JP2010506853A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010506853A5 JP2010506853A5 JP2009532605A JP2009532605A JP2010506853A5 JP 2010506853 A5 JP2010506853 A5 JP 2010506853A5 JP 2009532605 A JP2009532605 A JP 2009532605A JP 2009532605 A JP2009532605 A JP 2009532605A JP 2010506853 A5 JP2010506853 A5 JP 2010506853A5
- Authority
- JP
- Japan
- Prior art keywords
- heteroaryl
- aryl
- heterocyclyl
- aralkyl
- alkyl
- 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.)
- Withdrawn
Links
- 125000003118 aryl group Chemical group 0.000 claims description 660
- 125000001072 heteroaryl group Chemical group 0.000 claims description 650
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 619
- 125000000623 heterocyclic group Chemical group 0.000 claims description 598
- 125000000217 alkyl group Chemical group 0.000 claims description 594
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 484
- 125000001188 haloalkyl group Chemical group 0.000 claims description 478
- 229910052739 hydrogen Inorganic materials 0.000 claims description 403
- 239000001257 hydrogen Substances 0.000 claims description 403
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 375
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 367
- 150000002431 hydrogen Chemical class 0.000 claims description 362
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 346
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 345
- 125000005843 halogen group Chemical group 0.000 claims description 320
- 125000003342 alkenyl group Chemical group 0.000 claims description 223
- 125000000304 alkynyl group Chemical group 0.000 claims description 181
- 125000001424 substituent group Chemical group 0.000 claims description 164
- 150000001875 compounds Chemical class 0.000 claims description 152
- 125000003545 alkoxy group Chemical group 0.000 claims description 150
- -1 aralkenyl Chemical group 0.000 claims description 138
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 138
- 229910052757 nitrogen Inorganic materials 0.000 claims description 125
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 114
- 125000002947 alkylene group Chemical group 0.000 claims description 98
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 90
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 76
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 64
- 125000004450 alkenylene group Chemical group 0.000 claims description 58
- 125000004419 alkynylene group Chemical group 0.000 claims description 58
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
- 125000004043 oxo group Chemical group O=* 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 108010052164 Sodium Channels Proteins 0.000 claims description 3
- 102000018674 Sodium Channels Human genes 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- SJHDVMWBWHIRCU-UHFFFAOYSA-N 1'-[(5-chloro-1-methylimidazol-2-yl)methyl]-5-methoxyspiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1=NC=C(Cl)N1C SJHDVMWBWHIRCU-UHFFFAOYSA-N 0.000 claims description 2
- MXZOIHRFVGCWEH-UHFFFAOYSA-N 1'-[(5-chlorothiophen-2-yl)methyl]-5-methoxyspiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1=CC=C(Cl)S1 MXZOIHRFVGCWEH-UHFFFAOYSA-N 0.000 claims description 2
- ZHOGUJSKSATCOX-UHFFFAOYSA-N 1'-benzhydryl-5-methoxyspiro[2h-furo[2,3-c]pyridine-3,3'-indole]-2'-one Chemical compound C1=NC(OC)=CC2=C1OCC2(C1=CC=CC=C11)C(=O)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZHOGUJSKSATCOX-UHFFFAOYSA-N 0.000 claims description 2
