GB1463575A - Vinca alkaloid derivatives - Google Patents
Vinca alkaloid derivativesInfo
- Publication number
- GB1463575A GB1463575A GB1310174A GB1310174A GB1463575A GB 1463575 A GB1463575 A GB 1463575A GB 1310174 A GB1310174 A GB 1310174A GB 1310174 A GB1310174 A GB 1310174A GB 1463575 A GB1463575 A GB 1463575A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- formula
- compound
- alkanoyl
- chloroalkanoyl
- 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
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Fodder In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1463575 Novel amides, azides and hydrazides of vinca alkaloids ELI LILLY & CO 25 March 1974 [2 April 1973] 13101/74 Heading C2C Novel compounds of the Formula I wherein R is NH 2 , NH.NH 2 , N(CH 3 ) 3 , NHalk-X, NH(C 3-8 )cycloalkyl, NHalkAm, NHalk(OH) 1-3 or N 3 ; wherein alk is C 1-6 alkylene, Am is NH 2 , NHCH 3 or N(CH 3 ) 2 , X is hydrogen, CN, optionally substituted phenyl, carboxy, carbo- (C 1-3 )-alkoxy, or carboxamido; R<SP>1</SP> is H, alkanoyl or chloroalkanoyl; R<SP>11</SP> is hydrogen, C 1-3 alkyl, formyl or alkanoyl; and one of R<SP>111</SP> and R<SP>1111</SP> is hydroxy and the other is ethyl, in which alkanoyl groups have 1-3 carbon atoms in the alkane moiety, and salts thereof, may be prepared by reacting a compound of the Formula I wherein R is OCH 3 , R<SP>1</SP> is hydrogen or acetyl and R<SP>11</SP>, R<SP>111</SP> and R<SP>1111</SP> are as defined above with ammonia, methylamine or hydrazine to obtain a compound of Formula I wherein R is NH 2 , NHCH 3 or NH.NH 2 , and R<SP>1</SP> is hydrogen and, if desired, when R is NHNH 2 (a) reacting said compound with a nitrosating agent to form an azide in where R 3 N 3 and then reacting said azide with ammonia, an amine of the formula HN(CH 3 ) 2 , NH 2 alk-X, NH 2 -(C 3-8 )cycloalkyl, NH 2 alkAm or NH 2 alk(OH) 1-3 to obtain the corresponding compound of Formula I or (b) hydrogenolysing said compound with Raney nickel in an inert solvent to yield a compound of the Formula I wherein R is NH 2 , and/or, if desired, acylating a product in which R<SP>1</SP> is hydrogen to introduce an alkanoyl or chloroalkanoyl group at R<SP>1</SP>, and, if in the starting material R<SP>11</SP> is hydrogen, to introduce an alkanoyl or chloroalkanoyl at R<SP>11</SP>. Various by-products having the same ring systems as I are formed during some of the above reactions. Pharmaceutical compositions of the compounds I or salts thereof with the usual excipients may be administered orally or parenterally for treating neoplastic disease. The compounds also show antivral activity in vitro against herpes virus.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34727573A | 1973-04-02 | 1973-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1463575A true GB1463575A (en) | 1977-02-02 |
Family
ID=23363051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1310174A Expired GB1463575A (en) | 1973-04-02 | 1974-03-25 | Vinca alkaloid derivatives |
Country Status (28)
| Country | Link |
|---|---|
| JP (2) | JPS5919117B2 (en) |
| AR (2) | AR204004A1 (en) |
| AT (1) | AT340605B (en) |
| BE (1) | BE813168A (en) |
| BG (3) | BG21612A3 (en) |
| CA (1) | CA1042428A (en) |
| CH (1) | CH603669A5 (en) |
| CS (1) | CS185223B2 (en) |
| CY (1) | CY1044A (en) |
| DD (1) | DD113538A5 (en) |
| DE (1) | DE2415980A1 (en) |
| DK (1) | DK141511B (en) |
| ES (2) | ES424882A1 (en) |
| FR (1) | FR2223044B1 (en) |
| GB (1) | GB1463575A (en) |
| HK (1) | HK20180A (en) |
| HU (1) | HU171572B (en) |
| IE (1) | IE39071B1 (en) |
| IL (1) | IL44415A (en) |
| KE (1) | KE3028A (en) |
| MY (1) | MY8100025A (en) |
| NL (1) | NL181079C (en) |
| PH (1) | PH13623A (en) |
| RO (2) | RO77533A (en) |
| SE (1) | SE416206B (en) |
| SU (4) | SU731900A3 (en) |
| YU (3) | YU39719B (en) |
| ZA (1) | ZA741674B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2438052A1 (en) * | 1978-05-15 | 1980-04-30 | Lilly Co Eli | NOVEL PROCESS FOR THE PREPARATION OF BRIDGE DIMERES OF CATHARANTHUS ALKALOIDS AND INTERMEDIATE COMPOUNDS |
