Title:
8-AZA, 6-AZA AND 6,8-DIAZA-1,4-DIHYDROQUINOXALINE-2,3-DIONES AND THE USE THEREOF AS ANTAGONISTS FOR THE GLYCINE/NMDA RECEPTOR
Document Type and Number:
WIPO Patent Application WO1995018616
Kind Code:
A3
Abstract:
Disclosed is a method of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma or hypoglycemia. The method comprises administering to an animal a compound of the formula: hereof; wherein n is zero or 1; R4, R5, R6 are independently hydrogen, nitro, amino, halo, haloalkyl, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, azido, acylamino, alkylsulfonyl, aryl, substituted aryl, heteroaryl, alkoxy, trialkylsilyl-substituted alkoxy, aryloxy, substituted aryloxy, heteroaryloxy, a heterocyclic group, a heterocyclicoxy group, aralkoxy, or haloalkoxy; and Rc and Rd are defined in the specification. These compounds have high binding to the glycine site of the NMDA receptor.
Inventors:
CAI SUI XIONG
WEBER ECKARD
KEANA JOHN F W
WEBER ECKARD
KEANA JOHN F W
Application Number:
PCT/US1995/000214
Publication Date:
December 21, 1995
Filing Date:
January 03, 1995
Export Citation:
Assignee:
ACEA PHARM INC (US)
UNIV CALIFORNIA (US)
OREGON STATE (US)
UNIV CALIFORNIA (US)
OREGON STATE (US)
International Classes:
A61K31/495; C07D487/04; A61K31/4985; A61K31/519; A61P9/10; A61P21/00; A61P21/02; A61P25/00; A61P25/02; A61P25/04; A61P25/08; A61P25/14; A61P25/20; A61P25/22; A61P25/28; A61P25/36; A61P43/00; C07D471/04; C07D475/00; (IPC1-7): A61K31/495
Domestic Patent References:
| WO1991013878A1 | 1991-09-19 | |||
| WO1992007847A1 | 1992-05-14 |
Foreign References:
| EP0374534A1 | 1990-06-27 | |||
| EP0008864A1 | 1980-03-19 | |||
| EP0039920A2 | 1981-11-18 | |||
| EP0320136A2 | 1989-06-14 | |||
| EP0283162A2 | 1988-09-21 | |||
| EP0290819A2 | 1988-11-17 | |||
| EP0347146A2 | 1989-12-20 |
Other References:
M.KESSLER ET AL.: "A Glycine Site Associated with N-Methyl-D-Aspartic Acid Receptors: Characterization and Identification of a New Class of Antagonists", J.NEUROCHEM., vol. 52, no. 4, April 1989 (1989-04-01), pages 1319 - 1328
PATENT ABSTRACTS OF JAPAN vol. 16, no. 485 (C - 0993) 8 October 1992 (1992-10-08)
D.BOUTTE ET AL.: "Étude des mono et dihydroxy-pyrido-[2.3-b] et [3.4-b] pyrazines et synthèse de la dioxo-1.4 tétrahydro-1.2.3.4 pyrido-[2'.3':5.6]pyrazino-[2.3-d]pyridazine", C.R.ACAD.SCI., SER.C, vol. 273, no. 23, 1971, pages 1645 - 1648
M.D.MCFARLANE ET AL.: "A NEW ROUTE TO N-HYDROXYQUINOXALINE-2,3-DIONES AND SOME AZA-ANALOGUES", TETRAHEDRON LETT., vol. 28, no. 50, 1987, pages 6363 - 6366
R.GOTTLIEB ET AL.: "Synthese und elektrochemisches Verhalten von 6,7-Dioxo-tetrahydropteridinen und 2,3-Dioxotetrahydropyrido-pyrazinen", CHEM.BER., vol. 111, no. 5, 1978, pages 1763 - 1779
J.CLARK ET AL.: "Heterocyclic Sudies. Part X. 4-Phenylpteridine and Some Methyl Derivatives", J.CHEM.SOC. C, no. 14, 1969, pages 1883 - 1886
A.ALBERT ET AL.: "Pteridine Studies. Part XXXV. The Structure of the Hydrated Dimer Formed by the Action of Dilute Acid on 4-Methylpteridine", J.CHEM.SOC. C, no. 10, 1968, pages 1181 - 1187
J.CLARK ET AL.: "Heterocyclic Studies. Part VIII. 2-Phenylpteridine and Some Related Compounds", J.CHEM.SOC. C, no. 10, 1969, pages 1408 - 1412
J.WEINSTOCK ET AL.: "Pteridines. IX. Some Pteridine Isomers of Triamterene", J.MED.CHEM., vol. 11, no. 3, 1968, pages 565 - 568
CHEMICAL ABSTRACTS, vol. 56, no. 5, 5 March 1962, Columbus, Ohio, US; abstract no. 4753cd
CHEMICAL ABSTRACTS, vol. 51, no. 2, 25 January 1960, Columbus, Ohio, US; abstract no. 1978h
CHEMICAL ABSTRACTS, vol. 51, no. 2, 25 January 1960, Columbus, Ohio, US; abstract no. 6655ab
PATENT ABSTRACTS OF JAPAN vol. 16, no. 485 (C - 0993) 8 October 1992 (1992-10-08)
D.BOUTTE ET AL.: "Étude des mono et dihydroxy-pyrido-[2.3-b] et [3.4-b] pyrazines et synthèse de la dioxo-1.4 tétrahydro-1.2.3.4 pyrido-[2'.3':5.6]pyrazino-[2.3-d]pyridazine", C.R.ACAD.SCI., SER.C, vol. 273, no. 23, 1971, pages 1645 - 1648
M.D.MCFARLANE ET AL.: "A NEW ROUTE TO N-HYDROXYQUINOXALINE-2,3-DIONES AND SOME AZA-ANALOGUES", TETRAHEDRON LETT., vol. 28, no. 50, 1987, pages 6363 - 6366
R.GOTTLIEB ET AL.: "Synthese und elektrochemisches Verhalten von 6,7-Dioxo-tetrahydropteridinen und 2,3-Dioxotetrahydropyrido-pyrazinen", CHEM.BER., vol. 111, no. 5, 1978, pages 1763 - 1779
J.CLARK ET AL.: "Heterocyclic Sudies. Part X. 4-Phenylpteridine and Some Methyl Derivatives", J.CHEM.SOC. C, no. 14, 1969, pages 1883 - 1886
A.ALBERT ET AL.: "Pteridine Studies. Part XXXV. The Structure of the Hydrated Dimer Formed by the Action of Dilute Acid on 4-Methylpteridine", J.CHEM.SOC. C, no. 10, 1968, pages 1181 - 1187
J.CLARK ET AL.: "Heterocyclic Studies. Part VIII. 2-Phenylpteridine and Some Related Compounds", J.CHEM.SOC. C, no. 10, 1969, pages 1408 - 1412
J.WEINSTOCK ET AL.: "Pteridines. IX. Some Pteridine Isomers of Triamterene", J.MED.CHEM., vol. 11, no. 3, 1968, pages 565 - 568
CHEMICAL ABSTRACTS, vol. 56, no. 5, 5 March 1962, Columbus, Ohio, US; abstract no. 4753cd
CHEMICAL ABSTRACTS, vol. 51, no. 2, 25 January 1960, Columbus, Ohio, US; abstract no. 1978h
CHEMICAL ABSTRACTS, vol. 51, no. 2, 25 January 1960, Columbus, Ohio, US; abstract no. 6655ab
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