Title:
QUINOLINE COMPOUND, HNMT INHIBITOR, AND AGENT FOR PREVENTING/TREATING ADHD, NARCOLEPSY, OR ALZHEIMER'S DISEASE
Document Type and Number:
WIPO Patent Application WO/2022/191092
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a new method for increasing the intracerebral histamine concentration. The present invention provides a compound represented by general formula (I) or a salt thereof. [In the formula, the structures of respective groups are as described in the description.]
Inventors:
ARISAWA MIEKO (JP)
YOSHIKAWA TAKEO (JP)
YOSHIKAWA TAKEO (JP)
Application Number:
PCT/JP2022/009571
Publication Date:
September 15, 2022
Filing Date:
March 04, 2022
Export Citation:
Assignee:
UNIV TOHOKU (JP)
International Classes:
C07D215/42; A61K31/4706; A61K31/473; A61K31/565; A61K31/57; A61P25/00; A61P25/20; A61P25/26; A61P25/28; A61P43/00; C07D219/10; C07J43/00
Domestic Patent References:
| WO1997018193A1 | 1997-05-22 | |||
| WO2010020981A1 | 2010-02-25 |
Foreign References:
| US20030232856A1 | 2003-12-18 |
Other References:
DATABASE Registry CAS; ANONYMOUS : " Cyclopentanol, 2-[[(7-chloro-4-quinolinyl)amino]methyl]- (9CI) (CA INDEX NAME)", XP055966835, retrieved from STN
DATABASE Registry CAS; ANONYMOUS : "2-Cyclopentanediamine, N1-(7-chloro-4-quinolinyl)-(CA INDEX NAME) ", XP055966837, retrieved from STN
DATABASE Registry CAS; ANONYMOUS : "4-Quinolinamine, N-(cyclopentylmethyl)-(CA INDEX NAME)", XP055966852, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, 6-chloro-N-cyclopentyl-(CA INDEX NAME) ", XP055966854, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, 7-chloro-N-(2-cyclopentylethyl)-(CA INDEX NAME)", XP055966855, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, N-[(2-aminocyclopentyl)methyl]-7-chloro-(CA INDEX NAME) ", XP055966858, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, N-[(3-aminocyclopentyl)methyl]-7-chloro-(CA INDEX NAME) ", XP055966859, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, 7-chloro-N-(3-cyclopentylpropyl)-(CA INDEX NAME) ", XP055966860, retrieved from REGISTRY
DATABASE REGISTRY CAS; ANONYMOUS : "Cyclopentanol, 3-[[(7-chloro-4-quinolinyl)amino]methyl]-(CA INDEX NAME) ", XP055966862, retrieved from STN
COX, W. A.: "A note on a series of decamethylenebis[(4-substituted amino)quinaldinium] salts with potent antibacterial properties.", JOURNAL OF PHARMACY AND PHARMACOLOGY. SUPPLEMENT, PHARMACEUTICAL SOCIETY OF GREAT BRITAIN, LONDON, GB, vol. 19, no. 3, 1 March 1967 (1967-03-01), GB , pages 155 - 160, XP009539508, ISSN: 0373-1022, DOI: 10.1111/j.2042-7158.1967.tb08057.x
BINDRA J. S., ET AL.: "SYNTHESIS, PHARMACOLOGICAL ACTIVITIES & PHYSICO-CHEMICAL PROPERTIESOF 4-(SUBSTITUTED AMINO/N4-ARYLPIPERAZINYL/AMINOCARBONYL)-2,3- POLYMETHYLENEQUINOLINES.", INDIAN JOURNAL OF CHEMISTRY, JODHPUR, IN, vol. 26B., no. 04., 1 April 1987 (1987-04-01), IN , pages 318 - 329., XP000560899
CORRÊA SOARES JULIANA B. R., MENEZES DIEGO, VANNIER-SANTOS MARCOS A., FERREIRA-PEREIRA ANTONIO, ALMEIDA GIULLIANA T., VENANCIO THI: "Interference with Hemozoin Formation Represents an Important Mechanism of Schistosomicidal Action of Antimalarial Quinoline Methanols", PLOS NEGLECTED TROPICAL DISEASES, vol. 3, no. 7, 1 July 2009 (2009-07-01), pages e477, XP055966797, DOI: 10.1371/journal.pntd.0000477
HEITMAN L H; GÖBLYÖS A; ZWEEMER A M; BAKKER R; MULDER-KRIEGER T; VAN VELDHOVEN J P D; DE VRIES H; BRUSSEE J; IJZERMAN A P: "A Series of 2,4-Disubstituted Quinolines as a New Class of Allosteric Enhancers of the Adenosine A3 Receptor", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 52, no. 4, 26 February 2009 (2009-02-26), US , pages 926 - 931, XP008114805, ISSN: 0022-2623, DOI: 10.1021/jm8014052
MACEDO, B. ; KASCHULA, C.H. ; HUNTER, R. ; CHAVES, J.A.P. ; VAN DER MERWE, J.D. ; SILVA, J.L. ; EGAN, T.J. ; CORDEIRO, Y.: "Synthesis and anti-prion activity evaluation of aminoquinoline analogues", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 11, 1 November 2010 (2010-11-01), AMSTERDAM, NL , pages 5468 - 5473, XP027408968, ISSN: 0223-5234
BROMBERG KENNETH D, MITCHELL TAYLOR R H, UPADHYAY ANUP K, JAKOB CLARISSA G, JHALA MANISHA A, COMESS KENNETH M, LASKO LOREN M, LI C: "The SUV4-20 inhibitor A-196 verifies a role for epigenetics in genomic integrity", NATURE CHEMICAL BIOLOGY, NATURE PUBLISHING GROUP US, NEW YORK, vol. 13, no. 3, 1 March 2017 (2017-03-01), New York, pages 317 - 324, XP055966794, ISSN: 1552-4450, DOI: 10.1038/nchembio.2282
NAGANUMA FUMITO, NAKAMURA TADAHO, YOSHIKAWA TAKEO, IIDA TOMOMITSU, MIURA YAMATO, KÁRPÁTI ANIKÓ, MATSUZAWA TAKURO, YANAI ATUSHI, MO: "Histamine N-methyltransferase regulates aggression and the sleep-wake cycle", SCIENTIFIC REPORTS, vol. 7, no. 1, 1 December 2017 (2017-12-01), XP055966793, DOI: 10.1038/s41598-017-16019-8
CUMMING, P. ; REINER, P.B. ; VINCENT, S.R.: "Inhibition of rat brain histamine-N-methyltransferase by 9-amino-1,2,3,4-tetrahydroacridine (THA)", BIOCHEMICAL PHARMACOLOGY, ELSEVIER, US, vol. 40, no. 6, 15 September 1990 (1990-09-15), US , pages 1345 - 1350, XP025888578, ISSN: 0006-2952, DOI: 10.1016/0006-2952(90)90402-7
DATABASE Registry CAS; ANONYMOUS : "2-Cyclopentanediamine, N1-(7-chloro-4-quinolinyl)-(CA INDEX NAME) ", XP055966837, retrieved from STN
DATABASE Registry CAS; ANONYMOUS : "4-Quinolinamine, N-(cyclopentylmethyl)-(CA INDEX NAME)", XP055966852, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, 6-chloro-N-cyclopentyl-(CA INDEX NAME) ", XP055966854, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, 7-chloro-N-(2-cyclopentylethyl)-(CA INDEX NAME)", XP055966855, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, N-[(2-aminocyclopentyl)methyl]-7-chloro-(CA INDEX NAME) ", XP055966858, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, N-[(3-aminocyclopentyl)methyl]-7-chloro-(CA INDEX NAME) ", XP055966859, retrieved from STN
DATABASE REGISTRY CAS; ANONYMOUS : "4-Quinolinamine, 7-chloro-N-(3-cyclopentylpropyl)-(CA INDEX NAME) ", XP055966860, retrieved from REGISTRY
DATABASE REGISTRY CAS; ANONYMOUS : "Cyclopentanol, 3-[[(7-chloro-4-quinolinyl)amino]methyl]-(CA INDEX NAME) ", XP055966862, retrieved from STN
COX, W. A.: "A note on a series of decamethylenebis[(4-substituted amino)quinaldinium] salts with potent antibacterial properties.", JOURNAL OF PHARMACY AND PHARMACOLOGY. SUPPLEMENT, PHARMACEUTICAL SOCIETY OF GREAT BRITAIN, LONDON, GB, vol. 19, no. 3, 1 March 1967 (1967-03-01), GB , pages 155 - 160, XP009539508, ISSN: 0373-1022, DOI: 10.1111/j.2042-7158.1967.tb08057.x
BINDRA J. S., ET AL.: "SYNTHESIS, PHARMACOLOGICAL ACTIVITIES & PHYSICO-CHEMICAL PROPERTIESOF 4-(SUBSTITUTED AMINO/N4-ARYLPIPERAZINYL/AMINOCARBONYL)-2,3- POLYMETHYLENEQUINOLINES.", INDIAN JOURNAL OF CHEMISTRY, JODHPUR, IN, vol. 26B., no. 04., 1 April 1987 (1987-04-01), IN , pages 318 - 329., XP000560899
CORRÊA SOARES JULIANA B. R., MENEZES DIEGO, VANNIER-SANTOS MARCOS A., FERREIRA-PEREIRA ANTONIO, ALMEIDA GIULLIANA T., VENANCIO THI: "Interference with Hemozoin Formation Represents an Important Mechanism of Schistosomicidal Action of Antimalarial Quinoline Methanols", PLOS NEGLECTED TROPICAL DISEASES, vol. 3, no. 7, 1 July 2009 (2009-07-01), pages e477, XP055966797, DOI: 10.1371/journal.pntd.0000477
HEITMAN L H; GÖBLYÖS A; ZWEEMER A M; BAKKER R; MULDER-KRIEGER T; VAN VELDHOVEN J P D; DE VRIES H; BRUSSEE J; IJZERMAN A P: "A Series of 2,4-Disubstituted Quinolines as a New Class of Allosteric Enhancers of the Adenosine A3 Receptor", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 52, no. 4, 26 February 2009 (2009-02-26), US , pages 926 - 931, XP008114805, ISSN: 0022-2623, DOI: 10.1021/jm8014052
MACEDO, B. ; KASCHULA, C.H. ; HUNTER, R. ; CHAVES, J.A.P. ; VAN DER MERWE, J.D. ; SILVA, J.L. ; EGAN, T.J. ; CORDEIRO, Y.: "Synthesis and anti-prion activity evaluation of aminoquinoline analogues", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 11, 1 November 2010 (2010-11-01), AMSTERDAM, NL , pages 5468 - 5473, XP027408968, ISSN: 0223-5234
BROMBERG KENNETH D, MITCHELL TAYLOR R H, UPADHYAY ANUP K, JAKOB CLARISSA G, JHALA MANISHA A, COMESS KENNETH M, LASKO LOREN M, LI C: "The SUV4-20 inhibitor A-196 verifies a role for epigenetics in genomic integrity", NATURE CHEMICAL BIOLOGY, NATURE PUBLISHING GROUP US, NEW YORK, vol. 13, no. 3, 1 March 2017 (2017-03-01), New York, pages 317 - 324, XP055966794, ISSN: 1552-4450, DOI: 10.1038/nchembio.2282
NAGANUMA FUMITO, NAKAMURA TADAHO, YOSHIKAWA TAKEO, IIDA TOMOMITSU, MIURA YAMATO, KÁRPÁTI ANIKÓ, MATSUZAWA TAKURO, YANAI ATUSHI, MO: "Histamine N-methyltransferase regulates aggression and the sleep-wake cycle", SCIENTIFIC REPORTS, vol. 7, no. 1, 1 December 2017 (2017-12-01), XP055966793, DOI: 10.1038/s41598-017-16019-8
CUMMING, P. ; REINER, P.B. ; VINCENT, S.R.: "Inhibition of rat brain histamine-N-methyltransferase by 9-amino-1,2,3,4-tetrahydroacridine (THA)", BIOCHEMICAL PHARMACOLOGY, ELSEVIER, US, vol. 40, no. 6, 15 September 1990 (1990-09-15), US , pages 1345 - 1350, XP025888578, ISSN: 0006-2952, DOI: 10.1016/0006-2952(90)90402-7
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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