| WO1996031518A1 (en) * | 1995-04-04 | 1996-10-10 | MTA Enzimológiai Intézet | Novel tumor-inhibiting bisindole derivatives with calmodulin-liberator effect and pharmaceutical composition containing them |
| US5948750A (en) * | 1996-10-30 | 1999-09-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US7732491B2 (en) | 2007-11-12 | 2010-06-08 | Bipar Sciences, Inc. | Treatment of breast cancer with a PARP inhibitor alone or in combination with anti-tumor agents |
| US7994222B2 (en) | 2006-09-05 | 2011-08-09 | Bipar Sciences, Inc. | Monitoring of the inhibition of fatty acid synthesis by iodo-nitrobenzamide compounds |
| US8143447B2 (en) | 2006-09-05 | 2012-03-27 | Bipar Sciences, Inc. | Treatment of cancer |
| US8377985B2 (en) | 2005-07-18 | 2013-02-19 | Bipar Sciences, Inc. | Treatment of cancer |
| CN105121447A (en) * | 2013-04-19 | 2015-12-02 | 暨南大学 | Vinblastine derivatives, preparation method therefor and application thereof |
| CN113456797A (en) * | 2021-06-18 | 2021-10-01 | 暨南大学 | Application of vinblastine derivative in preparation of medicine for treating osteosarcoma and/or soft tissue sarcoma |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| GR69783B (en) * | 1976-09-08 | 1982-07-07 | Lilly Co Eli | |
| US4096148A (en) * | 1976-12-06 | 1978-06-20 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| USRE30560E (en) * | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| USRE30561E (en) | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Vinca alkaloid intermediates |
| US4203898A (en) | 1977-08-29 | 1980-05-20 | Eli Lilly And Company | Amide derivatives of VLB, leurosidine, leurocristine and related dimeric alkaloids |
| US4357334A (en) | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
| LU83822A1 (en) * | 1981-12-08 | 1983-09-01 | Omnichem Sa | N- (VINBLASTINOYL-23) DERIVATIVES OF AMINO ACIDS, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| OA06421A (en) * | 1980-06-10 | 1981-09-30 | Omnium Chimique Sa | Process for the preparation of N- (vinblastinoyl-23) derivatives of amino acids and peptides. |
| FR2623504B1 (en) * | 1987-11-25 | 1990-03-09 | Adir | NOVEL N- (VINBLASTINOYL-23) DERIVATIVES OF 1-AMINO METHYLPHOSPHONIC ACID, PROCESSES FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| US6326402B1 (en) | 1998-08-12 | 2001-12-04 | Octamer, Inc. | Methods for treating viral infections using a compound capable of inhibiting microtubules |
| JP5475234B2 (en) | 2005-01-21 | 2014-04-16 | アステックス・セラピューティクス・リミテッド | Pharmaceutical compounds |
| JP5528806B2 (en) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | Compound drug |
| JP5528807B2 (en) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | Compound drug |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097137A (en) * | 1960-05-19 | 1963-07-09 | Canadian Patents Dev | Vincaleukoblastine |
-
1974
- 1974-01-01 AR AR253105A patent/AR204004A1/en active
- 1974-03-13 IE IE532/74A patent/IE39071B1/en unknown
- 1974-03-13 IL IL44415A patent/IL44415A/en unknown
- 1974-03-13 ZA ZA00741674A patent/ZA741674B/en unknown
- 1974-03-22 CA CA195,760A patent/CA1042428A/en not_active Expired
- 1974-03-25 CY CY1044A patent/CY1044A/en unknown
- 1974-03-25 YU YU817/74A patent/YU39719B/en unknown
- 1974-03-25 GB GB1310174A patent/GB1463575A/en not_active Expired
- 1974-03-29 PH PH15676A patent/PH13623A/en unknown
- 1974-03-29 CH CH446374A patent/CH603669A5/xx active Protection Beyond IP Right Term
- 1974-03-29 FR FR7411519A patent/FR2223044B1/fr not_active Expired
- 1974-04-01 HU HU74EI00000538A patent/HU171572B/en unknown
- 1974-04-01 AT AT267974A patent/AT340605B/en not_active IP Right Cessation
- 1974-04-01 DK DK178774AA patent/DK141511B/en not_active IP Right Cessation
- 1974-04-01 CS CS7400002335A patent/CS185223B2/en unknown
- 1974-04-01 NL NLAANVRAGE7404423,A patent/NL181079C/en not_active IP Right Cessation
