PT96930B - Metodo para a utilizacao de guanidinas tri- e tetra-substituidas como antagonistas de amino-acidos excitadores - Google Patents
Metodo para a utilizacao de guanidinas tri- e tetra-substituidas como antagonistas de amino-acidos excitadores Download PDFInfo
- Publication number
- PT96930B PT96930B PT96930A PT9693091A PT96930B PT 96930 B PT96930 B PT 96930B PT 96930 A PT96930 A PT 96930A PT 9693091 A PT9693091 A PT 9693091A PT 96930 B PT96930 B PT 96930B
- Authority
- PT
- Portugal
- Prior art keywords
- guanidine
- naphthyl
- group
- substituted
- methyl
- Prior art date
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/435—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by selective application of radiation to a printing material or impression-transfer material
- B41J2/47—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by selective application of radiation to a printing material or impression-transfer material using the combination of scanning and modulation of light
- B41J2/471—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by selective application of radiation to a printing material or impression-transfer material using the combination of scanning and modulation of light using dot sequential main scanning by means of a light deflector, e.g. a rotating polygonal mirror
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
- G03G15/1665—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 by introducing the second base in the nip formed by the recording member and at least one transfer member, e.g. in combination with bias or heat
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- G03G15/168—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 by introducing the second base in the nip formed by the recording member and at least one transfer member, e.g. in combination with bias or heat at least one of the recording member or the transfer member being rotatable during the transfer with means for conditioning the transfer element, e.g. cleaning
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| US48703690A | 1990-03-02 | 1990-03-02 |
Publications (2)
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| PT96930A PT96930A (pt) | 1991-11-29 |
| PT96930B true PT96930B (pt) | 1998-06-30 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5824662A (en) | 1996-09-27 | 1998-10-20 | Guilford Pharmaceuticals Inc. | Treatment of global and focal ischemia using naaladase inhibitors |
| US6017903A (en) | 1996-09-27 | 2000-01-25 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating a glutamate abnormality and effecting a neuronal activity in an animal using NAALADase inhibitors |
| US6413948B1 (en) | 1996-09-27 | 2002-07-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of effecting a neuronal activity in an animal using naaladase inhibitors |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| EP0940139B1 (en) * | 1991-02-08 | 2005-02-02 | Scion Pharmaceuticals, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5298657A (en) * | 1992-03-20 | 1994-03-29 | Cambridge Neuroscience Inc. | Preparation of substituted guanidines |
| EP0690851B1 (en) * | 1993-03-23 | 1999-05-19 | Astra Aktiebolag | Guanidine derivatives useful in therapy |
| JP3610368B2 (ja) * | 1993-05-27 | 2005-01-12 | セネス リミティド | 治療用置換グアニジン |
| DE4327516A1 (de) * | 1993-08-17 | 1995-02-23 | Asta Medica Ag | Primäre und sekundäre neuroprotektive Wirkung bei neurodegenerativen Erkrankungen von Flupirtin |
| WO1995014461A1 (en) * | 1993-11-23 | 1995-06-01 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| AU1912595A (en) | 1994-02-03 | 1995-08-21 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
| GB2288732B (en) * | 1994-04-13 | 1998-04-29 | Quadrant Holdings Cambridge | Pharmaceutical compositions |
| US6756389B2 (en) * | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| US6875759B1 (en) | 1999-07-21 | 2005-04-05 | Kadmus Pharmaceuticals | Substituted guanidines and the use thereof |
| US6678548B1 (en) | 2000-10-20 | 2004-01-13 | The Trustees Of The University Of Pennsylvania | Unified probabilistic framework for predicting and detecting seizure onsets in the brain and multitherapeutic device |
| JP2005506292A (ja) * | 2001-03-08 | 2005-03-03 | エモリー ユニバーシティ | ｐＨに依存するＮＭＤＡレセプターアンタゴニスト |
| US6638981B2 (en) * | 2001-08-17 | 2003-10-28 | Epicept Corporation | Topical compositions and methods for treating pain |
| WO2007009462A2 (en) * | 2005-07-15 | 2007-01-25 | Region Hovedstaden V/Glostrup Hospital | Treatment of migraine and headaches |
| WO2009000038A1 (en) * | 2007-06-28 | 2008-12-31 | Cnsbio Pty Ltd | Combination methods and compositions for treatment of neuropathic pain |
| KR20100045983A (ko) | 2007-06-29 | 2010-05-04 | 에모리 유니버시티 | 신경보호를 위한 ｎｍｄａ 수용체 길항물질 |
| WO2009104080A2 (en) | 2008-02-20 | 2009-08-27 | Targia Pharmaceuticals | Cns pharmaceutical compositions and methods of use |
| AU2009296457A1 (en) | 2008-09-27 | 2010-04-01 | Taraxos Inc. | Topical formulations for treatment of neuropathy |
| NL2006875C2 (en) | 2011-05-31 | 2012-12-03 | Vereniging Voor Christelijk Hoger Onderwijs | N,n-substituted guanidine compound. |
| WO2017093354A1 (en) | 2015-11-30 | 2017-06-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Nmdar antagonists for the treatment of diseases associated with angiogenesis |
Family Cites Families (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1730388A (en) | 1929-10-08 | Winfield scott | ||
| US1677235A (en) | 1928-07-17 | Balph v | ||
| US2145214A (en) | 1939-01-24 | Parasiticide | ||
| US1422506A (en) | 1921-07-02 | 1922-07-11 | Dovan Chemical Corp | Process of making diphenylguanidine |
| US1642180A (en) | 1922-11-27 | 1927-09-13 | Du Pont | Di-para-xylylguanidine |
| US1597233A (en) | 1923-02-27 | 1926-08-24 | Albert C Burrage | Vulcanization of rubber |
| GB223410A (en) | 1923-11-01 | 1924-10-23 | British Dyestuffs Corp Ltd | Improvements in the manufacture of diarylguanidines |
| GB224376A (en) * | 1923-11-01 | 1924-11-13 | British Dyestuffs Corp Ltd | Improvements in the manufacture of triarylguanidines |
| GB258203A (en) | 1925-09-23 | 1926-09-16 | Silesia Ver Chemischer Fabrike | An improved process for the production of symmetrical di-arylguanidines |
| US1672431A (en) | 1925-11-30 | 1928-06-05 | Firm Chem Fab Auf Actien Vorma | Symmetrical diarylized guanidine compounds |
| US1795398A (en) | 1925-12-21 | 1931-03-10 | Huguenin Albert | Elevator for boats with constant draft |
| US1850682A (en) | 1927-01-10 | 1932-03-22 | Ig Farbenindustrie Ag | Substituted guanidines |
| DE514248C (de) * | 1927-09-13 | 1930-12-10 | Schering Kahlbaum Akt Ges | Verfahren zur Darstellung substituierter Guanidine |
| US1756315A (en) * | 1927-11-28 | 1930-04-29 | Rubber Service Lab Co | Rubber vulcanization process |
| US1915922A (en) | 1931-03-02 | 1933-06-27 | American Cyanamid Co | Mothproofing |
| GB478525A (en) | 1936-02-13 | 1938-01-20 | Georg Knoth | Process for the preparation of diphenylguanidine |
| US2254009A (en) | 1940-04-24 | 1941-08-26 | American Cyanamid Co | Symmetrical di-2-octyl-guanidine |
| US2274476A (en) | 1940-08-23 | 1942-02-24 | American Cyanamid Co | Insecticide and moth larvae repellent |
| US2362915A (en) | 1940-12-24 | 1944-11-14 | Courtaulds Ltd | Process for improving the fastness to washing of dyed cellulosic textile materials |
| US2289541A (en) * | 1941-01-18 | 1942-07-14 | American Cyanamid Co | Insecticide |
