Title:
IMINOPYRIDINE DERIVATIVE AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2008/050732
Kind Code:
A1
Abstract:
Disclosed are: an iminopyridine derivative which has a selective antagonistic
activity on an α1D adrenergic receptor and is useful as a prophylactic/therapeutic
agent for lower urinary tract disease or the like; and a method for the screening
of a compound having an antagonistic activity on an α1D adrenergic
receptor. Specifically disclosed are: an α1D adrenergic receptor
antagonist comprising a compound represented by the formula: [wherein each
symbol is as defined in the description] or a salt thereof; and a method for the
screening of a prophylactic/therapeutic agent for lower urinary tract disease
having an antagonistic activity on an α1D adrenergic receptor,
which comprises measuring the tension of a bladder smooth muscle in a rat having
bladder outlet obstruction.
Inventors:
YOSHIDA MASATO (JP)
SUZAKI TOMOHIKO (JP)
KOHARA YASUHISA (JP)
KUNO HARUHIKO (JP)
NAGABUKURO HIROSHI (US)
SAIKAWA REIKO (JP)
OKABE YUUICHI (JP)
IMAI SHIGEMITSU (JP)
SUZAKI TOMOHIKO (JP)
KOHARA YASUHISA (JP)
KUNO HARUHIKO (JP)
NAGABUKURO HIROSHI (US)
SAIKAWA REIKO (JP)
OKABE YUUICHI (JP)
IMAI SHIGEMITSU (JP)
Application Number:
PCT/JP2007/070581
Publication Date:
May 02, 2008
Filing Date:
October 22, 2007
Export Citation:
Assignee:
TAKEDA PHARMACEUTICAL (JP)
YOSHIDA MASATO (JP)
SUZAKI TOMOHIKO (JP)
KOHARA YASUHISA (JP)
KUNO HARUHIKO (JP)
NAGABUKURO HIROSHI (US)
SAIKAWA REIKO (JP)
OKABE YUUICHI (JP)
IMAI SHIGEMITSU (JP)
YOSHIDA MASATO (JP)
SUZAKI TOMOHIKO (JP)
KOHARA YASUHISA (JP)
KUNO HARUHIKO (JP)
NAGABUKURO HIROSHI (US)
SAIKAWA REIKO (JP)
OKABE YUUICHI (JP)
IMAI SHIGEMITSU (JP)
International Classes:
C07D213/82; A61K31/4545; A61K31/455; A61K31/497; A61K31/5377; A61P1/00; A61P1/02; A61P1/08; A61P1/12; A61P1/14; A61P1/16; A61P1/18; A61P3/00; A61P3/02; A61P3/04; A61P3/10; A61P5/00; A61P5/24; A61P5/40; A61P5/42; A61P7/00; A61P7/02; A61P7/06; A61P9/00; A61P9/02; A61P9/04; A61P9/06; A61P9/08; A61P9/10; A61P9/12; A61P11/00; A61P11/02; A61P11/04; A61P11/06; A61P11/10; A61P11/14; A61P13/00; A61P13/08; A61P13/10; A61P13/12; A61P15/00; A61P15/10; A61P15/12; A61P17/00; A61P17/04; A61P17/06; A61P19/00; A61P19/02; A61P19/10; A61P21/04; A61P25/00; A61P25/02; A61P25/08; A61P25/14; A61P25/16; A61P25/18; A61P25/22; A61P25/24; A61P25/28; A61P25/32; A61P25/36; A61P27/02; A61P27/06; A61P27/14; A61P27/16; A61P29/00; A61P31/00; A61P31/04; A61P31/06; A61P31/10; A61P31/16; A61P31/18; A61P31/22; A61P33/02; A61P35/00; A61P35/02; A61P37/02; A61P37/06; A61P37/08; A61P43/00; C07D401/06; C07D401/12; C07D405/06; C07D409/06
Domestic Patent References:
| WO2000004012A1 | 2000-01-27 | |||
| WO2000004027A1 | 2000-01-27 |
Foreign References:
| JPH08208614A | 1996-08-13 | |||
| JP2002503724A | 2002-02-05 | |||
| US3997666A | 1976-12-14 | |||
| DD263759A1 | 1989-01-11 | |||
| EP0047977A2 | 1982-03-24 | |||
| DD106377A1 | 1974-06-12 | |||
| JPS4840544B1 | 1973-12-01 | |||
| JPH09263545A | 1997-10-07 | |||
| JP2006287957A | 2006-10-19 |
Other References:
RUAN H. ET AL.: "Effects of Cl-channel blockers on Ca2+ influx induced by alpha1-adrenoceptor subtypes", CHINESE PHARMACOLOGICAL BULLETIN, vol. 17, no. 2, 2001, pages 147 - 150, XP003022386
SZELL E.A. ET AL.: "Smooth muscle and parasympathetic nerve terminals in the rat urinary bladder have different subtypes of alpha1 adrenoceptors", BRITISH JOURNAL OF PHARMACOLOGY, vol. 130, no. 7, 2000, pages 1685 - 1691, XP003022387
PLUKSE I. ET AL.: "deltaalpha,beta-Butenolides. XIII. Syntheses based on 2,4-pentadienoic acid derivatives", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, no. 4, 1986, pages 471 - 478, XP003022388
PLUKSE I. ET AL.: "deltaalpha,beta-Butenolides. X. Reactions of halobutenolides with aliphatic amines", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, no. 3, 1985, pages 351 - 358, XP003022389
See also references of EP 2077262A4
YAKUGAKU ZASSHI, vol. 126, 2006, pages 187 - 198
MOLECULAR BRAIN RESEARCH, vol. 63, 1999, pages 254 - 261
J. UROL., vol. 160, 1998, pages 937 - 943
J. UROL., vol. 174, 2005, pages 370 - 4
J. UROL., vol. 170, 2003, pages 649 - 653
J. UROL., vol. 167, 2002, pages 1513 - 1521
J. UROL., vol. 173, 2005, pages 657 - 61
EUR. J. PHARMACOL., vol. 272, 1995, pages R5 - R6
EUR. J. PHARMACOL., vol. 445, 2002, pages 21 - 29
HETEROATOM CHEMISTRY, vol. 15, no. 4, 2004, pages 293 - 299
LATVIJAS KIMIJAS ZURNALS, vol. 3-4, 1995, pages 109 - 113
ARZNEIMITTEL-FORSCHUNG, vol. 45, no. 9, 1995, pages 957 - 62
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 40, no. 2, 1993, pages 181 - 7
ZHURNAL STRUKTURNOI KHIMII, vol. 29, no. 5, 1988, pages 169 - 72
KIMIJAS SERIJA, LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, no. 4, 1986, pages 471 - 8 8
KIMIJAS SERIJA, LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, no. 3, 1985, pages 351 - 8
KIMIJAS SERIJA, LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, no. 2, 1985, pages 200 - 5
TETRAHEDRON, vol. 36, no. 6, 1980, pages 785 - 9
"Anorganische Chemie", ORGANISCHE CHEMIE, vol. 35B, no. 4, 1980, pages 490 - 3
TETRAHEDRON, vol. 35, no. 21, 1979, pages 2591 - 3
FETTE, SEIFEN, ANSTRICHMITTEL, vol. 82, no. 2, 1980, pages 82 - 6
TETRAHEDRON, vol. 35, no. 6, 1979, pages 809 - 12
JOURNAL OF CHEMICAL SOCIETY OF JAPAN, no. 5, 1978, pages 730 - 6
TETRAHEDRON LETTERS, no. 15, 1977, pages 1333 - 6
JOURNAL FUER PRAKTISCHE CHEMIE, vol. 318, no. 5, 1976, pages 705 - 30
ZEITSCHRIFT FUER CHEMIE, vol. 13, no. 9, 1973, pages 342 - 3
JOURNAL OF CHEMICAL SOCIETY [SECTION] C: ORGANIC, no. 10, 1971, pages 1892 - 5
ANGEWANDTE CHEMIE, INTERNATIONAL EDITION IN ENGLISH, vol. 10, no. 1, 1971, pages 68 - 70
CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 17, no. 11, 1969, pages 2209 - 16
CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 14, no. 8, 1966, pages 861 - 6
DOKLADY AKADEMII NAUK SSSR, vol. 66, 1949, pages 647 - 50
ANN., vol. 443, 1925, pages 272 - 309
J. AM. CHEM. SOC., vol. 75, 1953, pages 1909
J. ORG. CHEM., vol. 19, 1954, pages 1633
TETRAHEDRON. LETT., vol. 35, no. 32, 1994, pages 5775
CHEMICAL REVIEWS, vol. 95, 1995, pages 2457
THE METHOD DESCRIBED IN SYNTH. COMMUN., 24 June 1994 (1994-06-24), pages 887 - 890
"Protective Groups in Organic Synthesis, 3rd Ed. (1999)", 1999, WILEY-INTERSCIENCE
"Design of Molecules", vol. 7, 1990, HIROKAWA SHOTEN, article "IYAKUHIN no KAIHATSU", pages: 163 - 198
JOURNAL OF CLINICAL ONCOLOGY, vol. 12, 1994, pages 213 - 225
BRITISH JOURNAL OF CANCER, vol. 68, 1993, pages 314 - 318
MANIATIS ET AL., MOLECULAR CLONING, COLD SPRING HARBOR LABORATORY, 1989
DEBRA A. ET AL., J. PHARAMACOL. EXP. TER., vol. 272, 1995, pages 134 - 142
HASHIMOTO T; NAGABUKURO H; DOI T: "Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder outlet obstruction", J UROL., vol. 174, 2005, pages 1137 - 41, XP025377922, DOI: doi:10.1097/01.ju.0000168616.71956.a4
HASHIMOTO T; NAGABUKURO H; DOI T: "Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder ourlet obstruction", J UROL., vol. 174, 2005, pages 1137 - 41, XP025377922, DOI: doi:10.1097/01.ju.0000168616.71956.a4
TAKEI, R.; IKEGAKI, I.; SHIBATA, K. ET AL.: "Naftopidil, a novel alphal-adrenoceptor antagonist, displays selective inhibition of canine prostatic pressure and high affinity binding to cloned human alphal-adrenoceptors", JPN. J. PHARMACOL., vol. 79, 1999, pages 447
KONKEL, M. J.; WETZEL, J. M.; CAHIR, M. ET AL.: "Synthesis and structure-activity relationship of fluoro analogues of 8-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethyl}-8- azaspiro[4.5]decane-7,9-dione as selective alpha(ld)-adrenergic receptor antagonists", J. MED. CHEM., vol. 48, 2005, pages 3076
LEONARDI, A.; BARLOCCO, D.; MONTESANO, F. ET AL.: "Synthesis, screening, and molecular modeling of new potent and selective antagonists at the alpha ld adrenergic receptor", J. MED. CHEM., vol. 47, 2004, pages 1900, XP002651313, DOI: doi:10.1021/JM030944+
SZELL E.A. ET AL.: "Smooth muscle and parasympathetic nerve terminals in the rat urinary bladder have different subtypes of alpha1 adrenoceptors", BRITISH JOURNAL OF PHARMACOLOGY, vol. 130, no. 7, 2000, pages 1685 - 1691, XP003022387
PLUKSE I. ET AL.: "deltaalpha,beta-Butenolides. XIII. Syntheses based on 2,4-pentadienoic acid derivatives", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, no. 4, 1986, pages 471 - 478, XP003022388
PLUKSE I. ET AL.: "deltaalpha,beta-Butenolides. X. Reactions of halobutenolides with aliphatic amines", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, no. 3, 1985, pages 351 - 358, XP003022389
See also references of EP 2077262A4
YAKUGAKU ZASSHI, vol. 126, 2006, pages 187 - 198
MOLECULAR BRAIN RESEARCH, vol. 63, 1999, pages 254 - 261
J. UROL., vol. 160, 1998, pages 937 - 943
J. UROL., vol. 174, 2005, pages 370 - 4
J. UROL., vol. 170, 2003, pages 649 - 653
J. UROL., vol. 167, 2002, pages 1513 - 1521
J. UROL., vol. 173, 2005, pages 657 - 61
EUR. J. PHARMACOL., vol. 272, 1995, pages R5 - R6
EUR. J. PHARMACOL., vol. 445, 2002, pages 21 - 29
HETEROATOM CHEMISTRY, vol. 15, no. 4, 2004, pages 293 - 299
LATVIJAS KIMIJAS ZURNALS, vol. 3-4, 1995, pages 109 - 113
ARZNEIMITTEL-FORSCHUNG, vol. 45, no. 9, 1995, pages 957 - 62
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 40, no. 2, 1993, pages 181 - 7
ZHURNAL STRUKTURNOI KHIMII, vol. 29, no. 5, 1988, pages 169 - 72
KIMIJAS SERIJA, LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, no. 4, 1986, pages 471 - 8 8
KIMIJAS SERIJA, LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, no. 3, 1985, pages 351 - 8
KIMIJAS SERIJA, LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, no. 2, 1985, pages 200 - 5
TETRAHEDRON, vol. 36, no. 6, 1980, pages 785 - 9
"Anorganische Chemie", ORGANISCHE CHEMIE, vol. 35B, no. 4, 1980, pages 490 - 3
TETRAHEDRON, vol. 35, no. 21, 1979, pages 2591 - 3
FETTE, SEIFEN, ANSTRICHMITTEL, vol. 82, no. 2, 1980, pages 82 - 6
TETRAHEDRON, vol. 35, no. 6, 1979, pages 809 - 12
JOURNAL OF CHEMICAL SOCIETY OF JAPAN, no. 5, 1978, pages 730 - 6
TETRAHEDRON LETTERS, no. 15, 1977, pages 1333 - 6
JOURNAL FUER PRAKTISCHE CHEMIE, vol. 318, no. 5, 1976, pages 705 - 30
ZEITSCHRIFT FUER CHEMIE, vol. 13, no. 9, 1973, pages 342 - 3
JOURNAL OF CHEMICAL SOCIETY [SECTION] C: ORGANIC, no. 10, 1971, pages 1892 - 5
ANGEWANDTE CHEMIE, INTERNATIONAL EDITION IN ENGLISH, vol. 10, no. 1, 1971, pages 68 - 70
CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 17, no. 11, 1969, pages 2209 - 16
CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 14, no. 8, 1966, pages 861 - 6
DOKLADY AKADEMII NAUK SSSR, vol. 66, 1949, pages 647 - 50
ANN., vol. 443, 1925, pages 272 - 309
J. AM. CHEM. SOC., vol. 75, 1953, pages 1909
J. ORG. CHEM., vol. 19, 1954, pages 1633
TETRAHEDRON. LETT., vol. 35, no. 32, 1994, pages 5775
CHEMICAL REVIEWS, vol. 95, 1995, pages 2457
THE METHOD DESCRIBED IN SYNTH. COMMUN., 24 June 1994 (1994-06-24), pages 887 - 890
"Protective Groups in Organic Synthesis, 3rd Ed. (1999)", 1999, WILEY-INTERSCIENCE
"Design of Molecules", vol. 7, 1990, HIROKAWA SHOTEN, article "IYAKUHIN no KAIHATSU", pages: 163 - 198
JOURNAL OF CLINICAL ONCOLOGY, vol. 12, 1994, pages 213 - 225
BRITISH JOURNAL OF CANCER, vol. 68, 1993, pages 314 - 318
MANIATIS ET AL., MOLECULAR CLONING, COLD SPRING HARBOR LABORATORY, 1989
DEBRA A. ET AL., J. PHARAMACOL. EXP. TER., vol. 272, 1995, pages 134 - 142
HASHIMOTO T; NAGABUKURO H; DOI T: "Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder outlet obstruction", J UROL., vol. 174, 2005, pages 1137 - 41, XP025377922, DOI: doi:10.1097/01.ju.0000168616.71956.a4
HASHIMOTO T; NAGABUKURO H; DOI T: "Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder ourlet obstruction", J UROL., vol. 174, 2005, pages 1137 - 41, XP025377922, DOI: doi:10.1097/01.ju.0000168616.71956.a4
TAKEI, R.; IKEGAKI, I.; SHIBATA, K. ET AL.: "Naftopidil, a novel alphal-adrenoceptor antagonist, displays selective inhibition of canine prostatic pressure and high affinity binding to cloned human alphal-adrenoceptors", JPN. J. PHARMACOL., vol. 79, 1999, pages 447
KONKEL, M. J.; WETZEL, J. M.; CAHIR, M. ET AL.: "Synthesis and structure-activity relationship of fluoro analogues of 8-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethyl}-8- azaspiro[4.5]decane-7,9-dione as selective alpha(ld)-adrenergic receptor antagonists", J. MED. CHEM., vol. 48, 2005, pages 3076
LEONARDI, A.; BARLOCCO, D.; MONTESANO, F. ET AL.: "Synthesis, screening, and molecular modeling of new potent and selective antagonists at the alpha ld adrenergic receptor", J. MED. CHEM., vol. 47, 2004, pages 1900, XP002651313, DOI: doi:10.1021/JM030944+
Attorney, Agent or Firm:
TAKASHIMA, Hajime (1-1 Fushimimachi 4-chome, Chuo-k, Osaka-shi Osaka 44, JP)
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