GB1602684A - Substituted naphthalimides and their derivatives - Google Patents
Substituted naphthalimides and their derivatives Download PDFInfo
- Publication number
- GB1602684A GB1602684A GB37253/80A GB3725380A GB1602684A GB 1602684 A GB1602684 A GB 1602684A GB 37253/80 A GB37253/80 A GB 37253/80A GB 3725380 A GB3725380 A GB 3725380A GB 1602684 A GB1602684 A GB 1602684A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted naphthalimide
- naphthalimide
- substituted
- compound
- preparation
- 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
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 3-dimethylaminopropyl Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 claims 1
- 241000721267 Macara Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WAKUKXKZEXFXJP-UHFFFAOYSA-N 1-ethylpiperidin-3-amine Chemical compound CCN1CCCC(N)C1 WAKUKXKZEXFXJP-UHFFFAOYSA-N 0.000 description 1
- RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 1
- DYWWDZQRZYAPHQ-UHFFFAOYSA-N 3-benzoyl-4-ethyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one Chemical compound O1C(=O)C(CC)(C)N(C(=O)C=2C=CC=CC=2)C1C1=CC=CC=C1 DYWWDZQRZYAPHQ-UHFFFAOYSA-N 0.000 description 1
- CWVQFVQNUBOYEE-UHFFFAOYSA-N 5-nitrobenzo[de]isoquinoline-1,3-dione Chemical class C1=CC2=CC([N+](=O)[O-])=CC(C(=O)NC3=O)=C2C3=C1 CWVQFVQNUBOYEE-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- JABGXPCRNXUENL-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1N=CNC2=NC=N[C]12 JABGXPCRNXUENL-UHFFFAOYSA-N 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N purine-6-thione Natural products S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES459497A ES459497A1 (es) | 1977-06-04 | 1977-06-04 | Un metodo para la preparacion industrial de naftalimidas y sus derivados. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1602684A true GB1602684A (en) | 1981-11-11 |
Family
ID=8473948
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37253/80A Expired GB1602684A (en) | 1977-06-04 | 1978-05-26 | Substituted naphthalimides and their derivatives |
| GB23468/78A Expired GB1602683A (en) | 1977-06-04 | 1978-05-26 | Substituted naphthalimides and their derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23468/78A Expired GB1602683A (en) | 1977-06-04 | 1978-05-26 | Substituted naphthalimides and their derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4204063A (cg-RX-API-DMAC10.html) |
| JP (2) | JPS5439076A (cg-RX-API-DMAC10.html) |
| AR (1) | AR216945A1 (cg-RX-API-DMAC10.html) |
| CH (1) | CH634483A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2823987A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES459497A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2392978A2 (cg-RX-API-DMAC10.html) |
| GB (2) | GB1602684A (cg-RX-API-DMAC10.html) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3481120D1 (de) * | 1983-04-01 | 1990-03-01 | Warner Lambert Co | 3,6-disubstituierte-1,8-naphthalimide, verfahren zu ihrer herstellung und ihre verwendung. |
| US4614820A (en) * | 1983-04-01 | 1986-09-30 | Warner-Lambert Co. | 3,6-disubstituted-1,8-naphthalimides |
| US5183821A (en) * | 1983-09-19 | 1993-02-02 | Laboratories Knoll, S.A. | Method for treating leukemias using N-(2-dimethylaminoethyl)-3-amino-1,8-naphthalimide for treating leukemias and solid tumors |
| DE3604827A1 (de) * | 1986-02-15 | 1987-08-20 | Bayer Ag | Elektrophotographische toner |
| JPS6344707U (cg-RX-API-DMAC10.html) * | 1986-09-09 | 1988-03-25 | ||
