JP2010506853A5 - - Google Patents
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- 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.)
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- 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 (https=) | 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 (https=) |
| EP (1) | EP2076514A1 (https=) |
| JP (1) | JP2010506853A (https=) |
| AR (1) | AR063278A1 (https=) |
| AU (1) | AU2007307638A1 (https=) |
| BR (1) | BRPI0719857A2 (https=) |
| CA (1) | CA2666143A1 (https=) |
| CL (1) | CL2007002953A1 (https=) |
| MX (1) | MX2009003875A (https=) |
| RU (1) | RU2009117605A (https=) |
| TW (1) | TW200825091A (https=) |
| WO (1) | WO2008046049A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY145694A (en) | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| MY144968A (en) * | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| AR063280A1 (es) * | 2006-10-12 | 2009-01-21 | Xenon Pharmaceuticals Inc | Uso de compuestos de espiro-oxindol como agentes terapeuticos |
| CA2741024A1 (en) * | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
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- 2007-10-12 CA CA002666143A patent/CA2666143A1/en not_active Abandoned
- 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 US US12/445,270 patent/US20110294842A9/en not_active Abandoned
- 2007-10-12 CL CL200702953A patent/CL2007002953A1/es unknown
- 2007-10-12 BR BRPI0719857-4A patent/BRPI0719857A2/pt not_active IP Right Cessation
- 2007-10-12 RU RU2009117605/04A patent/RU2009117605A/ru not_active Application Discontinuation
- 2007-10-12 AU AU2007307638A patent/AU2007307638A1/en not_active Abandoned
- 2007-10-12 WO PCT/US2007/081244 patent/WO2008046049A1/en not_active Ceased
- 2007-10-12 TW TW096138359A patent/TW200825091A/zh unknown
- 2007-10-12 AR ARP070104539A patent/AR063278A1/es unknown
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