Title:
FUSED HETEROCYCLIC COMPOUND AND MEDICINAL USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2002/094790
Kind Code:
A1
Abstract:
A fused heterocyclic compound represented by the general formula (I): (I) (wherein the symbols are the same as defined in the description), optically active isomer thereof, pharmaceutically acceptable salt of any of these, hydrate of any of these, and water addition product of any of these. These compounds have poly(ADP−ribose) polymerase inhibitory activity and are useful as a remedy for brain infarction.
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Inventors:
FUJIO MASAKAZU (JP)
SATOH HIROYUKI (JP)
NUMATA ATUSHI (JP)
TAKANASHI SHINICHI (JP)
EGI YASUHIRO (JP)
TATSUMI RYOU (JP)
SATOH HIROYUKI (JP)
NUMATA ATUSHI (JP)
TAKANASHI SHINICHI (JP)
EGI YASUHIRO (JP)
TATSUMI RYOU (JP)
Application Number:
PCT/JP2002/004995
Publication Date:
November 28, 2002
Filing Date:
May 23, 2002
Export Citation:
Assignee:
MITSUBISHI PHARMA CORP (JP)
FUJIO MASAKAZU (JP)
SATOH HIROYUKI (JP)
NUMATA ATUSHI (JP)
TAKANASHI SHINICHI (JP)
EGI YASUHIRO (JP)
TATSUMI RYOU (JP)
FUJIO MASAKAZU (JP)
SATOH HIROYUKI (JP)
NUMATA ATUSHI (JP)
TAKANASHI SHINICHI (JP)
EGI YASUHIRO (JP)
TATSUMI RYOU (JP)
International Classes:
A61K31/4365; A61K31/4375; A61K31/472; A61K31/4725; A61K31/473; A61K31/496; A61K31/517; A61K31/5377; A61K31/55; A61K31/551; A61P3/10; A61P7/04; A61P9/10; A61P25/00; A61P25/14; A61P25/28; A61P29/00; A61P43/00; C07D217/24; C07D239/90; C07D401/04; C07D451/02; C07D453/02; C07D471/04; (IPC1-7): C07D217/24; C07D401/04; C07D451/02; C07D453/02; C07D471/04; C07D495/04; C07D239/88; A61K31/4365; A61K31/4375; A61K31/4725; A61K31/496; A61K31/5377; A61K31/551; A61K31/473; A61K31/472; A61K31/55; A61K31/517; A61P3/10; A61P7/04; A61P9/10; A61P25/00; A61P25/14; A61P25/28; A61P29/00; A61P43/00
Domestic Patent References:
| WO2000042025A1 | 2000-07-20 | |||
| WO2002048117A1 | 2002-06-20 | |||
| WO2002044157A2 | 2002-06-06 |
Foreign References:
| US3322756A | 1967-05-30 | |||
| JPS4880579A | 1973-10-29 | |||
| JPS4880580A | 1973-10-29 | |||
| US3939161A | 1976-02-17 | |||
| JPS4822483A | ||||
| JPS4819587A | ||||
| JPS4822482A | ||||
| JPS4822481A | ||||
| US4011324A | 1977-03-08 | |||
| US4159377A | 1979-06-26 | |||
| US4234581A | 1980-11-18 | |||
| US4054656A | 1977-10-18 |
Other References:
NUNAMI KEN-ICHI ET AL.: "One-step synthesis of 1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid derivatives", J. ORG. CHEM., vol. 44, no. 11, 1979, pages 1887 - 1888, XP002956340
UNVERFERTH KLAUS ET AL.: "Synthese und antikonvulsive aktivitaet von 3-Carbamoyl-4-aryl-isochinolin-1(2H)-onen", ARCH. PHARM., vol. 324, no. 10, 1991, pages 809 - 814, XP001070958
VITTORIO F. ET AL.: "Ricerche su derivati alchilici ed arilici della isochinolina", FARMACO ED. SC., vol. 39, no. 3, 1984, pages 217 - 228, XP002956341
MASAYUKI ISHIKAWA: "Ko domyaku kokazai no gosei kenkyu (dai 3 ho) chinazoline-rui no carbamate yudotai no gosei", REPORTS OF THE INSTITUTE FOR MEDICAL & DENTAL ENGINEERING, vol. 9, 1975, pages 169 - 181, XP002956342
SUESSE MANFRED ET AL.: "Chinazolinearbonsaeuren; Chinazolin-4-on-2-yl-essigsaeureamide", Z. CHEM., vol. 23, no. 11, 1983, pages 406 - 407, XP002956343
GRUPE RENATE ET AL.: "Untersuchungen zur antianaphylaktischen Wirksamkeit von Derivaten des 4-oxochinazolins, der 4-oxochinazolin-3-yl-benzoesaeure und der 4-Oxochinazolin-3-yl-essigsaeure an der Ratte", PHARMAZIE, vol. 39, no. 7, 1984, pages 484 - 486, XP002956344