- 1974-04-01 SE SE7404380A patent/SE416206B/en not_active IP Right Cessation
- 1974-04-01 SU SU742013753A patent/SU731900A3/en active
- 1974-04-02 BG BG028513A patent/BG21612A3/en unknown
- 1974-04-02 RO RO7498695A patent/RO77533A/en unknown
- 1974-04-02 BG BG026279A patent/BG22831A3/en unknown
- 1974-04-02 JP JP49037765A patent/JPS5919117B2/en not_active Expired
- 1974-04-02 ES ES424882A patent/ES424882A1/en not_active Expired
- 1974-04-02 BG BG028514A patent/BG21235A3/en unknown
- 1974-04-02 BE BE1005847A patent/BE813168A/en not_active IP Right Cessation
- 1974-04-02 RO RO78274A patent/RO73524B/en unknown
- 1974-04-02 DE DE2415980A patent/DE2415980A1/en active Granted
- 1974-04-02 DD DD177632A patent/DD113538A5/xx unknown
-
1975
- 1975-01-08 AR AR257228A patent/AR203882A1/en active
- 1975-07-04 SU SU752151512A patent/SU784783A3/en active
- 1975-07-09 SU SU752152020A patent/SU652896A3/en active
-
1976
- 1976-03-31 ES ES446571A patent/ES446571A1/en not_active Expired
- 1976-12-20 SU SU762429453A patent/SU623522A3/en active
-
1980
- 1980-02-27 KE KE3028A patent/KE3028A/en unknown
- 1980-04-17 HK HK201/80A patent/HK20180A/en unknown
- 1980-04-25 YU YU1138/80A patent/YU39875B/en unknown
- 1980-04-25 YU YU1139/80A patent/YU39876B/en unknown
-
1981
- 1981-12-30 MY MY25/81A patent/MY8100025A/en unknown
-
1983
- 1983-12-16 JP JP58238722A patent/JPS6033837B2/en not_active Expired
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2438052A1 (en) * | 1978-05-15 | 1980-04-30 | Lilly Co Eli | NOVEL PROCESS FOR THE PREPARATION OF BRIDGE DIMERES OF CATHARANTHUS ALKALOIDS AND INTERMEDIATE COMPOUNDS |
| EP0032756A2 (en) * | 1978-05-15 | 1981-07-29 | Eli Lilly And Company | Intermediates used in the preparation of bridged catharanthus alkaloid dimers |
| EP0033981A2 (en) * | 1978-05-15 | 1981-08-19 | Eli Lilly And Company | Preparation of bridged catharanthus alkaloid dimers |
| EP0033981A3 (en) * | 1978-05-15 | 1981-09-09 | Eli Lilly And Company | Preparation of bridged catharanthus alkaloid dimers |
| EP0032756A3 (en) * | 1978-05-15 | 1981-09-09 | Eli Lilly And Company | Intermediates used in the preparation of bridged catharanthus alkaloid dimers |
| WO1996031518A1 (en) * | 1995-04-04 | 1996-10-10 | MTA Enzimológiai Intézet | Novel tumor-inhibiting bisindole derivatives with calmodulin-liberator effect and pharmaceutical composition containing them |
| US5948750A (en) * | 1996-10-30 | 1999-09-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US8377985B2 (en) | 2005-07-18 | 2013-02-19 | Bipar Sciences, Inc. | Treatment of cancer |
| US7994222B2 (en) | 2006-09-05 | 2011-08-09 | Bipar Sciences, Inc. | Monitoring of the inhibition of fatty acid synthesis by iodo-nitrobenzamide compounds |
| US8143447B2 (en) | 2006-09-05 | 2012-03-27 | Bipar Sciences, Inc. | Treatment of cancer |
| US7732491B2 (en) | 2007-11-12 | 2010-06-08 | Bipar Sciences, Inc. | Treatment of breast cancer with a PARP inhibitor alone or in combination with anti-tumor agents |
| CN105121447A (en) * | 2013-04-19 | 2015-12-02 | 暨南大学 | Vinblastine derivatives, preparation method therefor and application thereof |
| EP2987794A4 (en) * | 2013-04-19 | 2016-11-30 | Univ Jinan | Vinblastine derivatives, preparation method therefor and application thereof |
| AU2014253584B2 (en) * | 2013-04-19 | 2017-02-02 | Jinan University | Vinca Alkaloid Derivatives, Preparation Method therefor and Application thereof |
| CN105121447B (en) * | 2013-04-19 | 2018-02-02 | 暨南大学 | Vinca derivative and its preparation method and application |
| CN113456797A (en) * | 2021-06-18 | 2021-10-01 | 暨南大学 | Application of vinblastine derivative in preparation of medicine for treating osteosarcoma and/or soft tissue sarcoma |
| CN113456797B (en) * | 2021-06-18 | 2024-03-08 | 暨南大学 | Application of vinblastine derivatives in preparation of medicines for treating osteosarcoma and/or soft tissue sarcoma |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19940324 |