Title:
テトラヒドロイソキノリン化合物、その調製方法、そのような化合物を含む医薬組成物およびその使用
Document Type and Number:
Japanese Patent JP2021513530
Kind Code:
A
Abstract:
本発明は、新規なテトラヒドロイソキノリン化合物およびその中間体の調製方法、医薬組成物および使用を開示する。本発明のテトラヒドロイソキノリン化合物は、ホスホジエステラーゼ（ＰＤＥ４）に対して良好な阻害効果を有し、ホスホジエステラーゼ活性または発現に関連する様々な疾患、特に乾癬および関節炎などのＰＤＥ４に関連する免疫および炎症性の予防、治療または補助治療のために使用することができる。【化１】
More Like This:
Inventors:
Shu, Yechun
Riu, Hong
Tan way
Chan, Shanley
Gu, Zanni
Ri, hen
Han, Shoe
Chu, von Hua
Feng, Chunlan
Dong, Gwanggyu
Chen, Tientien
Chen, Wuyang
Jen, Hua Liang
Chen, Kaysien
Riu, Hong
Tan way
Chan, Shanley
Gu, Zanni
Ri, hen
Han, Shoe
Chu, von Hua
Feng, Chunlan
Dong, Gwanggyu
Chen, Tientien
Chen, Wuyang
Jen, Hua Liang
Chen, Kaysien
Application Number:
JP2020542635A
Publication Date:
May 27, 2021
Filing Date:
February 03, 2019
Export Citation:
Assignee:
SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES
International Classes:
C07D217/06; A61K31/47; A61K31/4725; A61K31/5377; A61P11/00; A61P11/02; A61P11/06; A61P17/00; A61P17/06; A61P19/02; A61P25/14; A61P25/16; A61P25/24; A61P25/28; A61P29/00; A61P37/02; A61P37/08; A61P43/00; C07D401/06; C07D401/12; C07D401/14; C07D405/06; C07D405/14; C07D409/06; C07D413/06; C07D413/14; C07D417/14; C07D471/04
Domestic Patent References:
| JP2006521323A | 2006-09-21 | |||
| JP2007525531A | 2007-09-06 | |||
| JP2009530340A | 2009-08-27 | |||
| JP2017525740A | 2017-09-07 | |||
| JPS5035174A | 1975-04-03 | |||
| JP2013506692A | 2013-02-28 | |||
| JP2012502977A | 2012-02-02 |
Foreign References:
| WO2003041641A2 | 2003-05-22 | |||
| US4292320A | 1981-09-29 | |||
| US3326923A | 1967-06-20 | |||
| WO2015082616A1 | 2015-06-11 |
Other References:
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MORRISON, GLENN CURTIS; WAITE, RONALD O.; SHAVEL, JOHN, JR.: "Alternate precursors in biogenetic types of syntheses. III. Ring D indoline analog of the aporphin", JOURNAL OF ORGANIC CHEMISTRY, vol. 33(4),, JPN7021004253, 1968, pages 1663 - 4, ISSN: 0004611410
ZHU, ZHENGBO; SEIDEL, DANIEL: "An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step", ORGANIC LETTERS, vol. 18(4),, JPN7021004254, 2016, pages 631 - 633, ISSN: 0004611411
NGOUANSAVANH, TIFELLE; ZHU, JIEPING: "IBX-mediated oxidative Ugi-type multicomponent reactions: application to the N and C1 functionalizat", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 46(30),, JPN7021004230, 2007, pages 5775 - 5778, ISSN: 0004611412
SCHNEIDER, FERNAND; BERNAUER, KARL: "Natural and synthetic isoquinoline derivatives. 7. Synthesis of compounds with the homoproaporphin", HELVETICA CHIMICA ACTA, vol. 53(5),, JPN7021004231, 1970, pages 938 - 45, ISSN: 0004611413
BORGULYA, JANOS; GEROLD, MARCEL; SCHNEIDER, FERNAND; BERNAUER, KARL: "Natural and synthetic isoquinoline derivatives. 10. Chemical and pharmacological studies on deriva", HELVETICA CHIMICA ACTA, vol. 60(2),, JPN7021004232, 1977, pages 598 - 617, ISSN: 0004611414
KNABE, J.; ECKER, A.: "Dihydroisoquinoline rearrangement. 21. Mechanism of the 1,2-dihydroisoquinoline rearrangement", ARCHIV DER PHARMAZIE (WEINHEIM, GERMANY), vol. 307(9),, JPN7021004233, 1974, pages 727 - 31, ISSN: 0004611415
VACCHER, CLAUDE; BERTHELOT, PASCAL; DEBAERT, MICHEL; BARBRY, DIDIER: "A novel rearrangement reaction. A single-step conversion of tetrahydro-1-isoquinolinecarboxylic aci", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 21(4),, JPN7021004234, 1984, pages 1201 - 4, ISSN: 0004611416
HROMATKA, O.; GRAF, W.; KNOLLMUELLER, M.: "Piperazine-substituted isoquinoline derivatives", MONATSHEFTE FUER CHEMIE, vol. 97(1),, JPN7021004235, 1966, pages 19 - 32, ISSN: 0004611417
PEREGO, LUCA ALESSANDRO; BLIECK, REMI; GROUE, ANTOINE; MONNIER, FLORIAN;TAILLEFER, MARC; CIOFINI, IL: "Copper-Catalyzed Hydroamination of Allenes: from Mechanistic Understanding to Methodology Developme", ACS CATALYSIS, vol. 7(7),, JPN7021004236, 2017, pages 4253 - 4264, ISSN: 0004611418
ISHIWATA, SABURO; NOZAKI, TAIICHI: "Syntheses of isoquinoline derivatives. VI. Syntheses of alkyl derivatives of the pyridine nucleus. 3", YAKUGAKU ZASSHI, vol. 71, JPN7021004237, 1951, pages 1261 - 3, XP055732174, ISSN: 0004611419, DOI: 10.1248/yakushi1947.71.11_1261
ROSSETTI, ARIANNA; SACCHETTI, ALESSANDRO; GATTI, MARTA; PUGLIESE, ANDREA; RODA, GABRIELLA: "Rapid access to reverse-turn peptidomimetics by a three-component Ugi reaction of 3,4-dihydroisoquin", CHEMISTRY OF HETEROCYCLIC COMPOUNDS (NEW YORK, NY, UNITED STATES), vol. 53(11),, JPN7021004238, 2017, pages 1214 - 1219, ISSN: 0004611420
BOEKELHEIDE, V.; AINSWORTH, C.: "Curariform activity and chemical structure. VII. Some 1-skatylisoquinoline derivatives, and a novel", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 72,, JPN7021004239, 1950, pages 2134 - 7, ISSN: 0004611421
LIU, LEE TAI; LIN, YA-CHUAN; WANG, CHIA-LIN J.; LIN, MEI-SHEY; YEN, SU-CHEN; CHEN, HSIAO-JEN: "Synthesis and biological activities of a novel class of azole-containing antifungal agents", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 6(12),, JPN7021004240, 1996, pages 1335 - 1338, ISSN: 0004611422
ALMERICO, ANNA MARIA; TUTONE, MARCO; LAURIA, ANTONINO: "In-silico screening of new potential Bcl-2/Bcl-xl inhibitors as apoptosis modulators", JOURNAL OF MOLECULAR MODELING, vol. 15(4),, JPN7021004241, 2009, pages 349 - 355, ISSN: 0004611423
BOEHME, THOMAS M.; AUGELLI-SZAFRAN, CORINNE E.; HALLAK, HUSSEIN; SCHWARZ, ROY D.: "Analogs of M4 selective synthetic muscarinic receptor antagonists: synthesis, binding and pharmacoki", MEDICINAL CHEMISTRY RESEARCH, vol. 11(8),, JPN7021004242, 2002, pages 423 - 433, ISSN: 0004611424
SHISHIDO, HIDEO: "Synthesis of an isomer of domesticine ethyl ether", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 12,, JPN7021004243, 1937, pages 419 - 24, ISSN: 0004611425
VACCHER, CLAUDE; BERTHELOT, PASCAL; BARBRY, DIDIER; DEBAERT, MICHEL: "Unexpected reaction during the use of the mixed anhydride method in the isoquinoline series", BULLETIN DE LA SOCIETE DE PHARMACIE DE LILLE, vol. 41(1),, JPN7021004244, 1985, pages 63 - 72, ISSN: 0004611426
REGISTRY(STN)[ONLINE], JPN7021004245, ISSN: 0004611427
REGISTRY(STN)[ONLINE], JPN7021004246, ISSN: 0004611428
REGISTRY(STN)[ONLINE], JPN7021004247, ISSN: 0004611429
REGISTRY(STN)[ONLINE], JPN7021004248, ISSN: 0004611430
REGISTRY(STN)[ONLINE], JPN7021004249, ISSN: 0004611431
REGISTRY(STN)[ONLINE], JPN7021004250, ISSN: 0004611432
REGISTRY(STN)[ONLINE], JPN7021004251, ISSN: 0004611433
MORRISON, GLENN CURTIS; WAITE, RONALD O.; SHAVEL, JOHN, JR.: "Alternate precursors in biogenetic types of syntheses. III. Ring D indoline analog of the aporphin", JOURNAL OF ORGANIC CHEMISTRY, vol. 33(4),, JPN7021004253, 1968, pages 1663 - 4, ISSN: 0004611410
ZHU, ZHENGBO; SEIDEL, DANIEL: "An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step", ORGANIC LETTERS, vol. 18(4),, JPN7021004254, 2016, pages 631 - 633, ISSN: 0004611411
NGOUANSAVANH, TIFELLE; ZHU, JIEPING: "IBX-mediated oxidative Ugi-type multicomponent reactions: application to the N and C1 functionalizat", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 46(30),, JPN7021004230, 2007, pages 5775 - 5778, ISSN: 0004611412
SCHNEIDER, FERNAND; BERNAUER, KARL: "Natural and synthetic isoquinoline derivatives. 7. Synthesis of compounds with the homoproaporphin", HELVETICA CHIMICA ACTA, vol. 53(5),, JPN7021004231, 1970, pages 938 - 45, ISSN: 0004611413
BORGULYA, JANOS; GEROLD, MARCEL; SCHNEIDER, FERNAND; BERNAUER, KARL: "Natural and synthetic isoquinoline derivatives. 10. Chemical and pharmacological studies on deriva", HELVETICA CHIMICA ACTA, vol. 60(2),, JPN7021004232, 1977, pages 598 - 617, ISSN: 0004611414
KNABE, J.; ECKER, A.: "Dihydroisoquinoline rearrangement. 21. Mechanism of the 1,2-dihydroisoquinoline rearrangement", ARCHIV DER PHARMAZIE (WEINHEIM, GERMANY), vol. 307(9),, JPN7021004233, 1974, pages 727 - 31, ISSN: 0004611415
VACCHER, CLAUDE; BERTHELOT, PASCAL; DEBAERT, MICHEL; BARBRY, DIDIER: "A novel rearrangement reaction. A single-step conversion of tetrahydro-1-isoquinolinecarboxylic aci", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 21(4),, JPN7021004234, 1984, pages 1201 - 4, ISSN: 0004611416
HROMATKA, O.; GRAF, W.; KNOLLMUELLER, M.: "Piperazine-substituted isoquinoline derivatives", MONATSHEFTE FUER CHEMIE, vol. 97(1),, JPN7021004235, 1966, pages 19 - 32, ISSN: 0004611417
PEREGO, LUCA ALESSANDRO; BLIECK, REMI; GROUE, ANTOINE; MONNIER, FLORIAN;TAILLEFER, MARC; CIOFINI, IL: "Copper-Catalyzed Hydroamination of Allenes: from Mechanistic Understanding to Methodology Developme", ACS CATALYSIS, vol. 7(7),, JPN7021004236, 2017, pages 4253 - 4264, ISSN: 0004611418
ISHIWATA, SABURO; NOZAKI, TAIICHI: "Syntheses of isoquinoline derivatives. VI. Syntheses of alkyl derivatives of the pyridine nucleus. 3", YAKUGAKU ZASSHI, vol. 71, JPN7021004237, 1951, pages 1261 - 3, XP055732174, ISSN: 0004611419, DOI: 10.1248/yakushi1947.71.11_1261
ROSSETTI, ARIANNA; SACCHETTI, ALESSANDRO; GATTI, MARTA; PUGLIESE, ANDREA; RODA, GABRIELLA: "Rapid access to reverse-turn peptidomimetics by a three-component Ugi reaction of 3,4-dihydroisoquin", CHEMISTRY OF HETEROCYCLIC COMPOUNDS (NEW YORK, NY, UNITED STATES), vol. 53(11),, JPN7021004238, 2017, pages 1214 - 1219, ISSN: 0004611420
BOEKELHEIDE, V.; AINSWORTH, C.: "Curariform activity and chemical structure. VII. Some 1-skatylisoquinoline derivatives, and a novel", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 72,, JPN7021004239, 1950, pages 2134 - 7, ISSN: 0004611421
LIU, LEE TAI; LIN, YA-CHUAN; WANG, CHIA-LIN J.; LIN, MEI-SHEY; YEN, SU-CHEN; CHEN, HSIAO-JEN: "Synthesis and biological activities of a novel class of azole-containing antifungal agents", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 6(12),, JPN7021004240, 1996, pages 1335 - 1338, ISSN: 0004611422
ALMERICO, ANNA MARIA; TUTONE, MARCO; LAURIA, ANTONINO: "In-silico screening of new potential Bcl-2/Bcl-xl inhibitors as apoptosis modulators", JOURNAL OF MOLECULAR MODELING, vol. 15(4),, JPN7021004241, 2009, pages 349 - 355, ISSN: 0004611423
BOEHME, THOMAS M.; AUGELLI-SZAFRAN, CORINNE E.; HALLAK, HUSSEIN; SCHWARZ, ROY D.: "Analogs of M4 selective synthetic muscarinic receptor antagonists: synthesis, binding and pharmacoki", MEDICINAL CHEMISTRY RESEARCH, vol. 11(8),, JPN7021004242, 2002, pages 423 - 433, ISSN: 0004611424
SHISHIDO, HIDEO: "Synthesis of an isomer of domesticine ethyl ether", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 12,, JPN7021004243, 1937, pages 419 - 24, ISSN: 0004611425
VACCHER, CLAUDE; BERTHELOT, PASCAL; BARBRY, DIDIER; DEBAERT, MICHEL: "Unexpected reaction during the use of the mixed anhydride method in the isoquinoline series", BULLETIN DE LA SOCIETE DE PHARMACIE DE LILLE, vol. 41(1),, JPN7021004244, 1985, pages 63 - 72, ISSN: 0004611426
REGISTRY(STN)[ONLINE], JPN7021004245, ISSN: 0004611427
REGISTRY(STN)[ONLINE], JPN7021004246, ISSN: 0004611428
REGISTRY(STN)[ONLINE], JPN7021004247, ISSN: 0004611429
REGISTRY(STN)[ONLINE], JPN7021004248, ISSN: 0004611430
REGISTRY(STN)[ONLINE], JPN7021004249, ISSN: 0004611431
REGISTRY(STN)[ONLINE], JPN7021004250, ISSN: 0004611432
REGISTRY(STN)[ONLINE], JPN7021004251, ISSN: 0004611433
Attorney, Agent or Firm:
Kiyoji Kuzuwa