- ZTMUGZRESNMMNM-UHFFFAOYSA-N 1'-pentylspiro[2h-furo[3,2-c]pyridine-3,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCCCC)C(=O)C11C2=CN=CC=C2OC1 ZTMUGZRESNMMNM-UHFFFAOYSA-N 0.000 claims description 2
- KTHNAZDYAWQVFY-UHFFFAOYSA-N 1'-{[5-(trifluoromethyl)-2-furyl]methyl}spiro[1,3-dioxolo[4,5-b]furo[2,3-e]pyridine-5,3'-indol]-2'(1'h)-one Chemical compound O1C(C(F)(F)F)=CC=C1CN1C2=CC=CC=C2C2(C3=NC=4OCOC=4C=C3OC2)C1=O KTHNAZDYAWQVFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- ZZMVUMDGOMWVSB-UHFFFAOYSA-N 4'-(furan-3-yl)-5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=C(C2=COC=C2)C=CC=C11)C(=O)N1CC1=CC=C(C(F)(F)F)O1 ZZMVUMDGOMWVSB-UHFFFAOYSA-N 0.000 claims description 2
- OYKOUAWTZHABHV-UHFFFAOYSA-N 4'-bromo-5-methoxy-1'-[(2-propan-2-yl-1,3-thiazol-5-yl)methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=C(Br)C=CC=C11)C(=O)N1CC1=CN=C(C(C)C)S1 OYKOUAWTZHABHV-UHFFFAOYSA-N 0.000 claims description 2
- NVWFDLQVXIXCIE-UHFFFAOYSA-N 4'-bromo-5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=C(Br)C=CC=C11)C(=O)N1CC1=CC=C(C(F)(F)F)O1 NVWFDLQVXIXCIE-UHFFFAOYSA-N 0.000 claims description 2
- BXAJDQXJHVOHSD-UHFFFAOYSA-N 4'-chloro-5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=C(Cl)C=CC=C11)C(=O)N1CC1=CC=C(C(F)(F)F)O1 BXAJDQXJHVOHSD-UHFFFAOYSA-N 0.000 claims description 2
- VPRFWHZZICQOHE-UHFFFAOYSA-N 4-bromo-5'-methoxyspiro[1h-indole-3,3'-2h-furo[3,2-b]pyridine]-2-one Chemical compound O=C1NC2=CC=CC(Br)=C2C21COC1=CC=C(OC)N=C12 VPRFWHZZICQOHE-UHFFFAOYSA-N 0.000 claims description 2
- VCISRRKUQUZONU-UHFFFAOYSA-N 5'-fluoro-5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC(F)=CC=C11)C(=O)N1CC1=CC=C(C(F)(F)F)O1 VCISRRKUQUZONU-UHFFFAOYSA-N 0.000 claims description 2
- QVKFVTFAPBNNMR-UHFFFAOYSA-N 5'-methoxyspiro[1h-indole-3,3'-2h-furo[2,3-c]pyridine]-2-one Chemical compound O=C1NC2=CC=CC=C2C21COC1=C2C=C(OC)N=C1 QVKFVTFAPBNNMR-UHFFFAOYSA-N 0.000 claims description 2
- KZVVOAQYEOHGGD-UHFFFAOYSA-N 5-methoxy-1'-(oxan-4-ylmethyl)spiro[2h-furo[2,3-c]pyridine-3,3'-indole]-2'-one Chemical compound C1=NC(OC)=CC2=C1OCC2(C1=CC=CC=C11)C(=O)N1CC1CCOCC1 KZVVOAQYEOHGGD-UHFFFAOYSA-N 0.000 claims description 2
- HFDCBPAVYWSDHG-UHFFFAOYSA-N 5-methoxy-1'-(piperidin-4-ylmethyl)spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1CCNCC1 HFDCBPAVYWSDHG-UHFFFAOYSA-N 0.000 claims description 2
- STGMCBXIWDWKNF-UHFFFAOYSA-N 5-methoxy-1'-(pyridin-2-ylmethyl)spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1=CC=CC=N1 STGMCBXIWDWKNF-UHFFFAOYSA-N 0.000 claims description 2
- ZPBJZVCHEDJNGK-SZQRVLIRSA-N 5-methoxy-1'-[[(2s)-oxolan-2-yl]methyl]spiro[2h-furo[2,3-c]pyridine-3,3'-indole]-2'-one Chemical compound C1=NC(OC)=CC2=C1OCC2(C1=CC=CC=C11)C(=O)N1C[C@@H]1CCCO1 ZPBJZVCHEDJNGK-SZQRVLIRSA-N 0.000 claims description 2
- ZTAMUSSXAXYWPY-UHFFFAOYSA-N 5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2H-furo[2,3-c]pyridine-3,3'-2H-indole] Chemical compound COC=1C=C2C(=CN=1)OCC21CN(C2=CC=CC=C12)CC=1OC(=CC=1)C(F)(F)F ZTAMUSSXAXYWPY-UHFFFAOYSA-N 0.000 claims description 2
- AZYKTWWKNSJCFG-UHFFFAOYSA-N 5-oxido-1'-pentylspiro[2h-furo[3,2-c]pyridin-5-ium-3,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCCCC)C(=O)C11C2=C[N+]([O-])=CC=C2OC1 AZYKTWWKNSJCFG-UHFFFAOYSA-N 0.000 claims description 2
- YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims 13
- 238000006467 substitution reaction Methods 0.000 claims 9
- NXZXTRLIMWOUGS-UHFFFAOYSA-N 5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2H-furo[3,2-b]pyridine-3,3'-2H-indole] Chemical compound COC1=CC=C2C(=N1)C1(CN(C3=CC=CC=C13)CC=1OC(=CC=1)C(F)(F)F)CO2 NXZXTRLIMWOUGS-UHFFFAOYSA-N 0.000 claims 2
- 208000007914 Labor Pain Diseases 0.000 claims 2
- 208000035945 Labour pain Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- DDBQLGWNVMCVJL-UHFFFAOYSA-N 1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2H-furo[3,2-b]pyridine-3,3'-2H-indole] Chemical compound FC(C1=CC=C(O1)CN1CC2(C3=CC=CC=C13)COC=1C2=NC=CC=1)(F)F DDBQLGWNVMCVJL-UHFFFAOYSA-N 0.000 claims 1
- BZLHJHAEUYPNRL-UHFFFAOYSA-N 1'-pentylspiro[2,5-dihydrofuro[3,2-c]pyridine-3,3'-indole]-2',4-dione Chemical compound C12=CC=CC=C2N(CCCCC)C(=O)C11C(C(=O)NC=C2)=C2OC1 BZLHJHAEUYPNRL-UHFFFAOYSA-N 0.000 claims 1
- JKWMYJNZCOFMGT-UHFFFAOYSA-N 5-methoxy-1'-[(1-methylpiperidin-4-yl)methyl]spiro[2H-furo[3,2-b]pyridine-3,3'-2H-indole] Chemical compound COC1=CC=C2C(=N1)C1(CN(C3=CC=CC=C13)CC1CCN(CC1)C)CO2 JKWMYJNZCOFMGT-UHFFFAOYSA-N 0.000 claims 1
- OWVVUPLJBZOWBK-UHFFFAOYSA-N 5-methoxy-1'-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]spiro[2H-furo[3,2-b]pyridine-3,3'-2H-indole] Chemical compound COC1=CC=C2C(=N1)C1(CN(C3=CC=CC=C13)CC=1N=C(SC=1)C(C)C)CO2 OWVVUPLJBZOWBK-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 206010015150 Erythema Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 101000620451 Homo sapiens Leucine-rich glioma-inactivated protein 1 Proteins 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010020844 Hyperthermia malignant Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 102100022275 Leucine-rich glioma-inactivated protein 1 Human genes 0.000 claims 1
- 208000026709 Liddle syndrome Diseases 0.000 claims 1
- 208000018717 Malignant hyperthermia of anesthesia Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028372 Muscular weakness Diseases 0.000 claims 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
- 206010029279 Neurogenic bladder Diseases 0.000 claims 1
- 208000012075 Paroxysmal dystonia Diseases 0.000 claims 1
- 208000010886 Peripheral nerve injury Diseases 0.000 claims 1
- 208000004983 Phantom Limb Diseases 0.000 claims 1
- 206010056238 Phantom pain Diseases 0.000 claims 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 206010037113 Pseudoaldosteronism Diseases 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 206010039020 Rhabdomyolysis Diseases 0.000 claims 1
- 206010040744 Sinus headache Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000001871 Tachycardia Diseases 0.000 claims 1
- 206010057040 Temperature intolerance Diseases 0.000 claims 1
- 206010043269 Tension headache Diseases 0.000 claims 1
- 208000008548 Tension-Type Headache Diseases 0.000 claims 1
- 206010043994 Tonic convulsion Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 claims 1
- 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000025307 bipolar depression Diseases 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 208000010118 dystonia Diseases 0.000 claims 1
- 231100000321 erythema Toxicity 0.000 claims 1
- 230000004907 flux Effects 0.000 claims 1
- 230000008543 heat sensitivity Effects 0.000 claims 1
- 208000003532 hypothyroidism Diseases 0.000 claims 1
