KR20090103903A - 사이클로알킬아민 치환된 이소퀴놀론 및 이소퀴놀리논 유도체 - Google Patents
사이클로알킬아민 치환된 이소퀴놀론 및 이소퀴놀리논 유도체Info
- Publication number
- KR20090103903A KR20090103903A KR1020097013521A KR20097013521A KR20090103903A KR 20090103903 A KR20090103903 A KR 20090103903A KR 1020097013521 A KR1020097013521 A KR 1020097013521A KR 20097013521 A KR20097013521 A KR 20097013521A KR 20090103903 A KR20090103903 A KR 20090103903A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- alkylene
- aryl
- compound
- heterocyclyl
- 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
Links
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical class C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 title abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- -1 6-substituted isoquinoline Chemical class 0.000 claims abstract description 57
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 293
- 125000000623 heterocyclic group Chemical group 0.000 claims description 112
- 229910052736 halogen Inorganic materials 0.000 claims description 86
- 150000002367 halogens Chemical class 0.000 claims description 84
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 62
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 10
- 206010020772 Hypertension Diseases 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 206010019280 Heart failures Diseases 0.000 claims description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 230000004064 dysfunction Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 4
- 208000006029 Cardiomegaly Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 208000007101 Muscle Cramp Diseases 0.000 claims description 4
- 206010030043 Ocular hypertension Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 208000021328 arterial occlusion Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 4
- 230000002124 endocrine Effects 0.000 claims description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 208000017169 kidney disease Diseases 0.000 claims description 4
- 201000006370 kidney failure Diseases 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000002093 peripheral effect Effects 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 208000020431 spinal cord injury Diseases 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 206010019663 Hepatic failure Diseases 0.000 claims description 3
- 206010020880 Hypertrophy Diseases 0.000 claims description 3
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 3
- 206010053159 Organ failure Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 208000005107 Premature Birth Diseases 0.000 claims description 3
- 206010036590 Premature baby Diseases 0.000 claims description 3
- 208000004756 Respiratory Insufficiency Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 206010020718 hyperplasia Diseases 0.000 claims description 3
- 201000001881 impotence Diseases 0.000 claims description 3
- 208000023589 ischemic disease Diseases 0.000 claims description 3
- 230000000302 ischemic effect Effects 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 230000008816 organ damage Effects 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- 201000004193 respiratory failure Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 208000007903 liver failure Diseases 0.000 claims description 2
- 231100000835 liver failure Toxicity 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108010041788 rho-Associated Kinases Proteins 0.000 abstract description 15
- 102000000568 rho-Associated Kinases Human genes 0.000 abstract description 15
- 239000000203 mixture Substances 0.000 abstract description 12
- 230000026731 phosphorylation Effects 0.000 abstract description 6
- 238000006366 phosphorylation reaction Methods 0.000 abstract description 6
- 102000011131 Myosin-Light-Chain Phosphatase Human genes 0.000 abstract description 5
- 108010037801 Myosin-Light-Chain Phosphatase Proteins 0.000 abstract description 5
- 230000001404 mediated effect Effects 0.000 abstract description 4
- 230000006806 disease prevention Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000000651 prodrug Substances 0.000 description 10
- 229940002612 prodrug Drugs 0.000 description 10
- 238000007429 general method Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- ZDYXSEQHOVSTPA-UHFFFAOYSA-N 6-bromo-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C=2C1=CC(Br)=CC=2 ZDYXSEQHOVSTPA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VOAHGGQULSSGQW-UHFFFAOYSA-N 6-bromo-1-chloroisoquinoline Chemical compound BrC1=CC=C2C(Cl)=NC=CC2=C1 VOAHGGQULSSGQW-UHFFFAOYSA-N 0.000 description 7
- QNNTUJSIGVWFAS-UHFFFAOYSA-N 6-bromo-2-oxidoisoquinolin-2-ium Chemical compound C1=C(Br)C=CC2=C[N+]([O-])=CC=C21 QNNTUJSIGVWFAS-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000009739 binding Methods 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- IEMKXFLENZAFAZ-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]-2,2-dimethoxyethanamine Chemical compound COC(OC)CNCC1=CC=C(Br)C=C1 IEMKXFLENZAFAZ-UHFFFAOYSA-N 0.000 description 7
- BTUPJEUTBPAUHV-UHFFFAOYSA-N 6-bromo-2-[(4-methoxyphenyl)methyl]isoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C=C1 BTUPJEUTBPAUHV-UHFFFAOYSA-N 0.000 description 6
- ZTEATMVVGQUULZ-UHFFFAOYSA-N 6-bromoisoquinoline Chemical compound C1=NC=CC2=CC(Br)=CC=C21 ZTEATMVVGQUULZ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 208000001132 Osteoporosis Diseases 0.000 description 5
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
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- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical class C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 4
- YLHCMDNAKVPTIO-UHFFFAOYSA-N 2-(4-hydroxycyclohexyl)isoindole-1,3-dione Chemical compound C1CC(O)CCC1N1C(=O)C2=CC=CC=C2C1=O YLHCMDNAKVPTIO-UHFFFAOYSA-N 0.000 description 4
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 4
- GHVZZWBJRRTGHT-UHFFFAOYSA-N 6-bromo-7-chloro-2h-isoquinolin-1-one Chemical compound C1=C(Br)C(Cl)=CC2=C1C=CNC2=O GHVZZWBJRRTGHT-UHFFFAOYSA-N 0.000 description 4
- ABZAYLFRWGIRDU-UHFFFAOYSA-N 7-bromo-6-fluoroisoquinoline Chemical compound C1=NC=C2C=C(Br)C(F)=CC2=C1 ABZAYLFRWGIRDU-UHFFFAOYSA-N 0.000 description 4
- PTKVNYJGJSGOCB-UHFFFAOYSA-N 7-chloro-6-fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2=CC(Cl)=C(F)C=C2C=C1 PTKVNYJGJSGOCB-UHFFFAOYSA-N 0.000 description 4
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- QHXHQEANVDGNSF-UHFFFAOYSA-N n-[(4-bromo-3-chlorophenyl)methyl]-n-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(CC(OC)OC)CC1=CC=C(Br)C(Cl)=C1 QHXHQEANVDGNSF-UHFFFAOYSA-N 0.000 description 4
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06026895 | 2006-12-27 | ||
| EP06026895.0 | 2006-12-27 | ||
| PCT/EP2007/011166 WO2008077553A1 (en) | 2006-12-27 | 2007-12-19 | Cycloalkylamine substituted isoquinolone and isoquinolinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090103903A true KR20090103903A (ko) | 2009-10-01 |
Family
ID=38069270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097013521A Abandoned KR20090103903A (ko) | 2006-12-27 | 2007-12-19 | 사이클로알킬아민 치환된 이소퀴놀론 및 이소퀴놀리논 유도체 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20100056568A1 (enExample) |
