CA2640672A1 - 3 -deazapurine derivatives as tlr7 modulators - Google Patents
3 -deazapurine derivatives as tlr7 modulators Download PDFInfo
- Publication number
- CA2640672A1 CA2640672A1 CA002640672A CA2640672A CA2640672A1 CA 2640672 A1 CA2640672 A1 CA 2640672A1 CA 002640672 A CA002640672 A CA 002640672A CA 2640672 A CA2640672 A CA 2640672A CA 2640672 A1 CA2640672 A1 CA 2640672A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkylene
- compound
- formula
- cycloalkyl
- 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.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 claims abstract description 203
- 238000000034 method Methods 0.000 claims abstract description 46
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- 230000009385 viral infection Effects 0.000 claims abstract description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 85
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 84
- -1 tetrahydrofuranoxy Chemical group 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 61
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 239000012453 solvate Substances 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
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- 125000004429 atom Chemical group 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
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- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 9
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
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- 230000009467 reduction Effects 0.000 claims description 7
- GOOQRUJALRQYES-UHFFFAOYSA-N 4-amino-1-benzyl-6-cyclopropyl-3h-imidazo[4,5-c]pyridin-2-one Chemical compound O=C1NC=2C(N)=NC(C3CC3)=CC=2N1CC1=CC=CC=C1 GOOQRUJALRQYES-UHFFFAOYSA-N 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 6
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- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 241000711573 Coronaviridae Species 0.000 claims description 2
- 241000711950 Filoviridae Species 0.000 claims description 2
- 241000710831 Flavivirus Species 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 102000005741 Metalloproteases Human genes 0.000 claims description 2
- 108010006035 Metalloproteases Proteins 0.000 claims description 2
- 108060004795 Methyltransferase Proteins 0.000 claims description 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 2
- 241001631646 Papillomaviridae Species 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 102000012479 Serine Proteases Human genes 0.000 claims description 2
- 108010022999 Serine Proteases Proteins 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 241000701161 unidentified adenovirus Species 0.000 claims description 2
- 241001529453 unidentified herpesvirus Species 0.000 claims description 2
- 241001430294 unidentified retrovirus Species 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- YWWWOUJIAZDIRH-UHFFFAOYSA-N 4-amino-1-benzyl-6-(1,3-oxazol-2-yl)-3h-imidazo[4,5-c]pyridin-2-one Chemical compound O=C1NC=2C(N)=NC(C=3OC=CN=3)=CC=2N1CC1=CC=CC=C1 YWWWOUJIAZDIRH-UHFFFAOYSA-N 0.000 claims 1
- 101800000440 Non-structural protein NS3A Proteins 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 230
- 239000000543 intermediate Substances 0.000 abstract description 28
- 102000002689 Toll-like receptor Human genes 0.000 abstract description 9
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- 208000035473 Communicable disease Diseases 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 208000006454 hepatitis Diseases 0.000 abstract 1
- 231100000283 hepatitis Toxicity 0.000 abstract 1
- 230000028993 immune response Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 346
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 216
- 239000007787 solid Substances 0.000 description 189
- 239000000243 solution Substances 0.000 description 160
- 238000005481 NMR spectroscopy Methods 0.000 description 153
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 152
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 150
- 235000019439 ethyl acetate Nutrition 0.000 description 145
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 125
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 71
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
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- 239000002904 solvent Substances 0.000 description 62
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- 238000004440 column chromatography Methods 0.000 description 46
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 7
- MITDOYIDRUQMPY-UHFFFAOYSA-N ethyl n-(2-amino-6-bromo-3-nitropyridin-4-yl)-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(Br)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 MITDOYIDRUQMPY-UHFFFAOYSA-N 0.000 description 7
- UFSYMZWYMNKUHM-UHFFFAOYSA-N ethyl n-(2-amino-6-bromo-3-nitropyridin-4-yl)-n-benzylcarbamate Chemical compound C=1C(Br)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 UFSYMZWYMNKUHM-UHFFFAOYSA-N 0.000 description 7
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 7
