HRP20130174T1 - Derivati pirimidina za lijeäśenje astme, kopb, alergijskog rinitisa, alergijskog konjuktivitisa, atopijskog dermatitisa, karcinoma, hepatitisa b, hepatitisa c, hiv, hpv, bakterijskih infekcija i dermatoze - Google Patents
Derivati pirimidina za lijeäśenje astme, kopb, alergijskog rinitisa, alergijskog konjuktivitisa, atopijskog dermatitisa, karcinoma, hepatitisa b, hepatitisa c, hiv, hpv, bakterijskih infekcija i dermatoze Download PDFInfo
- Publication number
- HRP20130174T1 HRP20130174T1 HRP20130174AT HRP20130174T HRP20130174T1 HR P20130174 T1 HRP20130174 T1 HR P20130174T1 HR P20130174A T HRP20130174A T HR P20130174AT HR P20130174 T HRP20130174 T HR P20130174T HR P20130174 T1 HRP20130174 T1 HR P20130174T1
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- Croatia
- Prior art keywords
- methyl
- amino
- acetate
- phenyl
- pentylamino
- Prior art date
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- 208000035143 Bacterial infection Diseases 0.000 title claims 3
- 206010010744 Conjunctivitis allergic Diseases 0.000 title claims 3
- 206010012438 Dermatitis atopic Diseases 0.000 title claims 3
- 206010048768 Dermatosis Diseases 0.000 title claims 3
- 206010028980 Neoplasm Diseases 0.000 title claims 3
- 206010039085 Rhinitis allergic Diseases 0.000 title claims 3
- 208000002205 allergic conjunctivitis Diseases 0.000 title claims 3
- 201000010105 allergic rhinitis Diseases 0.000 title claims 3
- 208000006673 asthma Diseases 0.000 title claims 3
- 208000024998 atopic conjunctivitis Diseases 0.000 title claims 3
- 201000008937 atopic dermatitis Diseases 0.000 title claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 title claims 3
- 201000011510 cancer Diseases 0.000 title claims 3
- 208000017520 skin disease Diseases 0.000 title claims 3
- 208000006454 hepatitis Diseases 0.000 title 2
- 231100000283 hepatitis Toxicity 0.000 title 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- -1 cyano, hydroxyl Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- BYZABNXKJHIPDN-UHFFFAOYSA-N 4-(dimethylamino)butyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCCN(C)C)C=C1 BYZABNXKJHIPDN-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 208000022361 Human papillomavirus infectious disease Diseases 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000002672 hepatitis B Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- VYYKPSIXVXRLJH-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OC1CCN(C)CC1 VYYKPSIXVXRLJH-UHFFFAOYSA-N 0.000 claims 1
- VSFWCPUMFWQQEE-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[3-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-4-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OCC2CCN(C)CC2)=CC=C1OC VSFWCPUMFWQQEE-UHFFFAOYSA-N 0.000 claims 1
- TZVVODMWZXRQIJ-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[3-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=CC(CC(=O)OCC2CCN(C)CC2)=C1 TZVVODMWZXRQIJ-UHFFFAOYSA-N 0.000 claims 1
- GBXRUNJEPBUWFV-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]sulfanylphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1SC(C=C1)=CC=C1CC(=O)OCC1CCN(C)CC1 GBXRUNJEPBUWFV-UHFFFAOYSA-N 0.000 claims 1
- JSBYGNLUEWJVOE-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C(=C1)O)=CC=C1CC(=O)OCC1CCN(C)CC1 JSBYGNLUEWJVOE-UHFFFAOYSA-N 0.000 claims 1
- WHHYIHVELBUKCN-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C(=C1)OC)=CC=C1CC(=O)OCC1CCN(C)CC1 WHHYIHVELBUKCN-UHFFFAOYSA-N 0.000 claims 1
- IVBJQWBZUWGOLK-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCC1CCN(C)CC1 IVBJQWBZUWGOLK-UHFFFAOYSA-N 0.000 claims 1
- DKRNYHYMUISKST-NRFANRHFSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC(C(=C1)O)=CC=C1CC(=O)OCC1CCN(C)CC1 DKRNYHYMUISKST-NRFANRHFSA-N 0.000 claims 1
- QAEPBXISIAKTPX-QFIPXVFZSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC(C(=C1)OC)=CC=C1CC(=O)OCC1CCN(C)CC1 QAEPBXISIAKTPX-QFIPXVFZSA-N 0.000 claims 1
- VCCCSRKBSRKXDC-NRFANRHFSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-[[(2s)-2-hydroxybutyl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CC[C@H](O)CNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCC1CCN(C)CC1 VCCCSRKBSRKXDC-NRFANRHFSA-N 0.000 claims 1
- HXYISEZXXYWXGR-QFIPXVFZSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC(C(=C1)F)=CC=C1CC(=O)OCC1CCN(C)CC1 HXYISEZXXYWXGR-QFIPXVFZSA-N 0.000 claims 1
- VYLRUZOQUXMGDS-UHFFFAOYSA-N (1-methylpiperidin-4-yl)methyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCC1CCN(C)CC1 VYLRUZOQUXMGDS-UHFFFAOYSA-N 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- ADDAWDXCBUCWHX-QHCPKHFHSA-N 2-(1-methylpiperidin-4-yl)ethyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC(C(=C1)F)=CC=C1CC(=O)OCCC1CCN(C)CC1 ADDAWDXCBUCWHX-QHCPKHFHSA-N 0.000 claims 1
