JP2005511745A5 - - Google Patents
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- JP2005511745A5 JP2005511745A5 JP2003551142A JP2003551142A JP2005511745A5 JP 2005511745 A5 JP2005511745 A5 JP 2005511745A5 JP 2003551142 A JP2003551142 A JP 2003551142A JP 2003551142 A JP2003551142 A JP 2003551142A JP 2005511745 A5 JP2005511745 A5 JP 2005511745A5
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- JP
- Japan
- Prior art keywords
- imidazo
- pyridin
- amino
- ethoxymethyl
- alkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 37
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- -1 pyridin-1-yl Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- KJMFNFSIRKCPQO-UHFFFAOYSA-N 1-(2-aminoethyl)-2,6,7-trimethylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=C(C)C(C)=C2N(CCN)C(C)=NC2=C1N KJMFNFSIRKCPQO-UHFFFAOYSA-N 0.000 claims 1
- HOIOTYDCACFHCS-UHFFFAOYSA-N 1-(3-aminopropyl)-2,6,7-trimethylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=C(C)C(C)=C2N(CCCN)C(C)=NC2=C1N HOIOTYDCACFHCS-UHFFFAOYSA-N 0.000 claims 1
- VWHSOIVJZPDJKP-UHFFFAOYSA-N 1-(3-aminopropyl)-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=C(C)C(C)=C2N(CCCN)C(COCC)=NC2=C1N VWHSOIVJZPDJKP-UHFFFAOYSA-N 0.000 claims 1
- GWYPKAGIUPUIDF-UHFFFAOYSA-N 1-(4-aminobutyl)-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=C(C)C=C2N(CCCCN)C(COCC)=NC2=C1N GWYPKAGIUPUIDF-UHFFFAOYSA-N 0.000 claims 1
- CSMNYKIISWAVIS-UHFFFAOYSA-N 1-(4-aminobutyl)-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=CC(C)=C2N(CCCCN)C(COCC)=NC2=C1N CSMNYKIISWAVIS-UHFFFAOYSA-N 0.000 claims 1
- AXHSJWPORFKKRH-UHFFFAOYSA-N 1-(4-aminobutyl)-6,7-dimethylimidazo[4,5-c]pyridin-4-amine Chemical compound CC1=NC(N)=C2N=CN(CCCCN)C2=C1C AXHSJWPORFKKRH-UHFFFAOYSA-N 0.000 claims 1
- VGNKJMYCVGKMLK-UHFFFAOYSA-N 1-[2-(1-benzylpiperidin-4-yl)ethyl]-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1CC1=CC=CC=C1 VGNKJMYCVGKMLK-UHFFFAOYSA-N 0.000 claims 1
- JXMILQKKROYKJK-UHFFFAOYSA-N 1-[4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-2-methylpropan-1-one Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCN(C(=O)C(C)C)CC1 JXMILQKKROYKJK-UHFFFAOYSA-N 0.000 claims 1
- SXWSOTALVGQCCB-UHFFFAOYSA-N 1-[4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-2-phenylethanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)CC1=CC=CC=C1 SXWSOTALVGQCCB-UHFFFAOYSA-N 0.000 claims 1
- ZKSPOAXBKFOBTE-UHFFFAOYSA-N 1-[4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]pentan-1-one Chemical compound C1CN(C(=O)CCCC)CCC1CCN1C2=C(C)C(C)=NC(N)=C2N=C1COCC ZKSPOAXBKFOBTE-UHFFFAOYSA-N 0.000 claims 1
- LUTPLMJKWFCXMH-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCNCC1 LUTPLMJKWFCXMH-UHFFFAOYSA-N 0.000 claims 1
- BMPSRYJHZRZCOJ-UHFFFAOYSA-N 3-[4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidine-1-carbonyl]benzonitrile Chemical class CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1=CC=CC(C#N)=C1 BMPSRYJHZRZCOJ-UHFFFAOYSA-N 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- YDUBEYPVBXEWHN-UHFFFAOYSA-N [2-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethylamino]-2-oxoethyl] acetate Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)COC(=O)C)C(C)=NC2=C1N YDUBEYPVBXEWHN-UHFFFAOYSA-N 0.000 claims 1
- MSNHPKUKSSYIAP-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical class CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1=CC=C(F)C=C1 MSNHPKUKSSYIAP-UHFFFAOYSA-N 0.000 claims 1
- PWNUKFSQHYMANS-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-(6-chloropyridin-3-yl)methanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1=CC=C(Cl)N=C1 PWNUKFSQHYMANS-UHFFFAOYSA-N 0.000 claims 1
- HDWCCVFXDJYMJD-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1=CC=CC(C(F)(F)F)=C1 HDWCCVFXDJYMJD-UHFFFAOYSA-N 0.000 claims 1
- GOQVFTVKKQMNFZ-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 GOQVFTVKKQMNFZ-UHFFFAOYSA-N 0.000 claims 1
- XYEHTAPZOPTPPV-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-cyclohexylmethanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1CCCCC1 XYEHTAPZOPTPPV-UHFFFAOYSA-N 0.000 claims 1
- AGXLGCNKEUHLAC-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-cyclopropylmethanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1CC1 AGXLGCNKEUHLAC-UHFFFAOYSA-N 0.000 claims 1
- CNWUMGOQEPLGAQ-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-naphthalen-2-ylmethanone Chemical compound C1=CC=CC2=CC(C(=O)N3CCC(CC3)CCN3C4=C(C)C(C)=NC(N)=C4N=C3COCC)=CC=C21 CNWUMGOQEPLGAQ-UHFFFAOYSA-N 0.000 claims 1
- RSZTXMIGEHASAG-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-phenylmethanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)C1=CC=CC=C1 RSZTXMIGEHASAG-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- TYJARRZPGBOQSQ-UHFFFAOYSA-N methyl 6-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butylamino]-6-oxohexanoate Chemical compound N1=CC(C)=C2N(CCCCNC(=O)CCCCC(=O)OC)C(COCC)=NC2=C1N TYJARRZPGBOQSQ-UHFFFAOYSA-N 0.000 claims 1
- YXOZAXVENFQQNK-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-yl]acetamide Chemical compound N1=C(C)C(C)=C2N(CC(C)(C)NC(C)=O)C(COCC)=NC2=C1N YXOZAXVENFQQNK-UHFFFAOYSA-N 0.000 claims 1
- UTHXETHHWUBQRB-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-yl]benzamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CC(C)(C)NC(=O)C1=CC=CC=C1 UTHXETHHWUBQRB-UHFFFAOYSA-N 0.000 claims 1
- HONKLVLDAGJVAW-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-1,3-benzodioxole-5-carboxamide Chemical compound C1=C2OCOC2=CC(C(=O)NCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 HONKLVLDAGJVAW-UHFFFAOYSA-N 0.000 claims 1
- RFMUPRLKVKMXMN-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)C(C)C)C(C)=NC2=C1N RFMUPRLKVKMXMN-UHFFFAOYSA-N 0.000 claims 1
- CRSOSYXGWAAFFB-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylacetamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)CC1=CC=CC=C1 CRSOSYXGWAAFFB-UHFFFAOYSA-N 0.000 claims 1
- YYWOUYXZKHBWLH-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-2-thiophen-2-ylacetamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)CC1=CC=CS1 YYWOUYXZKHBWLH-UHFFFAOYSA-N 0.000 claims 1
- BZMNGSSWAOYBDM-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyanobenzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1=CC=CC(C#N)=C1 BZMNGSSWAOYBDM-UHFFFAOYSA-N 0.000 claims 1
- JNKOPVXMVLFKLX-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 JNKOPVXMVLFKLX-UHFFFAOYSA-N 0.000 claims 1
- BSAPKIFVIUFOPY-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylpropanamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)CCC1=CC=CC=C1 BSAPKIFVIUFOPY-UHFFFAOYSA-N 0.000 claims 1
- GMDVNTGCRYWOJE-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-cyanobenzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1=CC=C(C#N)C=C1 GMDVNTGCRYWOJE-UHFFFAOYSA-N 0.000 claims 1
- TYQIABKTIFCYBZ-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-fluorobenzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1=CC=C(F)C=C1 TYQIABKTIFCYBZ-UHFFFAOYSA-N 0.000 claims 1
- LQZHSYWMTYRSMK-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C LQZHSYWMTYRSMK-UHFFFAOYSA-N 0.000 claims 1
- UGCXFNBFAWTJEU-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-6-chloropyridine-3-carboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1=CC=C(Cl)N=C1 UGCXFNBFAWTJEU-UHFFFAOYSA-N 0.000 claims 1
- XLTORJIKKJGORG-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]acetamide Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)C)C(C)=NC2=C1N XLTORJIKKJGORG-UHFFFAOYSA-N 0.000 claims 1
- SNEZVZNGUZSPLQ-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]adamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C SNEZVZNGUZSPLQ-UHFFFAOYSA-N 0.000 claims 1
- NYTBHSKUIGYFCP-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]benzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1=CC=CC=C1 NYTBHSKUIGYFCP-UHFFFAOYSA-N 0.000 claims 1
- HQTNKAVVWLCHKL-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]cyclohexanecarboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1CCCCC1 HQTNKAVVWLCHKL-UHFFFAOYSA-N 0.000 claims 1
- NXEKGGRMBNEKIN-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]cyclopropanecarboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)C1CC1 NXEKGGRMBNEKIN-UHFFFAOYSA-N 0.000 claims 1
- UPPNIPMWBRKPON-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)NCCN3C4=C(C)C(C)=NC(N)=C4N=C3C)=CC=C21 UPPNIPMWBRKPON-UHFFFAOYSA-N 0.000 claims 1
- NGLNXYFPLNZBRM-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]pentanamide Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)CCCC)C(C)=NC2=C1N NGLNXYFPLNZBRM-UHFFFAOYSA-N 0.000 claims 1
- CNRYDWOIFDSGOW-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-2-methylpropanamide Chemical compound N1=C(C)C(C)=C2N(CCCNC(=O)C(C)C)C(C)=NC2=C1N CNRYDWOIFDSGOW-UHFFFAOYSA-N 0.000 claims 1
- QOKYOKCSUFCBIN-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-2-phenylacetamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)CC1=CC=CC=C1 QOKYOKCSUFCBIN-UHFFFAOYSA-N 0.000 claims 1
- WRQOPRPNSCKBNR-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-2-thiophen-2-ylacetamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)CC1=CC=CS1 WRQOPRPNSCKBNR-UHFFFAOYSA-N 0.000 claims 1
- IQNUKYBJDJJESF-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-cyanobenzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)C1=CC=CC(C#N)=C1 IQNUKYBJDJJESF-UHFFFAOYSA-N 0.000 claims 1
- QAGFDPDMLVQCCM-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 QAGFDPDMLVQCCM-UHFFFAOYSA-N 0.000 claims 1
- KSTXWINOVGTYQM-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylpropanamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)CCC1=CC=CC=C1 KSTXWINOVGTYQM-UHFFFAOYSA-N 0.000 claims 1
- PCRBQWKUAWPBJH-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-4-cyanobenzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)C1=CC=C(C#N)C=C1 PCRBQWKUAWPBJH-UHFFFAOYSA-N 0.000 claims 1
- PCPZBZVPZPXYDT-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-4-fluorobenzamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)C1=CC=C(F)C=C1 PCPZBZVPZPXYDT-UHFFFAOYSA-N 0.000 claims 1
- OILLMQGMZMHYRQ-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCCCN1C2=C(C)C(C)=NC(N)=C2N=C1C OILLMQGMZMHYRQ-UHFFFAOYSA-N 0.000 claims 1
- QXOVPQQMEWMKOT-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-6-chloropyridine-3-carboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)C1=CC=C(Cl)N=C1 QXOVPQQMEWMKOT-UHFFFAOYSA-N 0.000 claims 1
- TYWOWQTYHNBWAT-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]acetamide Chemical compound N1=C(C)C(C)=C2N(CCCNC(=O)C)C(C)=NC2=C1N TYWOWQTYHNBWAT-UHFFFAOYSA-N 0.000 claims 1
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| US10/016,073 US20020107262A1 (en) | 2000-12-08 | 2001-12-06 | Substituted imidazopyridines |
| PCT/US2002/018282 WO2003050118A1 (en) | 2001-12-06 | 2002-06-07 | Amide substituted imidazopyridines |
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| JP2005511745A JP2005511745A (ja) | 2005-04-28 |
