CA2923336A1 - 6- and 7-amino isoquinoline compounds and methods for making and using the same - Google Patents
6- and 7-amino isoquinoline compounds and methods for making and using the same Download PDFInfo
- Publication number
- CA2923336A1 CA2923336A1 CA2923336A CA2923336A CA2923336A1 CA 2923336 A1 CA2923336 A1 CA 2923336A1 CA 2923336 A CA2923336 A CA 2923336A CA 2923336 A CA2923336 A CA 2923336A CA 2923336 A1 CA2923336 A1 CA 2923336A1
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- CA
- Canada
- Prior art keywords
- group
- alkyl
- hydrogen
- aryl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- NGFCTYXFMDWFRQ-UHFFFAOYSA-N isoquinolin-6-amine Chemical compound C1=NC=CC2=CC(N)=CC=C21 NGFCTYXFMDWFRQ-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 44
- DRGUQIQEUWFBDE-UHFFFAOYSA-N isoquinolin-7-amine Chemical class C1=CN=CC2=CC(N)=CC=C21 DRGUQIQEUWFBDE-UHFFFAOYSA-N 0.000 title abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 114
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 27
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 14
- 230000009471 action Effects 0.000 claims abstract description 11
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- 208000008589 Obesity Diseases 0.000 claims abstract description 4
- 235000020824 obesity Nutrition 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000004429 atom Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- -1 amino, carbonyl Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 230000000699 topical effect Effects 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 21
- 125000001174 sulfone group Chemical group 0.000 claims description 18
- 230000009885 systemic effect Effects 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 16
- 125000004001 thioalkyl group Chemical group 0.000 claims description 16
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 229940124597 therapeutic agent Drugs 0.000 claims description 14
- 229910001868 water Inorganic materials 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 239000003086 colorant Substances 0.000 claims description 8
- 208000030533 eye disease Diseases 0.000 claims description 8
- 239000000796 flavoring agent Substances 0.000 claims description 8
- 235000019634 flavors Nutrition 0.000 claims description 8
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
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- 239000000375 suspending agent Substances 0.000 claims description 5
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
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- 208000035475 disorder Diseases 0.000 claims description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 3
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- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
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- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
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- 150000002431 hydrogen Chemical group 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 239000006196 drop Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 19
- 230000007423 decrease Effects 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
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- 125000002837 carbocyclic group Chemical group 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 235000002639 sodium chloride Nutrition 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007832 Na2SO4 Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000000049 pigment Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000007909 solid dosage form Substances 0.000 description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000003247 decreasing effect Effects 0.000 description 7
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
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- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C—CHEMISTRY; METALLURGY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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| US12/009,326 | 2008-01-17 | ||
| CA2712443A CA2712443C (en) | 2008-01-17 | 2009-01-15 | 6- and 7-amino isoquinoline compounds and methods for making and using the same |
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| CA2712443A Division CA2712443C (en) | 2008-01-17 | 2009-01-15 | 6- and 7-amino isoquinoline compounds and methods for making and using the same |
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| NZ577984A (en) | 2006-12-27 | 2011-03-31 | Sanofi Aventis | Cycloalkylamine substituted isoquinoline and isoquinolinone derivatives |
| US8455513B2 (en) * | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| WO2008124665A1 (en) * | 2007-04-10 | 2008-10-16 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US8455514B2 (en) * | 2008-01-17 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-and 7-amino isoquinoline compounds and methods for making and using the same |
| US8450344B2 (en) * | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| CA2929545C (en) | 2009-05-01 | 2019-04-09 | Aerie Pharmaceuticals, Inc. | Dual mechanism inhibitors for the treatment of disease |
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2008
- 2008-01-17 US US12/009,326 patent/US8455514B2/en active Active
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2009
- 2009-01-15 WO PCT/US2009/031117 patent/WO2009091898A2/en not_active Ceased
- 2009-01-15 EP EP12007092.5A patent/EP2546238B1/en active Active
- 2009-01-15 CA CA2712443A patent/CA2712443C/en active Active
- 2009-01-15 AU AU2009206075A patent/AU2009206075B2/en not_active Ceased
- 2009-01-15 EP EP09702189A patent/EP2252589B1/en active Active
- 2009-01-15 CA CA2923336A patent/CA2923336A1/en not_active Abandoned
- 2009-01-15 ES ES12007093.3T patent/ES2535716T3/es active Active
- 2009-01-15 ES ES12007092.5T patent/ES2465572T3/es active Active
- 2009-01-15 EP EP12007089A patent/EP2546237A1/en not_active Withdrawn
- 2009-01-15 EP EP12007093.3A patent/EP2546239B1/en active Active
- 2009-01-15 ES ES09702189T patent/ES2397928T3/es active Active
- 2009-01-15 JP JP2010543237A patent/JP5551613B2/ja active Active
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2010
- 2010-02-12 US US12/704,822 patent/US8871757B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2535716T3 (es) | 2015-05-14 |
| EP2546239B1 (en) | 2015-04-08 |
| AU2009206075A1 (en) | 2009-07-23 |
| EP2546238A1 (en) | 2013-01-16 |
| WO2009091898A2 (en) | 2009-07-23 |
| EP2252589B1 (en) | 2012-11-21 |
| CA2712443A1 (en) | 2009-07-23 |
| JP5551613B2 (ja) | 2014-07-16 |
| AU2009206075B2 (en) | 2014-06-12 |
| ES2465572T3 (es) | 2014-06-06 |
| EP2546237A1 (en) | 2013-01-16 |
| EP2252589A2 (en) | 2010-11-24 |
| ES2397928T3 (es) | 2013-03-12 |
| US8871757B2 (en) | 2014-10-28 |
| EP2546239A1 (en) | 2013-01-16 |
| WO2009091898A3 (en) | 2009-11-05 |
| US8455514B2 (en) | 2013-06-04 |
| US20090186917A1 (en) | 2009-07-23 |
| JP2011510014A (ja) | 2011-03-31 |
| US20100144713A1 (en) | 2010-06-10 |
| EP2546238B1 (en) | 2014-04-02 |
| CA2712443C (en) | 2016-05-03 |
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| Publication | Publication Date | Title |
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| CA2712443C (en) | 6- and 7-amino isoquinoline compounds and methods for making and using the same | |
| US10899714B2 (en) | 6-aminoisoquinoline compounds | |
| US7671205B2 (en) | 6-aminoisoquinoline compounds | |
| CA2731869C (en) | Beta-and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds | |
| US9963432B2 (en) | Beta-amino-isoquinolinyl amide compounds |
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