JP2008527007A5 - - Google Patents
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- JP2008527007A5 JP2008527007A5 JP2007551462A JP2007551462A JP2008527007A5 JP 2008527007 A5 JP2008527007 A5 JP 2008527007A5 JP 2007551462 A JP2007551462 A JP 2007551462A JP 2007551462 A JP2007551462 A JP 2007551462A JP 2008527007 A5 JP2008527007 A5 JP 2008527007A5
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- JP
- Japan
- Prior art keywords
- ring
- optionally substituted
- aliphatic
- alkyl
- independently
- 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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- 125000001931 aliphatic group Chemical group 0.000 claims description 120
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 150000002431 hydrogen Chemical class 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 32
- 125000004432 carbon atom Chemical group C* 0.000 claims 17
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000003107 substituted aryl group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000006413 ring segment Chemical group 0.000 claims 6
- -1 2-propynyloxy Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 150000003254 radicals Chemical class 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical group C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 2
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical group C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical group C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical group C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- QMWCKDKMPMTTNL-UHFFFAOYSA-N 3-[4-(3-cyano-6-propan-2-ylpyridin-2-yl)oxyphenyl]-n-(2,6-diethylphenyl)propanamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)CCC(C=C1)=CC=C1OC1=NC(C(C)C)=CC=C1C#N QMWCKDKMPMTTNL-UHFFFAOYSA-N 0.000 claims 1
- NOWHPSASVCTOLG-UHFFFAOYSA-N 4-[4-(4,5-dihydro-1,3-thiazol-2-ylamino)phenyl]-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)CCCC(C=C1)=CC=C1NC1=NCCS1 NOWHPSASVCTOLG-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical group C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical group C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical group N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical group C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- DMGXHJDDZDYXKU-UHFFFAOYSA-N n-(3-chloro-2-ethylpyridin-4-yl)-3-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]propanamide Chemical compound CCC1=NC=CC(NC(=O)CCC=2C=CC(OC=3N=CC(=CC=3)C(F)(F)F)=CC=2)=C1Cl DMGXHJDDZDYXKU-UHFFFAOYSA-N 0.000 claims 1
- NXFQMOGTBAJDER-UHFFFAOYSA-N n-(3-chloro-2-ethylpyridin-4-yl)-4-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]butanamide Chemical compound CCC1=NC=CC(NC(=O)CCCC=2C=CC(OC=3N=CC(=CC=3)C(F)(F)F)=CC=2)=C1Cl NXFQMOGTBAJDER-UHFFFAOYSA-N 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical group N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical group N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 102000009929 raf Kinases Human genes 0.000 claims 1
- 108010077182 raf Kinases Proteins 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 150000003852 triazoles Chemical group 0.000 claims 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical group C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64392805P | 2005-01-14 | 2005-01-14 | |
| US71063505P | 2005-08-23 | 2005-08-23 | |
| PCT/US2006/001490 WO2006076706A1 (en) | 2005-01-14 | 2006-01-12 | Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008527007A JP2008527007A (ja) | 2008-07-24 |
| JP2008527007A5 true JP2008527007A5 (https=) | 2009-01-08 |
Family
ID=36177938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007551462A Withdrawn JP2008527007A (ja) | 2005-01-14 | 2006-01-12 | Ｒａｆ−キナーゼ阻害活性を有するシンナミドおよびヒドロシンナミド誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7652041B2 (https=) |
| EP (1) | EP1856053A1 (https=) |
| JP (1) | JP2008527007A (https=) |
| AU (1) | AU2006204724A1 (https=) |
| CA (1) | CA2594860A1 (https=) |
| WO (1) | WO2006076706A1 (https=) |
Families Citing this family (56)
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| US7470787B2 (en) | 2005-07-11 | 2008-12-30 | Aerie Pharmaceuticals, Inc. | Isoquinoline compounds |
| AR057455A1 (es) * | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
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| KR102579582B1 (ko) | 2015-11-17 | 2023-09-15 | 에어리 파마슈티컬즈, 인코포레이티드 | 키나아제 억제제 및 이의 중간체의 제조 방법 |
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- 2006-01-12 AU AU2006204724A patent/AU2006204724A1/en not_active Abandoned
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- 2006-01-12 WO PCT/US2006/001490 patent/WO2006076706A1/en not_active Ceased
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