HRP20110115T1 - Derivati purina kao imunomodulatori - Google Patents
Derivati purina kao imunomodulatori Download PDFInfo
- Publication number
- HRP20110115T1 HRP20110115T1 HR20110115T HRP20110115T HRP20110115T1 HR P20110115 T1 HRP20110115 T1 HR P20110115T1 HR 20110115 T HR20110115 T HR 20110115T HR P20110115 T HRP20110115 T HR P20110115T HR P20110115 T1 HRP20110115 T1 HR P20110115T1
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- dihydro
- tetrahydro
- purin
- pyran
- Prior art date
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- 239000002955 immunomodulating agent Substances 0.000 title 1
- 229940121354 immunomodulator Drugs 0.000 title 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 239000012453 solvate Substances 0.000 claims abstract 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- -1 n-butylamino, n-butoxy Chemical group 0.000 claims 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 4
- MVWARGSQZIWHHV-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-(oxolan-3-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3COCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 MVWARGSQZIWHHV-UHFFFAOYSA-N 0.000 claims 3
- MRAUMDSWWQULRH-UHFFFAOYSA-N 6-amino-2-(butylamino)-9-(oxolan-3-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(NCCCC)=NC(N)=C2NC(=O)N1CC1CCOC1 MRAUMDSWWQULRH-UHFFFAOYSA-N 0.000 claims 3
- OFFICXUVHMCMEG-UHFFFAOYSA-N 6-amino-2-(butylamino)-9-[2-(oxan-3-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(NCCCC)=NC(N)=C2NC(=O)N1CCC1CCCOC1 OFFICXUVHMCMEG-UHFFFAOYSA-N 0.000 claims 3
- SIMTUGDZCSQGIQ-UHFFFAOYSA-N 6-amino-2-butoxy-9-(oxolan-3-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCOC1 SIMTUGDZCSQGIQ-UHFFFAOYSA-N 0.000 claims 3
- OQUINARFEBRLMU-UHFFFAOYSA-N 6-amino-2-butoxy-9-[(2,2-dimethyloxan-4-yl)methyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCOC(C)(C)C1 OQUINARFEBRLMU-UHFFFAOYSA-N 0.000 claims 3
- XFCGCPKSYGRQHC-UHFFFAOYSA-N 6-amino-2-butoxy-9-[2-(oxan-2-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCC1CCCCO1 XFCGCPKSYGRQHC-UHFFFAOYSA-N 0.000 claims 3
- DLHJROUHDUSMGR-UHFFFAOYSA-N 6-amino-2-butoxy-9-[2-(oxolan-2-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCC1CCCO1 DLHJROUHDUSMGR-UHFFFAOYSA-N 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- ONESKZROCAGAIN-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-(oxan-4-yl)ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CCC3CCOCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 ONESKZROCAGAIN-UHFFFAOYSA-N 0.000 claims 2
- ABCUXERROOXTLE-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[3-(oxan-4-yl)propyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCC3CCOCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 ABCUXERROOXTLE-UHFFFAOYSA-N 0.000 claims 2
- KXBFNUZOKHTGCZ-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[4-(oxan-4-yl)butyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCCC3CCOCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 KXBFNUZOKHTGCZ-UHFFFAOYSA-N 0.000 claims 2
- OGJFAWPIRPBLTI-UHFFFAOYSA-N 6-amino-2-(butylamino)-9-(oxolan-3-ylmethyl)-7h-purin-8-one;hydrochloride Chemical compound Cl.C12=NC(NCCCC)=NC(N)=C2NC(=O)N1CC1CCOC1 OGJFAWPIRPBLTI-UHFFFAOYSA-N 0.000 claims 2
- BTUPNFIVUXKROL-UHFFFAOYSA-N 6-amino-2-butoxy-9-[3-(oxan-4-yl)propyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCC1CCOCC1 BTUPNFIVUXKROL-UHFFFAOYSA-N 0.000 claims 2
- IJWKEDXCWCJJLD-UHFFFAOYSA-N 6-amino-2-butoxy-9-[4-(oxan-3-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCCOC1 IJWKEDXCWCJJLD-UHFFFAOYSA-N 0.000 claims 2
- JJXKGZFZGGRWGT-UHFFFAOYSA-N 6-amino-2-butoxy-9-[4-(oxan-4-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCOCC1 JJXKGZFZGGRWGT-UHFFFAOYSA-N 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000004968 inflammatory condition Effects 0.000 claims 2
- MKEPPSNIKULUQZ-UHFFFAOYSA-N 6-amino-2-(1-methoxypropan-2-yloxy)-9-(oxan-3-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OC(C)COC)=NC(N)=C2NC(=O)N1CC1CCCOC1 MKEPPSNIKULUQZ-UHFFFAOYSA-N 0.000 claims 1
- XWCKLWSVZQSFET-UHFFFAOYSA-N 6-amino-2-(1-methoxypropan-2-yloxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OC(C)COC)=NC(N)=C2NC(=O)N1CC1CCOCC1 XWCKLWSVZQSFET-UHFFFAOYSA-N 0.000 claims 1
- QLSVAYCZFUCFKB-UHFFFAOYSA-N 6-amino-2-(2,2-dimethylpentoxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCC(C)(C)CCC)=NC(N)=C2NC(=O)N1CC1CCOCC1 QLSVAYCZFUCFKB-UHFFFAOYSA-N 0.000 claims 1
- GFBMKIZYKVCGRZ-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3CCOCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 GFBMKIZYKVCGRZ-UHFFFAOYSA-N 0.000 claims 1
- RAJSZZXMHONNEH-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-(oxan-2-yl)ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CCC3OCCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 RAJSZZXMHONNEH-UHFFFAOYSA-N 0.000 claims 1
- BBSMITHHCRCDLZ-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-(oxan-3-yl)ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CCC3COCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 BBSMITHHCRCDLZ-UHFFFAOYSA-N 0.000 claims 1
- QVPDNUHUNVRRTP-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-(oxolan-2-yl)ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CCC3OCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 QVPDNUHUNVRRTP-UHFFFAOYSA-N 0.000 claims 1
- PMQPINGSUJOWFG-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-(oxolan-3-yl)ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CCC3COCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 PMQPINGSUJOWFG-UHFFFAOYSA-N 0.000 claims 1
- PMQPINGSUJOWFG-LLVKDONJSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-[(3r)-oxolan-3-yl]ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CC[C@H]3COCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 PMQPINGSUJOWFG-LLVKDONJSA-N 0.000 claims 1
- PMQPINGSUJOWFG-NSHDSACASA-N 6-amino-2-(2-cyclopropylethoxy)-9-[2-[(3s)-oxolan-3-yl]ethyl]-7h-purin-8-one Chemical compound N=1C=2N(CC[C@@H]3COCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 PMQPINGSUJOWFG-NSHDSACASA-N 0.000 claims 1
- HMCGTILHGMGUMK-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[3-(oxan-2-yl)propyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCC3OCCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 HMCGTILHGMGUMK-UHFFFAOYSA-N 0.000 claims 1
- WYPVGSRRKOLAOI-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[3-(oxolan-2-yl)propyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCC3OCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 WYPVGSRRKOLAOI-UHFFFAOYSA-N 0.000 claims 1
- XDIUAOIJZPBVDS-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[3-(oxolan-3-yl)propyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCC3COCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 XDIUAOIJZPBVDS-UHFFFAOYSA-N 0.000 claims 1
- UQVIBCJVUNSYTG-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[4-(oxan-2-yl)butyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCCC3OCCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 UQVIBCJVUNSYTG-UHFFFAOYSA-N 0.000 claims 1
- SUHQGECXZDFUDA-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[4-(oxan-3-yl)butyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCCC3COCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 SUHQGECXZDFUDA-UHFFFAOYSA-N 0.000 claims 1
- FJDSNCDPUQFYQR-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[4-(oxolan-2-yl)butyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCCC3OCCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 FJDSNCDPUQFYQR-UHFFFAOYSA-N 0.000 claims 1
- SBYDEQMKHAALFC-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethoxy)-9-[4-(oxolan-3-yl)butyl]-7h-purin-8-one Chemical compound N=1C=2N(CCCCC3COCC3)C(=O)NC=2C(N)=NC=1OCCC1CC1 SBYDEQMKHAALFC-UHFFFAOYSA-N 0.000 claims 1
- HPXXJHSZLPJIEB-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethylamino)-9-(oxan-3-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3COCCC3)C(=O)NC=2C(N)=NC=1NCCC1CC1 HPXXJHSZLPJIEB-UHFFFAOYSA-N 0.000 claims 1
- ZQKHUKKQOCMNHW-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethylamino)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3CCOCC3)C(=O)NC=2C(N)=NC=1NCCC1CC1 ZQKHUKKQOCMNHW-UHFFFAOYSA-N 0.000 claims 1
- CGIZYOAKHQGYSD-UHFFFAOYSA-N 6-amino-2-(2-cyclopropylethylamino)-9-(oxolan-3-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3COCC3)C(=O)NC=2C(N)=NC=1NCCC1CC1 CGIZYOAKHQGYSD-UHFFFAOYSA-N 0.000 claims 1
- GARPEDHKARXMTJ-UHFFFAOYSA-N 6-amino-2-(2-ethoxyethoxy)-9-(oxan-3-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCOCC)=NC(N)=C2NC(=O)N1CC1CCCOC1 GARPEDHKARXMTJ-UHFFFAOYSA-N 0.000 claims 1
- GENJONRXDMPJSQ-UHFFFAOYSA-N 6-amino-2-(2-ethoxyethoxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCOCC)=NC(N)=C2NC(=O)N1CC1CCOCC1 GENJONRXDMPJSQ-UHFFFAOYSA-N 0.000 claims 1
- IJKXVULVJLGAOD-UHFFFAOYSA-N 6-amino-2-(2-methoxyethoxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCOC)=NC(N)=C2NC(=O)N1CC1CCOCC1 IJKXVULVJLGAOD-UHFFFAOYSA-N 0.000 claims 1
- PFKCWSQFDGSQKE-UHFFFAOYSA-N 6-amino-2-(2-methoxyethoxy)-9-(oxolan-3-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCOC)=NC(N)=C2NC(=O)N1CC1CCOC1 PFKCWSQFDGSQKE-UHFFFAOYSA-N 0.000 claims 1
- KZUZGUPKNFYBQF-UHFFFAOYSA-N 6-amino-2-(2-methylbutoxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCC(C)CC)=NC(N)=C2NC(=O)N1CC1CCOCC1 KZUZGUPKNFYBQF-UHFFFAOYSA-N 0.000 claims 1
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- TXDSXCZUPNNIDU-UHFFFAOYSA-N 6-amino-2-(butylamino)-9-[4-(oxolan-3-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(NCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC1 TXDSXCZUPNNIDU-UHFFFAOYSA-N 0.000 claims 1
- SNFYDGOXTBVLID-UHFFFAOYSA-N 6-amino-2-(cyclohexylmethoxy)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3CCOCC3)C(=O)NC=2C(N)=NC=1OCC1CCCCC1 SNFYDGOXTBVLID-UHFFFAOYSA-N 0.000 claims 1
- KRVWYDVTNBAODI-UHFFFAOYSA-N 6-amino-2-(cyclohexylmethylamino)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3CCOCC3)C(=O)NC=2C(N)=NC=1NCC1CCCCC1 KRVWYDVTNBAODI-UHFFFAOYSA-N 0.000 claims 1
- ILOAJQDMRSAJTH-UHFFFAOYSA-N 6-amino-2-(cyclopentylmethylamino)-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound N=1C=2N(CC3CCOCC3)C(=O)NC=2C(N)=NC=1NCC1CCCC1 ILOAJQDMRSAJTH-UHFFFAOYSA-N 0.000 claims 1
- LBPGEAPSXSPOHI-UHFFFAOYSA-N 6-amino-2-butoxy-9-(oxan-2-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCCCO1 LBPGEAPSXSPOHI-UHFFFAOYSA-N 0.000 claims 1
- MQUIPJMIYGXXQY-UHFFFAOYSA-N 6-amino-2-butoxy-9-(oxan-3-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCCOC1 MQUIPJMIYGXXQY-UHFFFAOYSA-N 0.000 claims 1
- OMOVPCGGTUEFQK-UHFFFAOYSA-N 6-amino-2-butoxy-9-(oxan-4-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCOCC1 OMOVPCGGTUEFQK-UHFFFAOYSA-N 0.000 claims 1
