref) |
| JP (1) | JPS57134492A (ref) |
| KR (1) | KR830007704A (ref) |
| CA (1) | CA1166246A (ref) |
| GB (1) | GB2090254B (ref) |
| GR (1) | GR75128B (ref) |
| HU (1) | HU186800B (ref) |
| IL (1) | IL64617A0 (ref) |
| ZA (1) | ZA818905B (ref) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4952408A (en) * | 1988-05-23 | 1990-08-28 | Georgetown University | Liposome-encapsulated vinca alkaloids and their use in combatting tumors |
| CN116236461B (zh) * | 2021-12-08 | 2026-03-24 | 深圳先进技术研究院 | 一种氧化还原型纳米颗粒和活细胞载体及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR69783B (ref) * | 1976-09-08 | 1982-07-07 | Lilly Co Eli | |
| USRE30560E (en) | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| US4160767A (en) * | 1976-12-06 | 1979-07-10 | Eli Lilly And Company | Vinca alkaloid intermediates |
| US4096148A (en) * | 1976-12-06 | 1978-06-20 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| US4203898A (en) * | 1977-08-29 | 1980-05-20 | Eli Lilly And Company | Amide derivatives of VLB, leurosidine, leurocristine and related dimeric alkaloids |
| US4199504A (en) * | 1978-05-15 | 1980-04-22 | Eli Lilly And Company | Bridged cathranthus alkaloid dimers |
-
1980
- 1980-12-29 US US06/220,472 patent/US4362664A/en not_active Expired - Fee Related
-
1981
- 1981-12-11 GR GR66888A patent/GR75128B/el unknown
- 1981-12-22 IL IL64617A patent/IL64617A0/xx unknown
- 1981-12-23 GB GB8138763A patent/GB2090254B/en not_active Expired
- 1981-12-23 CA CA000393076A patent/CA1166246A/en not_active Expired
- 1981-12-23 EP EP81306075A patent/EP0055602A3/en not_active Ceased
- 1981-12-23 ZA ZA818905A patent/ZA818905B/xx unknown
- 1981-12-25 JP JP56216029A patent/JPS57134492A/ja active Pending
- 1981-12-28 HU HU813971A patent/HU186800B/hu unknown
- 1981-12-28 KR KR1019810005165A patent/KR830007704A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US4362664A (en) | 1982-12-07 |
| JPS57134492A (en) | 1982-08-19 |
| EP0055602A2 (en) | 1982-07-07 |
| ZA818905B (en) | 1983-08-31 |
| GR75128B (ref) | 1984-07-13 |
| GB2090254A (en) | 1982-07-07 |
| HU186800B (en) | 1985-09-30 |
| CA1166246A (en) | 1984-04-24 |
| IL64617A0 (en) | 1982-03-31 |
| EP0055602A3 (en) | 1982-10-13 |
| GB2090254B (en) | 1985-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19811228 |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19850827 Patent event code: PE09021S01D |
|
| PE0601 | Decision on rejection of patent |
Patent event date: 19851106 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19850827 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |