HRP20000652A2 - Quinolin -4-yl derivatives - Google Patents
Quinolin -4-yl derivatives Download PDFInfo
- Publication number
- HRP20000652A2 HRP20000652A2 HR20000652A HRP20000652A HRP20000652A2 HR P20000652 A2 HRP20000652 A2 HR P20000652A2 HR 20000652 A HR20000652 A HR 20000652A HR P20000652 A HRP20000652 A HR P20000652A HR P20000652 A2 HRP20000652 A2 HR P20000652A2
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- dihydro
- compounds
- isoquinolin
- Prior art date
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- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 65
- 150000003839 salts Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000004770 neurodegeneration Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 7
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- -1 hydroxy, amino Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- ZWZCUJOGAOTAMB-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-2-amine Chemical compound C1=CC=CC2=NC(N)=CC(N3CC4=CC=CC=C4CC3)=C21 ZWZCUJOGAOTAMB-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- BXAIQPPVOCFPQA-UHFFFAOYSA-N 1-aminopyrrolidin-3-ol Chemical compound NN1CCC(O)C1 BXAIQPPVOCFPQA-UHFFFAOYSA-N 0.000 claims description 2
- QSITUQDXTNRCQN-UHFFFAOYSA-N 3-[[4-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-2-yl]amino]propane-1,2-diol Chemical compound C1=CC=CC2=NC(NCC(O)CO)=CC(N3CC4=CC=CC=C4CC3)=C21 QSITUQDXTNRCQN-UHFFFAOYSA-N 0.000 claims description 2
- SPSXCZMMEURJOF-UHFFFAOYSA-N 4-(1,3-dihydroisoindol-2-yl)quinoline Chemical compound C1=CC=C2C(N3CC4=CC=CC=C4C3)=CC=NC2=C1 SPSXCZMMEURJOF-UHFFFAOYSA-N 0.000 claims description 2
- HRDFYQVITWAQGZ-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)quinoline Chemical compound C1=CC=C2C(N3CC4=CC=CC=C4CC3)=CC=NC2=C1 HRDFYQVITWAQGZ-UHFFFAOYSA-N 0.000 claims description 2
- DKDRUNMVVXRCDP-UHFFFAOYSA-N 4-(5-chloro-1,3-dihydroisoindol-2-yl)quinoline Chemical compound C1=CC=C2C(N3CC4=CC=C(C=C4C3)Cl)=CC=NC2=C1 DKDRUNMVVXRCDP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- HVVNJUAVDAZWCB-UHFFFAOYSA-N prolinol Chemical compound OCC1CCCN1 HVVNJUAVDAZWCB-UHFFFAOYSA-N 0.000 claims description 2
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- 150000002431 hydrogen Chemical class 0.000 claims 5
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- 239000000203 mixture Substances 0.000 description 6
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- 238000002474 experimental method Methods 0.000 description 3
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- KQKFXROIQIGLRC-UHFFFAOYSA-N 3-[[4-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-2-yl]amino]propane-1,2-diol;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(NCC(O)CO)=CC(N3CC4=CC=CC=C4CC3)=C21 KQKFXROIQIGLRC-UHFFFAOYSA-N 0.000 description 2
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- BEOVBLPXVFICSP-UHFFFAOYSA-N 4-chloro-6-methoxyquinoline Chemical compound N1=CC=C(Cl)C2=CC(OC)=CC=C21 BEOVBLPXVFICSP-UHFFFAOYSA-N 0.000 description 2
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 2
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- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000001767 medulla oblongata Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method 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
- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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
- C07D215/42—Nitrogen atoms attached in position 4
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99120131 | 1999-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000652A2 true HRP20000652A2 (en) | 2001-12-31 |
Family
ID=8239160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000652A HRP20000652A2 (en) | 1999-10-08 | 2000-10-03 | Quinolin -4-yl derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6339093B1 (es) |
| EP (1) | EP1090917B1 (es) |
| JP (1) | JP3385318B2 (es) |
| KR (1) | KR100398562B1 (es) |
| CN (1) | CN1162424C (es) |
| AR (1) | AR032601A1 (es) |
| AT (1) | ATE313538T1 (es) |
| AU (1) | AU777881B2 (es) |
| BR (1) | BR0004709A (es) |
| CA (1) | CA2322309C (es) |
| DE (1) | DE60024947T2 (es) |
| DK (1) | DK1090917T3 (es) |
| EG (1) | EG23872A (es) |
| ES (1) | ES2254095T3 (es) |
| HR (1) | HRP20000652A2 (es) |
| HU (1) | HUP0003938A2 (es) |
| ID (1) | ID27526A (es) |
| IL (1) | IL138916A0 (es) |
| MA (1) | MA26753A1 (es) |
| MX (1) | MXPA00009771A (es) |
| NO (1) | NO20005031L (es) |
| NZ (1) | NZ507303A (es) |
| PE (1) | PE20010660A1 (es) |
| PL (1) | PL343057A1 (es) |
| TR (1) | TR200002893A2 (es) |
| ZA (1) | ZA200005447B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6339093B1 (en) * | 1999-10-08 | 2002-01-15 | Hoffmann-La Roche Inc. | Isoquinoline derivatives |