| US2704710A (en) * | 1950-04-18 | 1955-03-22 | Gen Aniline & Film Corp | Precipitation of azo dyes in silver halide emulsions by means of guanidine and biguanide compounds containing long alkyl chains |
| US2633474A (en) | 1951-07-21 | 1953-03-31 | Monsanto Chemicals | 1, 3-bis (o-ethylphenyl) guanidine |
| US3117994A (en) * | 1959-12-03 | 1964-01-14 | Monsanto Canada Ltd | Nu, nu', nu'-trisubstituted guanidines |
| US3168562A (en) * | 1959-12-23 | 1965-02-02 | Burroughs Wellcome Co | Substituted benzylguanidines |
| GB952194A (en) | 1960-12-23 | 1964-03-11 | Smith Kline French Lab | New guanidine derivatives and processes for preparing the same |
| US3140231A (en) | 1961-08-14 | 1964-07-07 | Rohm & Haas | T-octylguanidines as antihypertensive agents |
| US3159676A (en) | 1962-02-07 | 1964-12-01 | Smith Kline French Lab | Naphthyl containing guanidines |
| US3248426A (en) | 1962-03-01 | 1966-04-26 | American Home Prod | Nu-(1-naphthylmethyl)-guanidine and acid addition salt thereof |
| US3301755A (en) | 1962-04-18 | 1967-01-31 | Ciba Geigy Corp | Allylic guanidines |
| CH433246A (de) * | 1962-06-25 | 1967-04-15 | Ciba Geigy | Verfahren zur Herstellung von Guanidinverbindungen |
| US3479437A (en) * | 1963-08-26 | 1969-11-18 | Stauffer Chemical Co | Guanidine complexes as fungicides |
| US3320229A (en) | 1963-08-26 | 1967-05-16 | Stauffer Chemical Co | Complexes of guanidines with completely halogenated acetones |
| GB1110947A (en) | 1963-12-13 | 1968-04-24 | Evans Medical Ltd | Guanidines |
| US3228975A (en) | 1964-04-10 | 1966-01-11 | American Cyanamid Co | Akyl-substituted cyclohexyl guanidines and biguanides |
| NL125066C (cg-RX-API-DMAC10.html) | 1964-07-31 | |||
| US3391189A (en) * | 1966-01-13 | 1968-07-02 | Ciba Geigy Corp | Nu-allyl-guanidines and salts thereof |
| US3639477A (en) | 1968-06-17 | 1972-02-01 | Parke Davis & Co | Novel propoxyguanidine compounds and means of producing the same |
| US3803324A (en) | 1968-07-09 | 1974-04-09 | Boehringer Mannheim Gmbh | Amino-guanidine derivatives useful for regulating blood pressure |
| GB1208252A (en) * | 1969-01-01 | 1970-10-14 | American Cyanamid Co | Use of alkylguanidine salts as viricides |
| US3547951A (en) | 1969-06-17 | 1970-12-15 | Waldo R Hardie | 1,3-dioxolan-4-yl-alkyl guanidines |
| AU1592270A (en) | 1969-06-17 | 1971-12-09 | Imperial Chemical Industries Limited | Antiviral processes and compositions |
| US3949089A (en) | 1969-06-23 | 1976-04-06 | Burroughs Wellcome Co. | Substituted guanidine compounds as antifibrillatory agents |
| US4060640A (en) | 1970-04-29 | 1977-11-29 | Shell Oil Company | Therapeutic agents |
| US3968243A (en) | 1970-06-05 | 1976-07-06 | Burroughs Wellcome Co. | Substituted guanidine compounds in the treating of arrythmias |
| NL7011683A (cg-RX-API-DMAC10.html) | 1970-08-07 | 1972-02-09 | ||
| US3908013A (en) | 1970-09-17 | 1975-09-23 | Armour Pharma | Pharmaceutical aromatic guanidine compositions and methods of using same |
| US3681459A (en) | 1970-10-01 | 1972-08-01 | Armour Pharma | Guanidine compounds and use of same |
| US3769427A (en) | 1970-10-01 | 1973-10-30 | Armour Pharma | Pharmaceutical compositions and methods of using same |
| US3976787A (en) | 1970-11-10 | 1976-08-24 | Armour Pharmaceutical Company | Pharmaceutical guanidine preparations and methods of using same |
| US3784643A (en) | 1970-12-11 | 1974-01-08 | Colgate Palmolive Co | Aryloxyalkylguanidines |
| DE2133056C3 (de) * | 1971-07-02 | 1980-10-23 | Vsesojuznyj Nautschno-Issledovatelskij Institut Chimitscheskich Sredstv Zaschtschity Rastenij, Moskau | Verwendung von NJS-di-alkyl-N'arylsubstituierten Guanidinen zur Bekämpfung von Mehltaupilzen und Grauschimmel der Pflanzen |
| US3795533A (en) | 1971-11-24 | 1974-03-05 | Research Corp | Preservation and strengthening of porous solids |