- KJBVRNQINPTFRU-UHFFFAOYSA-N 2-(1-methylpiperidin-4-yl)ethyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCC1CCN(C)CC1 KJBVRNQINPTFRU-UHFFFAOYSA-N 0.000 claims 1
- JZCKKOIBKLTZBS-UHFFFAOYSA-N 2-(4-methyl-1,3-thiazol-5-yl)ethyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C(=C1)OC)=CC=C1CC(=O)OCCC1=C(C)N=CS1 JZCKKOIBKLTZBS-UHFFFAOYSA-N 0.000 claims 1
- DMNPBOQSEXIFDT-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCN1CCN(C)CC1 DMNPBOQSEXIFDT-UHFFFAOYSA-N 0.000 claims 1
- XPQGDFIMNJFDAE-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCN(C)C)C=C1 XPQGDFIMNJFDAE-UHFFFAOYSA-N 0.000 claims 1
- MCPAXOJAQCOOFP-UHFFFAOYSA-N 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]-6-(1,1-dioxo-1,4-thiazinan-4-yl)hexanoic acid Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(C(CCCCN2CCS(=O)(=O)CC2)C(O)=O)C=C1 MCPAXOJAQCOOFP-UHFFFAOYSA-N 0.000 claims 1
- NODMYIIFUPVNHX-UHFFFAOYSA-N 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetic acid Chemical group CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(O)=O)C=C1 NODMYIIFUPVNHX-UHFFFAOYSA-N 0.000 claims 1
- CTBDABLNTBKPOJ-UHFFFAOYSA-N 2-hydroxyethyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCO)C=C1OC CTBDABLNTBKPOJ-UHFFFAOYSA-N 0.000 claims 1
- WAMNTNBSTRCWKC-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCN1CCOCC1 WAMNTNBSTRCWKC-UHFFFAOYSA-N 0.000 claims 1
- GISXEBIPMHPZOX-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCN1CCN(C)CC1 GISXEBIPMHPZOX-UHFFFAOYSA-N 0.000 claims 1
- FXQAXZWSLMXANH-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCN(C)C)C=C1 FXQAXZWSLMXANH-UHFFFAOYSA-N 0.000 claims 1
- HJEDJKUWIHVYHM-UHFFFAOYSA-N 3-hydroxypropyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCO)C=C1OC HJEDJKUWIHVYHM-UHFFFAOYSA-N 0.000 claims 1
- CRXIWMAAFKVAFF-UHFFFAOYSA-N 3-methylsulfonylpropyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCS(C)(=O)=O)C=C1OC CRXIWMAAFKVAFF-UHFFFAOYSA-N 0.000 claims 1
- LDWIIWMNVKHWOR-UHFFFAOYSA-N 3-morpholin-4-ylpropyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCN1CCOCC1 LDWIIWMNVKHWOR-UHFFFAOYSA-N 0.000 claims 1
- BXLDZNZUCNBWQA-DEOSSOPVSA-N 4-(4-methylpiperazin-1-yl)butyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC(C(=C1)F)=CC=C1CC(=O)OCCCCN1CCN(C)CC1 BXLDZNZUCNBWQA-DEOSSOPVSA-N 0.000 claims 1
- XXCBTNBISJVEMK-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)butyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCCN1CCN(C)CC1 XXCBTNBISJVEMK-UHFFFAOYSA-N 0.000 claims 1
- MNVAEQPGCYDFTH-UHFFFAOYSA-N 4-(dimethylamino)butyl 2-[3-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-4-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OCCCCN(C)C)=CC=C1OC MNVAEQPGCYDFTH-UHFFFAOYSA-N 0.000 claims 1
- LBDLBLLLGLBLIK-UHFFFAOYSA-N 4-(dimethylamino)butyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCCN(C)C)C=C1O LBDLBLLLGLBLIK-UHFFFAOYSA-N 0.000 claims 1
- CGBZYDZVVXAYDB-NRFANRHFSA-N 4-(dimethylamino)butyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCCN(C)C)C=C1 CGBZYDZVVXAYDB-NRFANRHFSA-N 0.000 claims 1
- RZYWNPKBUMWLMZ-NRFANRHFSA-N 4-(dimethylamino)butyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCCN(C)C)C=C1F RZYWNPKBUMWLMZ-NRFANRHFSA-N 0.000 claims 1
- CYJAIFLJNJHVDG-QFIPXVFZSA-N 4-(dimethylamino)butyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCCN(C)C)C=C1 CYJAIFLJNJHVDG-QFIPXVFZSA-N 0.000 claims 1
- DBUUCTYRHBFWBP-UHFFFAOYSA-N 4-[4-(dimethylamino)piperidin-1-yl]butyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C(=C1)OC)=CC=C1CC(=O)OCCCCN1CCC(N(C)C)CC1 DBUUCTYRHBFWBP-UHFFFAOYSA-N 0.000 claims 1
- UXAHLYRNZDNLHI-UHFFFAOYSA-N 4-[4-(dimethylamino)piperidin-1-yl]butyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCCN1CCC(N(C)C)CC1 UXAHLYRNZDNLHI-UHFFFAOYSA-N 0.000 claims 1
- JFUAWXPBHXKZGA-IBGZPJMESA-N 4-fluoro-2-[(4r)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C([C@@](O)(CC=1NC2=CN=CC=C2C=1)C(F)(F)F)C(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-IBGZPJMESA-N 0.000 claims 1
- PSFJKCHBPPPDNC-UHFFFAOYSA-N 4-hydroxybutyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCCCCO)C=C1OC PSFJKCHBPPPDNC-UHFFFAOYSA-N 0.000 claims 1
- QUHBBQJQZFDBSN-UHFFFAOYSA-N 4-morpholin-4-ylbutyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCCN1CCOCC1 QUHBBQJQZFDBSN-UHFFFAOYSA-N 0.000 claims 1
- XSDGRSBYBKKDBX-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutyl 2-[3-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=CC(CC(=O)OCCCCN2CCCC2)=C1 XSDGRSBYBKKDBX-UHFFFAOYSA-N 0.000 claims 1
- WZQIIPKEYHZMNV-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutyl 2-[4-[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]sulfanylphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1SC(C=C1)=CC=C1CC(=O)OCCCCN1CCCC1 WZQIIPKEYHZMNV-UHFFFAOYSA-N 0.000 claims 1
- INPUDRNJVKURSZ-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C(=C1)O)=CC=C1CC(=O)OCCCCN1CCCC1 INPUDRNJVKURSZ-UHFFFAOYSA-N 0.000 claims 1
