IL87457A - 2-Phenyl-4-quinoline carboxylic acids are converted and a process for their preparation - Google Patents
2-Phenyl-4-quinoline carboxylic acids are converted and a process for their preparationInfo
- Publication number
- IL87457A IL87457A IL8745788A IL8745788A IL87457A IL 87457 A IL87457 A IL 87457A IL 8745788 A IL8745788 A IL 8745788A IL 8745788 A IL8745788 A IL 8745788A IL 87457 A IL87457 A IL 87457A
- Authority
- IL
- Israel
- Prior art keywords
- hydroxy
- acid
- biphenyl
- fluoro
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title description 5
- YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical class N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000004305 biphenyl Substances 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 22
- -1 alkyKCj-Cg) Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 claims 1
- ZXMIFOJYMIDEPQ-UHFFFAOYSA-N 6,8-dichloro-2-(3,4-dichlorophenyl)-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(Cl)C=C(Cl)C=C2C(C(=O)O)=C(O)C=1C1=CC=C(Cl)C(Cl)=C1 ZXMIFOJYMIDEPQ-UHFFFAOYSA-N 0.000 claims 1
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 abstract description 6
- 230000005764 inhibitory process Effects 0.000 abstract description 4
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- 230000000750 progressive effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 13
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000000692 Student's t-test Methods 0.000 description 4
- LLDAQYHWVDTPPC-UHFFFAOYSA-N [2-oxo-2-(2-phenylphenyl)ethyl] acetate Chemical group CC(=O)OCC(=O)C1=CC=CC=C1C1=CC=CC=C1 LLDAQYHWVDTPPC-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- FSUWFRRQYMGYTP-UHFFFAOYSA-N 2-fluoro-3-hydroxyquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(F)=NC2=C1 FSUWFRRQYMGYTP-UHFFFAOYSA-N 0.000 description 3
- MFSHNFBQNVGXJX-UHFFFAOYSA-N 2-oxo-1,2-dihydroquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(=O)NC2=C1 MFSHNFBQNVGXJX-UHFFFAOYSA-N 0.000 description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- MHXUPMJCOAHSSV-UHFFFAOYSA-N 6-iodo-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(I)C=C2C(C(=O)O)=CC(=O)NC2=C1 MHXUPMJCOAHSSV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 208000009386 Experimental Arthritis Diseases 0.000 description 3
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- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 2
- VAJCSPZKMVQIAP-UHFFFAOYSA-N 5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1 VAJCSPZKMVQIAP-UHFFFAOYSA-N 0.000 description 2
- PHFJIUZKWPELKO-UHFFFAOYSA-N 6-bromo-3-hydroxyquinoline-4-carboxylic acid Chemical compound C1=C(Br)C=C2C(C(=O)O)=C(O)C=NC2=C1 PHFJIUZKWPELKO-UHFFFAOYSA-N 0.000 description 2
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000009696 proliferative response Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007886 soft shell capsule Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 210000001137 tarsal bone Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/090,996 US4847381A (en) | 1987-08-31 | 1987-08-31 | 2-Phenyl-4-quinoline carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL87457A0 IL87457A0 (en) | 1989-01-31 |
| IL87457A true IL87457A (en) | 1994-08-26 |
Family
ID=22225261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8745788A IL87457A (en) | 1987-08-31 | 1988-08-15 | 2-Phenyl-4-quinoline carboxylic acids are converted and a process for their preparation |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4847381A (no) |
| EP (1) | EP0305952B1 (no) |
| JP (1) | JP2760379B2 (no) |
| KR (1) | KR970005909B1 (no) |
| AR (1) | AR245698A1 (no) |
| AT (1) | ATE90079T1 (no) |
| AU (1) | AU613661B2 (no) |
| CA (1) | CA1333606C (no) |
| CS (1) | CS274434B2 (no) |
| DD (1) | DD282225A5 (no) |
| DE (1) | DE3881456T2 (no) |
| DK (1) | DK169473B1 (no) |
| ES (1) | ES2058191T3 (no) |
| FI (1) | FI92692C (no) |
| GR (1) | GR3008033T3 (no) |
| HU (1) | HU202498B (no) |
| IE (1) | IE65148B1 (no) |
| IL (1) | IL87457A (no) |
| NO (1) | NO174961C (no) |
| NZ (1) | NZ225924A (no) |
| PH (1) | PH26258A (no) |
| PL (1) | PL156232B1 (no) |
| PT (1) | PT88365B (no) |
| ZA (1) | ZA886443B (no) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968701A (en) * | 1988-04-26 | 1990-11-06 | E. I. Du Pont De Nemours And Company | 4-Quinoline carboxylic acid derivatives useful as immunosuppressive agents |
| US4918077A (en) * | 1989-01-25 | 1990-04-17 | E. I. Du Pont De Nemours & Co., Inc. | 3-phenyl-5,6-dihydrobenz(c)acridine-7-carboxylic acids and related compounds as cancer chemotherapeutic agents |
| US5204329A (en) * | 1990-06-11 | 1993-04-20 | Du Pont Merck Pharmaceutical Company | Treatment of organ transplantation rejection |
| US5135934A (en) * | 1990-07-06 | 1992-08-04 | Du Pont Merck Pharmaceutical Company | 3-phenyl-5,6-dihydrobenz(c) acridine-7-carboxylic acids and related compounds as immunosuppressive agents |
