Title:
2−IMINOIMIDAZOLE DERIVATIVES &lpar 1&rpar
Document Type and Number:
WIPO Patent Application WO/2002/088094
Kind Code:
A1
Abstract:
2−Iminoimidazole derivatives represented by the general formula (I) or salts thereof: (I) wherein C is a benzene ring, a pyridine ring, or the like&semi R1 is optionally substituted C1−6 alkyl or the like&semi R201 is hydrogen, halogeno, acyl, or the like&semi R6 is hydrogen, C1−6 alkyl, C1−6 alkyloxycarbonyl, or the like&semi Y1 is a single bond, −CH2−, or the like&semi Y2 is a single bond, −CO−, or the like&semi and Ar is hydrogen, a group represented by the general formula (II): (II) (wherein R10 to R14 are each hydrogen, C1−6 alkyl, hydroxyl, C1−6 alkoxy, or the like, or R11 and R12 or R12 and R13 may be united to form a 5− to 8−membered heterocycle), or the like.
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Inventors:
SUZUKI SHUICHI (JP)
KOTAKE MAKOTO (JP)
MIYAMOTO MITSUAKI (JP)
KAWAHARA TETSUYA
KOTAKE MAKOTO (JP)
MIYAMOTO MITSUAKI (JP)
KAWAHARA TETSUYA
Application Number:
PCT/JP2002/003952
Publication Date:
November 07, 2002
Filing Date:
April 19, 2002
Export Citation:
Assignee:
EISAI CO LTD (JP)
SUZUKI SHUICHI (JP)
KOTAKE MAKOTO (JP)
MIYAMOTO MITSUAKI (JP)
KAWAHARA TETSUYA
SUZUKI SHUICHI (JP)
KOTAKE MAKOTO (JP)
MIYAMOTO MITSUAKI (JP)
KAWAHARA TETSUYA
International Classes:
A61K31/403; A61K31/4035; A61K31/4178; A61K31/4184; A61K31/422; A61K31/437; A61K31/454; A61K31/496; A61K31/5377; A61K31/538; A61P7/02; A61P9/00; A61P9/10; A61P9/12; A61P11/00; A61P11/06; A61P13/12; A61P19/10; A61P25/00; A61P29/00; A61P35/00; A61P43/00; C07D207/22; C07D207/24; C07D207/263; C07D207/267; C07D207/34; C07D209/44; C07D209/52; C07D209/54; C07D209/62; C07D209/96; C07D213/73; C07D213/74; C07D233/46; C07D233/66; C07D233/88; C07D233/90; C07D235/30; C07D249/14; C07D261/14; C07D401/04; C07D401/06; C07D401/10; C07D401/12; C07D403/04; C07D403/06; C07D403/10; C07D403/12; C07D405/06; C07D409/04; C07D409/06; C07D409/10; C07D413/06; C07D413/10; C07D413/12; C07D413/14; C07D417/06; C07D417/10; C07D471/04; C07D487/04; C07D491/10; C07D498/04; C07D521/00; C07D207/26; A61K; A61P; C07D; (IPC1-7): C07D235/30; A61K31/4184; A61P7/02; A61P9/10; A61P9/12; A61P13/12; A61P19/10; A61P25/00; A61P29/00; A61P35/00; A61P43/00; A61P9/00; A61P11/00; A61P11/06
Domestic Patent References:
| WO2000001676A1 | 2000-01-13 |
Foreign References:
| US3989709A | 1976-11-02 | |||
| US4004016A | 1977-01-18 | |||
| JPS4842875B1 | 1973-12-14 | |||
| JP2002155060A | 2002-05-28 |
Other References:
KOVALEV G.V. ET AL.: "Synthesis and pharmacological properties of some disubstituted imidazo(1,2-a)benzimidazole derivatives", KHIM.-FARM. ZH., vol. 13, no. 8, 1979, pages 57 - 62, XP002954486
DIXON STEVEN L. ET AL.: "Bioactive diversity and screening library selection via affinity fingerprinting", CHEMICAL INFORMATION AND COMPUTER SCIENCES, vol. 38, no. 6, 1998, pages 1192 - 1203, XP000890397
KOSHCHIENKO YU.V. ET AL.: "New synthesis of imidazo(1,2-a)benzimidazole derivatives", GETEROTSIKL. SOEDIN., vol. 1, 1975, pages 140 - 141, XP002954487
KOSHCHIENKO YU.V. ET AL.: "Synthesis and antibacterial activity of 3-(alkoxymethyl)-2-amino-1-methylbenzimidazolium chlorides", KHIM.-FARM. ZH., vol. 11, no. 4, 1977, pages 14 - 17, XP002954488
YALE HARRY L. ET AL.: "Quaternary derivatives from 2-aminobenzimidazole and 2-phenylethyl- and phenyloxymethyl halides", J. HETEROCYCL. CHEMICAL, vol. 15, no. 3, 1978, pages 505 - 507, XP002954489
DA SETTIMO ANTONIO ET AL.: "Synthesis of 2-methylaminobenzimidazole derivatives tested for antiinflammatory activity", FARMACO, vol. 49, no. 12, 1994, pages 829 - 834, XP002954490
DA SETTIMO ANTONIO ET AL.: "Synthesis and anti-inflammatory properties of 2-aminobenzimidazole derivatives", FARMACO, vol. 47, no. 10, 1992, pages 1293 - 1313, XP002954491
ANISIMOVA V.A. ET AL.: "Imidazo (1,2-a)benzimidazole derivatives. X. Nitration of 2,9-disubstituted imidazo (1,2-a)benzimidazole", KHIM. GETEROTSIKL. SOEDIN., vol. 2, 1975, pages 258 - 262, XP002954492
REHSE KLAUS ET AL.: "New NO-donors with antithrombotic and vasodilating activities. XI. 2-Nitrosiminobenzimidazoles", ARCH. PHARM., vol. 328, no. 1, 1995, WEINHEIM, GER., pages 77 - 80, XP002954493
ALFAIA ANTONIO J.I. ET AL.: "Quaternization reaction of aromatic heterocyclic imines in methanol - a case of strong aromatic heterocyclic imines in methanol - a case of strong anti-reactivity selectivity principle with isoselective temperature", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 21, 2000, pages 3627 - 3631, XP002954494
CAROTI PAOLA ET AL.: "A facile synthesis of 5,7-dihydro-5-oxopyrido(3',2':5,6)pyrimido(1,2-a)benzimidazoles. A new heterocyclic ring system", J. HETEROCYCL. CHEMICAL, vol. 23, 1986, pages 1833 - 1836, XP002954495
ANISIMOVA V.A. ET AL.: "Imidazo(1,2-a)benzimidazole derivatives. 22. Synthesis of 2,3-dihydroimidazo(1,2-a)benzimidazoles from 3-(2-hydroxyethyl)-2-iminobenzimidazolines", KHIM. GETEROTSIKL. SOEDIN., vol. 7, 1986, pages 918 - 925, XP002954496
ANISIMOVA V.A. ET AL.: "Imidazo(1,2-a)benzimidazole derivatives. 25. Reaction of 2,9-disubstituted imidazo(1,2-a)benzimidazoles with acrylic acids and their derivatives", KHIM. GETEROTSIKL. SOEDIN., vol. 11, 1987, pages 1496 - 1502, XP002954497
KUZ'MENKO T.A. ET AL.: "Synthesis of 9-aminoimidazo(1,2-a)benzimidazoles and their deamination", KHIM. GETEROTSIKL. SOEDIN., vol. 11, 1990, pages 1517 - 1523, XP002954498
CHACKALAMANNIL S. ET AL.: "Potent, low molecular weight thrombin receptor antagonists", CHEMISTRY LETTERS, vol. 11, no. 21, November 2001 (2001-11-01), pages 2851 - 2853, XP002954499
SCIENTIFIC RESEARCH INSTITUTE OF PHYSICAL AND ORGANIC CHEMISTRY OF ROSTOV CITY UNIVERSITY AND VOLGOGRAD CITY MEDICAL INSTITUTE, 13 December 1978 (1978-12-13)
ANISIMOVA V.A.; AVDUNINA N.E.; SIMONOV A.M., CHEMICAL PHARMACOLOGY MAGAZINE, vol. 12, 1978, pages 40 - 45
SIMONOV A.M.; BELOUS A.A; ANISIMOVA V.A., CHEMICAL PHARMACOLOGY MAGAZINE, vol. 1, 1969, pages 7 - 10
KOVALEV G.V.; GOFMAN S.M.; IVANOVSKAYA S.V., PHARMACOLOGY AND TOXICOLOGY, vol. 2, 1973, pages 232 - 238
ANISIMOVA V.A.; SIMONOV A.M.; POHZARSKY A.F., CHEMISTRY OF HETEROCYCLIC COMPOUND, vol. 6, 1973, pages 797 - 802
ANISIMOVA V.A.; SIMONOV A.M.; BORISOVA T.A., CHEMISTRY OF HETEROCYCLIC COMPOUND, vol. 6, 1973, pages 791 - 796
BELENKY M.L.: "Elements of a quantitative estimation of pharmacological effect", 1936
SHEVCHUK M.E.; DOMBROVSKY A.V., LIFE OF GENERAL CHEMISTRY, vol. 33, 1963, pages 1135
SYNTHESES OF ORGANIC PREPARATIONS. MOSCOW, vol. 2, 1949, pages 102
SIMONOV A.M.; ANISIMOVA V.A.; CHUB N.K., HGS, no. 7, 1970, pages 977
SOMEI M. ET AL., CHEM. PHARM. BULL., vol. 26, 1973, pages 2522
ALONSO GARRIDO D.O. ET AL., J. ORG. CHEM., vol. 53, 1988, pages 403
SADYKOV A.S.; KURBATOV Y.V.; ZALYALIEVA S.V.: "N-Imines of pyridine basis - Tashkent", FAN, 1982, pages 35
KUZMENKO T.AS. ET AL., HGS, no. 9, 1988, pages 1226
POZHARSKY A.F.: "Theoretical bases of chemistry of heterocycles", MOSCOW: CHEM., 1985, pages 156
See also references of EP 1394152A4
DIXON STEVEN L. ET AL.: "Bioactive diversity and screening library selection via affinity fingerprinting", CHEMICAL INFORMATION AND COMPUTER SCIENCES, vol. 38, no. 6, 1998, pages 1192 - 1203, XP000890397
KOSHCHIENKO YU.V. ET AL.: "New synthesis of imidazo(1,2-a)benzimidazole derivatives", GETEROTSIKL. SOEDIN., vol. 1, 1975, pages 140 - 141, XP002954487
KOSHCHIENKO YU.V. ET AL.: "Synthesis and antibacterial activity of 3-(alkoxymethyl)-2-amino-1-methylbenzimidazolium chlorides", KHIM.-FARM. ZH., vol. 11, no. 4, 1977, pages 14 - 17, XP002954488
YALE HARRY L. ET AL.: "Quaternary derivatives from 2-aminobenzimidazole and 2-phenylethyl- and phenyloxymethyl halides", J. HETEROCYCL. CHEMICAL, vol. 15, no. 3, 1978, pages 505 - 507, XP002954489
DA SETTIMO ANTONIO ET AL.: "Synthesis of 2-methylaminobenzimidazole derivatives tested for antiinflammatory activity", FARMACO, vol. 49, no. 12, 1994, pages 829 - 834, XP002954490
DA SETTIMO ANTONIO ET AL.: "Synthesis and anti-inflammatory properties of 2-aminobenzimidazole derivatives", FARMACO, vol. 47, no. 10, 1992, pages 1293 - 1313, XP002954491
ANISIMOVA V.A. ET AL.: "Imidazo (1,2-a)benzimidazole derivatives. X. Nitration of 2,9-disubstituted imidazo (1,2-a)benzimidazole", KHIM. GETEROTSIKL. SOEDIN., vol. 2, 1975, pages 258 - 262, XP002954492
REHSE KLAUS ET AL.: "New NO-donors with antithrombotic and vasodilating activities. XI. 2-Nitrosiminobenzimidazoles", ARCH. PHARM., vol. 328, no. 1, 1995, WEINHEIM, GER., pages 77 - 80, XP002954493
ALFAIA ANTONIO J.I. ET AL.: "Quaternization reaction of aromatic heterocyclic imines in methanol - a case of strong aromatic heterocyclic imines in methanol - a case of strong anti-reactivity selectivity principle with isoselective temperature", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 21, 2000, pages 3627 - 3631, XP002954494
CAROTI PAOLA ET AL.: "A facile synthesis of 5,7-dihydro-5-oxopyrido(3',2':5,6)pyrimido(1,2-a)benzimidazoles. A new heterocyclic ring system", J. HETEROCYCL. CHEMICAL, vol. 23, 1986, pages 1833 - 1836, XP002954495
ANISIMOVA V.A. ET AL.: "Imidazo(1,2-a)benzimidazole derivatives. 22. Synthesis of 2,3-dihydroimidazo(1,2-a)benzimidazoles from 3-(2-hydroxyethyl)-2-iminobenzimidazolines", KHIM. GETEROTSIKL. SOEDIN., vol. 7, 1986, pages 918 - 925, XP002954496
ANISIMOVA V.A. ET AL.: "Imidazo(1,2-a)benzimidazole derivatives. 25. Reaction of 2,9-disubstituted imidazo(1,2-a)benzimidazoles with acrylic acids and their derivatives", KHIM. GETEROTSIKL. SOEDIN., vol. 11, 1987, pages 1496 - 1502, XP002954497
KUZ'MENKO T.A. ET AL.: "Synthesis of 9-aminoimidazo(1,2-a)benzimidazoles and their deamination", KHIM. GETEROTSIKL. SOEDIN., vol. 11, 1990, pages 1517 - 1523, XP002954498
CHACKALAMANNIL S. ET AL.: "Potent, low molecular weight thrombin receptor antagonists", CHEMISTRY LETTERS, vol. 11, no. 21, November 2001 (2001-11-01), pages 2851 - 2853, XP002954499
SCIENTIFIC RESEARCH INSTITUTE OF PHYSICAL AND ORGANIC CHEMISTRY OF ROSTOV CITY UNIVERSITY AND VOLGOGRAD CITY MEDICAL INSTITUTE, 13 December 1978 (1978-12-13)
ANISIMOVA V.A.; AVDUNINA N.E.; SIMONOV A.M., CHEMICAL PHARMACOLOGY MAGAZINE, vol. 12, 1978, pages 40 - 45
SIMONOV A.M.; BELOUS A.A; ANISIMOVA V.A., CHEMICAL PHARMACOLOGY MAGAZINE, vol. 1, 1969, pages 7 - 10
KOVALEV G.V.; GOFMAN S.M.; IVANOVSKAYA S.V., PHARMACOLOGY AND TOXICOLOGY, vol. 2, 1973, pages 232 - 238
ANISIMOVA V.A.; SIMONOV A.M.; POHZARSKY A.F., CHEMISTRY OF HETEROCYCLIC COMPOUND, vol. 6, 1973, pages 797 - 802
ANISIMOVA V.A.; SIMONOV A.M.; BORISOVA T.A., CHEMISTRY OF HETEROCYCLIC COMPOUND, vol. 6, 1973, pages 791 - 796
BELENKY M.L.: "Elements of a quantitative estimation of pharmacological effect", 1936
SHEVCHUK M.E.; DOMBROVSKY A.V., LIFE OF GENERAL CHEMISTRY, vol. 33, 1963, pages 1135
SYNTHESES OF ORGANIC PREPARATIONS. MOSCOW, vol. 2, 1949, pages 102
SIMONOV A.M.; ANISIMOVA V.A.; CHUB N.K., HGS, no. 7, 1970, pages 977
SOMEI M. ET AL., CHEM. PHARM. BULL., vol. 26, 1973, pages 2522
ALONSO GARRIDO D.O. ET AL., J. ORG. CHEM., vol. 53, 1988, pages 403
SADYKOV A.S.; KURBATOV Y.V.; ZALYALIEVA S.V.: "N-Imines of pyridine basis - Tashkent", FAN, 1982, pages 35
KUZMENKO T.AS. ET AL., HGS, no. 9, 1988, pages 1226
POZHARSKY A.F.: "Theoretical bases of chemistry of heterocycles", MOSCOW: CHEM., 1985, pages 156
See also references of EP 1394152A4
Attorney, Agent or Firm:
Hasegawa, Yoshiki (Okura-honkan 6-12, Ginza 2-chom, Chuo-ku Tokyo, JP)
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