- GBXARUMXIOCKEG-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C(=C1)OC)=CC=C1CC(=O)OCCCCN1CCCC1 GBXARUMXIOCKEG-UHFFFAOYSA-N 0.000 claims 1
- PMQLPEYHRWYHKP-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCCN1CCCC1 PMQLPEYHRWYHKP-UHFFFAOYSA-N 0.000 claims 1
- TZMUWCRBRBXMRT-QHCPKHFHSA-N 4-pyrrolidin-1-ylbutyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC(C(=C1)O)=CC=C1CC(=O)OCCCCN1CCCC1 TZMUWCRBRBXMRT-QHCPKHFHSA-N 0.000 claims 1
- WDFVFLWNFMKNDS-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCCCCN1CCCC1 WDFVFLWNFMKNDS-UHFFFAOYSA-N 0.000 claims 1
- 101100114469 Arabidopsis thaliana COR27 gene Proteins 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 1
- 102000009410 Chemokine receptor Human genes 0.000 claims 1
- 108050000299 Chemokine receptor Proteins 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 208000027771 Obstructive airways disease Diseases 0.000 claims 1
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- SJUSUUSNSBJWMG-UHFFFAOYSA-N [1-(2-methoxyethyl)piperidin-4-yl]methyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCC1CCN(CCOC)CC1 SJUSUUSNSBJWMG-UHFFFAOYSA-N 0.000 claims 1
- ZIOVBLKANPCWDJ-UHFFFAOYSA-N [3-(dimethylamino)-2,2-dimethylpropyl] 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OCC(C)(C)CN(C)C)C=C1 ZIOVBLKANPCWDJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 claims 1
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940112141 dry powder inhaler Drugs 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- XQWFKHJODHKTFG-SANMLTNESA-N methyl (2s)-1-[2-[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[[3-(2-methoxy-2-oxoethyl)phenyl]methyl]amino]-2-oxoethyl]pyrrolidine-2-carboxylate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1[C@@H](CCC1)C(=O)OC)CC1=CC=CC(CC(=O)OC)=C1 XQWFKHJODHKTFG-SANMLTNESA-N 0.000 claims 1
- LIXABKAVBPBYBQ-UHFFFAOYSA-N methyl 2-[3-[2-[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propylamino]-2-oxoethyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCNC(=O)CC1=CC=CC(CC(=O)OC)=C1 LIXABKAVBPBYBQ-UHFFFAOYSA-N 0.000 claims 1
- RUFSKWZCEBXHCJ-UHFFFAOYSA-N methyl 2-[3-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-4-hydroxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OC)=CC=C1O RUFSKWZCEBXHCJ-UHFFFAOYSA-N 0.000 claims 1
- NDNZWYMPRYTKEJ-UHFFFAOYSA-N methyl 2-[3-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-4-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OC)=CC=C1OC NDNZWYMPRYTKEJ-UHFFFAOYSA-N 0.000 claims 1
- VCVDUUJNDGWZQD-INIZCTEOSA-N methyl 2-[3-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-4-methoxyphenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OC)=CC=C1OC VCVDUUJNDGWZQD-INIZCTEOSA-N 0.000 claims 1
- VFCWXMJIAIXSKI-INIZCTEOSA-N methyl 2-[3-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-4-fluorophenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OC)=CC=C1F VFCWXMJIAIXSKI-INIZCTEOSA-N 0.000 claims 1
- VILWGDTWJBRESJ-UHFFFAOYSA-N methyl 2-[3-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]-4-hydroxyphenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OC)=CC=C1O VILWGDTWJBRESJ-UHFFFAOYSA-N 0.000 claims 1
- RQDKMQLSRZDIQV-UHFFFAOYSA-N methyl 2-[3-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]-4-methoxyphenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC(CC(=O)OC)=CC=C1OC RQDKMQLSRZDIQV-UHFFFAOYSA-N 0.000 claims 1
- NESHMLZUUOVDJG-UHFFFAOYSA-N methyl 2-[3-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=CC(CC(=O)OC)=C1 NESHMLZUUOVDJG-UHFFFAOYSA-N 0.000 claims 1
- KONPVEZKIOABPU-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-(1-methylimidazol-4-yl)sulfonylamino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(S(=O)(=O)C=1N=CN(C)C=1)CC1=CC=CC(CC(=O)OC)=C1 KONPVEZKIOABPU-UHFFFAOYSA-N 0.000 claims 1
- FYRLAQZCQZFTDU-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-(4-hydroxypiperidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1CCC(O)CC1)CC1=CC=CC(CC(=O)OC)=C1 FYRLAQZCQZFTDU-UHFFFAOYSA-N 0.000 claims 1
- VAPAUPMTRQPUOA-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1CCN(C)CC1)CC1=CC=CC(CC(=O)OC)=C1 VAPAUPMTRQPUOA-UHFFFAOYSA-N 0.000 claims 1
- HFPDLDLMCGOPQT-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN(C)C)CC1=CC=CC(CC(=O)OC)=C1 HFPDLDLMCGOPQT-UHFFFAOYSA-N 0.000 claims 1
- ADMVTAYTLGWNMQ-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-[2-hydroxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN(C)CCO)CC1=CC=CC(CC(=O)OC)=C1 ADMVTAYTLGWNMQ-UHFFFAOYSA-N 0.000 claims 1
- NZSFSXGQJZXQJW-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-[4-[3-(dimethylamino)propyl]piperazin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1CCN(CCCN(C)C)CC1)CC1=CC=CC(CC(=O)OC)=C1 NZSFSXGQJZXQJW-UHFFFAOYSA-N 0.000 claims 1
- RNGPSUUCDVRBHQ-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[3-(dimethylamino)propanoyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CCN(C)C)CC1=CC=CC(CC(=O)OC)=C1 RNGPSUUCDVRBHQ-UHFFFAOYSA-N 0.000 claims 1
- VUQWLQBFZLXNLL-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[4-(dimethylamino)butanoyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CCCN(C)C)CC1=CC=CC(CC(=O)OC)=C1 VUQWLQBFZLXNLL-UHFFFAOYSA-N 0.000 claims 1
- HIMJRJGIVBTRJC-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-methylsulfonylamino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(S(C)(=O)=O)CC1=CC=CC(CC(=O)OC)=C1 HIMJRJGIVBTRJC-UHFFFAOYSA-N 0.000 claims 1
- FZEQIZYCEYZRRR-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propylamino]methyl]phenoxy]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCNCC1=CC=CC(OCC(=O)OC)=C1 FZEQIZYCEYZRRR-UHFFFAOYSA-N 0.000 claims 1
- OFMDRXOBFRPNIK-UHFFFAOYSA-N methyl 2-[3-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propylamino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCNCC1=CC=CC(CC(=O)OC)=C1 OFMDRXOBFRPNIK-UHFFFAOYSA-N 0.000 claims 1
- KRKWMWOXTBWQQJ-UHFFFAOYSA-N methyl 2-[3-[[4-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]butylamino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCCNCC1=CC=CC(CC(=O)OC)=C1 KRKWMWOXTBWQQJ-UHFFFAOYSA-N 0.000 claims 1
- CZHMMVUCDGBBOT-UHFFFAOYSA-N methyl 2-[4-[2-[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propylamino]-2-oxoethyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCNC(=O)CC1=CC=C(CC(=O)OC)C=C1 CZHMMVUCDGBBOT-UHFFFAOYSA-N 0.000 claims 1
- FMVSYRYMESAHBX-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1O FMVSYRYMESAHBX-UHFFFAOYSA-N 0.000 claims 1
- WMRGREXQHLOXEC-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC WMRGREXQHLOXEC-UHFFFAOYSA-N 0.000 claims 1
- LTGWWJNPCNOBKY-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1 LTGWWJNPCNOBKY-UHFFFAOYSA-N 0.000 claims 1
- CFVPRJIBEINZNX-KRWDZBQOSA-N methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxyhexan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC CFVPRJIBEINZNX-KRWDZBQOSA-N 0.000 claims 1
- FRAWREFTINNZCA-KRWDZBQOSA-N methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxyhexan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1 FRAWREFTINNZCA-KRWDZBQOSA-N 0.000 claims 1
- OKMWFKVOJISTAK-HNNXBMFYSA-N methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1F OKMWFKVOJISTAK-HNNXBMFYSA-N 0.000 claims 1
- KIJOGUHGFXYHIQ-HNNXBMFYSA-N methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1O KIJOGUHGFXYHIQ-HNNXBMFYSA-N 0.000 claims 1
- TTYFFCJKAZFEPU-INIZCTEOSA-N methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC TTYFFCJKAZFEPU-INIZCTEOSA-N 0.000 claims 1
- GFWDCEMUNCSYLF-INIZCTEOSA-N methyl 2-[4-[[2-amino-4-[[(2s)-1-hydroxypentan-2-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCC[C@@H](CO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1 GFWDCEMUNCSYLF-INIZCTEOSA-N 0.000 claims 1
- LJCWGAFKPMAKIS-HNNXBMFYSA-N methyl 2-[4-[[2-amino-4-[[(2s)-2-hydroxybutyl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CC[C@H](O)CNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC LJCWGAFKPMAKIS-HNNXBMFYSA-N 0.000 claims 1
- ZEZZVRSKTPRDHO-KRWDZBQOSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyheptan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1F ZEZZVRSKTPRDHO-KRWDZBQOSA-N 0.000 claims 1
- IWSGKWLJZBEPNR-SFHVURJKSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyheptan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC IWSGKWLJZBEPNR-SFHVURJKSA-N 0.000 claims 1
- ITBBFOMZZKFSBU-SFHVURJKSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyheptan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1 ITBBFOMZZKFSBU-SFHVURJKSA-N 0.000 claims 1
- VOEPUDGAHQZNLR-INIZCTEOSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1F VOEPUDGAHQZNLR-INIZCTEOSA-N 0.000 claims 1
- HZVNYLLPQXXKPA-INIZCTEOSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-hydroxyphenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1O HZVNYLLPQXXKPA-INIZCTEOSA-N 0.000 claims 1
- VILGOZSKTAIFTC-KRWDZBQOSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC VILGOZSKTAIFTC-KRWDZBQOSA-N 0.000 claims 1
- RXADHRRCDAYERN-KRWDZBQOSA-N methyl 2-[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1 RXADHRRCDAYERN-KRWDZBQOSA-N 0.000 claims 1
- OHYUJDABQDCCFJ-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]-3-fluorophenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1F OHYUJDABQDCCFJ-UHFFFAOYSA-N 0.000 claims 1
- YWBUZOBEEKTTBM-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]-3-methoxyphenoxy]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(OCC(=O)OC)C=C1OC YWBUZOBEEKTTBM-UHFFFAOYSA-N 0.000 claims 1
- HIWQJYAWHHVTCG-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]-3-methoxyphenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1OC HIWQJYAWHHVTCG-UHFFFAOYSA-N 0.000 claims 1
- CGSDJZLYFVSPHW-UHFFFAOYSA-N methyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CC(=O)OC)C=C1 CGSDJZLYFVSPHW-UHFFFAOYSA-N 0.000 claims 1
- FYYSVFDVLUWSSB-DEOSSOPVSA-N methyl 2-[4-[[3-[2-amino-4-[[(3s)-1-hydroxyheptan-3-yl]amino]-6-methylpyrimidin-5-yl]propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 FYYSVFDVLUWSSB-DEOSSOPVSA-N 0.000 claims 1
- AWOUQNYJPWKMAF-NRFANRHFSA-N methyl 2-[4-[[3-[2-amino-4-[[(3s)-1-hydroxyheptan-3-yl]amino]-6-methylpyrimidin-5-yl]propylamino]methyl]phenyl]acetate Chemical compound CCCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CCCNCC1=CC=C(CC(=O)OC)C=C1 AWOUQNYJPWKMAF-NRFANRHFSA-N 0.000 claims 1
- QIBQHTOYFJCJSJ-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-(1-methylpiperidine-4-carbonyl)amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)C1CCN(C)CC1)CC1=CC=C(CC(=O)OC)C=C1 QIBQHTOYFJCJSJ-UHFFFAOYSA-N 0.000 claims 1
- LWQBGUQLUSBADZ-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-(2-methylsulfanylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CSC)CC1=CC=C(CC(=O)OC)C=C1 LWQBGUQLUSBADZ-UHFFFAOYSA-N 0.000 claims 1
- QBTADTBBDBDQNC-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-(2-morpholin-4-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1CCOCC1)CC1=CC=C(CC(=O)OC)C=C1 QBTADTBBDBDQNC-UHFFFAOYSA-N 0.000 claims 1
- UMECBZLEILSIMU-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-(2-piperidin-1-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1CCCCC1)CC1=CC=C(CC(=O)OC)C=C1 UMECBZLEILSIMU-UHFFFAOYSA-N 0.000 claims 1
- SDBDJKBDVUHIHD-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-(4-phenylpiperidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN1CCC(CC1)C=1C=CC=CC=1)CC1=CC=C(CC(=O)OC)C=C1 SDBDJKBDVUHIHD-UHFFFAOYSA-N 0.000 claims 1
- VURQKZCOEUNYNX-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 VURQKZCOEUNYNX-UHFFFAOYSA-N 0.000 claims 1
- JVLDENHNDNBENH-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[2-[2-methoxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CN(C)CCOC)CC1=CC=C(CC(=O)OC)C=C1 JVLDENHNDNBENH-UHFFFAOYSA-N 0.000 claims 1
- WOSYEPNXYFTHBO-UHFFFAOYSA-N methyl 2-[4-[[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propylamino]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCNCC1=CC=C(CC(=O)OC)C=C1 WOSYEPNXYFTHBO-UHFFFAOYSA-N 0.000 claims 1
- FXQKFFLMHTYUFX-UHFFFAOYSA-N methyl 4-[3-[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl-[[3-(2-methoxy-2-oxoethyl)phenyl]methyl]amino]-4-oxobutanoate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CCCN(C(=O)CCC(=O)OC)CC1=CC=CC(CC(=O)OC)=C1 FXQKFFLMHTYUFX-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- ZLUCFJCTDXPLIY-UHFFFAOYSA-N piperidin-4-ylmethyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate Chemical compound CCCCCNC1=NC(N)=NC(C)=C1CC(C=C1)=CC=C1CC(=O)OCC1CCNCC1 ZLUCFJCTDXPLIY-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000003637 steroidlike Effects 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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Claims (31)
1. Spoj sa formulom(I)
[image]
naznačen time da
R1 predstavlja C1-C6 alkil, C1-C6 alkoksi ili C1-C6 alkiltio;
R2 predstavlja ili
[image]
R3 predstavlja atom vodika ili C1-C3 alkilnu skupinu;
R4 predstavlja,
(i) C3-C8 cikloalkil, C1-C8 alkil, C2-C8 alkenil ili C2-C8 alkinil, svaki od kojih može biti proizvoljno supstituiran sa jednim ili više supstituenata neovisno odabranih između halogena, hidroksila, C1-C6 alkoksi, C1-C6 alkiltio i C3-C6 cikloalkila, ili
(ii) skupinu
[image]
gdje m je 1 ili 2, q je 0, 1 ili 2 i svaki R neovisno predstavlja atom halogena ili hidroksilnu, metilnu, cijano, trifluorometilnu, S(O)h-metilnu ili metoksi skupinu;
X1 predstavlja atom kisika ili sumpora ili skupinu NH ili CH2;
X2 i X4 svaki neovisno predstavlja vezu ili atom kisika ili sumpora;
R5 i R5a svaki neovisno predstavlja atom vodika ili C1-C3 alkilnu skupinu;
R6 predstavlja C1-C6 alkilnu skupinu proizvoljno supstituiranu sa jednim ili više supstituenata neovisno odabranih od halogena, cijano, hidroksila, C1-C3 alkoksi, metilsulfonila, metiltiazolila i NR10R11, ili R6 predstavlja zasićeni heterociklički prsten koji je proizvoljno supstituiran sa C1-C6 alkilom;
j je 1 ili 2;
svaki R7 neovisno predstavlja atom vodika ili halogena ili hidroksilnu, metilnu, cijano, halometoksi ili metoksi skupinu;
Z1 predstavlja C2-C6 alkilensku ili C3-C8 cikloalkilensku skupinu;
X3 predstavlja NR12, >N-COR12, CONR12, NR12CO, SC2NR12, >N-SO2R12, NR12SO2, NR12CONR13 ili NR13CONR12, S(O)p ili O;
p je 0, 1 ili 2;
Y1 predstavlja jednostruku vezu ili C1-C6alkilen;
A predstavlja monocikličku ili bicikličku C6-C10arilnu ili monocikličku ili bicikličku C5-C12heteroarilnu skupinu koja sadrži 1 do 3 prstenska heteroatoma;