| US5409886A (en) * | 1993-02-18 | 1995-04-25 | Mitsui Toatsu Chemicals, Incorporated | 3-pyrroline-2-one derivatives and herbicidal compositions containing same |
| US5428040A (en) * | 1993-08-31 | 1995-06-27 | The Du Pont Merck Pharmaceutical Company | Carbocyclic fused-ring quinolinecarboxylic acids useful as immunosuppressive agents |
| US5578609A (en) * | 1994-03-25 | 1996-11-26 | The Dupont Merck Pharmaceutical Company | 2-carbocyclic and 2-heterocyclic quinoline-4-carboxylic acids and salts thereof useful as immunosuppressive agents |
| ID18663A (id) | 1996-04-12 | 1998-04-30 | Novartis Ag | Komposisi farmasi berlapis enterik |
| US6376670B1 (en) | 1997-06-19 | 2002-04-23 | Sepracor Inc. | Quinoline-indole antimicrobial agents, uses and compositions related thereto |
| US6207679B1 (en) | 1997-06-19 | 2001-03-27 | Sepracor, Inc. | Antimicrobial agents uses and compositions related thereto |
| AU757059B2 (en) | 1997-06-19 | 2003-01-30 | Sepracor, Inc. | Quinoline-indole antimicrobial agents, uses and compositions related thereto |
| US6103905A (en) * | 1997-06-19 | 2000-08-15 | Sepracor, Inc. | Quinoline-indole antimicrobial agents, uses and compositions related thereto |
| WO1999038846A1 (en) * | 1998-01-30 | 1999-08-05 | Procept, Inc. | Immunosuppressive agents |
| SE9901366D0 (sv) * | 1999-04-16 | 1999-04-16 | Pharmacia & Upjohn Ab | Injector device and method for its operation |
| US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| WO2009016812A1 (ja) * | 2007-07-27 | 2009-02-05 | Kowa Company, Ltd. | ２－フェニルキノリン－４－カルボン酸誘導体を有効成分とする貧血の予防及び／又は治療剤 |
| MX2016006678A (es) | 2013-11-22 | 2016-09-13 | Genzyme Corp | Nuevos metodos para tratar enfermedades neurodegenerativas. |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776290A (en) * | 1957-01-01 | Hydroxy cevchoninates and carboxylic | ||
| US2008923A (en) * | 1931-07-09 | 1935-07-23 | Graham Patmore L | Cinchoninic acid salts of piperazines |
| US2077903A (en) * | 1933-12-15 | 1937-04-20 | Gen Aniline Works Inc | Process of preparing 3-amino-quinolines |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| BE502610A (no) * | 1950-04-18 | |||
| US2888346A (en) * | 1955-08-22 | 1959-05-26 | Gen Aniline & Film Corp | Ultra-violet absorbing compounds |
| DE1049701B (no) * | 1957-02-21 | |||
| FR6592M (no) * | 1967-10-31 | 1968-12-30 | ||
| BE794945A (fr) * | 1972-02-04 | 1973-08-02 | Sandoz Sa | Application de derives de la quinoleine pour stabiliser des matieres organiques contre les effets de la lumiere ultraviolette |
| US4009020A (en) * | 1975-05-06 | 1977-02-22 | Amchem Products, Inc. | Method of regulating plant growth |
| SU1109402A1 (ru) * | 1982-10-12 | 1984-08-23 | Предприятие П/Я Р-6496 | Способ получени производных 2-(хинолил-4)-5-арилоксазола |
| US4680299A (en) * | 1984-04-30 | 1987-07-14 | E.I. Du Pont De Nemours And Company | 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof |
| ZA845594B (en) * | 1983-07-22 | 1986-03-26 | Du Pont | Phenylquinolinecarboxylic acids and derivatives as antitumor agents |
-
1987
- 1987-08-31 US US07/090,996 patent/US4847381A/en not_active Expired - Lifetime
-
1988
- 1988-08-15 IL IL8745788A patent/IL87457A/en not_active IP Right Cessation
- 1988-08-24 NZ NZ225924A patent/NZ225924A/en unknown
- 1988-08-29 AT AT88114061T patent/ATE90079T1/de active
- 1988-08-29 ES ES88114061T patent/ES2058191T3/es not_active Expired - Lifetime
- 1988-08-29 EP EP88114061A patent/EP0305952B1/en not_active Expired - Lifetime
- 1988-08-29 DE DE88114061T patent/DE3881456T2/de not_active Expired - Fee Related
- 1988-08-29 PT PT88365A patent/PT88365B/pt not_active IP Right Cessation
- 1988-08-29 PH PH37473A patent/PH26258A/en unknown
- 1988-08-29 CA CA000575951A patent/CA1333606C/en not_active Expired - Fee Related
- 1988-08-30 JP JP63213853A patent/JP2760379B2/ja not_active Expired - Lifetime
- 1988-08-30 DK DK482688A patent/DK169473B1/da not_active IP Right Cessation
- 1988-08-30 IE IE262888A patent/IE65148B1/en not_active IP Right Cessation
- 1988-08-30 ZA ZA886443A patent/ZA886443B/xx unknown
- 1988-08-30 AR AR88311798A patent/AR245698A1/es active
- 1988-08-30 NO NO883865A patent/NO174961C/no not_active IP Right Cessation
- 1988-08-30 AU AU21678/88A patent/AU613661B2/en not_active Ceased
- 1988-08-30 HU HU884489A patent/HU202498B/hu not_active IP Right Cessation
- 1988-08-30 FI FI883997A patent/FI92692C/fi not_active IP Right Cessation
- 1988-08-30 KR KR1019880011111A patent/KR970005909B1/ko not_active IP Right Cessation
- 1988-08-31 CS CS587588A patent/CS274434B2/cs unknown
- 1988-08-31 PL PL1988274471A patent/PL156232B1/pl unknown
- 1988-08-31 DD DD88319347A patent/DD282225A5/de not_active IP Right Cessation
-
1993
- 1993-06-03 GR GR930400370T patent/GR3008033T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |