IE39071L - Vinca alkaloids - Google Patents
Vinca alkaloidsInfo
- Publication number
- IE39071L IE39071L IE740532A IE53274A IE39071L IE 39071 L IE39071 L IE 39071L IE 740532 A IE740532 A IE 740532A IE 53274 A IE53274 A IE 53274A IE 39071 L IE39071 L IE 39071L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen
- formula
- compound
- alkanoyl
- chloroalkanoyl
- Prior art date
Links
- 229940122803 Vinca alkaloid Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 125000001589 carboacyl group Chemical group 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 150000001540 azides Chemical class 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 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
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000001613 neoplastic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 241001529453 unidentified herpesvirus Species 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
-
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (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.
[GB1463575A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34727573A | 1973-04-02 | 1973-04-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39071L true IE39071L (en) | 1974-10-02 |
| IE39071B1 IE39071B1 (en) | 1978-08-02 |
Family
ID=23363051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE532/74A IE39071B1 (en) | 1973-04-02 | 1974-03-13 | 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) | BG22831A3 (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) | RO73524B (en) |
| SE (1) | SE416206B (en) |
| SU (4) | SU731900A3 (en) |
| YU (3) | YU39719B (en) |
| ZA (1) | ZA741674B (en) |
Families Citing this family (24)
| 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 | |
| USRE30561E (en) | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Vinca alkaloid intermediates |
| USRE30560E (en) * | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| 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 |
| US4210584A (en) | 1979-01-15 | 1980-07-01 | Eli Lilly And Company | Vindesine synthesis |
| US4357334A (en) | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
| 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. |
| LU83822A1 (en) * | 1981-12-08 | 1983-09-01 | Omnichem Sa | N- (VINBLASTINOYL-23) DERIVATIVES OF AMINO ACIDS, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| 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 |
| HUT76925A (en) * | 1995-04-04 | 1998-01-28 | MTA Enzimológiai Intézet | Bis-indole derivatives, process for the preparation thereof and pharmaceutical compositions containing them |
| US5948750A (en) * | 1996-10-30 | 1999-09-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US6326402B1 (en) | 1998-08-12 | 2001-12-04 | Octamer, Inc. | Methods for treating viral infections using a compound capable of inhibiting microtubules |
| KR101345002B1 (en) | 2005-01-21 | 2013-12-31 | 아스텍스 테라퓨틱스 리미티드 | Pharmaceutical compounds |
| NZ587586A (en) | 2005-07-18 | 2012-04-27 | Bipar Sciences Inc | Treatment of cancer |
| WO2008030891A2 (en) | 2006-09-05 | 2008-03-13 | Bipar Sciences, Inc. | Inhibition of fatty acid synthesis by parp inhibitors and methods of treatment thereof |
| WO2008030883A2 (en) | 2006-09-05 | 2008-03-13 | Bipar Sciences, Inc. | Treatment of cancer |
| EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| NZ586125A (en) | 2007-11-12 | 2012-12-21 | Bipar Sciences Inc | Treatment of breast cancer with a parp inhibitor alone or in combination with anti-tumor agents |
| AU2014253584B2 (en) * | 2013-04-19 | 2017-02-02 | Jinan University | Vinca Alkaloid Derivatives, Preparation Method therefor and Application thereof |
| 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 |
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 IL IL44415A patent/IL44415A/en unknown
- 1974-03-13 ZA ZA00741674A patent/ZA741674B/en unknown
- 1974-03-13 IE IE532/74A patent/IE39071B1/en unknown
- 1974-03-22 CA CA195,760A patent/CA1042428A/en not_active Expired
- 1974-03-25 GB GB1310174A patent/GB1463575A/en not_active Expired
- 1974-03-25 CY CY1044A patent/CY1044A/en unknown
- 1974-03-25 YU YU817/74A patent/YU39719B/en unknown
- 1974-03-29 PH PH15676A patent/PH13623A/en unknown
- 1974-03-29 CH CH446374A patent/CH603669A5/xx not_active IP Right Cessation
- 1974-03-29 FR FR7411519A patent/FR2223044B1/fr not_active Expired
- 1974-04-01 CS CS7400002335A patent/CS185223B2/en unknown
- 1974-04-01 DK DK178774AA patent/DK141511B/en not_active IP Right Cessation
- 1974-04-01 AT AT267974A patent/AT340605B/en not_active IP Right Cessation
- 1974-04-01 SE SE7404380A patent/SE416206B/en not_active IP Right Cessation
- 1974-04-01 HU HU74EI00000538A patent/HU171572B/en unknown
- 1974-04-01 SU SU742013753A patent/SU731900A3/en active
- 1974-04-01 NL NLAANVRAGE7404423,A patent/NL181079C/en not_active IP Right Cessation
- 1974-04-02 RO RO78274A patent/RO73524B/en unknown
- 1974-04-02 BG BG026279A patent/BG22831A3/en unknown
- 1974-04-02 BG BG028514A patent/BG21235A3/en unknown
- 1974-04-02 ES ES424882A patent/ES424882A1/en not_active Expired
- 1974-04-02 DD DD177632A patent/DD113538A5/xx unknown
- 1974-04-02 BG BG028513A patent/BG21612A3/en unknown
- 1974-04-02 RO RO7498695A patent/RO77533A/en unknown
- 1974-04-02 JP JP49037765A patent/JPS5919117B2/en not_active Expired
- 1974-04-02 BE BE1005847A patent/BE813168A/en not_active IP Right Cessation
- 1974-04-02 DE DE2415980A patent/DE2415980A1/en active Granted
-
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 YU1139/80A patent/YU39876B/en unknown
- 1980-04-25 YU YU1138/80A patent/YU39875B/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
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