IL41259A - 3-((4-methyl-1-piperazinyl carbonyl)oxy)-2-(2-quinolyl)-1-isoindoline derivatives,process for their preparation and pharmaceutical compositions containing the same - Google Patents
3-((4-methyl-1-piperazinyl carbonyl)oxy)-2-(2-quinolyl)-1-isoindoline derivatives,process for their preparation and pharmaceutical compositions containing the sameInfo
- Publication number
- IL41259A IL41259A IL41259A IL4125973A IL41259A IL 41259 A IL41259 A IL 41259A IL 41259 A IL41259 A IL 41259A IL 4125973 A IL4125973 A IL 4125973A IL 41259 A IL41259 A IL 41259A
- Authority
- IL
- Israel
- Prior art keywords
- isoindoline
- general formula
- isoindolin
- preparation
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 20
- -1 4-Methylpiperazin-l-yl Chemical group 0.000 claims description 17
- 238000007792 addition Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- YXMGZCXDCLYIET-UHFFFAOYSA-N (3-oxo-2-quinolin-2-yl-1H-isoindol-1-yl) 4-methylpiperazine-1-carboxylate Chemical compound CN1CCN(CC1)C(=O)OC1N(C(C2=CC=CC=C12)=O)C1=NC2=CC=CC=C2C=C1 YXMGZCXDCLYIET-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 239000008016 pharmaceutical coating Substances 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- UAXOJHPDLDHQDN-UHFFFAOYSA-N [2-(7-methoxyquinolin-2-yl)-3-oxo-1H-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound CN1CCN(CC1)C(=O)OC1N(C(C2=CC=CC=C12)=O)C1=NC2=CC(=CC=C2C=C1)OC UAXOJHPDLDHQDN-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000155 melt Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
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- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PBGQDNSMFBXURC-UHFFFAOYSA-N 2-chloro-7-nitroquinoline Chemical compound C1=CC(Cl)=NC2=CC([N+](=O)[O-])=CC=C21 PBGQDNSMFBXURC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VOGBOMUONXLUTI-UHFFFAOYSA-N 2,7-dichloroquinoline Chemical compound C1=CC(Cl)=NC2=CC(Cl)=CC=C21 VOGBOMUONXLUTI-UHFFFAOYSA-N 0.000 description 2
- GEQNFRFUGCASIF-UHFFFAOYSA-N 2-(7-chloroquinolin-2-yl)isoindole-1,3-dione Chemical compound ClC1=CC=C2C=CC(=NC2=C1)N1C(C=2C(C1=O)=CC=CC2)=O GEQNFRFUGCASIF-UHFFFAOYSA-N 0.000 description 2
- CBAYEOALFAPPRY-UHFFFAOYSA-N 2-(7-nitroquinolin-2-yl)isoindole-1,3-dione Chemical compound [N+](=O)([O-])C1=CC=C2C=CC(=NC2=C1)N1C(C=2C(C1=O)=CC=CC2)=O CBAYEOALFAPPRY-UHFFFAOYSA-N 0.000 description 2
- FOARXBSDMBUBEG-UHFFFAOYSA-N 2-chloro-7-methoxyquinoline Chemical compound C1=CC(Cl)=NC2=CC(OC)=CC=C21 FOARXBSDMBUBEG-UHFFFAOYSA-N 0.000 description 2
- BETUAUWPUGRBOG-UHFFFAOYSA-N 2-chloro-7-methylquinoline Chemical compound C1=CC(Cl)=NC2=CC(C)=CC=C21 BETUAUWPUGRBOG-UHFFFAOYSA-N 0.000 description 2
- OKAQPKGNWDDQRC-UHFFFAOYSA-N 2-quinolin-2-ylisoindole-1,3-dione Chemical compound C1=CC=CC2=NC(N3C(C4=CC=CC=C4C3=O)=O)=CC=C21 OKAQPKGNWDDQRC-UHFFFAOYSA-N 0.000 description 2
- ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 2
- CVUUCFIVYYDLHL-UHFFFAOYSA-N 7-chloroquinolin-2-amine Chemical compound C1=CC(Cl)=CC2=NC(N)=CC=C21 CVUUCFIVYYDLHL-UHFFFAOYSA-N 0.000 description 2
- STVRCCRLJQADFZ-UHFFFAOYSA-N 7-nitroquinolin-2-amine Chemical compound C1=CC([N+]([O-])=O)=CC2=NC(N)=CC=C21 STVRCCRLJQADFZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
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- 229920002472 Starch Polymers 0.000 description 2
- DPXCJHBBCLQKQH-UHFFFAOYSA-N [2-(7-chloroquinolin-2-yl)-3-oxo-1H-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound CN1CCN(CC1)C(=O)OC1N(C(C2=CC=CC=C12)=O)C1=NC2=CC(=CC=C2C=C1)Cl DPXCJHBBCLQKQH-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
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- PCJXDBQPRPOFFV-UHFFFAOYSA-N 1-methyl-7-nitroquinolin-2-one Chemical compound CN1C(=O)C=CC2=CC=C(C=C12)[N+]([O-])=O PCJXDBQPRPOFFV-UHFFFAOYSA-N 0.000 description 1
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- AUHADULCABPIFC-UHFFFAOYSA-N 7-methoxy-1h-quinolin-2-one Chemical compound C1=CC(=O)NC2=CC(OC)=CC=C21 AUHADULCABPIFC-UHFFFAOYSA-N 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 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