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- JVFDPSSRCVBVIR-UHFFFAOYSA-N ethyl 4-ethyl-1,3-oxazole-5-carboxylate 4-ethyl-1,3-oxazole-5-carboxylic acid Chemical compound C(C)OC(=O)C1=C(N=CO1)CC.C(C)C=1N=COC1C(=O)O JVFDPSSRCVBVIR-UHFFFAOYSA-N 0.000 description 1
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- VMCGGJYUSVWETI-UHFFFAOYSA-N ethyl 5-propan-2-yl-1,3-oxazole-4-carboxylate 5-propan-2-yl-1,3-oxazole Chemical compound C(C)OC(=O)C=1N=COC1C(C)C.C(C)(C)C1=CN=CO1 VMCGGJYUSVWETI-UHFFFAOYSA-N 0.000 description 1
- OWXYPMFXNHHLKE-UHFFFAOYSA-N ethyl 6-cyclopropyl-4-hydroxy-2-oxo-1h-pyridine-3-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=C(O)C=C1C1CC1 OWXYPMFXNHHLKE-UHFFFAOYSA-N 0.000 description 1
- CPGWYUDAERZMHM-UHFFFAOYSA-N ethyl n-(2,6-dibromo-3-nitropyridin-4-yl)-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(Br)=NC(Br)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 CPGWYUDAERZMHM-UHFFFAOYSA-N 0.000 description 1
- LWGVDCVEVOEFBR-UHFFFAOYSA-N ethyl n-(2,6-dibromo-3-nitropyridin-4-yl)-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]carbamate Chemical compound C=1C(Br)=NC(Br)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C(F)(F)F)N=C1 LWGVDCVEVOEFBR-UHFFFAOYSA-N 0.000 description 1
- KFATWOQNHFAQHS-UHFFFAOYSA-N ethyl n-(2,6-dichloro-3-nitropyridin-4-yl)carbamate Chemical compound CCOC(=O)NC1=CC(Cl)=NC(Cl)=C1[N+]([O-])=O KFATWOQNHFAQHS-UHFFFAOYSA-N 0.000 description 1
- DPQMBOXFXFUXBG-UHFFFAOYSA-N ethyl n-(2-amino-6-methylsulfanyl-3-nitropyridin-4-yl)-n-benzylcarbamate Chemical compound C=1C(SC)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 DPQMBOXFXFUXBG-UHFFFAOYSA-N 0.000 description 1
- IVFPNSHMAYYVDT-UHFFFAOYSA-N ethyl n-[(3-cyanophenyl)methyl]-n-(2,6-dibromo-3-nitropyridin-4-yl)carbamate Chemical compound C=1C(Br)=NC(Br)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC(C#N)=C1 IVFPNSHMAYYVDT-UHFFFAOYSA-N 0.000 description 1
- CYMGBQHHDKDEAI-UHFFFAOYSA-N ethyl n-[2-(benzylamino)-3-nitro-6-(trifluoromethyl)pyridin-4-yl]carbamate Chemical compound CCOC(=O)NC1=CC(C(F)(F)F)=NC(NCC=2C=CC=CC=2)=C1[N+]([O-])=O CYMGBQHHDKDEAI-UHFFFAOYSA-N 0.000 description 1
- DIHIMZYEVAEPGN-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(1,3-oxazol-2-yl)pyridin-4-yl]-n-[(3-cyanophenyl)methyl]carbamate Chemical compound C=1C(C=2OC=CN=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC(C#N)=C1 DIHIMZYEVAEPGN-UHFFFAOYSA-N 0.000 description 1
- HOSZSKAPLVHWNF-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(1,3-thiazol-2-yl)pyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C=2SC=CN=2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 HOSZSKAPLVHWNF-UHFFFAOYSA-N 0.000 description 1
- LEBOMZHLLLYYKS-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(propylamino)pyridin-4-yl]-n-benzylcarbamate Chemical compound NC1=NC(NCCC)=CC(N(CC=2C=CC=CC=2)C(=O)OCC)=C1[N+]([O-])=O LEBOMZHLLLYYKS-UHFFFAOYSA-N 0.000 description 1
- AWDYXSREPLLVRG-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(triazol-1-yl)pyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=NC=C2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 AWDYXSREPLLVRG-UHFFFAOYSA-N 0.000 description 1
- PQVLSOPBGACXEF-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(triazol-2-yl)pyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(N2N=CC=N2)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 PQVLSOPBGACXEF-UHFFFAOYSA-N 0.000 description 1
- FKPNCHRHFMAFFO-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(trifluoromethyl)pyridin-4-yl]-n-[(6-methylpyridin-3-yl)methyl]carbamate Chemical compound C=1C(C(F)(F)F)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=C(C)N=C1 FKPNCHRHFMAFFO-UHFFFAOYSA-N 0.000 description 1
- CKYRAMREDLSSRT-UHFFFAOYSA-N ethyl n-[2-amino-3-nitro-6-(trifluoromethyl)pyridin-4-yl]-n-benzylcarbamate Chemical compound C=1C(C(F)(F)F)=NC(N)=C([N+]([O-])=O)C=1N(C(=O)OCC)CC1=CC=CC=C1 CKYRAMREDLSSRT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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| PCT/IB2007/000368 WO2007093901A1 (en) | 2006-02-17 | 2007-02-05 | 3 -deazapurine derivatives as tlr7 modulators |
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| US9040556B2 (en) | 2007-03-20 | 2015-05-26 | Curis, Inc. | Fused amino pyridine as HSP90 inhibitors |
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| US9040556B2 (en) | 2007-03-20 | 2015-05-26 | Curis, Inc. | Fused amino pyridine as HSP90 inhibitors |
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| AR059481A1 (es) | 2008-04-09 |
| KR20080085232A (ko) | 2008-09-23 |
| AU2007216247A1 (en) | 2007-08-23 |
| BRPI0707945A2 (pt) | 2011-05-17 |
| EP1987030A1 (en) | 2008-11-05 |
| US7691877B2 (en) | 2010-04-06 |
| NL2000480A1 (nl) | 2007-08-20 |
| PE20070983A1 (es) | 2007-10-24 |
| IL193173A0 (en) | 2009-02-11 |
| EP1987030B1 (en) | 2011-11-09 |
| UY30169A1 (es) | 2007-09-28 |
| WO2007093901A1 (en) | 2007-08-23 |
| JP2009528989A (ja) | 2009-08-13 |
| MX2008010611A (es) | 2008-11-12 |
| TW200800995A (en) | 2008-01-01 |
| ATE532784T1 (de) | 2011-11-15 |
| US20070197478A1 (en) | 2007-08-23 |
| ES2374455T3 (es) | 2012-02-16 |
| NL2000480C2 (nl) | 2012-09-17 |
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