JP2010514721A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010514721A5 JP2010514721A5 JP2009543377A JP2009543377A JP2010514721A5 JP 2010514721 A5 JP2010514721 A5 JP 2010514721A5 JP 2009543377 A JP2009543377 A JP 2009543377A JP 2009543377 A JP2009543377 A JP 2009543377A JP 2010514721 A5 JP2010514721 A5 JP 2010514721A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- isoquinolin
- aryl
- chloro
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- -1 chloro, bromo, methyl Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 155
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 67
- 125000002947 alkylene group Chemical group 0.000 claims 45
- 229910052736 halogen Inorganic materials 0.000 claims 34
- 150000002367 halogens Chemical class 0.000 claims 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 17
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- VQRVPAVBZKORPH-UHFFFAOYSA-N 6-(4-amino-4-benzylcyclohexyl)oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(N)CC1=CC=CC=C1 VQRVPAVBZKORPH-UHFFFAOYSA-N 0.000 claims 1
- KIFSYDCZKXYTBM-UHFFFAOYSA-N 6-(4-amino-4-phenylcyclohexyl)oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(N)C1=CC=CC=C1 KIFSYDCZKXYTBM-UHFFFAOYSA-N 0.000 claims 1
- KHXBQZITYUJRMU-UHFFFAOYSA-N 6-[(1-amino-4-bicyclo[2.2.2]octanyl)oxy]-7-chloro-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C(C=C2Cl)=C1C=C2OC1(CC2)CCC2(N)CC1 KHXBQZITYUJRMU-UHFFFAOYSA-N 0.000 claims 1
- DRIVXCAUALAPCG-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(3,4-dichlorophenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(CN)C1=CC=C(Cl)C(Cl)=C1 DRIVXCAUALAPCG-UHFFFAOYSA-N 0.000 claims 1
- YQTHQGAWGJYBQU-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(3,4-dimethoxyphenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C1(CN)CCC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CC1 YQTHQGAWGJYBQU-UHFFFAOYSA-N 0.000 claims 1
- GITGRQCWFHTEGH-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(3-chlorophenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(CN)C1=CC=CC(Cl)=C1 GITGRQCWFHTEGH-UHFFFAOYSA-N 0.000 claims 1
- YHFSMARAKOSCAV-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(3-methylphenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound CC1=CC=CC(C2(CN)CCC(CC2)OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)=C1 YHFSMARAKOSCAV-UHFFFAOYSA-N 0.000 claims 1
- XDQASUXTOJJMCZ-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(4-chlorophenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(CN)C1=CC=C(Cl)C=C1 XDQASUXTOJJMCZ-UHFFFAOYSA-N 0.000 claims 1
- JQBDVFMSMFKFIU-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(4-fluorophenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(CN)C1=CC=C(F)C=C1 JQBDVFMSMFKFIU-UHFFFAOYSA-N 0.000 claims 1
- JJKIFVWUOCEGCD-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(4-methoxyphenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1C1(CN)CCC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CC1 JJKIFVWUOCEGCD-UHFFFAOYSA-N 0.000 claims 1
- HQHBWBAFDIXHBN-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-(4-methylphenyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1=CC(C)=CC=C1C1(CN)CCC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CC1 HQHBWBAFDIXHBN-UHFFFAOYSA-N 0.000 claims 1
- AOMYLCRSEQEVCW-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-phenylcyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(CN)C1=CC=CC=C1 AOMYLCRSEQEVCW-UHFFFAOYSA-N 0.000 claims 1
- CONJEOHHKBJXHM-UHFFFAOYSA-N 6-[4-amino-4-(2,3-dihydroxypropyl)cyclohexyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CC(N)(CC(O)CO)CCC1OC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 CONJEOHHKBJXHM-UHFFFAOYSA-N 0.000 claims 1
- BPZATNXUWRXOFR-UHFFFAOYSA-N 6-[5-amino-5-(2,3-dihydroxypropyl)cyclooctyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CCC(N)(CC(O)CO)CCCC1OC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 BPZATNXUWRXOFR-UHFFFAOYSA-N 0.000 claims 1
- QLBYVJQLFXDTAY-UHFFFAOYSA-N 6-[5-amino-5-(3-hydroxypropyl)cyclooctyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CCC(N)(CCCO)CCCC1OC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 QLBYVJQLFXDTAY-UHFFFAOYSA-N 0.000 claims 1
- RSDBMUXVVFBHFP-UHFFFAOYSA-N 6-[5-amino-5-(3-methoxypropyl)cyclooctyl]oxy-7-chloro-2h-isoquinolin-1-one Chemical compound C1CCC(CCCOC)(N)CCCC1OC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 RSDBMUXVVFBHFP-UHFFFAOYSA-N 0.000 claims 1
- WPSDTAMLHYYWJL-UOYQGRGCSA-N 6-[[(1r,5r)-2-amino-6-bicyclo[3.3.1]nonanyl]oxy]-4-benzyl-7-methyl-2h-isoquinolin-1-one Chemical compound C([C@]1(C(CC[C@]2([H])C1)N)[H])CC2OC(C(=CC=1C(=O)NC=2)C)=CC=1C=2CC1=CC=CC=C1 WPSDTAMLHYYWJL-UOYQGRGCSA-N 0.000 claims 1
- XCNFSJZIYIUKAZ-CPWXYTRJSA-N 6-[[(1r,5r)-2-amino-6-bicyclo[3.3.1]nonanyl]oxy]-7-chloro-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C(C=C2Cl)=C1C=C2OC1CC[C@@]2([H])C(N)CC[C@]1([H])C2 XCNFSJZIYIUKAZ-CPWXYTRJSA-N 0.000 claims 1
- ODGPSQQDTKODQC-QBBMROGASA-N 6-[[(1r,5r)-2-amino-6-bicyclo[3.3.1]nonanyl]oxy]-7-methyl-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C(C=C2C)=C1C=C2OC1CC[C@@]2([H])C(N)CC[C@]1([H])C2 ODGPSQQDTKODQC-QBBMROGASA-N 0.000 claims 1
- VPSYCISPBILXNB-UHFFFAOYSA-N 7-chloro-6-[4-cyclopropyl-4-(ethylamino)cyclohexyl]oxy-2h-isoquinolin-1-one Chemical compound C1CC(OC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCC1(NCC)C1CC1 VPSYCISPBILXNB-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010019663 Hepatic failure Diseases 0.000 claims 1
- 206010020880 Hypertrophy Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010053159 Organ failure Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000031481 Pathologic Constriction Diseases 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000003143 atherosclerotic effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000002124 endocrine Effects 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 206010061989 glomerulosclerosis Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000001286 intracranial vasospasm Diseases 0.000 claims 1
- 230000004410 intraocular pressure Effects 0.000 claims 1
- 208000023589 ischemic disease Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 208000007903 liver failure Diseases 0.000 claims 1
- 231100000835 liver failure Toxicity 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 230000000250 revascularization Effects 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000037804 stenosis Diseases 0.000 claims 1
- 230000036262 stenosis Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- BBAWTPDTGRXPDG-UHFFFAOYSA-N [1,3]thiazolo[4,5-b]pyridine Chemical compound C1=CC=C2SC=NC2=N1 BBAWTPDTGRXPDG-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004623 carbolinyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
- 125000005438 isoindazolyl group Chemical group 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- QNNHQVPFZIFNFK-UHFFFAOYSA-N oxazolo[4,5-b]pyridine Chemical compound C1=CC=C2OC=NC2=N1 QNNHQVPFZIFNFK-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005494 pyridonyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06026897.6 | 2006-12-27 | ||
| EP06026897 | 2006-12-27 | ||
| PCT/EP2007/011169 WO2008077556A1 (en) | 2006-12-27 | 2007-12-19 | Cycloalkylamine substituted isoquinoline and isoquinolinone derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010514721A JP2010514721A (ja) | 2010-05-06 |
| JP2010514721A5 true JP2010514721A5 (enExample) | 2011-02-03 |
| JP5318779B2 JP5318779B2 (ja) | 2013-10-16 |
Family
ID=38050127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009543377A Expired - Fee Related JP5318779B2 (ja) | 2006-12-27 | 2007-12-19 | シクロアルキルアミン置換イソキノリン及びイソキノリノン誘導体 |
Country Status (37)
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1899322B1 (en) | 2005-06-28 | 2009-09-02 | Sanofi-Aventis | Isoquinoline derivatives as inhibitors of rho-kinase |
| ES2580108T3 (es) | 2005-07-11 | 2016-08-19 | Aerie Pharmaceuticals, Inc | Compuestos de isoquinolina |
| HRP20110839T1 (hr) | 2005-07-26 | 2011-12-31 | Sanofi | Derivati cikloheksaminizokinolona kao inhibitori rho-kinaze |
| PT1910333E (pt) | 2005-07-26 | 2013-08-01 | Sanofi Sa | Derivados de isoquinolona substituída com piperidinilo como inibidores da rho-cinase |
| EP2526948A1 (en) | 2006-09-20 | 2012-11-28 | Aerie Pharmaceuticals, Inc. | RHO kinase inhibitors |
| EP2102164B1 (en) | 2006-12-27 | 2010-12-01 | Sanofi-Aventis | Cycloalkylamine substituted isoquinoline and isoquinolinone derivatives |
| JP5421783B2 (ja) | 2006-12-27 | 2014-02-19 | サノフイ | Ｒｈｏキナーゼ阻害剤としての置換イソキノロン及びイソキノリノン誘導体 |
| KR20090094338A (ko) | 2006-12-27 | 2009-09-04 | 사노피-아벤티스 | 치환된 이소퀴놀린 및 이소퀴놀리논 유도체 |
| AU2007338410B2 (en) | 2006-12-27 | 2012-08-16 | Sanofi-Aventis | Cycloalkylamine substituted isoquinoline derivatives |
| ATE502027T1 (de) | 2006-12-27 | 2011-04-15 | Sanofi Aventis | Substituierte isochinoline und ihre verwendung als rho-kinase-inhibitoren |
| CN101595094B (zh) | 2006-12-27 | 2013-02-20 | 塞诺菲-安万特股份有限公司 | 环烷基胺取代的异喹诺酮衍生物 |
| 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 |
| SI2303845T1 (sl) * | 2008-06-24 | 2013-12-31 | Sanofi | Bi- in policiklični substituirani izokinolin in izokinolinski derivati kot inhibitorji rho-kinaze |
| PL2313374T3 (pl) | 2008-06-24 | 2014-03-31 | Sanofi Sa | 6-podstawione izochinoliny i izochinolinony |
| PE20110059A1 (es) | 2008-06-24 | 2011-02-15 | Sanofi Aventis | Isoquinolinas e isoquinolinonas sustituidas en calidad de inhibidores de la rho-quinasa |
| US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| MX2011009568A (es) * | 2009-03-09 | 2011-12-06 | Surface Logix Inc | Inhibidores de la rho cinasa. |
| WO2010126626A2 (en) | 2009-05-01 | 2010-11-04 | Aerie Pharmaceuticals, Inc. | Dual mechanism inhibitors for the treatment of disease |
| US20130225615A1 (en) | 2010-09-01 | 2013-08-29 | Ambit Biosciences Corporation | 2-cycloquinazoline derivatives and methods of use thereof |
| EP3238722B1 (en) * | 2011-01-10 | 2019-03-13 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinones |
| US9447025B2 (en) | 2013-03-14 | 2016-09-20 | Kalyra Pharmaceuticals, Inc. | Bicyclic analgesic compounds |
| BR112015021386A2 (pt) * | 2013-03-14 | 2017-07-18 | Bristol Myers Squibb Co | moduladores de ácido biciclo [2.2.2] gpr120 |
| MY181020A (en) | 2013-03-15 | 2020-12-16 | Sanofi Sa | Heteroaryl compounds and uses thereof |
| ES2776199T3 (es) | 2013-03-15 | 2020-07-29 | Aerie Pharmaceuticals Inc | Conjugados de compuestos de isoquinolina y prostaglandinas |
| TWI647220B (zh) | 2013-03-15 | 2019-01-11 | 美商西建卡爾有限責任公司 | 雜芳基化合物及其用途 |
| EP3290407B1 (en) | 2013-10-18 | 2020-01-01 | Celgene Quanticel Research, Inc | Bromodomain inhibitors |
| US10189780B2 (en) | 2013-12-12 | 2019-01-29 | Zeno Royalties & Milestones, LLC | Bicyclic alkyl compounds and synthesis |
| FR3017868A1 (fr) | 2014-02-21 | 2015-08-28 | Servier Lab | Derives d'isoquinoleine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN106232567B (zh) | 2014-03-07 | 2021-11-02 | 里科瑞尔姆Ip控股有限责任公司 | 螺桨烷衍生物及合成 |
| MA38393B1 (fr) * | 2014-03-13 | 2018-11-30 | Sanofi Sa | Composés hétéroaryle et utilisations associées |
| CN106999451B (zh) | 2014-09-17 | 2021-04-02 | 里科瑞尔姆Ip控股有限责任公司 | 双环化合物 |
| AR104259A1 (es) | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| US9643927B1 (en) | 2015-11-17 | 2017-05-09 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| WO2017086941A1 (en) | 2015-11-17 | 2017-05-26 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| US20190060257A1 (en) * | 2016-03-16 | 2019-02-28 | Zeno Royalties & Milestones, LLC | Analgesic compounds |
| AU2017252276A1 (en) | 2016-04-18 | 2018-11-15 | Celgene Quanticel Research, Inc. | Therapeutic compounds |
| US10150754B2 (en) | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| WO2018045091A1 (en) | 2016-08-31 | 2018-03-08 | Aerie Pharmaceuticals, Inc. | Ophthalmic compositions |
| CA3057872A1 (en) | 2017-03-31 | 2018-10-04 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| EP3628043A4 (en) | 2017-05-15 | 2021-04-28 | Recurium IP Holdings, LLC | ANALGESIC COMPOUNDS |
| AU2019337703B2 (en) | 2018-09-14 | 2023-02-02 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| CA3212840A1 (en) * | 2021-04-05 | 2022-10-13 | Justin KIM | Bioorthogonal reaction suitable for click/unclick applications |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2485537B2 (fr) | 1977-04-13 | 1986-05-16 | Anvar | Dipyrido(4,3-b)(3,4-f)indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant |
| HU178522B (en) * | 1979-04-11 | 1982-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing amino-isoquinoline derivatives |
| EP0541559A1 (en) | 1990-07-31 | 1993-05-19 | E.I. Du Pont De Nemours And Company | Catalytic equilibration of selected halocarbons |
| 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 |
| GB9516709D0 (en) | 1995-08-15 | 1995-10-18 | Zeneca Ltd | Medicament |
| ZA9610741B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Substituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| PT956865E (pt) | 1996-08-12 | 2007-07-30 | Mitsubishi Pharma Corp | Medicamentos compreendendo inibidores da rho cinase. |
| JPH1087629A (ja) | 1996-09-18 | 1998-04-07 | Fujisawa Pharmaceut Co Ltd | 新規イソキノリン誘導体、およびその医薬用途 |
| JP2001514259A (ja) | 1997-08-29 | 2001-09-11 | ゼネカ・リミテッド | アミノメチルオキソオキサゾリジニルベンゼン誘導体 |
| TW575567B (en) | 1998-10-23 | 2004-02-11 | Akzo Nobel Nv | Serine protease inhibitor |
| GB9912701D0 (en) | 1999-06-01 | 1999-08-04 | Smithkline Beecham Plc | Novel compounds |
| US6541456B1 (en) | 1999-12-01 | 2003-04-01 | Isis Pharmaceuticals, Inc. | Antimicrobial 2-deoxystreptamine compounds |
| IL150650A0 (en) * | 2000-01-20 | 2003-02-12 | Eisai Co Ltd | Piperidine derivatives and pharmaceutical compositions containing 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 |
| US20040171533A1 (en) | 2000-02-29 | 2004-09-02 | Barbara Zehentner | Methods and compositions for regulating adiopocytes |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| AR033517A1 (es) | 2000-04-08 | 2003-12-26 | Astrazeneca Ab | Derivados de piperidina, proceso para su preparacion y uso de estos derivados en la fabricacion de medicamentos |
| GB0013060D0 (en) | 2000-05-31 | 2000-07-19 | Astrazeneca Ab | Chemical compounds |
| SK322003A3 (en) * | 2000-07-12 | 2003-06-03 | Akzo Nobel Nv | Thrombin inhibitors comprising an aminoisoquinoline group |
| AU2001296008A1 (en) | 2000-10-27 | 2002-05-06 | Takeda Chemical Industries Ltd. | Process for preparing substituted aromatic compounds and intermediates therefor |
| JP2004520347A (ja) | 2001-01-15 | 2004-07-08 | グラクソ グループ リミテッド | Ｌｄｌ−受容体発現のインデューサーとしてのアリールピペリジンおよびピペラジン誘導体 |
| SE0101038D0 (sv) | 2001-03-23 | 2001-03-23 | Astrazeneca Ab | Novel compounds |
| JP2004534017A (ja) | 2001-04-27 | 2004-11-11 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｂａｃｅのインヒビター |
| EP1403255A4 (en) | 2001-06-12 | 2005-04-06 | Sumitomo Pharma | RHO KINASE INHIBITORS |
| GB0117899D0 (en) | 2001-07-23 | 2001-09-12 | Astrazeneca Ab | Chemical compounds |
| WO2003024450A1 (en) | 2001-09-20 | 2003-03-27 | Eisai Co., Ltd. | Methods for treating prion diseases |
| SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New compounds |
| AU2003281623B8 (en) * | 2002-07-22 | 2009-06-11 | Asahi Kasei Pharma Corporation | 5-substituted isoquinoline derivative |
| CA2502583A1 (en) | 2002-09-12 | 2004-03-25 | Kirin Beer Kabushiki Kaisha | Isoquinoline derivatives having kinase inhibitory activity and medicament containing the same |
| WO2004106325A1 (en) | 2003-05-29 | 2004-12-09 | Schering Aktiengesellschaft | Prodrugs of 1-(1-hydroxy-5-isoquinolinesulfonyl)homopiperazine |
| EP1638939A2 (en) | 2003-06-24 | 2006-03-29 | Neurosearch A/S | Aza-ring derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| WO2005030130A2 (en) | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinoline potassium channel inhibitors |
| US7723352B2 (en) | 2003-09-23 | 2010-05-25 | Merck Sharp & Dohme | Isoquinolinone potassium channel inhibitors |
| US20050067037A1 (en) | 2003-09-30 | 2005-03-31 | Conocophillips Company | Collapse resistant composite riser |
| EP1671962A1 (en) * | 2003-10-10 | 2006-06-21 | Ono Pharmaceutical Co., Ltd. | Novel fused heterocyclic compound and use thereof |
| EP1689719A1 (en) | 2003-11-25 | 2006-08-16 | Eli Lilly And Company | 7-phenyl-isoquinoline-5-sulfonylamino derivatives as inhibitors of akt (proteinkinase b) |
| JP2005232175A (ja) * | 2004-01-21 | 2005-09-02 | Asahi Kasei Pharma Kk | ５−置換イソキノリン医薬 |
| WO2005074535A2 (en) | 2004-01-30 | 2005-08-18 | Eisai Co., Ltd. | Cholinesterase inhibitors for spinal cord disorders |
| US20080312189A1 (en) | 2004-03-05 | 2008-12-18 | Eisai Co., Ltd. | Cadasil Treatment with Cholinesterase Inhibitors |
| SE0400850D0 (sv) | 2004-03-30 | 2004-03-31 | Astrazeneca Ab | Novel Compounds |
| US7517991B2 (en) * | 2004-10-12 | 2009-04-14 | Bristol-Myers Squibb Company | N-sulfonylpiperidine cannabinoid receptor 1 antagonists |
| HRP20110839T1 (hr) | 2005-07-26 | 2011-12-31 | Sanofi | Derivati cikloheksaminizokinolona kao inhibitori rho-kinaze |
| PT1910333E (pt) | 2005-07-26 | 2013-08-01 | Sanofi Sa | Derivados de isoquinolona substituída com piperidinilo como inibidores da rho-cinase |
| TW200745101A (en) | 2005-09-30 | 2007-12-16 | Organon Nv | 9-Azabicyclo[3.3.1]nonane derivatives |
| US7618985B2 (en) * | 2005-12-08 | 2009-11-17 | N.V. Organon | Isoquinoline derivatives |
| TW200738682A (en) | 2005-12-08 | 2007-10-16 | Organon Nv | Isoquinoline derivatives |
| US7893088B2 (en) | 2006-08-18 | 2011-02-22 | N.V. Organon | 6-substituted isoquinoline derivatives |
| EP2102164B1 (en) | 2006-12-27 | 2010-12-01 | Sanofi-Aventis | Cycloalkylamine substituted isoquinoline and isoquinolinone derivatives |
| ATE502027T1 (de) | 2006-12-27 | 2011-04-15 | Sanofi Aventis | Substituierte isochinoline und ihre verwendung als rho-kinase-inhibitoren |
-
2007
- 2007-12-19 EP EP07856892A patent/EP2102164B1/en active Active
- 2007-12-19 WO PCT/EP2007/011169 patent/WO2008077556A1/en not_active Ceased
- 2007-12-19 BR BRPI0720859-6A patent/BRPI0720859A2/pt not_active IP Right Cessation
- 2007-12-19 RS RS20110096A patent/RS51655B/sr unknown
- 2007-12-19 AU AU2007338412A patent/AU2007338412B2/en not_active Ceased
- 2007-12-19 PT PT07856892T patent/PT2102164E/pt unknown
- 2007-12-19 HR HR20100705T patent/HRP20100705T1/hr unknown
- 2007-12-19 ES ES07856892T patent/ES2355534T3/es active Active
- 2007-12-19 JP JP2009543377A patent/JP5318779B2/ja not_active Expired - Fee Related
- 2007-12-19 DE DE602007010981T patent/DE602007010981D1/de active Active
- 2007-12-19 PL PL07856892T patent/PL2102164T3/pl unknown
- 2007-12-19 CA CA2673922A patent/CA2673922C/en not_active Expired - Fee Related
- 2007-12-19 AT AT07856892T patent/ATE490243T1/de active
- 2007-12-19 KR KR1020097013327A patent/KR101494452B1/ko not_active Expired - Fee Related
- 2007-12-19 NZ NZ577984A patent/NZ577984A/en not_active IP Right Cessation
- 2007-12-19 SI SI200730505T patent/SI2102164T1/sl unknown
- 2007-12-19 MX MX2009005967A patent/MX2009005967A/es active IP Right Grant
- 2007-12-19 DK DK07856892.0T patent/DK2102164T3/da active
