Title:
NAPHTHALENE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO2002042248
Kind Code:
A3
Abstract:
The present invention relates to naphthalene derivatives of formula (I), wherein X is S, S(O), S(O)2, S(O)2NH, P(O)OCH3, P(O)OH, NH, N(CH3), NHC(O)NH, C(O), C(O)O, NHC(O), CH(OH), CH=N, CH=CH, CH2NH, C(=NH); R<1> is aryl or heteroaryl; R<2> is hydrogen, OR<4> or NR<5>R<6> and the other variables are as defined in the description, and the preparation thereof. The compounds of formula (I) are useful as pharmaceuticals in treating or preventing a disease or condition in which cannobinoid receptor activation plays a rôle or is implicated. (I)
Inventors:
BRAIN CHRISTOPHER THOMAS (GB)
CULSHAW ANDREW JAMES (GB)
DZIADULEWICZ EDWARD KAROL (GB)
SCHOPFER ULRICH (DE)
CULSHAW ANDREW JAMES (GB)
DZIADULEWICZ EDWARD KAROL (GB)
SCHOPFER ULRICH (DE)
Application Number:
PCT/EP2001/013605
Publication Date:
December 19, 2002
Filing Date:
November 22, 2001
Export Citation:
Assignee:
NOVARTIS AG (CH)
NOVARTIS ERFIND VERWALT GMBH (AT)
BRAIN CHRISTOPHER THOMAS (GB)
CULSHAW ANDREW JAMES (GB)
DZIADULEWICZ EDWARD KAROL (GB)
SCHOPFER ULRICH (DE)
NOVARTIS ERFIND VERWALT GMBH (AT)
BRAIN CHRISTOPHER THOMAS (GB)
CULSHAW ANDREW JAMES (GB)
DZIADULEWICZ EDWARD KAROL (GB)
SCHOPFER ULRICH (DE)
International Classes:
A61K31/085; A61K31/10; A61K31/12; A61K31/136; A61K31/15; A61K31/166; A61K31/167; A61K31/17; A61K31/18; A61K31/185; A61K31/192; A61K31/198; A61K31/216; A61K31/235; A61K31/275; A61K31/41; A61K31/415; A61K31/4164; A61K31/4184; A61K31/4196; A61K31/4245; A61K31/433; A61K31/47; A61K31/472; A61K31/4965; A61K31/5375; A61K31/662; A61K45/00; A61P7/10; A61P17/04; A61P17/06; A61P19/02; A61P19/04; A61P19/06; A61P25/00; C07D249/08; A61P25/04; A61P29/00; A61P41/00; A61P43/00; C07C43/20; C07C43/23; C07C45/46; C07C45/68; C07C49/84; C07C65/40; C07C67/39; C07C69/017; C07C69/157; C07C69/63; C07C69/712; C07C69/76; C07C69/94; C07C205/45; C07C217/76; C07C217/94; C07C225/22; C07C233/65; C07C235/84; C07C243/28; C07C251/24; C07C255/56; C07C257/18; C07C259/18; C07C275/32; C07C311/08; C07C311/13; C07C311/29; C07C311/37; C07C317/22; C07C317/34; C07C323/21; C07C323/38; C07C323/42; C07D215/08; C07D215/20; C07D215/26; C07D215/32; C07D215/48; C07D215/58; C07D217/02; C07D217/04; C07D217/16; C07D231/12; C07D233/60; C07D235/16; C07D235/26; C07D235/30; C07D257/04; C07D271/10; C07D271/12; C07D285/14; C07D295/08; C07D295/092; C07D295/096; C07D295/10; C07D295/12; C07D521/00; C07F9/12; C07F9/30; C07F9/32; C07F9/572; C07F9/60; (IPC1-7): C07C43/215; C07C43/23; C07C49/84; C07C65/40; C07C69/712; C07C69/767; C07C205/34; C07C217/76; C07C217/94; C07C225/22; C07C231/12; C07C233/60; C07C235/84; C07C249/08; C07C251/24; C07C255/56; C07C259/18; C07C275/32; C07C311/08; C07C311/29; C07C317/22; C07C323/21; C07C323/42; C07D215/08; C07D215/20; C07D215/32; C07D215/58; C07D217/02; C07D271/12; C07D285/14; C07D295/10; C07F9/30; C07F9/32; A61K31/00; A61P29/00
Foreign References:
| US5939429A | 1999-08-17 | |||
| DE1016717B | 1957-10-03 | |||
| US1874581A | 1932-08-30 | |||
| GB1200273A | 1970-07-29 |
Other References:
Y. KITA, ET AL.: "Novel and direct nucleophilic sulphenylation and thiocyanation of phenol ethers using a hypervalent iodine(III) reagent", JOURNAL OF ORGANIC CHEMISTRY, vol. 60, no. 22, 3 November 1995 (1995-11-03), American Chemical Society, Washington, DC, US, pages 7144 - 7148, XP002206002, ISSN: 0022-3263
H.E. ZIEGER, ET AL.: "2-Chloro-3-dimethylamino-6-phenylsulphon- ylphenyllithium", JOURNAL OF ORGANIC CHEMISTRY, vol. 27, no. 9, September 1962 (1962-09-01), American Chemical Society, Washington, DC, US, pages 3270 - 3273, XP002206003, ISSN: 0022-3263
G. SCHROETER: "Über Acyierung von Anilin-sulfosäuren", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 39, 1906, Verlag Chemie, Weinheim, DE, pages 1559 - 1570, XP002206004
R. HUISIGEN, ET AL.: "Zur Thermolyse des 2-Azido-4,6-dimethyl-pyrimidins; Reaktionen des Azens", TETRAHEDRON LETTERS, no. 30, June 1969 (1969-06-01), Elsevier Science Publishers, Amsterdam, NL, pages 2595 - 2598, XP002206005, ISSN: 0040-4039
F. KURZER: "The conversion of arylamines into symmetrical diarylureas. The melting points of certain substituted ureas", JOURNAL OF THE CHEMICAL SOCIETY, 1949, Royal Society of Chemistry, Letchworth, GB, pages 2292 - 2295, XP002206006
R. NEIDLEIN, ET AL.: "Heterocyclische 12-pi- und 14-pi-systeme, 34. Untersuchungen zum Reaktionsverhalten von 2-Phenyl-5H-naphtho[1,8-bc]furan-2-on (Oxapseudophenalenon)", LIEBIGS ANNALEN DER CHEMIE, no. 7, 30 July 1979 (1979-07-30), Verlag Chemie, Weinheim, DE, pages 959 - 964, XP002206007, ISSN: 0170-2041
T. NAKAYMA, ET AL.: "Synthesis and structure-activity study of protease inhibitors. II. Amino- and guanidino-substituted naphthoates and tetrahydronaphthoates", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 32, no. 10, October 1984 (1984-10-01), Pharmaceutical Society of Japan, Tokyo, JP, pages 3968 - 3980, XP002206219, ISSN: 0009-2363
G.O. DOAK, ET AL.: "Arsene oxides of naphthalene and biphenyl", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 64, no. 5, May 1942 (1942-05-01), American Chemical Society, Washington, DC, US, pages 1064 - 1066, XP002206008, ISSN: 0002-7863
W.A. DENNY, ET AL.: "Potential antitumour agents. 29. Quantitative structure-activity relationships for the antileukaemic bisquaternary ammonium heterocycles", JOURNAL OF MEDICINAL CHEMISTRY, vol. 22, no. 2, February 1979 (1979-02-01), American Chemical Society, Washington, DC, US, pages 134 - 150, XP002139936, ISSN: 0022-2623
W.F. MICHNE, ET AL.: "Novel inhibitors of potassium ion channels on human T lymphocytes", JOURNAL OF MEDICINAL CHEMISTRY, vol. 11, no. 38, 26 May 1995 (1995-05-26), American Chemical Society, Washington, DC, US, pages 1877 - 1883, XP002079143, ISSN: 0022-2623
A. GANGJEE, ET AL.: "2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductases", JOURNAL OF MEDICINAL CHEMISTRY, vol. 39, no. 7, 29 March 1996 (1996-03-29), American Chemical Society, Washington, DC, US, pages 1438 - 1446, XP002206009, ISSN: 0022-2623
A. GANGJEE, ET AL.: "6-Substituted 2,4-diamino-5-methylpyrido[2,3-d]pyrimidines as inhibitors of dihydrofolate reductases from Pneumocystis carinii and Toxoplasma gondii and as antitumour agents", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, no. 10, 12 May 1995 (1995-05-12), American Chemical Society, Washington, DC, US, pages 1778 - 1785, XP002206010, ISSN: 0022-2623
D. TANIYAMA, ET AL.: "A facile and efficient asymmetric synthesis of (+)-salsolidine", TETRAHEDRON LETTERS, vol. 41, no. 29, 15 July 2000 (2000-07-15), Elsevier Science Publishers, Amsterdam, NL, pages 5533 - 5536, XP004209507, ISSN: 0040-4039
E. NOELTING, ET AL.: "Über FArbstoffe der Naphtyl-diphenyl-methan-, Dinaphtyl-diphenyl-methan- und Trinaphtyl-methan-Reihen", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 37, 1904, Verlag Chemie, Weinheim, DE, pages 1899 - 1920, XP002206011
V.A. CHAUZOV: "Stereospecific transition from phenyl(1-naphthyl)phosphinothioic acid to S-ethyl phenyl(1-naphthyl)phosphinothioate, methyl phenyl(1-naphthyl)phosphinate, and N,N-diethyl-P-phenyl-P-(1-naphthyl)phosphinic amide", JOURNAL OF GENERAL CHEMISTRY OF THE USSR, vol. 51, no. 8, pt. 2, August 1981 (1981-08-01), Consultants Bureau, New York, US, pages 1650, XP002206012
K.H. GRELLMANN, ET AL.: "Reactivity and decay pathways of photoexcited anilinonaphthalenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 104, no. 23, 17 November 1982 (1982-11-17), American Chemical Society, Washington, DC, US, pages 6267 - 6272, XP002206013, ISSN: 0002-7863
C.J. CAVALLITO, ET AL.: "Choline acetyltransferase inhibitors. Styrylpyridine analogues with nitrogen-atom modifications", JOURNAL OF MEDICINAL CHEMISTRY, vol. 14, no. 2, February 1971 (1971-02-01), American Chemical Society, Washington, DC, US, pages 130 - 133, XP002206014, ISSN: 0022-2623
H.E. ZIEGER, ET AL.: "2-Chloro-3-dimethylamino-6-phenylsulphon- ylphenyllithium", JOURNAL OF ORGANIC CHEMISTRY, vol. 27, no. 9, September 1962 (1962-09-01), American Chemical Society, Washington, DC, US, pages 3270 - 3273, XP002206003, ISSN: 0022-3263
G. SCHROETER: "Über Acyierung von Anilin-sulfosäuren", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 39, 1906, Verlag Chemie, Weinheim, DE, pages 1559 - 1570, XP002206004
R. HUISIGEN, ET AL.: "Zur Thermolyse des 2-Azido-4,6-dimethyl-pyrimidins; Reaktionen des Azens", TETRAHEDRON LETTERS, no. 30, June 1969 (1969-06-01), Elsevier Science Publishers, Amsterdam, NL, pages 2595 - 2598, XP002206005, ISSN: 0040-4039
F. KURZER: "The conversion of arylamines into symmetrical diarylureas. The melting points of certain substituted ureas", JOURNAL OF THE CHEMICAL SOCIETY, 1949, Royal Society of Chemistry, Letchworth, GB, pages 2292 - 2295, XP002206006
R. NEIDLEIN, ET AL.: "Heterocyclische 12-pi- und 14-pi-systeme, 34. Untersuchungen zum Reaktionsverhalten von 2-Phenyl-5H-naphtho[1,8-bc]furan-2-on (Oxapseudophenalenon)", LIEBIGS ANNALEN DER CHEMIE, no. 7, 30 July 1979 (1979-07-30), Verlag Chemie, Weinheim, DE, pages 959 - 964, XP002206007, ISSN: 0170-2041
T. NAKAYMA, ET AL.: "Synthesis and structure-activity study of protease inhibitors. II. Amino- and guanidino-substituted naphthoates and tetrahydronaphthoates", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 32, no. 10, October 1984 (1984-10-01), Pharmaceutical Society of Japan, Tokyo, JP, pages 3968 - 3980, XP002206219, ISSN: 0009-2363
G.O. DOAK, ET AL.: "Arsene oxides of naphthalene and biphenyl", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 64, no. 5, May 1942 (1942-05-01), American Chemical Society, Washington, DC, US, pages 1064 - 1066, XP002206008, ISSN: 0002-7863
W.A. DENNY, ET AL.: "Potential antitumour agents. 29. Quantitative structure-activity relationships for the antileukaemic bisquaternary ammonium heterocycles", JOURNAL OF MEDICINAL CHEMISTRY, vol. 22, no. 2, February 1979 (1979-02-01), American Chemical Society, Washington, DC, US, pages 134 - 150, XP002139936, ISSN: 0022-2623
W.F. MICHNE, ET AL.: "Novel inhibitors of potassium ion channels on human T lymphocytes", JOURNAL OF MEDICINAL CHEMISTRY, vol. 11, no. 38, 26 May 1995 (1995-05-26), American Chemical Society, Washington, DC, US, pages 1877 - 1883, XP002079143, ISSN: 0022-2623
A. GANGJEE, ET AL.: "2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductases", JOURNAL OF MEDICINAL CHEMISTRY, vol. 39, no. 7, 29 March 1996 (1996-03-29), American Chemical Society, Washington, DC, US, pages 1438 - 1446, XP002206009, ISSN: 0022-2623
A. GANGJEE, ET AL.: "6-Substituted 2,4-diamino-5-methylpyrido[2,3-d]pyrimidines as inhibitors of dihydrofolate reductases from Pneumocystis carinii and Toxoplasma gondii and as antitumour agents", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, no. 10, 12 May 1995 (1995-05-12), American Chemical Society, Washington, DC, US, pages 1778 - 1785, XP002206010, ISSN: 0022-2623
D. TANIYAMA, ET AL.: "A facile and efficient asymmetric synthesis of (+)-salsolidine", TETRAHEDRON LETTERS, vol. 41, no. 29, 15 July 2000 (2000-07-15), Elsevier Science Publishers, Amsterdam, NL, pages 5533 - 5536, XP004209507, ISSN: 0040-4039
E. NOELTING, ET AL.: "Über FArbstoffe der Naphtyl-diphenyl-methan-, Dinaphtyl-diphenyl-methan- und Trinaphtyl-methan-Reihen", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 37, 1904, Verlag Chemie, Weinheim, DE, pages 1899 - 1920, XP002206011
V.A. CHAUZOV: "Stereospecific transition from phenyl(1-naphthyl)phosphinothioic acid to S-ethyl phenyl(1-naphthyl)phosphinothioate, methyl phenyl(1-naphthyl)phosphinate, and N,N-diethyl-P-phenyl-P-(1-naphthyl)phosphinic amide", JOURNAL OF GENERAL CHEMISTRY OF THE USSR, vol. 51, no. 8, pt. 2, August 1981 (1981-08-01), Consultants Bureau, New York, US, pages 1650, XP002206012
K.H. GRELLMANN, ET AL.: "Reactivity and decay pathways of photoexcited anilinonaphthalenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 104, no. 23, 17 November 1982 (1982-11-17), American Chemical Society, Washington, DC, US, pages 6267 - 6272, XP002206013, ISSN: 0002-7863
C.J. CAVALLITO, ET AL.: "Choline acetyltransferase inhibitors. Styrylpyridine analogues with nitrogen-atom modifications", JOURNAL OF MEDICINAL CHEMISTRY, vol. 14, no. 2, February 1971 (1971-02-01), American Chemical Society, Washington, DC, US, pages 130 - 133, XP002206014, ISSN: 0022-2623
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