- C07D215/16—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
- C07D215/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07D215/20—Oxygen atoms
-
- 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
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G15/00—Apparatus for electrographic processes using a charge pattern
- G03G15/14—Apparatus for electrographic processes using a charge pattern for transferring a pattern to a second base
- G03G15/16—Apparatus for electrographic processes using a charge pattern for transferring a pattern to a second base of a toner pattern, e.g. a powder pattern, e.g. magnetic transfer
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7200650A FR2167217A1 (en) | 1972-01-10 | 1972-01-10 | Isoindolino-quinoline derivs - useful as tranquillizers and anticonvulsants |
| FR7241272A FR2206936A2 (en) | 1972-11-21 | 1972-11-21 | Isoindolino-quinoline derivs - useful as tranquillizers and anticonvulsants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41259A0 IL41259A0 (en) | 1973-03-30 |
| IL41259A true IL41259A (en) | 1976-09-30 |
Family
ID=26216826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41259A IL41259A (en) | 1972-01-10 | 1973-01-09 | 3-((4-methyl-1-piperazinyl carbonyl)oxy)-2-(2-quinolyl)-1-isoindoline derivatives,process for their preparation and pharmaceutical compositions containing the same |
Country Status (22)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2286642A2 (fr) * | 1974-03-14 | 1976-04-30 | Rhone Poulenc Ind | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| US3992382A (en) * | 1973-06-15 | 1976-11-16 | The Upjohn Company | Quinolylaminobenzoylpiperazine-1-oxides |
| FR2322601A1 (fr) * | 1975-09-04 | 1977-04-01 | Rhone Poulenc Ind | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| AR208414A1 (es) * | 1974-11-07 | 1976-12-27 | Rhone Poulenc Ind | Procedimiento para obtener nuevos derivados de la((acil-4piperazinil-1)carboniloxi-5 pirrolinona-2) |
| FR2607503B1 (fr) * | 1986-12-02 | 1989-02-24 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US20050232983A1 (en) * | 2004-04-14 | 2005-10-20 | Indevus Pharmaceuticals, Inc. | Transdermal patch |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3466297A (en) * | 1967-03-14 | 1969-09-09 | American Home Prod | 2-(2-aminophenyl)isoindolines |
| FR2101081B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-08-19 | 1974-01-11 | Rhone Poulenc Sa | |
| FR2117740B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-12-14 | 1974-04-12 | Rhone Poulenc Sa |
-
0
- BE BE793851D patent/BE793851A/xx not_active IP Right Cessation
-
1972
- 1972-12-29 US US319879A patent/US3884921A/en not_active Expired - Lifetime
-
1973
- 1973-01-02 NL NLAANVRAGE7300024,A patent/NL178690C/xx not_active IP Right Cessation
- 1973-01-08 GB GB92873A patent/GB1367589A/en not_active Expired
- 1973-01-08 IE IE24/73A patent/IE37088B1/xx unknown
- 1973-01-08 PH PH14239*UA patent/PH9482A/en unknown
- 1973-01-08 JP JP475773A patent/JPS5610315B2/ja not_active Expired
- 1973-01-09 AR AR246040A patent/AR197485A1/es active
- 1973-01-09 CA CA160,876A patent/CA991184A/fr not_active Expired
- 1973-01-09 IL IL41259A patent/IL41259A/en unknown
- 1973-01-09 NO NO84/73A patent/NO136840C/no unknown
- 1973-01-09 YU YU40/73A patent/YU35765B/xx unknown
- 1973-01-09 CH CH22673A patent/CH554353A/fr not_active IP Right Cessation
- 1973-01-09 LU LU66810A patent/LU66810A1/xx unknown
- 1973-01-09 HU HURO693A patent/HU164822B/hu unknown
- 1973-01-09 SE SE7300262A patent/SE384510B/xx unknown
- 1973-01-09 CH CH912874A patent/CH554354A/fr not_active IP Right Cessation
- 1973-01-09 DK DK11273AA patent/DK138117B/da not_active IP Right Cessation
- 1973-01-10 AT AT528274A patent/AT325626B/de not_active IP Right Cessation
- 1973-01-10 FI FI67/73A patent/FI55198C/fi active
- 1973-01-10 AT AT18773A patent/AT325622B/de not_active IP Right Cessation
- 1973-01-10 DD DD168163A patent/DD102697A5/xx unknown
- 1973-01-10 DE DE2301069A patent/DE2301069C2/de not_active Expired
- 1973-01-10 OA OA54803A patent/OA04286A/xx unknown
Also Published As
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