Title:
AROMATIC AMINE DERIVATIVES HAVING NOS INHIBITORY EFFECT
Document Type and Number:
WIPO Patent Application WO/1998/028257
Kind Code:
A1
Abstract:
Compounds represented by general formula (1) which have NOS inhibitory activities and are useful as drugs, for example, remedies for cerebrovascular disorders, wherein R�1? and R�2? represent each hydrogen, etc.; R�3? and R�4? represent each hydrogen, lower alkyl, etc.; R�5? represents hydrogen, etc.; X�1?, X�2?, X�3? and X�4? represent each hydrogen, lower alkoxyl, etc.; A represents an optionally substituted pyridine ring, etc.; and m and n are each 0 or 1.
Inventors:
ESAKI TORU (JP)
MAKINO TOSHIHIKO (JP)
NISHIMURA YOSHIKAZU (JP)
NAGAFUJI TOSHIAKI (JP)
MAKINO TOSHIHIKO (JP)
NISHIMURA YOSHIKAZU (JP)
NAGAFUJI TOSHIAKI (JP)
Application Number:
PCT/JP1997/004762
Publication Date:
July 02, 1998
Filing Date:
December 24, 1997
Export Citation:
Assignee:
CHUGAI PHARMACEUTICAL CO LTD (JP)
ESAKI TORU (JP)
MAKINO TOSHIHIKO (JP)
NISHIMURA YOSHIKAZU (JP)
NAGAFUJI TOSHIAKI (JP)
ESAKI TORU (JP)
MAKINO TOSHIHIKO (JP)
NISHIMURA YOSHIKAZU (JP)
NAGAFUJI TOSHIAKI (JP)
International Classes:
A61K31/137; A61K31/40; A61K31/44; A61K31/4965; A61K31/50; A61K31/505; A61P9/10; C07C209/10; C07C211/55; C07C211/56; C07C217/92; C07C229/58; C07C229/60; C07C271/20; C07C323/09; C07D207/34; C07D207/42; C07D213/74; C07D213/75; C07D213/76; C07D213/78; C07D213/80; C07D213/803; C07D213/82; C07D213/85; C07D231/14; C07D231/16; C07C215/56; C07D237/12; C07D237/20; C07D237/24; C07D239/42; C07D241/16; C07D241/24; C07D263/48; C07D277/42; C07D521/00; (IPC1-7): C07C211/54; C07C211/56; C07C209/10; C07D239/42; C07D241/20; C07D263/48; C07D207/335; C07D207/337; C07D401/12; C07D205/04; C07D203/12; C07D277/42; C07D295/12; C07D233/88; C07D213/74; C07D213/79; C07D213/81; C07D213/85; A61K31/135; A61K31/42; A61K31/505; A61K31/40; A61K31/44; A61K31/395; A61K31/425; A61K31/445; A61K31/415
Domestic Patent References:
| WO1994012163A1 | 1994-06-09 | |||
| WO1994025448A1 | 1994-11-10 | |||
| WO1996036620A1 | 1996-11-21 |
Foreign References:
| US5362747A | 1994-11-08 | |||
| JPH08501096A | 1996-02-06 | |||
| JPH05186431A | 1993-07-27 | |||
| JPH08505646A | 1996-06-18 | |||
| JPH0761983A | 1995-03-07 | |||
| JPH05221989A | 1993-08-31 | |||
| JPH0558998A | 1993-03-09 | |||
| JPH04249551A | 1992-09-04 | |||
| JPH0273071A | 1990-03-13 | |||
| US4892578A | 1990-01-09 | |||
| JPS63316775A | 1988-12-26 | |||
| JPS6065067A | 1985-04-13 | |||
| JPS57140783A | 1982-08-31 | |||
| JPS5618969A | 1981-02-23 | |||
| US3705127A | 1972-12-05 | |||
| JPS4842054B1 | 1973-12-10 | |||
| JPS469248B1 | ||||
| US3388099A | 1968-06-11 |
Other References:
EUR. J. MED. CHEM. - CHIM. THER., (1977), 12(3), MIOCQUE MARCEL et al., "Imipramine Derivatives: Amino-Methylation of Diphenylamine and Iminodibenzyl", pages 219-225.
COYNE W. E., CUSIC J. W.: "3,4-DIHYDRO-2(1H)-QUINAZOLINONES.", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 11., no. 06., 1 January 1968 (1968-01-01), US, pages 1208 - 1213., XP000909664, ISSN: 0022-2623, DOI: 10.1021/jm00312a022
J. CHEM. SOC., PERKIN TRANS. 1, (1973), (1), BOWMAN R.E. et al., "Syntheses of Flufenamic Acid Metabolites I and II and Other N-Aryl-Anthranilic Acids", pages 1-4.
NUSSBAUMER P, ET AL.: "Synthesis and Struc ture-Activity Relationships of Phenyl-Substituted Benzylamine Anti-Mycotics: A Novel Benzylbenzylamine Antifungal Agent for Systematic Treatment", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 36, no. 15, 1 January 1993 (1993-01-01), US, pages 2115 - 2120, XP002979877, ISSN: 0022-2623, DOI: 10.1021/jm00067a010
KATO N, ET AL.: "Synthesis of the Acridone Alkaloid Citrusinine-I and Its Derivatives", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 41, no. 3, 1 March 1993 (1993-03-01), JP, pages 445 - 452, XP002979890, ISSN: 0009-2363
NINFANT'EV E.E. ET AL: "1,3,2-Diazaphosphor inanes. VIII. Synthesis, Structure and Chemical Transformations of 1,3-Dialkyl(Aryl)-4,5-Benzo-1,3,2-Diazaphosphorinanes", ZHURNAL OBSHCHEI KHIMII, NAUKA, RUSSIA, vol. 62, no. 2, 1 January 1992 (1992-01-01), Russia, pages 289 - 302, XP008035251, ISSN: 0044-460X
MATHEW A E, ET AL.: "Amino-Substituted P-Benzo quinones", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 29, no. 9, 1 January 1986 (1986-01-01), US, pages 1792 - 1795, XP002979878, ISSN: 0022-2623, DOI: 10.1021/jm00159a041
IL' INA I G, ET AL.: "Synthesis and Chiroptic al Properties of Electron Acceptors of the Picryl Series", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 21, no. 12, 1 January 1985 (1985-01-01), MOSCOW, RU, pages 2529 - 2532, XP002979889, ISSN: 0514-7492
J. LEHMANN ET. AL.: "Zur reduzierenden Spaltung von Chinazolin-2,4-dionen.", ARCHIV DER PHARMAZIE, WILEY VERLAG, WEINHEIM, vol. 315, no. 11, 1 January 1982 (1982-01-01), Weinheim, pages 967 - 969, XP002139157, ISSN: 0365-6233
HORI T, ET AL.: "STUDIES ON ANTITUMOR-ACTIVE 2,3-DIOXOPIPERAZINE DERIVATIVES. III. SYNTHESIS AND STRUCTURE-ANTITUMOR ACTIVITY RALATIONSHIP OF 1-(4-AMINOBENZYL)-2,3-DIOXOPIPERAZINE DERIVATIVES", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 29, no. 05, 1 January 1981 (1981-01-01), JP, pages 1253 - 1266, XP001063113, ISSN: 0009-2363
SINGH P, GUPTA I S: "Study in Nitrogen Mus tards: I. Some 3-ÄN,N-Bis(2-Haloethyl)AminomethylÜ-4-Alkoxyaniline and 3-ÄN-(2-Haloethyl)AminomethylÜ-4-Alkoxyaniline Derivatives of Carboxyamides, Sulfonamides and Certain Other Substituted Compounds", INDIAN JOURNAL OF CHEMISTRY. SECTION B, COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (C S I R), IN, vol. 13, no. 5, 1 January 1975 (1975-01-01), IN, pages 473 - 476, XP002980703, ISSN: 0019-5103
J. CHEM. SOC., PERKIN TRANS. 1, (1972), (3), IRWIN W.J., "Reduction of Fused Benzo(d)-and Pyrido(3,2-d) Pyridinones", pages 353-355.
GALE D M, KRESPAN C G: "FLUOROALKYLAMINES", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 33, 1 March 1968 (1968-03-01), US, pages 1002 - 1008, XP001109380, ISSN: 0022-3263, DOI: 10.1021/jo01267a013
CHEMICAL ABSTRACTS, (1961), Vol. 55, No. 16, 7 August 1961, (Columbus, Ohio, USA), Abstract No. 15940, SCHWANDER H.R. et al., "Monoazo Dyes"; & US,A,2 975 167 (14 March 1961).
CHEMICAL ABSTRACTS, (1958), Vol. 52, No. 21, 10 November 1958, (Columbus, Ohio, USA), Abstract No. 18318d, STERLING J.D. et al., "Derivatives of 4-Anilino-3-Nitrobenzenesulfonamide"; & US,A,2 834 794 (13 May 1958).
CHEMICAL ABSTRACTS, (1957), Vol. 51, No. 4, 25 February 1957, (Columbus, Ohio, USA), Abstract No. 2881i-2882b, COPP F.C., "Pyridine Derivatives"; & GB,A,750 925 (20 June 1956).
See also references of EP 0949242A4
COYNE W. E., CUSIC J. W.: "3,4-DIHYDRO-2(1H)-QUINAZOLINONES.", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 11., no. 06., 1 January 1968 (1968-01-01), US, pages 1208 - 1213., XP000909664, ISSN: 0022-2623, DOI: 10.1021/jm00312a022
J. CHEM. SOC., PERKIN TRANS. 1, (1973), (1), BOWMAN R.E. et al., "Syntheses of Flufenamic Acid Metabolites I and II and Other N-Aryl-Anthranilic Acids", pages 1-4.
NUSSBAUMER P, ET AL.: "Synthesis and Struc ture-Activity Relationships of Phenyl-Substituted Benzylamine Anti-Mycotics: A Novel Benzylbenzylamine Antifungal Agent for Systematic Treatment", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 36, no. 15, 1 January 1993 (1993-01-01), US, pages 2115 - 2120, XP002979877, ISSN: 0022-2623, DOI: 10.1021/jm00067a010
KATO N, ET AL.: "Synthesis of the Acridone Alkaloid Citrusinine-I and Its Derivatives", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 41, no. 3, 1 March 1993 (1993-03-01), JP, pages 445 - 452, XP002979890, ISSN: 0009-2363
NINFANT'EV E.E. ET AL: "1,3,2-Diazaphosphor inanes. VIII. Synthesis, Structure and Chemical Transformations of 1,3-Dialkyl(Aryl)-4,5-Benzo-1,3,2-Diazaphosphorinanes", ZHURNAL OBSHCHEI KHIMII, NAUKA, RUSSIA, vol. 62, no. 2, 1 January 1992 (1992-01-01), Russia, pages 289 - 302, XP008035251, ISSN: 0044-460X
MATHEW A E, ET AL.: "Amino-Substituted P-Benzo quinones", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 29, no. 9, 1 January 1986 (1986-01-01), US, pages 1792 - 1795, XP002979878, ISSN: 0022-2623, DOI: 10.1021/jm00159a041
IL' INA I G, ET AL.: "Synthesis and Chiroptic al Properties of Electron Acceptors of the Picryl Series", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 21, no. 12, 1 January 1985 (1985-01-01), MOSCOW, RU, pages 2529 - 2532, XP002979889, ISSN: 0514-7492
J. LEHMANN ET. AL.: "Zur reduzierenden Spaltung von Chinazolin-2,4-dionen.", ARCHIV DER PHARMAZIE, WILEY VERLAG, WEINHEIM, vol. 315, no. 11, 1 January 1982 (1982-01-01), Weinheim, pages 967 - 969, XP002139157, ISSN: 0365-6233
HORI T, ET AL.: "STUDIES ON ANTITUMOR-ACTIVE 2,3-DIOXOPIPERAZINE DERIVATIVES. III. SYNTHESIS AND STRUCTURE-ANTITUMOR ACTIVITY RALATIONSHIP OF 1-(4-AMINOBENZYL)-2,3-DIOXOPIPERAZINE DERIVATIVES", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 29, no. 05, 1 January 1981 (1981-01-01), JP, pages 1253 - 1266, XP001063113, ISSN: 0009-2363
SINGH P, GUPTA I S: "Study in Nitrogen Mus tards: I. Some 3-ÄN,N-Bis(2-Haloethyl)AminomethylÜ-4-Alkoxyaniline and 3-ÄN-(2-Haloethyl)AminomethylÜ-4-Alkoxyaniline Derivatives of Carboxyamides, Sulfonamides and Certain Other Substituted Compounds", INDIAN JOURNAL OF CHEMISTRY. SECTION B, COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (C S I R), IN, vol. 13, no. 5, 1 January 1975 (1975-01-01), IN, pages 473 - 476, XP002980703, ISSN: 0019-5103
J. CHEM. SOC., PERKIN TRANS. 1, (1972), (3), IRWIN W.J., "Reduction of Fused Benzo(d)-and Pyrido(3,2-d) Pyridinones", pages 353-355.
GALE D M, KRESPAN C G: "FLUOROALKYLAMINES", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 33, 1 March 1968 (1968-03-01), US, pages 1002 - 1008, XP001109380, ISSN: 0022-3263, DOI: 10.1021/jo01267a013
CHEMICAL ABSTRACTS, (1961), Vol. 55, No. 16, 7 August 1961, (Columbus, Ohio, USA), Abstract No. 15940, SCHWANDER H.R. et al., "Monoazo Dyes"; & US,A,2 975 167 (14 March 1961).
CHEMICAL ABSTRACTS, (1958), Vol. 52, No. 21, 10 November 1958, (Columbus, Ohio, USA), Abstract No. 18318d, STERLING J.D. et al., "Derivatives of 4-Anilino-3-Nitrobenzenesulfonamide"; & US,A,2 834 794 (13 May 1958).
CHEMICAL ABSTRACTS, (1957), Vol. 51, No. 4, 25 February 1957, (Columbus, Ohio, USA), Abstract No. 2881i-2882b, COPP F.C., "Pyridine Derivatives"; & GB,A,750 925 (20 June 1956).
See also references of EP 0949242A4
Attorney, Agent or Firm:
Shamoto, Ichio (Section 206 New Ohtemachi Building, 2-1,
Ohtemachi 2-chom, Chiyoda-ku Tokyo, JP)
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