R8 predstavlja C1-C6 alkilnu skupinu proizvoljno supstituiranu sa jednim ili više supstituenata koji su neovisno odabrani od halogena, cijano, hidroksila, NR10R11 i C1-C3 alkoksi;
n je 0, 1 ili 2;
svaki R9 neovisno predstavlja halogen, cijano, hidroksi, tiol, C1-C3alkil, C1-C3hidroksialkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfonil ili C1-C3alkilsulfinil;
R10 i R11 svaki neovisno predstavlja vodik, C1-C6 alkil ili C3-C6 cikloalkil, ili R10 i R11 zajedno sa atomom dušika na koji su spojeni tvore 4- do 7-člani zasićeni heterociklički prsten koji proizvoljno može sadržavati dodatni prstenski heteroatom koji je odabran od kisika, S(O)v ili NR36, te je heterociklički prsten proizvoljno supstituiran sa C1-C6alkilom (koji je sam proizvoljno supstituiran sa C1-C6 alkoksi) ili di-C1-C6 alkilamino;
R12 predstavlja atom vodika, 3- do 8-člani zasićeni ili nezasićeni heterociklički prsten koji sadrži barem jednu prstensku skupinu O, S(O)t, N ili NR14, C1-C6 alkilnu skupinu ili C3-C6 cikloalkilnu skupinu, pri čemu su zadnje dvije skupine proizvoljno supstituirane sa jednim ili više supstituenata neovisno odabranih od NR15 R16 i R17, ili
R12 je C1-C6alkilen koji može biti povezan sa atomom ugljika unutar C2-C6 alkilen skupine Z1 tako da tvori 4- do 7-člani prsten koji sadrži dušik;
R14, R22 i R35 svaki neovisno predstavlja atom vodika, CO2R18, S(O)wR18 , COR19, ili C1-C6 alkilnu, C2-C6 alkenilnu, C2-C6 alkinilnu ili C3-C8 cikloalkilnu skupinu,
između kojih svaka može biti proizvoljno supstituirana sa jednim ili više supstituenata neovisno odabranih od halogena, cijano, OR20 i NR20 R21;
R15 i R16 svaki neovisno predstavlja atom vodika, 3- do 8-člani zasićeni heterociklički prsten koji sadrži barem jednu prstensku skupinu O, S(O)z ili NR22, C1-C6 alkilnu ili C3-C6 cikloalkilnu skupinu, pri čemu su zadnje dvije skupine proizvoljno supstituirane sa jednim ili više supstituenata neovisno odabranih od halogena, cijano, S(O)aR23, OR24, CO2R24, OC(O)R24, SO2NR24R25, CONR24 R25, NR24R25, NR24SO2R26, NR24COR25, ili 3- do 8-člani zasićen heterociklički prsten koji sadrži barem jednu prstensku skupinu O, S(O)b ili NR25, ili
R15 i R16 zajedno sa atomom dušika na koji su povezani tvore 3- do 8-člani zasićeni heterociklički prsten koji sadrži atom dušika u prstenu i proizvoljno jedan ili više dodatnih heteroatoma u prstenu neovisno odabranih od dušika, kisika, sumpora i sulfonila, te je heterociklički prsten proizvoljno supstituiran sa jednim ili više supstituenata neovisno odabranih od halogena, cijano, S(O)dR27 , OR27, CO2R27 , COR27, OC(O)R27, SO2NR27R28, CONR27R28, NR27R28, NR27SO2, R29, NR27COR28, C1-C6 haloalkila, C3-C8 cikloalkila, C1-C6 alkila, arila i heteroarila, pri čemu su posljednje četiri skupine proizvoljno supstituirane sa jednim ili više supstituenata neovisno odabranih od halogena, cijano, S(O)fR30, OR30, CO2R30, SO2NR30R31, CONR30R31 i NR30R31;
R17 predstavlja halogen, cijano, C1-C3 haloalkoksi, CO2R32, S(O)gR32, OR32, SO2NR32R34, CONR32R34, NR32SO2R33, NR32CO2R33, NR32COR34 ili 3- do 8-člani zasićeni heterociklički prsten koji sadrži prstensku skupinu NR35;
a, b, d, f, g, h, t, v, w i z svaki neovisno predstavlja 0, 1 ili 2;
R18 , R26, R29 i R33 svaki neovisno predstavlja C1-C6 alkilnu ili C3-C6 cikloalkilnu skupinu;
R13, R19, R20, R21, R23, R24, R25, R27, R28, R30, R31, R32 i R34 svaki neovisno predstavlja atom vodika ili C1-C6 alkilnu ili C3-C6 cikloalkilnu skupinu; i
R36 predstavlja atom vodika ili C1-C3 alkilnu skupinu;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1, naznačen time da R1 predstavlja C1-C6 alkil.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, naznačen time da R3 predstavlja atom vodika.
4. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da R4 predstavlja C1-C8alkil proizvoljno supstituiran sa jednim ili više supstituenata koji su neovisno odabrani od halogena, hidroksila, C1-C6alkoksi, C1-C6alkiltio i C3-C6cikloalkila.
5. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da R2 predstavlja skupinu sa formulom (Ia).
6. Spoj prema zahtjevu 5, naznačen time da X1 predstavlja CH2, X2 predstavlja vezu i R5 predstavlja atom vodika.
7. Spoj prema zahtjevu 5 ili zahtjevu 6, naznačen time da j je 1 i R7 predstavlja vodik, hidroksil, fluor ili metoksi.
8. Spoj prema bilo kojem zahtjevu od 1 do 4, naznačen time da R2 predstavlja skupinu sa formulom (Ib).
9. Spoj prema zahtjevu 8, naznačen time da Z1 predstavlja C2-C6alkilen.
10. Spoj prema zahtjevu 8 ili zahtjevu 9, naznačen time da X3 predstavlja NR12, >N-COR12, NR12CO ili >N-SO2R12.
11. Spoj prema bilo kojem zahtjevu od 8 do 10, naznačen time da Y1 predstavlja C1-C6 alkilen.
12. Spoj prema bilo kojem zahtjevu od 8 do 11, naznačen time da A predstavlja monociklički ili biciklički C6-C10 aril odabran od fenila.
13. Spoj prema bilo kojem zahtjevu od 8 do 12, naznačen time da R8 predstavlja C1-C6 alkil.
14. Spoj prema zahtjevu 1 naznačen time da je
Metil 2-(3-((3-(2-Amino-4-metil-6-(pentilamino)pirimidin-5-il)propilamino)metil)fenil)acetat,
Metil 2-(4-((3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propilamino)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(dimetilamino)acetamido)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(dimetilamino)acetamido)metil)fenil)acetat,
(S)-Metil1-(2-((3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)(3-(2-metoksi-2-oksoetil)benzil)amino)-2-oksoetil)pirolidine-2-karboksilate,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(4-metilpiperazin-1-il)acetamido)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(4-hidroksipiperidin-1-il)acetamido)metil)fenil)acetat,
Metil 2-(3-((2-(4-acetil-1,4-diazepan-1-il)-N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)acetamido)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(4-(3-(dimetilamino)propil)piperazin-1-il)acetamido)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-((2-hidroksietil)(metil)amino)acetamido)metil)fenil)acetat,
Metil 4-((3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)(3-(2-metoksi-2-oksoetil)benzil)amino)-4-oksobutanoate,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-4-(dimetilamino)butanamido)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)metilsulfonamido)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-1-metil-1H-imidazole-4-sulfonamido)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-((2-metoksietil)(metil)amino)acetamido)metil)fenil)acetat,
Metil 2-(3-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-3-(dimetilamino)propanamido)metil)fenil)acetat,
Metil 2-(3-((4-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)butilamino)metil)fenil)acetat,
(S)-Metil 2-(4-((3-(2-amino-4-(1-hidroksiheptan-3-ilamino)-6-metilpirimidin-5-il)propilamino)metil)fenil)acetat,
(S)-Metil 2-(4-((N-(3-(2-amino-4-(1-hidroksiheptan-3-ilamino)-6-metilpirimidin-5-il)propil)-2-(dimetilamino)acetamido)metil)fenil)acetat,
Metil 2-(3-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
Metil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)-3-metoksifenil)acetat,
Metil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)-3-fluorofenil)acetat,
Metil 2-(4-(2-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propilamino)-2-oksoetil)fenil)acetat,
Metil 2-(3-(2-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propilamino)-2-oksoetil)fenil)acetat,
Metil 2-(3-((3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propilamino)metil)fenoksi)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(3-(4-(metilsulfonil)fenil)piperidin-1-il)acetamido)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-morfolinoacetamido)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(4-fenilpiperidin-1-il)acetamido)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(piperidin-1-il)acetamido)metil)fenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheptan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheksan-2-ilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheptan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
Metil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil) acetat,
2-Morfolinoetil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
2-(Dimetilamino)etil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
3-(Dimetilamino)propil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
2-(4-Metilpiperazin-1-il)etil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
Metil 2-(3-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)-4-hidroksifenil)acetat,
Metil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)-3-metoksifenoksi)acetat,
Metil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)fenil) acetat,
(S)-Metil 2-(3-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-4-fluorofenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheksan-2-ilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
Metil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheptan-3-ilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-1-metilpiperidin-4-karboksamido)metil)fenil)acetat,
Metil 2-(4-((N-(3-(2-amino-4-metil-6-(pentilamino)pirimidin-5-il)propil)-2-(metiltio)acetamido)metil)fenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(2-hidroksibutilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
Metil 2-(3-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)-4-metoksifenil)acetat,
3-(Dimetilamino)-2,2-dimetilpropil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
3-(4-Metilpiperazin-1-il)propil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
4-(Dimetilamino)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
3-Morfolinopropil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
1-Metilpiperidin-4-il 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
4-(Pirolidin-1-il)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
(1-(2-Metoksietil)piperidin-4-il)metil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
4-(4-Metilpiperazin-1-il)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
4-(1,1-Dioksidotiomorfolin-4-il)butil(4-{[2-amino-4-metil-6-(pentilamino)pirimidin-5-il]metil}fenil)acetat,
4-Morfolinobutil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
2-(1-Metilpiperidin-4-il)etil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
Piperidin-4-ilmetil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
4-(4-(Dimetilamino)piperidin-1-il)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(S)-4-(Dimetilamino)butil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(S)-(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
4-(Pirolidin-1-il)butil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
(S)-(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
Metil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
(S)-4-(Pirolidin-1-il)butil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
4-(Pirolidin-1-il)butil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
(S)-Metil 2-(3-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)-4-metoksifenil)acetat,
(S)-(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(2-hidroksibutilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
4-(Pirolidin-1-il)butil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(3-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-4-metoksifenil)acetat,
4-(Pirolidin-1-il)butil 2-(3-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(3-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat,
(S)-4-(Dimetilamino)butil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
(S)-4-(4-Metilpiperazin-1-il)butil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
(S)-Metil 2-(4-((2-amino-4-(1-hidroksipentan-2-ilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
2-Hidroksietil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
4-(4-(Dimetilamino)piperidin-1-il)butil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
4-Hidroksibutil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
3-(Metilsulfonil)propil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
3-Hidroksipropil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(S)-4-(Dimetilamino)butil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)fenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(4-(2-amino-4-(butilamino)-6-metilpirimidin-5-iltio)fenil)acetat,
4-(Pirolidin-1-il)butil 2-(4-(2-amino-4-(butilamino)-6-metilpirimidin-5-iltio)fenil)acetat,
4-(Dimetilamino)butil 2-(3-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-4-metoksifenil)acetat,
Metil 2-(3-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-4-metoksifenil)acetat,
Metil 2-(3-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-4-hidroksifenil)acetat,
(S)-2-(1-Metilpiperidin-4-il)etil 2-(4-((2-amino-4-(1-hidroksiheksan-3-ilamino)-6-metilpirimidin-5-il)metil)-3-fluorofenil)acetat,
2-(4-Metiltiazol-5-il)etil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-metoksifenil)acetat,
(1-Metilpiperidin-4-il)metil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
4-(Dimetilamino)butil 2-(4-((2-amino-4-(butilamino)-6-metilpirimidin-5-il)metil)-3-hidroksifenil)acetat,
ili farmaceutski prihvatljiva sol bilo kojeg od njih.
15. Spoj prema zahtjevu 1 naznačen time da je 4-(dimetilamino)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat, ili njegova farmaceutski prihvatljiva sol.
16. Spoj prema zahtjevu 1 naznačen time da je 4-(dimetilamino)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat.
17. Spoj prema zahtjevu 1 naznačen time da je farmaceutski prihvatljiva sol 4-(dimetilamino)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetata.
