AP877A - Tetrahydroquinoline derivatives as EAA antagonists. - Google Patents
Tetrahydroquinoline derivatives as EAA antagonists. Download PDFInfo
- Publication number
- AP877A AP877A APAP/P/1999/001459A AP9901459A AP877A AP 877 A AP877 A AP 877A AP 9901459 A AP9901459 A AP 9901459A AP 877 A AP877 A AP 877A
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- AP
- ARIPO
- Prior art keywords
- group
- formula
- compound
- carboxylic acid
- hydrogen
- Prior art date
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- 239000003194 amino acid receptor blocking agent Substances 0.000 title description 3
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- -1 hydroxy, methoxy, amino Chemical group 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
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- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims abstract description 4
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- 125000006239 protecting group Chemical group 0.000 claims description 24
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
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- 229950006874 kainic acid Drugs 0.000 description 1
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- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- RLHBCXKHVSXMKY-UHFFFAOYSA-N n-(4-aminophenyl)-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC=C(N)C=C1 RLHBCXKHVSXMKY-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 208000033300 perinatal asphyxia Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
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- 230000000069 prophylactic effect Effects 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61P25/28—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9617305.9A GB9617305D0 (en) | 1996-08-17 | 1996-08-17 | Heterocyclic compounds |
| PCT/EP1997/004440 WO1998007704A1 (en) | 1996-08-17 | 1997-08-14 | Tetrahydroquinoline derivatives as eaa antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9901459A0 AP9901459A0 (en) | 1999-03-31 |
| AP877A true AP877A (en) | 2000-09-27 |
Family
ID=10798623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1999/001459A AP877A (en) | 1996-08-17 | 1997-08-14 | Tetrahydroquinoline derivatives as EAA antagonists. |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6479488B1 (cs) |
| EP (1) | EP0922034B1 (cs) |
| JP (1) | JP4108129B2 (cs) |
| KR (1) | KR100552864B1 (cs) |
| CN (1) | CN1131214C (cs) |
| AP (1) | AP877A (cs) |
| AR (1) | AR008296A1 (cs) |
| AT (1) | ATE221052T1 (cs) |
| AU (1) | AU724473B2 (cs) |
| BR (1) | BR9711311B1 (cs) |
| CA (1) | CA2264118C (cs) |
| CO (1) | CO4900066A1 (cs) |
| CZ (1) | CZ296250B6 (cs) |
| DE (1) | DE69714265T2 (cs) |
| DK (1) | DK0922034T3 (cs) |
| EA (1) | EA001704B1 (cs) |
| ES (1) | ES2181030T3 (cs) |
| GB (1) | GB9617305D0 (cs) |
| HU (1) | HU225797B1 (cs) |
| ID (1) | ID18095A (cs) |
| IL (1) | IL128141A0 (cs) |
| IS (1) | IS4953A (cs) |
| MY (1) | MY116952A (cs) |
| NO (1) | NO312241B1 (cs) |
| NZ (1) | NZ333812A (cs) |
| PE (1) | PE107098A1 (cs) |
| PL (1) | PL194532B1 (cs) |
| PT (1) | PT922034E (cs) |
| SI (1) | SI0922034T1 (cs) |
| TR (1) | TR199900336T2 (cs) |
| TW (1) | TW449582B (cs) |
| WO (1) | WO1998007704A1 (cs) |
| YU (1) | YU6799A (cs) |
| ZA (1) | ZA977326B (cs) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9706294D0 (en) * | 1997-03-26 | 1997-05-14 | Glaxo Wellcome Spa | Heterocyclic compound |
| MY125037A (en) * | 1998-06-10 | 2006-07-31 | Glaxo Wellcome Spa | 1,2,3,4 tetrahydroquinoline derivatives |
| US6455734B1 (en) | 2000-08-09 | 2002-09-24 | Magnesium Diagnostics, Inc. | Antagonists of the magnesium binding defect as therapeutic agents and methods for treatment of abnormal physiological states |
| GB9929037D0 (en) | 1999-12-08 | 2000-02-02 | Glaxo Wellcome Spa | Heterocyclic derivatives |
| DE10132725A1 (de) | 2001-07-05 | 2006-08-03 | Grünenthal GmbH | Substituierte γ-Lactonverbindungen |
| DE60206198T2 (de) * | 2001-12-28 | 2006-06-14 | Acadia Pharm Inc | Tetrahydrochinolinderivate als muscarinische agonisten |
| AU2004206931A1 (en) * | 2003-01-23 | 2004-08-05 | Acadia Pharmaceuticals Inc. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20050085463A1 (en) * | 2003-01-23 | 2005-04-21 | Weiner David M. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20050250767A1 (en) * | 2003-01-23 | 2005-11-10 | Weiner David M | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20060233843A1 (en) * | 2003-02-19 | 2006-10-19 | Conn P J | Treatment of psychosis with a muscarinic m1 receptor ectopic activator |
| BRPI0417749A (pt) * | 2003-12-22 | 2007-04-10 | Acadia Pharm Inc | composto, método de sintese de composto, bibliotecas combinatórias, composições farmacêuticas e métodos de tratamento de disfunções neuropsiquiátricas |