| JP2005511745A5 true JP2005511745A5 (enExample) | 2006-01-05 |
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| KR (3) | KR20040105695A (enExample) |
| CN (4) | CN101220028A (enExample) |
| AU (3) | AU2002315006B2 (enExample) |
| BR (3) | BR0214749A (enExample) |
| CA (3) | CA2468164A1 (enExample) |
| HR (3) | HRP20040504A2 (enExample) |
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| MX (3) | MXPA04005412A (enExample) |
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| PL (3) | PL370702A1 (enExample) |
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| UA (3) | UA77711C2 (enExample) |
| WO (3) | WO2003050119A2 (enExample) |
| ZA (3) | ZA200405336B (enExample) |
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| CA2540598C (en) | 2003-10-03 | 2013-09-24 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| EP1678137A1 (en) * | 2003-10-15 | 2006-07-12 | Chiron Corporation | Compositions and methods for viral inhibition |
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| EP1685129A4 (en) * | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
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| JP2007512349A (ja) * | 2003-11-25 | 2007-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミンおよびオキシム置換した、イミダゾキノリン、イミダゾピリジン、およびイミダゾナフチリジン |
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| US20080149123A1 (en) * | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
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| CN101239978A (zh) * | 2008-03-05 | 2008-08-13 | 南方医科大学 | 一种咪唑并吡啶类化合物 |
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| US8802666B2 (en) * | 2009-12-21 | 2014-08-12 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Inhibitors of cyclophilins and uses thereof |
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| EP3366311B1 (en) | 2011-06-03 | 2020-02-26 | 3M Innovative Properties Co. | Hydrazino-1h-imidazoquinolin-4-amines and conjugates made therefrom |
| WO2015023958A1 (en) * | 2013-08-15 | 2015-02-19 | The University Of Kansas | Toll-like receptor agonists |
| ES2995737T3 (en) | 2015-01-06 | 2025-02-11 | Arena Pharm Inc | Compound for use in treating conditions related to the s1p1 receptor |
| MA42807A (fr) | 2015-06-22 | 2018-07-25 | Arena Pharm Inc | Sel l-arginine cristallin d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclo-penta[b]indol-3-yl)acétique (composé 1) pour une utilisation dans des troubles associés au récepteur de s1p1 |
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| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| CA3086439A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| EP3801459B1 (en) | 2018-06-06 | 2024-08-07 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0708772B1 (en) * | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | IMIDAZO [4,5-c]PYRIDIN-4-AMINES |
| US6039969A (en) * | 1996-10-25 | 2000-03-21 | 3M Innovative Properties Company | Immune response modifier compounds for treatment of TH2 mediated and related diseases |
| US6541485B1 (en) * | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6376669B1 (en) * | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| UA74593C2 (en) * | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
-
2001
- 2001-12-06 US US10/016,073 patent/US20020107262A1/en not_active Abandoned
-
2002
- 2002-06-07 CN CNA2008100030374A patent/CN101220028A/zh active Pending
- 2002-06-07 RU RU2004117161/04A patent/RU2004117161A/ru not_active Application Discontinuation
- 2002-06-07 MX MXPA04005412A patent/MXPA04005412A/es not_active Application Discontinuation
- 2002-06-07 CA CA002468164A patent/CA2468164A1/en not_active Abandoned