| US3976643A (en) | 1973-07-13 | 1976-08-24 | William H. Rorer, Inc. | Guanidines |
| NL7315350A (nl) | 1973-11-09 | 1975-05-13 | Akzo Nv | Nieuwe aminoguanidine verbindingen. |
| US4007181A (en) * | 1974-02-11 | 1977-02-08 | The Upjohn Company | Adamantyl containing guanidines |
| US4052455A (en) | 1974-04-08 | 1977-10-04 | Mead Johnson & Company | Styrylamidines |
| US4014934A (en) | 1974-04-15 | 1977-03-29 | Armour Pharmaceutical Company | Substituted 4'-hydroxyphenyl guanidines and methods of using the same |
| US4109014A (en) | 1974-10-29 | 1978-08-22 | Armour Pharmaceutical Company | Pharmaceutical, compositions containing substituted 4'-hydroxyphenyl guanidines and methods of using same |
| US4130663A (en) | 1975-08-04 | 1978-12-19 | Mead Johnson & Company | Styrylamidines |
| US4169154A (en) | 1976-04-15 | 1979-09-25 | Hoffmann-La Roche Inc. | Method of treating depression with thiourea derivatives |
| US4051256A (en) | 1976-09-19 | 1977-09-27 | Imperial Chemical Industries Limited | Guanidine derivatives |
| US4101659A (en) | 1977-08-29 | 1978-07-18 | Mcneil Laboratories, Incorporated | Benzhydryl guanidines |
| US4172204A (en) | 1977-10-07 | 1979-10-23 | Syntex (U.S.A.) Inc. | Method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and intermediates thereof |
| PL135545B1 (en) | 1980-03-01 | 1985-11-30 | Wyeth John & Brother Ltd | Process for preparing novel derivatives of piperidine |
| DE3108564A1 (de) * | 1981-03-06 | 1982-11-18 | Bayer Ag, 5090 Leverkusen | N-tert-butyl-phenyl-n'-cyclohexyl-quanidine, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| US4393077A (en) * | 1981-07-02 | 1983-07-12 | William H. Rorer, Inc. | 1-Methylene-1-phenylguanidine compounds |
| FR2509724B1 (fr) * | 1981-07-15 | 1985-10-25 | Centre Nat Rech Scient | Nouvelles guanidines a fort encombrement sterique et procedes pour leur preparation |
| US4742054A (en) * | 1982-11-23 | 1988-05-03 | Naftchi Nosrat E | Treatment of mammals suffering from damage to the central nervous system |
| JPS60231755A (ja) * | 1984-04-02 | 1985-11-18 | Mitsubishi Rayon Co Ltd | エポキシ樹脂用添加剤 |
| US4663263A (en) | 1984-10-19 | 1987-05-05 | Canon Kabushiki Kaisha | Toner, charge-imparting material and composition containing substituted guanidine compound for electrophotography |
| DE3501383A1 (de) | 1985-01-17 | 1986-07-17 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von n,n'-disubstituierten guanidinen |
| EP0259371B1 (en) * | 1986-01-28 | 1992-05-13 | JOHN WYETH & BROTHER LIMITED | Preparation of 3-dimethylamino-7-methyl-1,2,4-benzotriazine-1-oxide and azapropazone |
| US5093525A (en) | 1986-07-10 | 1992-03-03 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US5385946A (en) | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
| US5312840A (en) | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US4906779A (en) * | 1986-07-10 | 1990-03-06 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US4709094A (en) * | 1986-07-10 | 1987-11-24 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Sigma brain receptor ligands and their use |
| US5190976A (en) | 1986-07-10 | 1993-03-02 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And University Of Oregon | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| JPS63215034A (ja) * | 1987-03-04 | 1988-09-07 | エルナ−株式会社 | 固体電解コンデンサ |
| US4837218A (en) | 1987-10-23 | 1989-06-06 | Washington University | Alkylated bicycloalkaneamines for treatment of neurotoxic injury |
| DE69011859T2 (de) | 1989-05-02 | 1994-12-15 | Oregon State | Verwendung von sigma-rezeptor-liganden zur herstellung eines anxiolytikums. |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5336689A (en) | 1990-03-02 | 1994-08-09 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| JPH05508836A (ja) * | 1990-05-25 | 1993-12-09 | オレゴン州 | シグマ受容体に対して高い結合性を有する置換グアニジンおよびその使用 |