| EP (1) | EP2125744B1 (enExample) |
| JP (1) | JP5318778B2 (enExample) |
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Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2580108T3 (es) | 2005-07-11 | 2016-08-19 | Aerie Pharmaceuticals, Inc | Compuestos de isoquinolina |
| ES2729424T3 (es) | 2006-09-20 | 2019-11-04 | Aerie Pharmaceuticals Inc | Inhibidores de Rho cinasa |
| US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| 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 |
| PE20110054A1 (es) * | 2008-06-24 | 2011-02-15 | Sanofi Aventis | Isoquinolinas e isoquinolinonas 6-sustituidas |
| US8541449B2 (en) * | 2008-06-24 | 2013-09-24 | Sanofi | Substituted isoquinolines and isoquinolinones as Rho kinase inhibitors |
| PL2303845T3 (pl) * | 2008-06-24 | 2014-03-31 | Sanofi Sa | Bi- i policykliczne podstawione pochodne izochinoliny i izochinolinonu jako inhibitory kinazy Rho |
| US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| CA2760562C (en) | 2009-05-01 | 2016-07-19 | Aerie Pharmaceuticals, Inc. | Dual mechanism inhibitors for the treatment of disease |
| HUE028684T2 (en) | 2009-06-19 | 2016-12-28 | D Western Therapeutics Inst Inc | Substituted isoquinoline derivatives |
| CN105688214A (zh) * | 2011-10-26 | 2016-06-22 | 艾米丽·A·斯坦 | 用于影响神经功能的药剂、方法和设备 |
| PT3811943T (pt) | 2013-03-15 | 2023-03-15 | Aerie Pharmaceuticals Inc | Composto para uso no tratamento de distúrbios oculares |
| FR3017868A1 (fr) | 2014-02-21 | 2015-08-28 | Servier Lab | Derives d'isoquinoleine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US10308650B2 (en) | 2014-12-11 | 2019-06-04 | Syngenta Participations Ag | Pesticidally active tetracyclic derivatives with sulfur containing substituents |
| TW202237569A (zh) | 2014-12-24 | 2022-10-01 | 美商基利科學股份有限公司 | 喹唑啉化合物 |
| EA032430B1 (ru) | 2014-12-24 | 2019-05-31 | Джилид Сайэнс, Инк. | Конденсированные пиримидины для лечения вич |
| BR112017013440A2 (pt) | 2014-12-24 | 2018-01-09 | Gilead Sciences, Inc. | compostos de isoquinolina para o tratamento de hiv |
| US9643927B1 (en) | 2015-11-17 | 2017-05-09 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| JP6832946B2 (ja) | 2015-11-17 | 2021-02-24 | アエリエ ファーマシューティカルズ インコーポレイテッド | キナーゼ阻害剤およびその中間体の調製方法 |
| CN109640966A (zh) | 2016-08-31 | 2019-04-16 | 爱瑞制药公司 | 眼用组合物 |
| SG11201908179UA (en) | 2017-03-31 | 2019-10-30 | Aerie Pharmaceuticals Inc | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| WO2020056345A1 (en) | 2018-09-14 | 2020-03-19 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| US12398118B2 (en) | 2018-11-09 | 2025-08-26 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising same, and use thereof |
| CN110670090B (zh) * | 2019-11-13 | 2021-06-29 | 广西师范大学 | 一种基于电化学合成异喹啉酮类化合物的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5480883A (en) * | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| TW575567B (en) * | 1998-10-23 | 2004-02-11 | Akzo Nobel Nv | Serine protease inhibitor |
| HUP0204496A3 (en) * | 2000-01-20 | 2004-07-28 | Eisai Co Ltd | Novel piperidine compounds and pharmaceutical compositions containing the same and process for preparation the same |
| US7217722B2 (en) * | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| EP1403255A4 (en) * | 2001-06-12 | 2005-04-06 | Sumitomo Pharma | RHO KINASE INHIBITORS |
| SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New compounds |
| CN100354264C (zh) * | 2002-07-22 | 2007-12-12 | 旭化成制药株式会社 | 5－取代异喹啉衍生物及含有它们的药物 |