| EP1436258A4 (en) * | 2001-03-08 | 2005-03-23 | Univ Emory | PH VALVE DEPENDENT NMDA RECEPTOR ANTAGONISTS |
| US6831087B2 (en) | 2001-11-09 | 2004-12-14 | Hoffmann-La Roche Inc. | Pyridine substituted isoquinoline derivatives |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| US8110681B2 (en) | 2006-03-17 | 2012-02-07 | The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Compounds for the treatment of spinal muscular atrophy and other uses |
| MY146992A (en) * | 2007-06-18 | 2012-10-15 | Richter Gedeon Nyrt | Sulfonyl-quinoline derivatives |
| JP2010532382A (ja) * | 2007-06-29 | 2010-10-07 | エモリー・ユニバーシテイ | 神経保護のためのｎｍｄａ受容体拮抗薬 |
| AU2008304231A1 (en) * | 2007-09-27 | 2009-04-02 | Albany Molecular Research, Inc. | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| US9938269B2 (en) | 2011-06-30 | 2018-04-10 | Abbvie Inc. | Inhibitor compounds of phosphodiesterase type 10A |
| LT3386591T (lt) | 2015-12-09 | 2020-10-12 | Cadent Therapeutics, Inc. | Heteroaromatiniai nmda receptoriaus moduliatoriai ir jų panaudojimas |
| EP3452465B1 (en) * | 2016-05-04 | 2020-11-04 | Genoscience Pharma | Substituted 2, 4-diamino-quinoline derivatives for use in the treatment of proliferative diseases |
| US11274107B2 (en) | 2016-12-22 | 2022-03-15 | Cadent Therapeutics, Inc. | NMDA receptor modulators and uses thereof |
| JP7319369B2 (ja) | 2018-08-03 | 2023-08-01 | ノバルティス アーゲー | ヘテロ芳香族ｎｍｄａ受容体モジュレーターおよびその使用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8409745D0 (en) * | 1984-04-14 | 1984-05-23 | Beecham Group Plc | Active compounds |
| US4560692A (en) * | 1984-07-18 | 1985-12-24 | Hoffmann-La Roche Inc. | 4-Piperidino-2-phenylquinolines |
| GB8716972D0 (en) * | 1987-07-17 | 1987-08-26 | Pfizer Ltd | Treatment of cardiac arrhythmias |
| JPH0262875A (ja) | 1988-05-23 | 1990-03-02 | Wakunaga Pharmaceut Co Ltd | 新規イソインドリン誘導体 |
| US4992448A (en) * | 1989-10-24 | 1991-02-12 | Hoechst-Roussel Pharmaceuticals Inc. | Benzocycloalkylaminopyridinamines and related compounds as topical antiinflammatory agents for the treatment of skin disorders |
| US5304554A (en) * | 1990-04-27 | 1994-04-19 | Emory University | 4-[(alkyl or dialkyl)amino]quinolines and their method of preparation |
| GB9203798D0 (en) * | 1992-02-21 | 1992-04-08 | Fujisawa Pharmaceutical Co | Quinolylbenzofuran derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
| GB9305644D0 (en) * | 1993-03-18 | 1993-05-05 | Merck Sharp & Dohme | Therapeutic agents |
| US5567718A (en) * | 1994-08-11 | 1996-10-22 | Hoechst Marion Roussel Inc. | 2,3-dihydro-1h-isoindole derivatives and their use as serotonin reuptake inhibitors |
| ZA9610738B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| US6339093B1 (en) * | 1999-10-08 | 2002-01-15 | Hoffmann-La Roche Inc. | Isoquinoline derivatives |
-
2000
- 2000-09-26 US US09/669,648 patent/US6339093B1/en not_active Expired - Fee Related
- 2000-09-29 CN CNB001290843A patent/CN1162424C/zh not_active Expired - Fee Related
- 2000-10-02 ES ES00121561T patent/ES2254095T3/es not_active Expired - Lifetime
- 2000-10-02 AT AT00121561T patent/ATE313538T1/de not_active IP Right Cessation
- 2000-10-02 DK DK00121561T patent/DK1090917T3/da active
- 2000-10-02 EP EP00121561A patent/EP1090917B1/en not_active Expired - Lifetime
- 2000-10-02 DE DE60024947T patent/DE60024947T2/de not_active Expired - Lifetime
- 2000-10-03 HR HR20000652A patent/HRP20000652A2/hr not_active Application Discontinuation
- 2000-10-03 PE PE2000001045A patent/PE20010660A1/es not_active Application Discontinuation
- 2000-10-03 NZ NZ507303A patent/NZ507303A/xx unknown
- 2000-10-04 ID IDP20000858D patent/ID27526A/id unknown
- 2000-10-04 CA CA002322309A patent/CA2322309C/en not_active Expired - Fee Related
- 2000-10-04 TR TR2000/02893A patent/TR200002893A2/xx unknown
- 2000-10-04 JP JP2000304354A patent/JP3385318B2/ja not_active Expired - Fee Related
- 2000-10-04 MA MA26080A patent/MA26753A1/fr unknown
- 2000-10-04 EG EG20001265A patent/EG23872A/xx active
- 2000-10-05 IL IL13891600A patent/IL138916A0/xx unknown
- 2000-10-05 ZA ZA200005447A patent/ZA200005447B/xx unknown
- 2000-10-05 MX MXPA00009771A patent/MXPA00009771A/es active IP Right Grant
- 2000-10-05 AR ARP000105238A patent/AR032601A1/es not_active Application Discontinuation
- 2000-10-06 HU HU0003938A patent/HUP0003938A2/hu unknown
- 2000-10-06 BR BR0004709-0A patent/BR0004709A/pt not_active Application Discontinuation
- 2000-10-06 AU AU64100/00A patent/AU777881B2/en not_active Ceased
- 2000-10-06 NO NO20005031A patent/NO20005031L/no not_active Application Discontinuation
- 2000-10-07 KR KR10-2000-0059049A patent/KR100398562B1/ko not_active Expired - Fee Related
- 2000-10-09 PL PL00343057A patent/PL343057A1/xx not_active Application Discontinuation
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