JOSHI VIDYA ET AL.: "Synthesis of some new 4-quinazolinone-2-carboxy esters, 2-carboxamides, 2-carboxyhydrazides & their tosyl derivatives hving potential biological activity", INDIAN J. CHEM., vol. 26B, 1987, pages 602 - 604, XP002956345
SPIRKOVA K. ET AL.: "Synthesis and biological activity of some 2-substituted quinazolin-4-ones", CHEM. PAPERS, vol. 53, no. 4, 1999, pages 272 - 275, XP002956346
HORI MANABU ET AL.: "Effects of a 2-substituent on the ratio of N- and O-alkylation of 4(3H)-quinazolinones", CHEM. PHARM. BULL., vol. 41, no. 6, 1993, pages 1114 - 1117, XP002956347
RASTOGI RASHMI ET AL.: "Synthesis of 2-substituted quinazolines & quinazolones as potential anthelmintics", INDIAN J. CHEM., vol. 21B, 1982, pages 744 - 746, XP002956348
VAIDYA V.P. ET AL.: "Studies on benzofurans: Part XII - synthesis & reactions of 2-chloromethyl-3,4-dihydro-4-oxobenzofuro(3,2-d)pyrimidine", INDIAN J. CHEM., vol. 20B, 1981, pages 780 - 783, XP002944144
MUSATOVA I.S. ET AL.: "The synthesis and properties of 4-oxo-3,4-dihydrobenzo(g)pteridine-2-carboxylic acid derivatives", KHIM.-FARM. ZH., vol. 20, no. 2, 1986, pages 182 - 187, XP002956349
CRESPO MARIA I. ET AL.: "Design, synthesis and biological activities of new thieno(3,2-d)pyrimidines as selective type 4 phosphodiesterase inhibitors", J. MED. CHEM., vol. 41, 1998, pages 4021 - 4035, XP002173938
REPORTS OF THE INSTITUTE FOR MEDICAL & DENTAL ENGINEERING, vol. 8, 1974, pages 9 - 20, XP000654632
MEKUSKIENE G. ET AL.: "Synthesis and anti-monoamine oxidase activity of 1-(4-quinazolone-2-carbonyl)-2-alkyl (or aralkyl) hydrazines", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, vol. 32, no. 10, 1998, pages 10 - 12, XP002956350
CHIBANI A. ET AL.: "Reduction electrochimique de N-(o-nitrobenzoyl) et de N-(o-nitrobenzyl)amides ou imides obtention de derives de la quinazoline", BULL. SOC. CHIM. FR., vol. 128, 1991, pages 814 - 822, XP002956351
NAGASAKA TATSUO ET AL.: "The reaction of o-ethyl succinimide with primary and secondary amines. A simple synthesis of some 4(3H)-quinazolones and quinazolines having propionic acid at 2-position", HETEROCYCLES, vol. 9, no. 10, 1978, pages 1375 - 1380, XP002956352
CORBIN PERRY S. ET AL.: "Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers", J. AM. CHEM. SOC., vol. 120, 1998, pages 9710 - 9711, XP002956353
REDDY P.S.N. ET AL.: "Synthesis of 2-(4-(3H)-oxoquinazolin-2-yl)-4-aryl-1,3,4-oxadiazoles", INDIAN J. CHEM., vol. 29B, 1990, pages 564 - 565, XP002956354
REDDY V, GOPAL ET AL.: "Synthesis of some new 2-azaheteryl and 2,3-azahetero-annelated quinazolinones", INDIAN J. CHEM., vol. 31B, November 1992 (1992-11-01), pages 764 - 767, XP002956355
USIFOH CYRIL O. ET AL.: "Synthesis and anticonvulsant activity of acetylenic quinazolinone derivatives", ARCHIV. DER PHARMAZIE, vol. 333, no. 8, 2000, pages 261 - 266, XP002956356
ELIASSON MIKAEL J.L. ET AL.: "Poly(ADP-ribose) polymerase gene disruption renders mice resistant to cerebral ischemia", NATURE MEDICINE, vol. 3, no. 10, 1997, pages 1089 - 1095, XP002956357
UNVERFERTH KLAUS ET AL.: "Synthese und antikonvulsive aktivitaet von 3-Carbamoyl-4-aryl-isochinolin-1(2H)-onen", ARCH. PHARM., vol. 324, no. 10, 1991, pages 809 - 814, XP001070958
VITTORIO F. ET AL.: "Ricerche su derivati alchilici ed arilici della isochinolina", FARMACO ED. SC., vol. 39, no. 3, 1984, pages 217 - 228, XP002956341
MASAYUKI ISHIKAWA: "Ko domyaku kokazai no gosei kenkyu (dai 3 ho) chinazoline-rui no carbamate yudotai no gosei", REPORTS OF THE INSTITUTE FOR MEDICAL & DENTAL ENGINEERING, vol. 9, 1975, pages 169 - 181, XP002956342