| KR20070007888A (ko) * | 2004-04-01 | 2007-01-16 | 아카디아 파마슈티칼스 인코포레이티드 | 결정질 ｎ-데스메틸클로자핀 |
| KR20110093948A (ko) * | 2005-07-22 | 2011-08-18 | 모찌다 세이야쿠 가부시끼가이샤 | 신규 헤테로시클리덴 아세트아미드 유도체 |
| RU2451014C2 (ru) * | 2005-07-22 | 2012-05-20 | Мотида Фармасьютикал Ко., Лтд. | Новое производное гетероциклиден ацетамида |
| US8435224B2 (en) | 2005-09-12 | 2013-05-07 | Abela Pharmaceuticals, Inc. | Materials for facilitating administration of dimethyl sulfoxide (DMSO) and related compounds |
| EP1966229B1 (en) | 2005-09-12 | 2015-10-21 | Abela Pharmaceuticals, Inc. | Systems for removing dimethyl sulfoxide (dmso) or related compounds, or odors associated with same |
| US8480797B2 (en) | 2005-09-12 | 2013-07-09 | Abela Pharmaceuticals, Inc. | Activated carbon systems for facilitating use of dimethyl sulfoxide (DMSO) by removal of same, related compounds, or associated odors |
| US9427419B2 (en) | 2005-09-12 | 2016-08-30 | Abela Pharmaceuticals, Inc. | Compositions comprising dimethyl sulfoxide (DMSO) |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| BRPI0921494A2 (pt) | 2008-11-03 | 2018-10-30 | Prad Reasearch And Development Ltd | método de planejamento de uma operação de amostragem para uma formação subterrãnea, método de contolar uma operação de amostragem de formação subterrânea, método de controlar uma operação de perfuração para uma formação subterrãnea, e método de realizar uma amostragem durante a operação de perfuração. |
| AU2010313253B2 (en) | 2009-10-30 | 2015-02-19 | Abela Pharmaceuticals, Inc. | Dimethyl sulfoxide (DMSO) and methylsulfonylmethane (MSM) formulations to treat osteoarthritis |
| WO2013055386A2 (en) | 2011-10-03 | 2013-04-18 | The University Of Utah Research Foundation | Application of 5-ht6 receptor antagonists for the alleviation of cognitive deficits of down syndrome |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0386839A2 (en) * | 1989-03-08 | 1990-09-12 | Merck Sharp & Dohme Ltd. | Tetrahydroquinoline derivatives useful for neurodegenerative disorders |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4108123B2 (ja) * | 1995-09-29 | 2008-06-25 | グラクソスミスクライン・ソシエタ・ペル・アチオニ | Ｎｍｄａアンタゴニストとしてのテトラヒドロキノリン |
-
1996
- 1996-08-17 GB GBGB9617305.9A patent/GB9617305D0/en active Pending
-
1997
- 1997-08-14 ES ES97943809T patent/ES2181030T3/es not_active Expired - Lifetime
- 1997-08-14 EA EA199900121A patent/EA001704B1/ru not_active IP Right Cessation
- 1997-08-14 DE DE69714265T patent/DE69714265T2/de not_active Expired - Lifetime
- 1997-08-14 HU HU9903108A patent/HU225797B1/hu not_active IP Right Cessation
- 1997-08-14 CO CO97046782A patent/CO4900066A1/es unknown
- 1997-08-14 MY MYPI97003742A patent/MY116952A/en unknown
- 1997-08-14 DK DK97943809T patent/DK0922034T3/da active
- 1997-08-14 AT AT97943809T patent/ATE221052T1/de not_active IP Right Cessation
- 1997-08-14 EP EP97943809A patent/EP0922034B1/en not_active Expired - Lifetime
- 1997-08-14 AU AU45518/97A patent/AU724473B2/en not_active Ceased
- 1997-08-14 IL IL12814197A patent/IL128141A0/xx not_active IP Right Cessation
- 1997-08-14 ID IDP972834A patent/ID18095A/id unknown
- 1997-08-14 YU YU6799A patent/YU6799A/sh unknown
- 1997-08-14 CZ CZ0052999A patent/CZ296250B6/cs not_active IP Right Cessation
- 1997-08-14 TR TR1999/00336T patent/TR199900336T2/xx unknown
- 1997-08-14 PE PE1997000718A patent/PE107098A1/es not_active Application Discontinuation
- 1997-08-14 JP JP51037298A patent/JP4108129B2/ja not_active Expired - Fee Related
- 1997-08-14 ZA ZA977326A patent/ZA977326B/xx unknown
- 1997-08-14 PT PT97943809T patent/PT922034E/pt unknown
- 1997-08-14 AP APAP/P/1999/001459A patent/AP877A/en active
- 1997-08-14 PL PL97331562A patent/PL194532B1/pl not_active IP Right Cessation
- 1997-08-14 WO PCT/EP1997/004440 patent/WO1998007704A1/en active IP Right Grant
- 1997-08-14 US US09/147,568 patent/US6479488B1/en not_active Expired - Fee Related
- 1997-08-14 BR BRPI9711311-5A patent/BR9711311B1/pt not_active IP Right Cessation
- 1997-08-14 CN CN97197233A patent/CN1131214C/zh not_active Expired - Fee Related
- 1997-08-14 NZ NZ333812A patent/NZ333812A/xx active Application Revival
- 1997-08-14 AR ARP970103703A patent/AR008296A1/es active IP Right Grant
- 1997-08-14 SI SI9730404T patent/SI0922034T1/xx unknown
- 1997-08-14 KR KR1019997001280A patent/KR100552864B1/ko not_active Expired - Fee Related
- 1997-08-14 CA CA002264118A patent/CA2264118C/en not_active Expired - Fee Related
- 1997-08-30 TW TW086112442A patent/TW449582B/zh not_active IP Right Cessation
-
1999
- 1999-01-22 IS IS4953A patent/IS4953A/is unknown
- 1999-02-16 NO NO19990723A patent/NO312241B1/no not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0386839A2 (en) * | 1989-03-08 | 1990-09-12 | Merck Sharp & Dohme Ltd. | Tetrahydroquinoline derivatives useful for neurodegenerative disorders |
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