- 2002-06-07 HR HRP20040504 patent/HRP20040504A2/hr not_active Application Discontinuation
- 2002-06-07 JP JP2003551141A patent/JP2005513052A/ja active Pending
- 2002-06-07 AU AU2002315006A patent/AU2002315006B2/en not_active Expired - Fee Related
- 2002-06-07 NZ NZ532926A patent/NZ532926A/en unknown
- 2002-06-07 IL IL16194502A patent/IL161945A0/xx unknown
- 2002-06-07 EP EP02739783A patent/EP1453829A1/en not_active Withdrawn
- 2002-06-07 JP JP2003551143A patent/JP2005511746A/ja active Pending
- 2002-06-07 PL PL02370702A patent/PL370702A1/xx not_active Application Discontinuation
- 2002-06-07 EP EP02744260A patent/EP1451187A1/en not_active Withdrawn
- 2002-06-07 IL IL16178702A patent/IL161787A0/xx unknown
- 2002-06-07 PL PL02374260A patent/PL374260A1/xx not_active Application Discontinuation
- 2002-06-07 CA CA002468174A patent/CA2468174A1/en not_active Abandoned
- 2002-06-07 CA CA002468659A patent/CA2468659A1/en not_active Abandoned
- 2002-06-07 WO PCT/US2002/018284 patent/WO2003050119A2/en not_active Ceased
- 2002-06-07 EP EP02741939A patent/EP1451186A2/en not_active Withdrawn
- 2002-06-07 BR BR0214749-1A patent/BR0214749A/pt not_active IP Right Cessation
- 2002-06-07 HR HRP20040506 patent/HRP20040506A2/hr not_active Application Discontinuation
- 2002-06-07 PL PL02370738A patent/PL370738A1/xx not_active Application Discontinuation
- 2002-06-07 KR KR10-2004-7008676A patent/KR20040105695A/ko not_active Ceased
- 2002-06-07 RU RU2004117156/04A patent/RU2004117156A/ru not_active Application Discontinuation
- 2002-06-07 NZ NZ532927A patent/NZ532927A/en unknown
- 2002-06-07 NZ NZ532770A patent/NZ532770A/en unknown
- 2002-06-07 CN CNB028242858A patent/CN100402528C/zh not_active Expired - Fee Related
- 2002-06-07 AU AU2002345615A patent/AU2002345615B2/en not_active Expired - Fee Related
- 2002-06-07 RU RU2004117159/04A patent/RU2004117159A/ru not_active Application Discontinuation
- 2002-06-07 BR BR0214999-0A patent/BR0214999A/pt not_active IP Right Cessation
- 2002-06-07 HR HRP20040503 patent/HRP20040503A2/hr not_active Application Discontinuation
- 2002-06-07 AU AU2002312414A patent/AU2002312414B2/en not_active Expired - Fee Related
- 2002-06-07 JP JP2003551142A patent/JP2005511745A/ja active Pending
- 2002-06-07 WO PCT/US2002/018220 patent/WO2003050117A1/en not_active Ceased
- 2002-06-07 MX MXPA04005331A patent/MXPA04005331A/es unknown
- 2002-06-07 BR BR0214752-1A patent/BR0214752A/pt not_active IP Right Cessation
- 2002-06-07 CN CNB028242874A patent/CN100387597C/zh not_active Expired - Fee Related
- 2002-06-07 WO PCT/US2002/018282 patent/WO2003050118A1/en not_active Ceased
- 2002-06-07 MX MXPA04005363A patent/MXPA04005363A/es unknown
- 2002-06-07 KR KR10-2004-7008644A patent/KR20040105694A/ko not_active Ceased
- 2002-06-07 KR KR10-2004-7008686A patent/KR20040105696A/ko not_active Ceased
- 2002-06-07 CN CNB028242866A patent/CN100372846C/zh not_active Expired - Fee Related
- 2002-06-07 IL IL16194602A patent/IL161946A0/xx unknown
- 2002-07-06 UA UA20040604343A patent/UA77711C2/uk unknown
- 2002-07-06 UA UA20040604342A patent/UA77710C2/uk unknown
- 2002-07-06 UA UA20040604339A patent/UA77709C2/uk unknown
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2004
- 2004-06-22 NO NO20042621A patent/NO20042621L/no not_active Application Discontinuation
- 2004-06-24 NO NO20042661A patent/NO20042661L/no not_active Application Discontinuation
- 2004-06-29 NO NO20042755A patent/NO20042755L/no not_active Application Discontinuation
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- 2004-07-05 ZA ZA200405337A patent/ZA200405337B/en unknown
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