GB1538921A - Amide derivatives of dimeric alkaloids - Google Patents
Amide derivatives of dimeric alkaloidsInfo
- Publication number
- GB1538921A GB1538921A GB281/76A GB28176A GB1538921A GB 1538921 A GB1538921 A GB 1538921A GB 281/76 A GB281/76 A GB 281/76A GB 28176 A GB28176 A GB 28176A GB 1538921 A GB1538921 A GB 1538921A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amide derivatives
- compounds
- converted
- dimeric
- alkaloids
- 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.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 title abstract 3
- 229930013930 alkaloid Natural products 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 229940034982 antineoplastic agent Drugs 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical class 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-CFWMRBGOSA-N 0.000 abstract 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
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Novel amide derivatives of dimeric vinblastin alkaloids of formula <IMAGE> wherein the substituents are defined in Claim 1, are prepared. These compounds are obtained by reacting corresponding compounds in which R denotes methoxy and R<1> represents H, OH or acetoxy, with ammonia, methylamine or hydrazine. Resulting compounds in which R denotes an NH-NH2 group can be converted by reaction with a nitrosylating agent into the azide, which can subsequently be converted by means of primary or secondary amines into further amide derivatives. The novel compounds may be used as antiviral or antineoplastic agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53968175A | 1975-01-09 | 1975-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1538921A true GB1538921A (en) | 1979-01-24 |
Family
ID=24152219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB281/76A Expired GB1538921A (en) | 1975-01-09 | 1976-01-06 | Amide derivatives of dimeric alkaloids |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5195100A (en) |
| BE (1) | BE837390A (en) |
| CA (1) | CA1067073A (en) |
| CH (1) | CH624962A5 (en) |
| CS (1) | CS199615B2 (en) |
| DE (1) | DE2558027A1 (en) |
| FR (1) | FR2297043A1 (en) |
| GB (1) | GB1538921A (en) |
| HU (1) | HU176226B (en) |
| IE (1) | IE42385B1 (en) |
| IL (1) | IL48685A (en) |
| NL (1) | NL7515253A (en) |
| PH (1) | PH17563A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2019396A (en) * | 1978-04-20 | 1979-10-31 | Lilly Co Eli | 4-desacetyl containinig them and their use as pharmaceuticals |
| USRE30561E (en) | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Vinca alkaloid intermediates |
| US4357334A (en) | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR69783B (en) * | 1976-09-08 | 1982-07-07 | Lilly Co Eli | |
| BG33293A3 (en) * | 1977-01-19 | 1983-01-14 | Eli Lilly And Company | Method for obtaining of 4- dezacetyldimer indoldihydrondol |
| US4191688A (en) | 1977-08-08 | 1980-03-04 | Eli Lilly And Company | Amides of leurosine, leuroformine, desacetylleurosine and desacetylleuroformine |
| US4195022A (en) | 1978-03-27 | 1980-03-25 | Eli Lilly And Company | 4-Desacetoxy-4α-hydroxyvinblastine and related compounds |
| US4199504A (en) * | 1978-05-15 | 1980-04-22 | Eli Lilly And Company | Bridged cathranthus alkaloid dimers |
| AR225153A1 (en) * | 1978-10-10 | 1982-02-26 | Lilly Co Eli | A PROCEDURE FOR THE PREPARATION OF VINDESINE SULPHATE |
| LU83822A1 (en) * | 1981-12-08 | 1983-09-01 | Omnichem Sa | N- (VINBLASTINOYL-23) DERIVATIVES OF AMINO ACIDS, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204004A1 (en) * | 1973-04-02 | 1975-11-12 | Lilly Co Eli | PROCEDURES FOR PREPARING VINBLASTIN LEUROSIDINE AND LEUROCRISTINE DERIVATIVES |
-
1975
- 1975-12-17 IL IL48685A patent/IL48685A/en unknown
- 1975-12-18 CA CA242,012A patent/CA1067073A/en not_active Expired
- 1975-12-19 IE IE2775/75A patent/IE42385B1/en unknown
- 1975-12-19 PH PH17891A patent/PH17563A/en unknown
- 1975-12-22 DE DE19752558027 patent/DE2558027A1/en not_active Ceased
- 1975-12-29 CH CH1684075A patent/CH624962A5/en not_active IP Right Cessation
- 1975-12-31 NL NL7515253A patent/NL7515253A/en not_active Application Discontinuation
-
1976
- 1976-01-06 GB GB281/76A patent/GB1538921A/en not_active Expired
- 1976-01-07 CS CS7699A patent/CS199615B2/en unknown
- 1976-01-08 HU HU76EI664A patent/HU176226B/en not_active IP Right Cessation
- 1976-01-08 BE BE1007122A patent/BE837390A/en not_active IP Right Cessation
- 1976-01-09 FR FR7600519A patent/FR2297043A1/en active Granted
- 1976-01-09 JP JP51002380A patent/JPS5195100A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30561E (en) | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Vinca alkaloid intermediates |
| GB2019396A (en) * | 1978-04-20 | 1979-10-31 | Lilly Co Eli | 4-desacetyl containinig them and their use as pharmaceuticals |
| US4357334A (en) | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
Also Published As
| Publication number | Publication date |
|---|---|
| IE42385L (en) | 1976-07-09 |
| CS199615B2 (en) | 1980-07-31 |
| FR2297043A1 (en) | 1976-08-06 |
| HU176226B (en) | 1981-01-28 |
| CA1067073A (en) | 1979-11-27 |
| DE2558027A1 (en) | 1976-07-15 |
| IE42385B1 (en) | 1980-07-30 |
| CH624962A5 (en) | 1981-08-31 |
| PH17563A (en) | 1984-10-01 |
| JPS5195100A (en) | 1976-08-20 |
| IL48685A0 (en) | 1976-02-29 |
| FR2297043B1 (en) | 1978-08-11 |
| BE837390A (en) | 1976-07-08 |
| IL48685A (en) | 1980-03-31 |
| NL7515253A (en) | 1976-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |