HRP20000904A2 - Farnesyl protein transferase inhibitors for treating arthropathies - Google Patents
Farnesyl protein transferase inhibitors for treating arthropathies Download PDFInfo
- Publication number
- HRP20000904A2 HRP20000904A2 HR20000904A HRP20000904A HRP20000904A2 HR P20000904 A2 HRP20000904 A2 HR P20000904A2 HR 20000904 A HR20000904 A HR 20000904A HR P20000904 A HRP20000904 A HR P20000904A HR P20000904 A2 HRP20000904 A2 HR P20000904A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- alkyloxy
- amino
- methyl
- hydroxy
- Prior art date
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- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title claims description 20
- 208000012659 Joint disease Diseases 0.000 title claims description 14
- 208000036487 Arthropathies Diseases 0.000 title claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 238
- 239000001257 hydrogen Substances 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 79
- -1 C1-6-alkyloxy Chemical group 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 206010003246 arthritis Diseases 0.000 claims description 32
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
- 125000004951 trihalomethoxy group Chemical group 0.000 claims description 11
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
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- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- PLHJCIYEEKOWNM-UHFFFAOYSA-N 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-UHFFFAOYSA-N 0.000 claims description 4
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- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 3
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 3
- WOYOASASOHZEDR-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-[(4-chlorophenyl)-hydroxy-(3-methylimidazol-4-yl)methyl]-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 WOYOASASOHZEDR-UHFFFAOYSA-N 0.000 claims description 2
- ZMLMGCPNMBRTKN-UHFFFAOYSA-N 6-[(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-ethoxyphenyl)-1-methylquinolin-2-one;hydrate;hydrochloride Chemical compound O.Cl.CCOC1=CC=CC(C=2C3=CC(=CC=C3N(C)C(=O)C=2)C(C=2N(C=NC=2)C)C=2C=CC(Cl)=CC=2)=C1 ZMLMGCPNMBRTKN-UHFFFAOYSA-N 0.000 claims description 2
- QOFQBGVDXIFFKM-UHFFFAOYSA-N 6-[(4-chlorophenyl)-hydroxy-(3-methylimidazol-4-yl)methyl]-4-(3-ethoxyphenyl)-1-methylquinolin-2-one Chemical compound CCOC1=CC=CC(C=2C3=CC(=CC=C3N(C)C(=O)C=2)C(O)(C=2N(C=NC=2)C)C=2C=CC(Cl)=CC=2)=C1 QOFQBGVDXIFFKM-UHFFFAOYSA-N 0.000 claims description 2
- ALKQAQOKGRWMSJ-UHFFFAOYSA-N 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-ethoxyphenyl)-1-methylquinolin-2-one Chemical compound CCOC1=CC=CC(C=2C3=CC(=CC=C3N(C)C(=O)C=2)C(N)(C=2N(C=NC=2)C)C=2C=CC(Cl)=CC=2)=C1 ALKQAQOKGRWMSJ-UHFFFAOYSA-N 0.000 claims description 2
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- 201000005569 Gout Diseases 0.000 claims description 2
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- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- 208000024891 symptom Diseases 0.000 description 7
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- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98202258 | 1998-07-06 | ||
| PCT/EP1999/004546 WO2000001386A1 (en) | 1998-07-06 | 1999-06-30 | Farnesyl protein transferase inhibitors for treating arthropathies |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000904A2 true HRP20000904A2 (en) | 2001-12-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| HR20000904A HRP20000904A2 (en) | 1998-07-06 | 2000-12-28 | Farnesyl protein transferase inhibitors for treating arthropathies |
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| UA (1) | UA64797C2 (xx) |
| WO (1) | WO2000001386A1 (xx) |
| ZA (1) | ZA200100152B (xx) |
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