- 2007-12-19 RU RU2009128652/04A patent/RU2468011C2/ru not_active IP Right Cessation
- 2007-12-19 CN CN2007800484652A patent/CN101578266B/zh not_active Expired - Fee Related
- 2007-12-19 MY MYPI20092206A patent/MY154767A/en unknown
- 2007-12-25 TW TW096149807A patent/TWI423803B/zh not_active IP Right Cessation
- 2007-12-26 CL CL200703820A patent/CL2007003820A1/es unknown
- 2007-12-26 UY UY30845A patent/UY30845A1/es unknown
- 2007-12-26 AR ARP070105898A patent/AR064531A1/es unknown
-
2009
- 2009-05-20 CR CR10811A patent/CR10811A/es not_active Application Discontinuation
- 2009-05-22 ZA ZA200903555A patent/ZA200903555B/xx unknown
- 2009-06-04 NI NI200900111A patent/NI200900111A/es unknown
- 2009-06-12 CO CO09061604A patent/CO6210815A2/es active IP Right Grant
- 2009-06-18 US US12/487,503 patent/US8710077B2/en not_active Expired - Fee Related
- 2009-06-23 SV SV2009003314A patent/SV2009003314A/es unknown
- 2009-06-24 MA MA32040A patent/MA31076B1/fr unknown
- 2009-06-26 EC EC2009009468A patent/ECSP099468A/es unknown
- 2009-06-26 GT GT200900183A patent/GT200900183A/es unknown
- 2009-06-26 TN TNP2009000274A patent/TN2009000274A1/fr unknown
- 2009-07-01 NO NO20092488A patent/NO20092488L/no not_active Application Discontinuation
-
2011
- 2011-02-04 CY CY20111100131T patent/CY1111323T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010514718A5 (enExample) | ||
| JP2010514719A5 (enExample) | ||
| JP2010514716A5 (enExample) | ||
| JP2010514717A5 (enExample) | ||
| JP2010514720A5 (enExample) | ||
| JP2010514715A5 (enExample) | ||
| AU766081B2 (en) | Phthalazine derivatives for treating inflammatory diseases | |
| CN105503862B (zh) | 流感病毒复制抑制剂 | |
| ES2393630T3 (es) | Derivados de N-(AMINO-HETEROARIL)-1H-INDOL-2-CARBOXAMIDAS, su preparación y su aplicación en terapéutica | |
| ES2702182T3 (es) | Compuestos aromáticos multisustituidos como inhibidores de la serina proteasa | |
| TW530048B (en) | New hydroxyindoles, their use as inhibitors of phosphodiesterase 4 and processes for their preparation | |
| AU2020374957A1 (en) | Small molecule degraders of Helios and methods of use | |
| ES2852351T3 (es) | Pirrolamidas como inhibidores de la integrina alfa V | |
| ES2704704T3 (es) | Nuevos derivados de azaindol como inhibidores selectivos de la histona desacetilasa (HDAC) y composiciones farmacéuticas que los comprenden | |
| RU2009128652A (ru) | Замещенные циклоалкиламином производные изохинолина и изохинолинона | |
| JP2021519766A (ja) | ＸＩＩａ因子インヒビター | |
| IL301690A (en) | Piperidinyl small molecule degraders of helios and methods of use | |
| CN102093320B (zh) | 一种可溶性环氧化物水解酶抑制剂 | |
| ES2535212T3 (es) | Carboxamido-4-[(4-piridil)amino]-pirimidinas para el tratamiento de la hepatitis C | |
| RU2009128693A (ru) | Замещенные производные изохинолина и изохинолинона | |
| JP2006502112A5 (enExample) | ||
| JP2019537603A (ja) | アルファｖインテグリン阻害剤としてのアゾールアミドおよびアミン | |
| TW200307545A (en) | Nicotinamide derivatives and a tiotropium salt in combination for the treatment of diseases | |
| EP4153175A1 (en) | Piperidine-2,6-diones as small molecule degraders of helios and methods of use | |
| WO2003106429A1 (ja) | プロドラッグおよびその製造法 |