| DE3635711A1 (de) * | 1986-10-21 | 1988-04-28 | Knoll Ag | 5-nitrobenzo(de)isochinolin-1,3-dione, ihre herstellung und verwendung |
| DE3707651A1 (de) * | 1987-03-10 | 1988-09-22 | Knoll Ag | Bis-naphthalimide, ihre herstellung und verwendung |
| DE8715181U1 (de) * | 1987-10-17 | 1987-12-03 | Ledermann Gmbh + Co, 7240 Horb | Spannvorrichtung |
| US5420137A (en) * | 1989-07-11 | 1995-05-30 | Knoll Ag | Amonafide salts |
| DE3922771A1 (de) * | 1989-07-11 | 1991-01-24 | Knoll Ag | Amonafide-salze |
| CA2030129A1 (en) * | 1989-11-29 | 1991-05-30 | Thomas Saupe | 1,8-napthalenedicarboximides as antidotes |
| DE3942280A1 (de) * | 1989-12-21 | 1991-06-27 | Knoll Ag | N-substituierte naphthalimide, ihre herstellung und verwendung |
| US5202318A (en) * | 1990-05-14 | 1993-04-13 | Syntex (U.S.A.) Inc. | Tricyclic compounds acting at serotonin receptor subtypes |
| WO1994006771A1 (en) * | 1992-09-11 | 1994-03-31 | Research Corporation Technologies, Inc. | 1,2 DIHYDRO-3-H-DIBENZ(de,h) ISOQUINOLINE 1,3 DIONE AND THEIR USE AS ANTICANCER AGENTS |
| US5635506A (en) * | 1990-06-26 | 1997-06-03 | Research Corporation Technologies, Inc. | 1, 2-dihydro-3H-dibenzisoquinoline-1,3-dione anticancer agents |
| JP2992769B2 (ja) * | 1990-06-26 | 1999-12-20 | リサーチ コーポレーション テクノロジーズ インコーポレーテッド | １，２―ジヒドロ―３ｈ―ジベンズイソキノリン―１，３―ジオン抗ガン剤 |
| FR2673944B1 (fr) * | 1991-03-13 | 1995-03-10 | Sanofi Elf | Derives de l'1,8-naphtalimide, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| US5206250A (en) * | 1991-03-27 | 1993-04-27 | Du Pont Merck Pharmaceutical Company | Bis-naphthalimides containing amide and thioamide linkers as anticancer agents |
| JPH07581U (ja) * | 1993-05-31 | 1995-01-06 | 株式会社遠藤製作所 | 浴槽用浄水器 |
| NZ335291A (en) * | 1996-10-21 | 2001-02-23 | Allelix Biopharma | Neurotrophin antagonist compositions |
| SK7022001A3 (en) * | 1998-11-25 | 2002-09-10 | Merck Patent Gmbh | Derivative of benzo[de]isoquinoline-1,3-dione, process for the preparation thereof, use thereof and pharmaceutical composition comprising the same |
| US6492380B1 (en) * | 1999-05-17 | 2002-12-10 | Queen's University At Kingston | Method of inhibiting neurotrophin-receptor binding |
| US6468990B1 (en) | 1999-05-17 | 2002-10-22 | Queen's University At Kingston | Method of inhibiting binding of nerve growth factor to p75 NTR receptor |
| US20050239816A1 (en) * | 2002-04-22 | 2005-10-27 | Xanthus Life Sciences, Inc. | Amonafide salts |
| US6693198B2 (en) * | 2002-04-22 | 2004-02-17 | Xanthus Life Sciences, Inc. | Amonafide salts |
| CA2491673A1 (en) * | 2002-07-08 | 2004-01-15 | Chemgenex Pharmaceuticals, Inc. | Naphthalimide synthesis including amonafide synthesis and pharmaceutical preparations thereof |
| EP1711634A4 (en) * | 2004-01-30 | 2008-04-02 | Chemgenex Pharmaceuticals Inc | NAPHTHALIMIDE ASSAY BY GENOTYPING N-ACETYL TRANSFERASE |
| WO2005105753A2 (en) * | 2004-05-05 | 2005-11-10 | Unibioscreen S.A. | Naphthalimide derivatives, methods for their production and pharmaceutical compositions therefrom |
| WO2005117893A2 (en) * | 2004-06-04 | 2005-12-15 | Chemgenex Pharmaceuticals, Inc. | Methods of treating cellular proliferative disease using naphthalimide and parp-1 inhibitors |
| JP2009507861A (ja) | 2005-09-15 | 2009-02-26 | ペインセプター ファーマ コーポレーション | ニューロトロフィン媒介性活性を調節する方法 |
| CA2883306C (en) * | 2012-08-27 | 2021-10-19 | University Of Tennessee Research Foundation | Lpa2 receptor-specific benzoic acid derivatives |