| AU2004276236B2 (en) * | 2003-09-23 | 2008-01-24 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| JPWO2005035516A1 (ja) * | 2003-10-10 | 2006-12-21 | 小野薬品工業株式会社 | 新規縮合複素環化合物およびその用途 |
| US7449477B2 (en) * | 2003-11-25 | 2008-11-11 | Eli Lilly And Company | 7-phenyl-isoquinoline-5-sulfonylamino derivatives as inhibitors of akt (protein kinase B) |
| JP2005232175A (ja) * | 2004-01-21 | 2005-09-02 | Asahi Kasei Pharma Kk | ５−置換イソキノリン医薬 |
| US7517991B2 (en) * | 2004-10-12 | 2009-04-14 | Bristol-Myers Squibb Company | N-sulfonylpiperidine cannabinoid receptor 1 antagonists |
| MX2008000017A (es) * | 2005-06-28 | 2008-03-26 | Sanofi Aventis | Derivados de isoquinolina como inhibidores de rho-cinasa. |
| US7618985B2 (en) * | 2005-12-08 | 2009-11-17 | N.V. Organon | Isoquinoline derivatives |
| US7893088B2 (en) | 2006-08-18 | 2011-02-22 | N.V. Organon | 6-substituted isoquinoline derivatives |
-
2007
- 2007-12-19 CN CN2007800485212A patent/CN101573338B/zh not_active Expired - Fee Related
- 2007-12-19 JP JP2009543374A patent/JP5318778B2/ja not_active Expired - Fee Related
- 2007-12-19 WO PCT/EP2007/011166 patent/WO2008077553A1/en not_active Ceased
- 2007-12-19 RU RU2009128688/04A patent/RU2009128688A/ru not_active Application Discontinuation
- 2007-12-19 MX MX2009005828A patent/MX2009005828A/es active IP Right Grant
- 2007-12-19 DE DE602007013950T patent/DE602007013950D1/de active Active
- 2007-12-19 ES ES07856889T patent/ES2364511T3/es active Active
- 2007-12-19 MY MYPI20092205A patent/MY148514A/en unknown
- 2007-12-19 AT AT07856889T patent/ATE505458T1/de active
- 2007-12-19 BR BRPI0720710-7A2A patent/BRPI0720710A2/pt not_active IP Right Cessation
- 2007-12-19 AU AU2007338409A patent/AU2007338409B2/en not_active Ceased
- 2007-12-19 DK DK07856889.6T patent/DK2125744T3/da active
- 2007-12-19 KR KR1020097013521A patent/KR20090103903A/ko not_active Abandoned
- 2007-12-19 PT PT07856889T patent/PT2125744E/pt unknown
- 2007-12-19 CA CA2673919A patent/CA2673919C/en not_active Expired - Fee Related
- 2007-12-19 EP EP07856889A patent/EP2125744B1/en active Active
-
2009
- 2009-05-22 ZA ZA200903553A patent/ZA200903553B/xx unknown
- 2009-06-12 CO CO09061596A patent/CO6210725A2/es not_active Application Discontinuation
- 2009-06-18 US US12/487,525 patent/US20100056568A1/en not_active Abandoned
- 2009-06-24 IL IL199536A patent/IL199536A/en not_active IP Right Cessation
- 2009-06-24 MA MA32038A patent/MA31023B1/fr unknown
- 2009-06-26 NO NO20092431A patent/NO20092431L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2673919C (en) | 2015-06-23 |
| CO6210725A2 (es) | 2010-10-20 |
| DE602007013950D1 (de) | 2011-05-26 |
| JP5318778B2 (ja) | 2013-10-16 |
| WO2008077553A1 (en) | 2008-07-03 |
| CA2673919A1 (en) | 2008-07-03 |
| CN101573338B (zh) | 2013-03-20 |
| JP2010514718A (ja) | 2010-05-06 |
| AU2007338409A1 (en) | 2008-07-03 |
| AU2007338409B2 (en) | 2012-12-13 |
| IL199536A (en) | 2014-07-31 |
| NO20092431L (no) | 2009-09-21 |
| MA31023B1 (fr) | 2009-12-01 |
| ATE505458T1 (de) | 2011-04-15 |
| ES2364511T3 (es) | 2011-09-05 |
| US20100056568A1 (en) | 2010-03-04 |
| CN101573338A (zh) | 2009-11-04 |
| EP2125744A1 (en) | 2009-12-02 |
| ZA200903553B (en) | 2010-04-28 |
| MX2009005828A (es) | 2009-06-16 |
| MY148514A (en) | 2013-04-30 |
| EP2125744B1 (en) | 2011-04-13 |
| PT2125744E (pt) | 2011-07-01 |
| HK1138583A1 (en) | 2010-08-27 |
| BRPI0720710A2 (pt) | 2014-12-23 |
| RU2009128688A (ru) | 2011-02-10 |
| DK2125744T3 (da) | 2011-08-01 |
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