- 230000002989 hypothyroidism Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 201000007004 malignant hyperthermia Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000036473 myasthenia Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 230000004112 neuroprotection Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 208000019865 paroxysmal extreme pain disease Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 230000002085 persistent effect Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- NHNDASBNYPKGID-UHFFFAOYSA-N spiro[1H-indole-3,3'-2H-furo[2,3-c]pyridine]-2-one Chemical compound N1C(C2(C3=CC=CC=C13)COC1=CN=CC=C12)=O NHNDASBNYPKGID-UHFFFAOYSA-N 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- 239000002435 venom Substances 0.000 claims 1
- 210000001048 venom Anatomy 0.000 claims 1
- 231100000611 venom Toxicity 0.000 claims 1
- 208000003663 ventricular fibrillation Diseases 0.000 claims 1
- 208000009935 visceral pain Diseases 0.000 claims 1
- AAJMBUNHJRDMPE-UHFFFAOYSA-N 5'-methoxyspiro[1h-indole-3,3'-2h-furo[3,2-b]pyridine]-2-one Chemical compound O=C1NC2=CC=CC=C2C21COC1=CC=C(OC)N=C12 AAJMBUNHJRDMPE-UHFFFAOYSA-N 0.000 description 1
- AWQZHUDDUMVDST-UHFFFAOYSA-N 5-methoxy-1'-[(1-methylpiperidin-4-yl)methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1CCN(C)CC1 AWQZHUDDUMVDST-UHFFFAOYSA-N 0.000 description 1
- ZDJYTQQELONEPI-UHFFFAOYSA-N 5-methoxy-1'-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1=CSC(C(C)C)=N1 ZDJYTQQELONEPI-UHFFFAOYSA-N 0.000 description 1
- ZPBJZVCHEDJNGK-CRIUFTBBSA-N 5-methoxy-1'-[[(2r)-oxolan-2-yl]methyl]spiro[2h-furo[2,3-c]pyridine-3,3'-indole]-2'-one Chemical compound C1=NC(OC)=CC2=C1OCC2(C1=CC=CC=C11)C(=O)N1C[C@H]1CCCO1 ZPBJZVCHEDJNGK-CRIUFTBBSA-N 0.000 description 1
- KFNVAIUTZXCDKO-UHFFFAOYSA-N 5-methoxy-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[2h-furo[3,2-b]pyridine-3,3'-indole]-2'-one Chemical compound C12=NC(OC)=CC=C2OCC1(C1=CC=CC=C11)C(=O)N1CC1=CC=C(C(F)(F)F)O1 KFNVAIUTZXCDKO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85123706P | 2006-10-12 | 2006-10-12 | |
| US95558207P | 2007-08-13 | 2007-08-13 | |
| PCT/US2007/081244 WO2008046049A1 (en) | 2006-10-12 | 2007-10-12 | Spiro (furo [3, 2-c] pyridine-3-3 ' -indol) -2' (1'h)-one derivatives and related compounds for the treatment of sodium-channel mediated diseases, such as pain |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010506853A JP2010506853A (ja) | 2010-03-04 |
| JP2010506853A5 true JP2010506853A5 (enExample) | 2011-11-24 |
Family
ID=39047542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009532605A Withdrawn JP2010506853A (ja) | 2006-10-12 | 2007-10-12 | 疼痛などのナトリウムチャネル媒介性の疾患の処置のための、スピロ（［３，２−フロ］ピリジン−３，３’−インドール）−２’（１’ｈ）−オン誘導体および関連化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20110294842A9 (enExample) |
| EP (1) | EP2076514A1 (enExample) |
| JP (1) | JP2010506853A (enExample) |
| AR (1) | AR063278A1 (enExample) |
| AU (1) | AU2007307638A1 (enExample) |
| BR (1) | BRPI0719857A2 (enExample) |
| CA (1) | CA2666143A1 (enExample) |
| CL (1) | CL2007002953A1 (enExample) |
| MX (1) | MX2009003875A (enExample) |
| RU (1) | RU2009117605A (enExample) |
| TW (1) | TW200825091A (enExample) |
| WO (1) | WO2008046049A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR053710A1 (es) | 2005-04-11 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos espiroheterociclicos y sus usos como agentes terapeuticos |
| MY144968A (en) | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| MX2009003876A (es) | 2006-10-12 | 2009-05-11 | Xenon Pharmaceuticals Inc | Uso de compuestos de espiro-oxindol como agentes terapeuticos. |
| WO2010045197A1 (en) * | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals, Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| PT2350090E (pt) | 2008-10-17 | 2015-11-13 | Xenon Pharmaceuticals Inc | Composto espiro-oxindol e suas utilizações como agentes terapêuticos |
| WO2010078307A1 (en) | 2008-12-29 | 2010-07-08 | Xenon Pharmaceuticals Inc. | Spiro-oxindole-derivatives as sodium channel blockers |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| PE20121350A1 (es) | 2009-10-14 | 2012-10-20 | Xenon Pharmaceuticals Inc | Metodos sinteticos para compuestos espiro-oxoindol |
| US20110086899A1 (en) * | 2009-10-14 | 2011-04-14 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
| PE20121699A1 (es) | 2010-02-26 | 2012-12-22 | Xenon Pharmaceuticals Inc | Composiciones farmaceuticas del compuesto espiro-oxindol para administracion topica |
| WO2012049555A1 (en) | 2010-10-13 | 2012-04-19 | Lupin Limited | Spirocyclic compounds as voltage-gated sodium channel modulators |
| KR101880966B1 (ko) * | 2011-06-10 | 2018-07-23 | 메르크 파텐트 게엠베하 | Btk 억제 활성을 갖는 피리미딘 및 피리딘 화합물의 조성물 및 제조방법 |
| WO2013154712A1 (en) | 2012-04-12 | 2013-10-17 | Xenon Pharmaceuticals Inc. | Asymmetric syntheses for spiro-oxindole compounds useful as therapeutic agents |
| GB201209015D0 (en) | 2012-05-22 | 2012-07-04 | Convergence Pharmaceuticals | Novel compounds |
| US20170137415A1 (en) | 2014-03-29 | 2017-05-18 | Lupin Limited | Sulfonamide compounds as voltage gated sodium channel modulators |
| BR112016028888A2 (pt) | 2014-06-12 | 2017-08-22 | Adamed Sp Zoo | compostos que compreendem o sistema 1,1',2,5'-tetra hidro espiro [indol-3,2'-pirrol]-2,5'-diona como inibidores de interação proteína-proteína p53-mdm2 |
| TW201636017A (zh) | 2015-02-05 | 2016-10-16 | 梯瓦製藥國際有限責任公司 | 以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法 |
| TW201722938A (zh) | 2015-09-04 | 2017-07-01 | 魯賓有限公司 | 作為電位閘控鈉通道調節子之磺醯胺化合物 |
| WO2017218920A1 (en) | 2016-06-16 | 2017-12-21 | Teva Pharmaceuticals International Gmbh | Asymmetric synthesis of funapide |
| WO2018163077A1 (en) | 2017-03-08 | 2018-09-13 | Lupin Limited | Indanyl compounds as voltage gated sodium channel modulators |
| WO2019075073A2 (en) | 2017-10-10 | 2019-04-18 | Biogen Inc. | PROCESS FOR THE PREPARATION OF SPIRO DERIVATIVES |
| CN108299451B (zh) * | 2018-04-04 | 2020-11-24 | 四川理工学院 | 一种螺[吲哚啉-3,3’-吡喃[2,3-b]芳杂环]-2-酮化合物及其制备方法 |
Family Cites Families (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189617A (en) * | 1961-02-03 | 1965-06-15 | Sterling Drug Inc | 1-aryloxindoles and their preparation |
| US3723459A (en) * | 1971-04-23 | 1973-03-27 | Mc Neil Labor Inc | 2-oxospiro (indoline -3,4{40 -thiochroman) derivatives |
| US3845770A (en) * | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| SE400966B (sv) * | 1975-08-13 | 1978-04-17 | Robins Co Inc A H | Forfarande for framstellning av 2-amino-3-(eller 5-)bensoyl-fenylettiksyror |
| US4670566A (en) * | 1979-07-12 | 1987-06-02 | A. H. Robins Company, Incorporated | 3-methyl-hio-4-(5-, 6-, or 7-)phenylindolindolin-2-ones |
| US4326525A (en) * | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US4440785A (en) * | 1980-10-30 | 1984-04-03 | A. H. Robins Company, Inc. | Methods of using 2-aminobiphenylacetic acids, esters, and metal salts thereof to treat inflammation |
| US4438130A (en) * | 1981-11-12 | 1984-03-20 | The Upjohn Company | Analgesic 1-oxa-, aza- and thia-spirocyclic compounds |
| JPS6130554A (ja) * | 1984-07-23 | 1986-02-12 | Ono Pharmaceut Co Ltd | プロスタグランジン類似化合物のある特定の立体配置を有する異性体及びそれらを有効成分として含有する治療剤 |
| DE3608088C2 (de) * | 1986-03-07 | 1995-11-16 | Schering Ag | Pharmazeutische Präparate, enthaltend Cyclodextrinclathrate von Carbacyclinderivaten |
| EP0299914B2 (de) * | 1987-07-17 | 2003-04-23 | Schering Aktiengesellschaft | 9-Halogen-(Z)-prostaglandinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US5182289A (en) * | 1988-06-14 | 1993-01-26 | Schering Corporation | Heterobicyclic compounds having antiinflammatory activity |
| US5023265A (en) * | 1990-06-01 | 1991-06-11 | Schering Corporation | Substituted 1-H-pyrrolopyridine-3-carboxamides |
| US5116854A (en) * | 1991-06-28 | 1992-05-26 | Pfizer Inc. | Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles |
| US5663431A (en) * | 1992-01-30 | 1997-09-02 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| US5849780A (en) * | 1992-01-30 | 1998-12-15 | Sanofi | 1-benzenesulfonyl-1-1,3-dihydroindol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| US5686624A (en) * | 1992-01-30 | 1997-11-11 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| US5278162A (en) * | 1992-09-18 | 1994-01-11 | The Du Pont Merck Pharmaceutical Company | 3,3'-disubstituted-1,3-dihydro-2H-pyrrolo[2,3-b]heterocyclic-2-one useful in the treatment of cognitive disorders of man |
| US5296478A (en) * | 1992-10-07 | 1994-03-22 | The Dupont Merck Pharmaceutical Co. | 1-substituted oxindoles as cognition enhancers |
| US5776936A (en) * | 1992-11-13 | 1998-07-07 | Pharmacia & Upjohn Company | Marcfortine/paraherquamide derivatives useful as antiparasitic agents |
| DE4242451A1 (de) * | 1992-12-16 | 1994-06-23 | Basf Ag | Verfahren zur Herstellung von 5-Ringheterocyclen |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| AT400950B (de) * | 1994-02-04 | 1996-04-25 | Immodal Pharmaka Gmbh | Verfahren zur technischen herstellung definierter isomerengemische aus verbindungen mit spirozyklischen - aminocarboxyl- und/oder spirozyklischen - aminocarbonyl-systemen |
| AU2310895A (en) * | 1994-04-07 | 1995-10-30 | Cemaf | Novel spiro{indole-pyrrolidine} derivatives as melatoninergic agonists, method for preparing same and use thereofas a drug |
| US5618819A (en) * | 1994-07-07 | 1997-04-08 | Adir Et Compagnie | 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one and oxazolo[4,5-b]pyridin-2-(3H)-one compounds |
| US5726332A (en) * | 1995-09-21 | 1998-03-10 | Witco Gmbh | Synthesis of novel organometallics and their use in olefin polymerization |
| FR2740136B1 (fr) * | 1995-10-24 | 1998-01-09 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
| FR2757157B1 (fr) * | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| DE59814452D1 (de) * | 1997-01-20 | 2010-06-24 | Immodal Pharmaka Gmbh | Verfahren und stoffe zur freisetzung eines wachstumsfaktors aus endothelzellen, und nach dem verfahren freigesetzter wachstumsfaktor sowie seine verwendung |
| NO317155B1 (no) * | 1997-02-04 | 2004-08-30 | Ono Pharmaceutical Co | <omega>-cykloalkyl-prostagladin-E<N>2</N>-derivater |
| ATE237587T1 (de) * | 1997-02-10 | 2003-05-15 | Ono Pharmaceutical Co | 11,15-o-dialkylprostaglandin-e-derivate, verfahren zu ihrer herstellung und arzneimittel, die diese als aktiven inhaltsstoff enthalten |
| WO1999033794A1 (en) * | 1997-12-25 | 1999-07-08 | Ono Pharmaceutical Co., Ltd. | φ-CYCLOALKYL-PROSTAGLANDIN E2 DERIVATIVES |
| JP4087938B2 (ja) * | 1998-02-04 | 2008-05-21 | 高砂香料工業株式会社 | ヒノキチオ−ル類の分岐サイクロデキストリン包接化合物からなる抗菌剤およびそれを含有する組成物 |
| US20040038970A1 (en) * | 1998-06-12 | 2004-02-26 | Societe De Conseils De Recherches Etd' Application Scientifiques, S.A.S. A Paris, France Corp. | Beta-carboline compounds |
| US6235780B1 (en) * | 1998-07-21 | 2001-05-22 | Ono Pharmaceutical Co., Ltd. | ω-cycloalkyl-prostaglandin E1 derivatives |
| US6355648B1 (en) * | 1999-05-04 | 2002-03-12 | American Home Products Corporation | Thio-oxindole derivatives |
| US6407101B1 (en) * | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| US6414153B1 (en) * | 1999-07-21 | 2002-07-02 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1-phenylpydrrolidin-2-ones and -thiones and 1-(4-pyridyl)pydrrolidin-2-ones and -thiones which are useful in the treatment of inflammatory disease |
| US6566372B1 (en) * | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| US6670357B2 (en) * | 2000-11-17 | 2003-12-30 | Bristol-Myers Squibb Company | Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors |
| ES2262817T3 (es) * | 2001-08-14 | 2006-12-01 | Eli Lilly And Company | Agonistas beta-3 oxindol 3-sustituidos. |
| WO2003044016A1 (en) * | 2001-11-20 | 2003-05-30 | Eli Lilly And Company | 3-SUBSTITUTED OXINDOLE β3 AGONISTS |
| SE0104341D0 (sv) * | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New use |
| US6995144B2 (en) * | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| WO2004100956A1 (en) * | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Method for enhancing cognition using ziprasidone |
| JP2007516955A (ja) * | 2003-05-16 | 2007-06-28 | ファイザー・プロダクツ・インク | 双極性障害および関連症候の治療 |
| BRPI0410378A (pt) * | 2003-05-16 | 2006-06-13 | Pfizer Prod Inc | tratamento de distúrbios psicóticos e depressivos |
| BRPI0410419A (pt) * | 2003-05-16 | 2006-05-30 | Pfizer Prod Inc | tratamento para a ansiedade com ziprasidona |
| DE10337184A1 (de) * | 2003-08-13 | 2005-03-10 | Gruenenthal Gmbh | Substituierte 3-Pyrrolidin-Indol-Derivate |
| WO2005016913A1 (en) * | 2003-08-19 | 2005-02-24 | Pfizer Japan, Inc. | Tetrahydroisoquinoline or isochroman compounds as orl-1 receptor ligands for the treatment of pain and cns disorders |
| GT200500063A (es) * | 2004-04-01 | 2005-10-14 | Metodo para tratar la esquizofrenia y/o anormalidades glucoregulatorias | |
| CA2562399A1 (en) * | 2004-04-08 | 2005-10-20 | Topotarget A/S | Diphenyl - indol-2-on compounds and their use in the treatment of cancer |
| JP2007537235A (ja) * | 2004-05-14 | 2007-12-20 | ファイザー・プロダクツ・インク | 異常細胞増殖の治療用ピリミジン誘導体 |
| MY144968A (en) * | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| AR053710A1 (es) * | 2005-04-11 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos espiroheterociclicos y sus usos como agentes terapeuticos |
| AR056317A1 (es) * | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| AR053713A1 (es) * | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
| CN101166722A (zh) * | 2005-04-29 | 2008-04-23 | 惠氏公司 | 制备3,3-二取代的羟吲哚和硫代羟吲哚的方法 |
| EP1888581A2 (en) * | 2005-05-16 | 2008-02-20 | Gilead Sciences, Inc. | Hiv-integrase inhibitor compounds |
| MX2008002733A (es) * | 2005-09-01 | 2008-03-26 | Hoffmann La Roche | Diaminopirimidinas como moduladores p2x3 y p2x2/3. |