| CN119409634B (zh) * | 2024-10-31 | 2025-09-26 | 河北大学 | 一类hsa荧光探针及其合成与应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3330834A (en) * | 1967-07-11 | Naphthalimide whitening agents anb method of making same | ||
| US1796012A (en) * | 1928-04-12 | 1931-03-10 | Gen Aniline Works Inc | Amino-naphthalimido-sulphonic acid compounds and process of preparing same |
| GB309552A (en) | 1928-04-12 | 1930-06-26 | Ig Farbenindustrie Ag | Manufacture of acid wool dyestuffs |
| US1886797A (en) * | 1928-05-18 | 1932-11-08 | Gen Aniline Works Inc | Naphthalimide dyestuffs and process of preparing them |
| DE530906C (de) * | 1929-07-02 | 1931-08-01 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von sauren Wollfarbstoffen |
| US3625947A (en) * | 1957-01-30 | 1971-12-07 | Nippon Kayaku Kk | N heterocyclic ethyl naphthalimides |
| US3310564A (en) * | 1961-01-21 | 1967-03-21 | Kasai Toshiyasu | Novel 4-alkoxy naphthalimides |
| GB1003083A (en) * | 1961-01-21 | 1965-09-02 | Toshiyasu Kasai | Novel 4-alkoxynaphthalimides |
| GB962019A (en) * | 1961-04-12 | 1964-06-24 | Mitsubishi Chem Ind | Naphthalimide optical whitening agents |
| AT257528B (de) * | 1964-08-08 | 1967-10-10 | Bayer Ag | Aufhellungsmittel |
| US3308127A (en) * | 1964-08-24 | 1967-03-07 | Mitsubishi Chem Ind | Process for the production of naphthalic acid derivatives |
| FR1557945A (cg-RX-API-DMAC10.html) * | 1967-01-30 | 1969-02-21 | ||
| US3798224A (en) * | 1969-12-30 | 1974-03-19 | Sumitomo Chemical Co | Naphthalimide hydrazinamides |
| DE2423547A1 (de) * | 1974-05-15 | 1975-12-04 | Hoechst Ag | Basische farbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| DE2423548C2 (de) * | 1974-05-15 | 1984-08-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von 4-Amino1,8-naphthalimid-Verbindungen |
| GB1435238A (en) * | 1974-07-24 | 1976-05-12 | Made Labor Sa | Substituted naphthalimides and processes for their preparation |
| FR2279396A1 (fr) * | 1974-07-25 | 1976-02-20 | Made Labor Sa | Naphtalimides substitues |
| JPS5116674A (en) * | 1974-08-01 | 1976-02-10 | Made Labor Sa | Nafutaruimidoruino seizoho |
| JPS5851024B2 (ja) * | 1975-05-26 | 1983-11-14 | 帝人株式会社 | ユウシヨクカゴウブツノセイゾウホウ |
| GB1520944A (en) * | 1975-06-12 | 1978-08-09 | Teijin Ltd | Quinoline derivatives for use als colouring agents |
-
1977
- 1977-06-04 ES ES459497A patent/ES459497A1/es not_active Expired
-
1978
- 1978-03-28 AR AR271557A patent/AR216945A1/es active
- 1978-05-25 FR FR7815612A patent/FR2392978A2/fr active Granted
- 1978-05-26 GB GB37253/80A patent/GB1602684A/en not_active Expired
- 1978-05-26 GB GB23468/78A patent/GB1602683A/en not_active Expired
- 1978-05-30 CH CH587678A patent/CH634483A5/fr not_active IP Right Cessation
- 1978-06-01 DE DE19782823987 patent/DE2823987A1/de active Granted
- 1978-06-02 JP JP6588978A patent/JPS5439076A/ja active Pending
- 1978-06-02 US US05/911,801 patent/US4204063A/en not_active Expired - Lifetime
-
1980
- 1980-10-22 JP JP55147009A patent/JPS5835995B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES459497A1 (es) | 1978-04-16 |
| GB1602683A (en) | 1981-11-11 |
| CH634483A5 (fr) | 1983-02-15 |
| DE2823987A1 (de) | 1978-12-07 |
| JPS56103166A (en) | 1981-08-18 |
| JPS5835995B2 (ja) | 1983-08-05 |
| JPS5439076A (en) | 1979-03-24 |
| AR216945A1 (es) | 1980-02-15 |
| US4204063A (en) | 1980-05-20 |
| DE2823987C2 (cg-RX-API-DMAC10.html) | 1990-08-02 |
| FR2392978B2 (cg-RX-API-DMAC10.html) | 1982-07-02 |
| FR2392978A2 (fr) | 1978-12-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980525 |