JP4843608B2 - カゼイン・キナーゼIε阻害剤としての3−置換−5−及び6−アミノアルキルインドール−2−カルボン酸アミド及び関連する類似化合物 - Google Patents
カゼイン・キナーゼIε阻害剤としての3−置換−5−及び6−アミノアルキルインドール−2−カルボン酸アミド及び関連する類似化合物 Download PDFInfo
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- JP4843608B2 JP4843608B2 JP2007527928A JP2007527928A JP4843608B2 JP 4843608 B2 JP4843608 B2 JP 4843608B2 JP 2007527928 A JP2007527928 A JP 2007527928A JP 2007527928 A JP2007527928 A JP 2007527928A JP 4843608 B2 JP4843608 B2 JP 4843608B2
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- Prior art keywords
- indole
- phenylsulfanyl
- carboxylic acid
- 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.)
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- 102000005403 Casein Kinases Human genes 0.000 title description 22
- 108010031425 Casein Kinases Proteins 0.000 title description 22
- 239000003112 inhibitor Substances 0.000 title description 14
- -1 His Chemical compound 0.000 claims description 177
- 150000001875 compounds Chemical class 0.000 claims description 163
- 125000000623 heterocyclic group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 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 10
- 239000003937 drug carrier Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 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
- 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
- HORQAWFOJKHFQG-UHFFFAOYSA-N tert-butyl n-[(2-carbamoyl-3-phenylsulfanyl-1h-indol-6-yl)methyl]carbamate Chemical compound NC(=O)C=1NC2=CC(CNC(=O)OC(C)(C)C)=CC=C2C=1SC1=CC=CC=C1 HORQAWFOJKHFQG-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
- KSZFGVPYJPGQDB-UHFFFAOYSA-N 3-amino-4-[(2-carbamoyl-3-phenylsulfanyl-1h-indol-6-yl)methylamino]-4-oxobutanoic acid Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(CC(O)=O)N)=CC=C2C=1SC1=CC=CC=C1 KSZFGVPYJPGQDB-UHFFFAOYSA-N 0.000 claims description 3
- BXJWUHNROITKOB-UHFFFAOYSA-N 3-phenylsulfanyl-5-(piperidin-1-ylmethyl)-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCCCC1 BXJWUHNROITKOB-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
- ZVSMVUSAVZIXCE-UHFFFAOYSA-N 3-phenylsulfanyl-6-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=C(C(F)(F)F)C=C1 ZVSMVUSAVZIXCE-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
- VIQIAMCXYSBYQY-UHFFFAOYSA-N 5-[(1-hydroxypropan-2-ylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(CO)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 VIQIAMCXYSBYQY-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
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- 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
- CCUHUKCNAKYYIH-UHFFFAOYSA-N 5-[[(1-amino-1-oxopropan-2-yl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(C)C(N)=O)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 CCUHUKCNAKYYIH-UHFFFAOYSA-N 0.000 claims description 3
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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Applications Claiming Priority (3)
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| 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 |
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| JP2008510017A JP2008510017A (ja) | 2008-04-03 |
| JP2008510017A5 JP2008510017A5 (enExample) | 2008-09-04 |
| JP4843608B2 true JP4843608B2 (ja) | 2011-12-21 |
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| EP (1) | EP1794122B1 (enExample) |
| JP (1) | JP4843608B2 (enExample) |
| KR (2) | KR20130038409A (enExample) |
| CN (1) | CN101006055B (enExample) |
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| UY (1) | UY29078A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
Citations (2)
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| JP2003501074A (ja) * | 1999-06-08 | 2003-01-14 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 概日リズムタンパク質の変化に関するスクリーニング方法 |
| WO2004014851A2 (en) * | 2002-08-09 | 2004-02-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296471A (en) | 1992-12-22 | 1994-03-22 | Glycomed Incorporated | Method for controlling o-desulfation of heparin and compositions produced thereby |
| TWI310035B (en) * | 2000-04-28 | 2009-05-21 | Acadia Pharm Inc | Muscarinic agonists |
| 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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- 2007-02-13 US US11/674,385 patent/US7629376B2/en not_active Expired - Lifetime
- 2007-03-14 MA MA29757A patent/MA28863B1/fr unknown
- 2007-03-19 NO NO20071466A patent/NO20071466L/no not_active Application Discontinuation
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2008
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003501074A (ja) * | 1999-06-08 | 2003-01-14 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 概日リズムタンパク質の変化に関するスクリーニング方法 |
| WO2004014851A2 (en) * | 2002-08-09 | 2004-02-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
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