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
- 229940122803 Vinca alkaloid Drugs 0.000 title abstract 2
- 150000003797 alkaloid derivatives Chemical class 0.000 title 1
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Oncology (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.
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) | RO73524B (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 (15)
| 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 |
| 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 |
| US4203898A (en) | 1977-08-29 | 1980-05-20 | Eli Lilly And Company | Amide derivatives of VLB, leurosidine, leurocristine and related dimeric alkaloids |
| 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 |
| 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 |
| EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
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 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 not_active IP Right Cessation
- 1974-03-29 FR FR7411519A patent/FR2223044B1/fr not_active Expired
- 1974-04-01 HU HU74EI00000538A patent/HU171572B/en unknown
- 1974-04-01 SE SE7404380A patent/SE416206B/en not_active IP Right Cessation
- 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 NL NLAANVRAGE7404423,A patent/NL181079C/en not_active IP Right Cessation
- 1974-04-01 SU SU742013753A patent/SU731900A3/en active
- 1974-04-01 AT AT267974A patent/AT340605B/en not_active IP Right Cessation
- 1974-04-02 DE DE2415980A patent/DE2415980A1/en active Granted
- 1974-04-02 ES ES424882A patent/ES424882A1/en not_active Expired
- 1974-04-02 BG BG028513A patent/BG21612A3/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 JP JP49037765A patent/JPS5919117B2/en not_active Expired
- 1974-04-02 DD DD177632A patent/DD113538A5/xx unknown
- 1974-04-02 BG BG026279A patent/BG22831A3/en unknown
- 1974-04-02 BG BG028514A patent/BG21235A3/en unknown
- 1974-04-02 RO RO7498695A patent/RO77533A/en 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 (15)
| 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 |
| EP0032756A3 (en) * | 1978-05-15 | 1981-09-09 | Eli Lilly And Company | Intermediates used in the preparation of bridged catharanthus alkaloid dimers |
| EP0033981A3 (en) * | 1978-05-15 | 1981-09-09 | Eli Lilly And Company | 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, PROCESS FOR THEIR SYNTHESIS AND THEIR APPLICATION |
| 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 | Vinblastine derivatives and their preparation methods and applications |
| 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 |