| JP2010522690A (ja) * | 2006-10-12 | 2010-07-08 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 三環式スピロオキシインドール誘導体および治療薬としてのその使用 |
| MX2009003876A (es) * | 2006-10-12 | 2009-05-11 | Xenon Pharmaceuticals Inc | Uso de compuestos de espiro-oxindol como agentes terapeuticos. |
| WO2010045197A1 (en) * | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals, Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| PT2350090E (pt) * | 2008-10-17 | 2015-11-13 | Xenon Pharmaceuticals Inc | Composto espiro-oxindol e suas utilizações como agentes terapêuticos |
| AR077252A1 (es) * | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| PE20121350A1 (es) * | 2009-10-14 | 2012-10-20 | Xenon Pharmaceuticals Inc | Metodos sinteticos para compuestos espiro-oxoindol |
| US20110086899A1 (en) * | 2009-10-14 | 2011-04-14 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
-
2007
- 2007-10-12 MX MX2009003875A patent/MX2009003875A/es not_active Application Discontinuation
- 2007-10-12 EP EP07844225A patent/EP2076514A1/en not_active Withdrawn
- 2007-10-12 CA CA002666143A patent/CA2666143A1/en not_active Abandoned
- 2007-10-12 CL CL200702953A patent/CL2007002953A1/es unknown
- 2007-10-12 TW TW096138359A patent/TW200825091A/zh unknown
- 2007-10-12 JP JP2009532605A patent/JP2010506853A/ja not_active Withdrawn
- 2007-10-12 AU AU2007307638A patent/AU2007307638A1/en not_active Abandoned
- 2007-10-12 RU RU2009117605/04A patent/RU2009117605A/ru not_active Application Discontinuation
- 2007-10-12 AR ARP070104539A patent/AR063278A1/es unknown
- 2007-10-12 US US12/445,270 patent/US20110294842A9/en not_active Abandoned
- 2007-10-12 BR BRPI0719857-4A patent/BRPI0719857A2/pt not_active IP Right Cessation
- 2007-10-12 WO PCT/US2007/081244 patent/WO2008046049A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010506853A5 (enExample) | ||
| JP2008535916A5 (enExample) | ||
| RU2009117605A (ru) | ПРОИЗВОДНЫЕ СПИРО-(ФУРО[3,2-c]ПИРИДИН-3-3'-ИНДОЛ)-2'(1'H)-ОНА И РОДСТВЕННЫЕ ИМ СОЕДИНЕНИЯ ДЛЯ ЛЕЧЕНИЯ ОПОСРЕДОВАННЫХ НАТРИЕВЫМИ КАНАЛАМИ ЗАБОЛЕВАНИЙ, ТАКИХ КАК БОЛЬ | |
| AU2019283921B2 (en) | Indole carboxamide compounds useful as kinase inhibitors | |
| RU2007141633A (ru) | Спирогетероциклические соединения и их применение в качестве терапевтических средств | |
| CN110891935B (zh) | 双环化合物及其在癌症治疗中的用途 | |
| JP7349359B2 (ja) | 二環式ピリドンラクタム及びその使用方法。 | |
| JP2022548095A (ja) | 接着分解剤及びその使用方法 | |
| EP3337802A1 (en) | Heteroaryl derivatives as parp inhibitors | |
| JP2010506854A5 (enExample) | ||
| CA3082856A1 (en) | Sulphur substituted 3-oxo-2,3-dihydropyridazine-4-carboxamides | |
| TWI805595B (zh) | 二環酮化合物及其使用方法 | |
| AU2017269870A1 (en) | 3-oxo-2,6-diphenyl-2,3-dihydropyridazine-4-carboxamides | |
| JP2014506599A5 (enExample) | ||
| TW202227435A (zh) | 用於治療ｈｂｖ感染或ｈｂｖ誘發的疾病之稠合環嘧啶酮衍生物 | |
| RU2004126671A (ru) | Гетероарилсоединения, полезные в качестве ингибиторов gsk-3 | |
| JP2023509495A (ja) | ＲＯＲγｔ阻害剤、その製造方法及び使用 | |
| RU2011116230A (ru) | Пиразолопиридиновые производные как ингибиторы надфн-оксидазы | |
| RU2003115490A (ru) | Амидные производные в качестве антагонистов nmda рецептора | |
| JP2007521287A5 (enExample) | ||
| AU2015335783B2 (en) | Tricyclic atropisomer compounds | |
| JP2010504352A5 (enExample) | ||
| JP2016517409A5 (enExample) | ||
| KR20170075756A (ko) | 카르바졸 유도체 | |
| CA3082857A1 (en) | 3-oxo-6-heteroaryl-2-phenyl-2,3-dihydropyridazine-4-carboxamides |