18. Spoj prema zahtjevu 1 naznačen time da je sol 4-(dimetilamino)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetat bi benzen sulfonske kiseline.
19. Spoj prema zahtjevu 1 naznačen time da je monosaharinska sol 4-(dimetilamino)butil 2-(4-((2-amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)acetata.
20. Postupak za dobivanje spoja sa formulom(I) ili njegove farmaceutski prihvatljive soli kako je definirano u zahtjevu 1 naznačen time da sadrži,
(a) kada R2 predstavlja skupinu sa formulom (Ia), reakciju spoja sa formulom(II)
[image]
pri čemu j, X1, X2, R1, R3, R4, R5 i R7 su kako je definirano u zahtjevu 1, sa spojem sa formulom(III), R6-OH, gdje R6 je kako je definirano u zahtjevu 1; ili
(b) kada R2 predstavlja skupinu sa formulom (Ib), reakciju spoja sa formulom (IV)
[image]
pri čemu su n, A, X3, X4, Y1, Z1, R1, R3, R4, R5a i R9 kako je definirano u zahtjevu 1, sa spojem sa formulom(V), R8-OH, gdje R8 je kako je definirano u zahtjevu 1; ili
(c) kada R2 predstavlja skupinu sa formulom (Ib) gdje X3 predstavlja NH i Y1 predstavlja C1-C6 alkilen, reakciju spoja sa formulom (VI)
[image]
pri čemu R1, R3, R4 i Z1 su kako je definirano u zahtjevu 1, sa spojem sa formulom (VII)
[image]
pri čemu Y2 predstavlja -(C1-C5 alkil)j-CHO, j je 0 ili 1, i A, n, X4, R5a, R8 i R9 su kako je definirano u zahtjevu 1;
i proizvoljno nakon koraka (a), (b) ili (c) provođenje jednog ili više od slijedećih postupaka:
• konverziju spoja sa formulom(I) u drugi spoj sa formulom (I)
• uklanjanje bilo koje zaštitne skupine
• tvorbu farmaceutski prihvatljive soli.
21. Farmaceutski pripravak naznačen time da sadrži spoj sa formulom(I) prema bilo kojem zahtjevu od 1 do 15 ili njegovu farmaceutski prihvatljivu sol zajedno sa farmaceutski prihvatljivim adjuvantom, razrjeđivačem ili nosačem.
22. Farmaceutski pripravak prema zahtjevu 21, naznačen time da je u obliku heptafluoroalkanskog aerosola pogodnog za davanje oralnim putem ili nazalnu inhalaciju.
23. Farmaceutski pripravak prema zahtjevu 21, naznačen time da je formulacija suhog praha pogodna za davanje oralnim putem ili nazalnu inhalaciju.
24. Inhalator suhog praha naznačen time da sadrži spoj sa formulom (I) prema bilo kojem zahtjevu od 1 do 15 ili njegovu farmaceutski prihvatljivu sol, ili pripravak prema zahtjevu 23.
25. Spoj sa formulom (I) prema bilo kojem zahtjevu od 1 do 15, ili njegova farmaceutski prihvatljiva sol, naznačen time da je za uporabu kod liječenja.
26. Spoj sa formulom (I) prema bilo kojem zahtjevu od 1 do 15 ili njegova farmaceutski prihvatljiva sol naznačen time da je za uporabu kod liječenja astme, KOPB, alergijskog rinitisa, alergijskog konjunktivitisa, atopijskog dermatitisa, raka, hepatitisa B, hepatitisa C, HIV, HPV, bakterijskih infekcija ili dermatoze.
27. Uporaba spoja sa formulom (I) prema bilo kojem zahtjevu od 1 do 15 ili njegove farmaceutski prihvatljive soli za proizvodnju lijeka za uporabu kod liječenja astme KOPB, alergijskog rinitisa, alergijskog konjunktivitisa, atopijskog dermatitisa, raka, hepatitisa B, hepatitisa C, HIV, HPV, bakterijskih infekcija ili dermatoze.
28. Uporaba spoja sa formulom (I) prema bilo kojem zahtjevu od 1 do 15 ili njegove farmaceutski prihvatljive soli za proizvodnju lijeka za uporabu kod liječenja opstruktivne bolesti dišnih puteva.
29. Kombinacija spoja sa formulom (I) prema bilo kojem zahtjevu od 1 do 15 ili njegove farmaceutski prihvatljive soli i jednog ili više sredstava koja su neovisno odabrana od:
• agonist ne-steroidalnog glukokortikoidnog receptora;
• selektivni agonist β2 adrenoceptora;
• inhibitor fosfodiesteraze;
• inhibitor proteaze;
• glukokortikoid;
• anti-kolinergijsko sredstvo;
• modulator funkcije kemokinskog receptora; i
• inhibitor funkcije kinaze.
30. Spoj sa formulom (II):
[image]
naznačen time da R1, R3, R4, R7 i j su kako je definirano u zahtjevu 1.
31. Spoj naznačen time da je 2-(4-((2-Amino-4-metil-6-(pentilamino)pirimidin-5-il)metil)fenil)octena kiselina.
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SE0702577 | 2007-11-22 | ||
US1369907P | 2007-12-14 | 2007-12-14 | |
PCT/SE2008/051334 WO2009067081A1 (en) | 2007-11-22 | 2008-11-21 | Pyrimidine derivatives for the treatment of asthma, copd, allergic rhinitis, allergic conjunctivitis, atopic dermatitis, cancer, hepatitis b, hepatitis c, hiv, hpv, bacterial infections and dermatosis |
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HRP20130174AT HRP20130174T1 (hr) | 2007-11-22 | 2013-02-28 | Derivati pirimidina za lijeäśenje astme, kopb, alergijskog rinitisa, alergijskog konjuktivitisa, atopijskog dermatitisa, karcinoma, hepatitisa b, hepatitisa c, hiv, hpv, bakterijskih infekcija i dermatoze |
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- 2008-11-21 CL CL2008003480A patent/CL2008003480A1/es unknown
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