| CA2089261A1 (en) | 1990-08-30 | 1992-03-01 | John F.W. Keana | Substituted amidines having high binding to the sigma receptor and the use thereof |
| EP0940139B1 (en) * | 1991-02-08 | 2005-02-02 | Scion Pharmaceuticals, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5298657A (en) | 1992-03-20 | 1994-03-29 | Cambridge Neuroscience Inc. | Preparation of substituted guanidines |
-
1991
- 1991-03-04 IE IE071991A patent/IE910719A1/en not_active IP Right Cessation
- 1991-03-04 EP EP91906702A patent/EP0517852B1/en not_active Expired - Lifetime
- 1991-03-04 JP JP50716391A patent/JP3298875B2/ja not_active Expired - Lifetime
- 1991-03-04 WO PCT/US1991/001447 patent/WO1991012797A1/en not_active Ceased
- 1991-03-04 AT AT91906702T patent/ATE220320T1/de not_active IP Right Cessation
- 1991-03-04 PT PT96930A patent/PT96930B/pt active IP Right Grant
- 1991-03-04 ES ES91906702T patent/ES2181668T3/es not_active Expired - Lifetime
- 1991-03-04 SG SG1996007226A patent/SG73414A1/en unknown
- 1991-03-04 AU AU75796/91A patent/AU655176B2/en not_active Ceased
- 1991-03-04 DK DK91906702T patent/DK0517852T3/da active
- 1991-03-04 DE DE69133065T patent/DE69133065T2/de not_active Expired - Fee Related
- 1991-03-04 ZA ZA911553A patent/ZA911553B/xx unknown
- 1991-03-04 CA CA002076664A patent/CA2076664C/en not_active Expired - Lifetime
- 1991-03-04 KR KR1019920702108A patent/KR100353486B1/ko not_active Expired - Fee Related
-
1995
- 1995-06-06 US US08/468,028 patent/US6251948B1/en not_active Expired - Fee Related
-
2001
- 2001-05-23 JP JP2001154124A patent/JP3341000B2/ja not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5824662A (en) | 1996-09-27 | 1998-10-20 | Guilford Pharmaceuticals Inc. | Treatment of global and focal ischemia using naaladase inhibitors |
| US5985855A (en) | 1996-09-27 | 1999-11-16 | Guilford Pharmaceuticals Inc. | Treatment of global and focal ischemia using NAALADase inhibitors |
| US6004946A (en) | 1996-09-27 | 1999-12-21 | Guilford Pharmaceuticals Inc. | Treatment of global and focal ischemia using naaladase inhibitors |
| US6017903A (en) | 1996-09-27 | 2000-01-25 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating a glutamate abnormality and effecting a neuronal activity in an animal using NAALADase inhibitors |
| US6413948B1 (en) | 1996-09-27 | 2002-07-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of effecting a neuronal activity in an animal using naaladase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1991012797A1 (en) | 1991-09-05 |
| JP3298875B2 (ja) | 2002-07-08 |
| ATE220320T1 (de) | 2002-07-15 |
| CA2076664C (en) | 2004-01-13 |
| KR100353486B1 (ko) | 2003-01-06 |
| AU7579691A (en) | 1991-09-18 |
| ZA911553B (en) | 1991-12-24 |
| JP2002020361A (ja) | 2002-01-23 |
| EP0517852A4 (cg-RX-API-DMAC10.html) | 1994-03-02 |
| JPH05507062A (ja) | 1993-10-14 |
| DE69133065D1 (de) | 2002-08-14 |
| IE910719A1 (en) | 1991-09-11 |
| PT96930A (pt) | 1991-11-29 |
| AU655176B2 (en) | 1994-12-08 |
| DE69133065T2 (de) | 2003-02-27 |
| SG73414A1 (en) | 2000-06-20 |
| EP0517852A1 (en) | 1992-12-16 |
| JP3341000B2 (ja) | 2002-11-05 |
| CA2076664A1 (en) | 1991-09-03 |
| DK0517852T3 (da) | 2002-10-07 |
| EP0517852B1 (en) | 2002-07-10 |
| US6251948B1 (en) | 2001-06-26 |
| ES2181668T3 (es) | 2003-03-01 |
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Legal Events
| Date | Code | Title | Description |
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| BB1A | Laying open of patent application |
Effective date: 19910925 |
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| FG3A | Patent granted, date of granting |
Effective date: 19980331 |