SUESSE MANFRED ET AL.: "Chinazolinearbonsaeuren; Chinazolin-4-on-2-yl-essigsaeureamide", Z. CHEM., vol. 23, no. 11, 1983, pages 406 - 407, XP002956343
GRUPE RENATE ET AL.: "Untersuchungen zur antianaphylaktischen Wirksamkeit von Derivaten des 4-oxochinazolins, der 4-oxochinazolin-3-yl-benzoesaeure und der 4-Oxochinazolin-3-yl-essigsaeure an der Ratte", PHARMAZIE, vol. 39, no. 7, 1984, pages 484 - 486, XP002956344
JOSHI VIDYA ET AL.: "Synthesis of some new 4-quinazolinone-2-carboxy esters, 2-carboxamides, 2-carboxyhydrazides & their tosyl derivatives hving potential biological activity", INDIAN J. CHEM., vol. 26B, 1987, pages 602 - 604, XP002956345
SPIRKOVA K. ET AL.: "Synthesis and biological activity of some 2-substituted quinazolin-4-ones", CHEM. PAPERS, vol. 53, no. 4, 1999, pages 272 - 275, XP002956346
HORI MANABU ET AL.: "Effects of a 2-substituent on the ratio of N- and O-alkylation of 4(3H)-quinazolinones", CHEM. PHARM. BULL., vol. 41, no. 6, 1993, pages 1114 - 1117, XP002956347
RASTOGI RASHMI ET AL.: "Synthesis of 2-substituted quinazolines & quinazolones as potential anthelmintics", INDIAN J. CHEM., vol. 21B, 1982, pages 744 - 746, XP002956348
VAIDYA V.P. ET AL.: "Studies on benzofurans: Part XII - synthesis & reactions of 2-chloromethyl-3,4-dihydro-4-oxobenzofuro(3,2-d)pyrimidine", INDIAN J. CHEM., vol. 20B, 1981, pages 780 - 783, XP002944144
MUSATOVA I.S. ET AL.: "The synthesis and properties of 4-oxo-3,4-dihydrobenzo(g)pteridine-2-carboxylic acid derivatives", KHIM.-FARM. ZH., vol. 20, no. 2, 1986, pages 182 - 187, XP002956349
CRESPO MARIA I. ET AL.: "Design, synthesis and biological activities of new thieno(3,2-d)pyrimidines as selective type 4 phosphodiesterase inhibitors", J. MED. CHEM., vol. 41, 1998, pages 4021 - 4035, XP002173938
REPORTS OF THE INSTITUTE FOR MEDICAL & DENTAL ENGINEERING, vol. 8, 1974, pages 9 - 20, XP000654632
MEKUSKIENE G. ET AL.: "Synthesis and anti-monoamine oxidase activity of 1-(4-quinazolone-2-carbonyl)-2-alkyl (or aralkyl) hydrazines", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, vol. 32, no. 10, 1998, pages 10 - 12, XP002956350
CHIBANI A. ET AL.: "Reduction electrochimique de N-(o-nitrobenzoyl) et de N-(o-nitrobenzyl)amides ou imides obtention de derives de la quinazoline", BULL. SOC. CHIM. FR., vol. 128, 1991, pages 814 - 822, XP002956351
NAGASAKA TATSUO ET AL.: "The reaction of o-ethyl succinimide with primary and secondary amines. A simple synthesis of some 4(3H)-quinazolones and quinazolines having propionic acid at 2-position", HETEROCYCLES, vol. 9, no. 10, 1978, pages 1375 - 1380, XP002956352
CORBIN PERRY S. ET AL.: "Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers", J. AM. CHEM. SOC., vol. 120, 1998, pages 9710 - 9711, XP002956353
REDDY P.S.N. ET AL.: "Synthesis of 2-(4-(3H)-oxoquinazolin-2-yl)-4-aryl-1,3,4-oxadiazoles", INDIAN J. CHEM., vol. 29B, 1990, pages 564 - 565, XP002956354
REDDY V, GOPAL ET AL.: "Synthesis of some new 2-azaheteryl and 2,3-azahetero-annelated quinazolinones", INDIAN J. CHEM., vol. 31B, November 1992 (1992-11-01), pages 764 - 767, XP002956355
USIFOH CYRIL O. ET AL.: "Synthesis and anticonvulsant activity of acetylenic quinazolinone derivatives", ARCHIV. DER PHARMAZIE, vol. 333, no. 8, 2000, pages 261 - 266, XP002956356
ELIASSON MIKAEL J.L. ET AL.: "Poly(ADP-ribose) polymerase gene disruption renders mice resistant to cerebral ischemia", NATURE MEDICINE, vol. 3, no. 10, 1997, pages 1089 - 1095, XP002956357
Attorney, Agent or Firm:
Takashima, Hajime (2-14 Fushimimachi 4-chome, Chuo-k, Osaka-shi Osaka, JP)
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