CA2577667C - 3-substituted-5- and 6-aminoalkyl indole-2-carboxylic acid amides and related analogs as inhibitors of casein kinase ie - Google Patents
3-substituted-5- and 6-aminoalkyl indole-2-carboxylic acid amides and related analogs as inhibitors of casein kinase ie Download PDFInfo
- Publication number
- CA2577667C CA2577667C CA2577667A CA2577667A CA2577667C CA 2577667 C CA2577667 C CA 2577667C CA 2577667 A CA2577667 A CA 2577667A CA 2577667 A CA2577667 A CA 2577667A CA 2577667 C CA2577667 C CA 2577667C
- Authority
- CA
- Canada
- Prior art keywords
- indole
- carboxylic acid
- phenylsulfanyl
- acid amide
- methyl
- 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.)
- Expired - Fee Related
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- 108010031425 Casein Kinases Proteins 0.000 title claims description 34
- 102000005403 Casein Kinases Human genes 0.000 title claims description 34
- 239000003112 inhibitor Substances 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- 208000019116 sleep disease Diseases 0.000 claims abstract description 25
- 208000019022 Mood disease Diseases 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 102000008122 Casein Kinase I Human genes 0.000 claims abstract description 5
- 108010049812 Casein Kinase I Proteins 0.000 claims abstract description 5
- -1 Cl-C6alkoxycarbonyl Chemical group 0.000 claims description 173
- 125000000623 heterocyclic group Chemical group 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- 230000000694 effects Effects 0.000 claims description 32
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 230000027288 circadian rhythm Effects 0.000 claims description 22
- 208000035475 disorder Diseases 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 208000024714 major depressive disease Diseases 0.000 claims description 18
- 230000005764 inhibitory process Effects 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 208000020401 Depressive disease Diseases 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 208000020925 Bipolar disease Diseases 0.000 claims description 11
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 9
- 208000028683 bipolar I disease Diseases 0.000 claims description 8
- 208000022257 bipolar II disease Diseases 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 229910052736 halogen Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 208000020685 sleep-wake disease Diseases 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- JLYRSHVVQADSID-UHFFFAOYSA-N 3-phenylsulfanyl-5-(propylaminomethyl)-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 JLYRSHVVQADSID-UHFFFAOYSA-N 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- 201000007034 advanced sleep phase syndrome Diseases 0.000 claims description 5
- 230000001668 ameliorated effect Effects 0.000 claims description 5
- 201000001098 delayed sleep phase syndrome Diseases 0.000 claims description 5
- 208000033921 delayed sleep phase type circadian rhythm sleep disease Diseases 0.000 claims description 5
- ZRSYJRIKLSTZMT-UHFFFAOYSA-N 5-(aminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CN)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 ZRSYJRIKLSTZMT-UHFFFAOYSA-N 0.000 claims description 4
- TZYCYPZBYDYRQB-UHFFFAOYSA-N 5-(methylaminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 TZYCYPZBYDYRQB-UHFFFAOYSA-N 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 4
- GXSKHMNBZZVSSQ-UHFFFAOYSA-N tert-butyl n-[(2-carbamoyl-3-phenylsulfanyl-1h-indol-5-yl)methyl]carbamate Chemical compound C12=CC(CNC(=O)OC(C)(C)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 GXSKHMNBZZVSSQ-UHFFFAOYSA-N 0.000 claims description 4
- ZRUUVAXNJWUIJO-UHFFFAOYSA-N 1-methyl-5-(methylaminomethyl)-3-phenylsulfanylindole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2N(C)C(C(N)=O)=C1SC1=CC=CC=C1 ZRUUVAXNJWUIJO-UHFFFAOYSA-N 0.000 claims description 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 3
- PHTVYNGDFBACTF-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfanyl-5-(methylaminomethyl)-1h-indole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC(Cl)=C1 PHTVYNGDFBACTF-UHFFFAOYSA-N 0.000 claims description 3
- OJFWSLXLAIEZSO-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanyl-5-(methylaminomethyl)-1h-indole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC(F)=C1 OJFWSLXLAIEZSO-UHFFFAOYSA-N 0.000 claims description 3
- YUDYVWVBVNISFO-UHFFFAOYSA-N 3-phenylsulfanyl-5-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCN1C1=NC=CC=N1 YUDYVWVBVNISFO-UHFFFAOYSA-N 0.000 claims description 3
- JUQZGNJVJIHARC-UHFFFAOYSA-N 3-phenylsulfanyl-5-[(propan-2-ylamino)methyl]-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(C)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 JUQZGNJVJIHARC-UHFFFAOYSA-N 0.000 claims description 3
- PQWRIVOWPXRRJX-UHFFFAOYSA-N 3-phenylsulfanyl-5-[(quinolin-6-ylamino)methyl]-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(CNC=3C=C4C=CC=NC4=CC=3)C=C2C=1SC1=CC=CC=C1 PQWRIVOWPXRRJX-UHFFFAOYSA-N 0.000 claims description 3
- LRKWJJYDPQPEEQ-UHFFFAOYSA-N 3-phenylsulfanyl-5-[[3-(trifluoromethyl)anilino]methyl]-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CNC1=CC=CC(C(F)(F)F)=C1 LRKWJJYDPQPEEQ-UHFFFAOYSA-N 0.000 claims description 3
- SHKMPRXGCZCJQL-UHFFFAOYSA-N 5-(1,4-diazepan-1-ylmethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCCNCC1 SHKMPRXGCZCJQL-UHFFFAOYSA-N 0.000 claims description 3
- SYZDABMIUZMPPL-UHFFFAOYSA-N 5-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylmethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCC21OCCO2 SYZDABMIUZMPPL-UHFFFAOYSA-N 0.000 claims description 3
- UDUXBKHRALVKNO-UHFFFAOYSA-N 5-(butylaminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 UDUXBKHRALVKNO-UHFFFAOYSA-N 0.000 claims description 3
- HLZRKWABRSXWTB-UHFFFAOYSA-N 5-(ethylaminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 HLZRKWABRSXWTB-UHFFFAOYSA-N 0.000 claims description 3
- XLAUWVOGJHPJML-UHFFFAOYSA-N 5-(morpholin-4-ylmethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCOCC1 XLAUWVOGJHPJML-UHFFFAOYSA-N 0.000 claims description 3
- RYWSGPKTJTWPJH-UHFFFAOYSA-N 5-[(2,3-dihydroxypropylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(CNCC(O)CO)C=C2C=1SC1=CC=CC=C1 RYWSGPKTJTWPJH-UHFFFAOYSA-N 0.000 claims description 3
- LCFUECWRWISTPP-UHFFFAOYSA-N 5-[(2-cyano-4,5-dimethoxyanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC(NCC=2C=C3C(SC=4C=CC=CC=4)=C(C(N)=O)NC3=CC=2)=C1C#N LCFUECWRWISTPP-UHFFFAOYSA-N 0.000 claims description 3
- WWFKUELLAFXIEG-UHFFFAOYSA-N 5-[(2-fluoroanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CNC1=CC=CC=C1F WWFKUELLAFXIEG-UHFFFAOYSA-N 0.000 claims description 3
- LARCNPWNXCRVKY-UHFFFAOYSA-N 5-[(3-carbamoylpiperidin-1-yl)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1C(C(=O)N)CCCN1CC1=CC=C(NC(C(N)=O)=C2SC=3C=CC=CC=3)C2=C1 LARCNPWNXCRVKY-UHFFFAOYSA-N 0.000 claims description 3
- WVKHZVHKRFIYHU-UHFFFAOYSA-N 5-[(3-methoxyanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound COC1=CC=CC(NCC=2C=C3C(SC=4C=CC=CC=4)=C(C(N)=O)NC3=CC=2)=C1 WVKHZVHKRFIYHU-UHFFFAOYSA-N 0.000 claims description 3
- VRUDQDCPQOQGDE-UHFFFAOYSA-N 5-[(4-butylanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=CC(CCCC)=CC=C1NCC1=CC=C(NC(C(N)=O)=C2SC=3C=CC=CC=3)C2=C1 VRUDQDCPQOQGDE-UHFFFAOYSA-N 0.000 claims description 3
- IPEWRCABZMBLLR-UHFFFAOYSA-N 5-[(benzylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CNCC1=CC=CC=C1 IPEWRCABZMBLLR-UHFFFAOYSA-N 0.000 claims description 3
- DAAPUDXKYYZXKS-UHFFFAOYSA-N 5-[(heptylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 DAAPUDXKYYZXKS-UHFFFAOYSA-N 0.000 claims description 3
- OCICEAWBXNDPAL-UHFFFAOYSA-N 5-[(pentylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 OCICEAWBXNDPAL-UHFFFAOYSA-N 0.000 claims description 3
- BBVKPLPOVHBJGO-UHFFFAOYSA-N 5-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(CO)(CO)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 BBVKPLPOVHBJGO-UHFFFAOYSA-N 0.000 claims description 3
- BKPVPPGKGHXIJE-UHFFFAOYSA-N 5-[[4-(3-phenylprop-1-enyl)piperazin-1-yl]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCN1C=CCC1=CC=CC=C1 BKPVPPGKGHXIJE-UHFFFAOYSA-N 0.000 claims description 3
- CWKFMXVKGKBRJP-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCN1C1=CC=C(F)C=C1 CWKFMXVKGKBRJP-UHFFFAOYSA-N 0.000 claims description 3
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- LUMOFRIFMDHOOY-UHFFFAOYSA-N 6-[(2-aminopropanoylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)C)=CC=C2C=1SC1=CC=CC=C1 LUMOFRIFMDHOOY-UHFFFAOYSA-N 0.000 claims description 3
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- RREKJZCVYBLDDA-UHFFFAOYSA-N 6-[[(2-amino-3-methylpentanoyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)C(C)CC)=CC=C2C=1SC1=CC=CC=C1 RREKJZCVYBLDDA-UHFFFAOYSA-N 0.000 claims description 3
- WEQYXTUOZWXXHA-UHFFFAOYSA-N 6-[[(2-amino-3-phenylpropanoyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(N)=O)NC2=CC=1CNC(=O)C(N)CC1=CC=CC=C1 WEQYXTUOZWXXHA-UHFFFAOYSA-N 0.000 claims description 3
- MYTUDELNCGATRF-UHFFFAOYSA-N 6-[[(2-amino-4-methylsulfanylbutanoyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)CCSC)=CC=C2C=1SC1=CC=CC=C1 MYTUDELNCGATRF-UHFFFAOYSA-N 0.000 claims description 3
- AAECZAPATSJXKY-UHFFFAOYSA-N 6-[[(2-aminoacetyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)CN)=CC=C2C=1SC1=CC=CC=C1 AAECZAPATSJXKY-UHFFFAOYSA-N 0.000 claims description 3
- NNXGDKGCTQFQHZ-UHFFFAOYSA-N 6-[[(2-methoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound COC1=CC=CC=C1CNCC1=CC=C(C(SC=2C=CC=CC=2)=C(N2)C(N)=O)C2=C1 NNXGDKGCTQFQHZ-UHFFFAOYSA-N 0.000 claims description 3
- SJZNOQDCSSUVCX-UHFFFAOYSA-N 6-[[(2-methylphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound CC1=CC=CC=C1CNCC1=CC=C(C(SC=2C=CC=CC=2)=C(N2)C(N)=O)C2=C1 SJZNOQDCSSUVCX-UHFFFAOYSA-N 0.000 claims description 3
- MKIJAGJRNHRXFV-UHFFFAOYSA-N 6-[[(3,5-dichloro-2-hydroxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC(Cl)=CC(Cl)=C1O MKIJAGJRNHRXFV-UHFFFAOYSA-N 0.000 claims description 3
- GESOVJVFJICPLO-UHFFFAOYSA-N 6-[[(3-methoxy-4-phenylmethoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1CNCC(C=C1NC=2C(N)=O)=CC=C1C=2SC1=CC=CC=C1 GESOVJVFJICPLO-UHFFFAOYSA-N 0.000 claims description 3
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- YSYBLLPQACHVMA-UHFFFAOYSA-N 6-[[[4-(2-phenylethenyl)phenyl]methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC(C=C1)=CC=C1C=CC1=CC=CC=C1 YSYBLLPQACHVMA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
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- PXMWRAAMGAHXFZ-UHFFFAOYSA-N tert-butyl 1h-1,4-diazepine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CN=CC=CN1 PXMWRAAMGAHXFZ-UHFFFAOYSA-N 0.000 description 1
- HEZMSIJTFGHAKX-UHFFFAOYSA-N tert-butyl 2-(aminomethyl)-1h-indole-6-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=C2C=C(CN)NC2=C1 HEZMSIJTFGHAKX-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- USPJCQGOONDJAG-UHFFFAOYSA-N tert-butyl n-[(2-carbamoyl-1h-indol-5-yl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C2NC(C(N)=O)=CC2=C1 USPJCQGOONDJAG-UHFFFAOYSA-N 0.000 description 1
- KPOWODVZVBAOQC-UHFFFAOYSA-N tert-butyl n-[(2-carbamoyl-1h-indol-6-yl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C2C=C(C(N)=O)NC2=C1 KPOWODVZVBAOQC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60338004P | 2004-08-19 | 2004-08-19 | |
| US60/603,380 | 2004-08-19 | ||
| PCT/US2005/029053 WO2006023467A1 (en) | 2004-08-19 | 2005-08-16 | 3-SUBSTITUTED-5- AND 6-AMINOALKYL INDOLE-2-CARBOXYLIC ACID AMIDES AND RELATED ANALOGS AS INHIBITORS OF CASEIN KINASE Iϵ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2577667A1 CA2577667A1 (en) | 2006-03-02 |
| CA2577667C true CA2577667C (en) | 2011-01-04 |
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|---|---|---|---|
| CA2577667A Expired - Fee Related CA2577667C (en) | 2004-08-19 | 2005-08-16 | 3-substituted-5- and 6-aminoalkyl indole-2-carboxylic acid amides and related analogs as inhibitors of casein kinase ie |
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| US (2) | US7629376B2 (enExample) |
| EP (1) | EP1794122B1 (enExample) |
| JP (1) | JP4843608B2 (enExample) |
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| AT (1) | ATE508112T1 (enExample) |
| AU (1) | AU2005277523B2 (enExample) |
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| DE (1) | DE602005027858D1 (enExample) |
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| MA (1) | MA28863B1 (enExample) |
| MX (1) | MX2007001382A (enExample) |
| NO (1) | NO20071466L (enExample) |
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| PE (1) | PE20060498A1 (enExample) |
| RU (1) | RU2369599C2 (enExample) |
| SV (1) | SV2006002192A (enExample) |
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| JP4748823B2 (ja) * | 2009-02-12 | 2011-08-17 | 株式会社ファルマデザイン | カゼインキナーゼ１δ及びカゼインキナーゼ１ε阻害剤 |
| SG175210A1 (en) * | 2009-04-17 | 2011-11-28 | Cylene Pharmaceuticals Inc | Method of treating disorders associated with protein kinase ck2 activity |
| CA2877589C (en) | 2012-06-27 | 2019-11-26 | 4Sc Ag | Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders |
| JP2021511364A (ja) | 2018-01-29 | 2021-05-06 | カディラ ヘルスケア リミティド | 抗菌剤として有用な複素環式化合物 |
| WO2022006377A2 (en) | 2020-07-02 | 2022-01-06 | Mbq Pharma | Heterocyclic inhibitors of rho gtpases for the treatment of disease |
| US12209078B2 (en) | 2021-10-06 | 2025-01-28 | Mbq Pharma | Crystalline forms of carbazole inhibitors of RhoGTPase for the treatment of disease |
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| US5296471A (en) | 1992-12-22 | 1994-03-22 | Glycomed Incorporated | Method for controlling o-desulfation of heparin and compositions produced thereby |
| KR100722176B1 (ko) | 1999-06-08 | 2007-05-29 | 아벤티스 파마슈티칼스 인크. | 일주기 리듬 단백질을 변화시키기 위한 스크리닝 방법 |
| TWI310035B (en) * | 2000-04-28 | 2009-05-21 | Acadia Pharm Inc | Muscarinic agonists |
| CA2494962C (en) * | 2002-08-09 | 2011-06-14 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| CN100439367C (zh) * | 2003-12-11 | 2008-12-03 | 安万特药物公司 | 作为酪蛋白激酶Iε抑制剂的取代的1H-吡咯并[3,2-b、3,2-c和2,3-c]吡啶-2-甲酰胺以及相关类似物 |
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- 2005-08-09 GT GT200500214A patent/GT200500214A/es unknown
- 2005-08-10 SV SV2005002192A patent/SV2006002192A/es active IP Right Grant
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