- ZKUGYRSLIUMWNO-UHFFFAOYSA-N 6-amino-2-butoxy-9-(oxolan-2-ylmethyl)-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCCO1 ZKUGYRSLIUMWNO-UHFFFAOYSA-N 0.000 claims 1
- NGSOTZGUNHREFY-UHFFFAOYSA-N 6-amino-2-butoxy-9-(oxolan-3-ylmethyl)-7h-purin-8-one;hydrochloride Chemical compound Cl.C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC1CCOC1 NGSOTZGUNHREFY-UHFFFAOYSA-N 0.000 claims 1
- MKCLAQMINGJUQB-UHFFFAOYSA-N 6-amino-2-butoxy-9-[2-(2,2-dimethyloxan-4-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCC1CCOC(C)(C)C1 MKCLAQMINGJUQB-UHFFFAOYSA-N 0.000 claims 1
- QICHIOQGNQGVNB-UHFFFAOYSA-N 6-amino-2-butoxy-9-[2-(oxan-3-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCC1CCCOC1 QICHIOQGNQGVNB-UHFFFAOYSA-N 0.000 claims 1
- IOAXHGACYRWNGO-UHFFFAOYSA-N 6-amino-2-butoxy-9-[2-(oxan-4-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCC1CCOCC1 IOAXHGACYRWNGO-UHFFFAOYSA-N 0.000 claims 1
- SVFBIRSGZWGKKF-UHFFFAOYSA-N 6-amino-2-butoxy-9-[2-(oxolan-3-yl)ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCC1CCOC1 SVFBIRSGZWGKKF-UHFFFAOYSA-N 0.000 claims 1
- SVFBIRSGZWGKKF-SNVBAGLBSA-N 6-amino-2-butoxy-9-[2-[(3r)-oxolan-3-yl]ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC[C@@H]1CCOC1 SVFBIRSGZWGKKF-SNVBAGLBSA-N 0.000 claims 1
- SVFBIRSGZWGKKF-JTQLQIEISA-N 6-amino-2-butoxy-9-[2-[(3s)-oxolan-3-yl]ethyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CC[C@H]1CCOC1 SVFBIRSGZWGKKF-JTQLQIEISA-N 0.000 claims 1
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- LFQAFLSMDSGGJA-UHFFFAOYSA-N 6-amino-2-butoxy-9-[3-(oxolan-2-yl)propyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCC1CCCO1 LFQAFLSMDSGGJA-UHFFFAOYSA-N 0.000 claims 1
- YWAKIRWCKYOCCA-UHFFFAOYSA-N 6-amino-2-butoxy-9-[3-(oxolan-3-yl)propyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCC1CCOC1 YWAKIRWCKYOCCA-UHFFFAOYSA-N 0.000 claims 1
- MFXNKCNOVQQHEL-UHFFFAOYSA-N 6-amino-2-butoxy-9-[4-(2,2-dimethyloxan-4-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC(C)(C)C1 MFXNKCNOVQQHEL-UHFFFAOYSA-N 0.000 claims 1
- MFRCGVPWKBJJAF-UHFFFAOYSA-N 6-amino-2-butoxy-9-[4-(oxan-2-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCCCO1 MFRCGVPWKBJJAF-UHFFFAOYSA-N 0.000 claims 1
- GPUYPNFHCLMCFI-UHFFFAOYSA-N 6-amino-2-butoxy-9-[4-(oxolan-2-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCCO1 GPUYPNFHCLMCFI-UHFFFAOYSA-N 0.000 claims 1
- BDGOZKLNJHTCIA-UHFFFAOYSA-N 6-amino-2-butoxy-9-[4-(oxolan-3-yl)butyl]-7h-purin-8-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC1 BDGOZKLNJHTCIA-UHFFFAOYSA-N 0.000 claims 1
- TYQYAWLPFNJYOW-UHFFFAOYSA-N 6-amino-9-(oxan-4-ylmethyl)-2-(2-propan-2-yloxyethoxy)-7h-purin-8-one Chemical compound C12=NC(OCCOC(C)C)=NC(N)=C2NC(=O)N1CC1CCOCC1 TYQYAWLPFNJYOW-UHFFFAOYSA-N 0.000 claims 1
- NUSGNGZCIRJYIT-UHFFFAOYSA-N 6-amino-9-(oxan-4-ylmethyl)-2-(oxolan-2-ylmethoxy)-7h-purin-8-one Chemical compound N=1C=2N(CC3CCOCC3)C(=O)NC=2C(N)=NC=1OCC1CCCO1 NUSGNGZCIRJYIT-UHFFFAOYSA-N 0.000 claims 1
- KWDXJSIZNIYPLJ-UHFFFAOYSA-N 6-amino-9-(oxan-4-ylmethyl)-2-(pentan-2-ylamino)-7h-purin-8-one Chemical compound C12=NC(NC(C)CCC)=NC(N)=C2NC(=O)N1CC1CCOCC1 KWDXJSIZNIYPLJ-UHFFFAOYSA-N 0.000 claims 1
- PAVCIFRJGSOFJP-UHFFFAOYSA-N 6-amino-9-(oxan-4-ylmethyl)-2-(pentylamino)-7h-purin-8-one Chemical compound C12=NC(NCCCCC)=NC(N)=C2NC(=O)N1CC1CCOCC1 PAVCIFRJGSOFJP-UHFFFAOYSA-N 0.000 claims 1
- YJFQEPHNAAJFDK-UHFFFAOYSA-N 6-amino-9-(oxan-4-ylmethyl)-2-pentan-2-yloxy-7h-purin-8-one Chemical compound C12=NC(OC(C)CCC)=NC(N)=C2NC(=O)N1CC1CCOCC1 YJFQEPHNAAJFDK-UHFFFAOYSA-N 0.000 claims 1
- RRBWHCJRNKUDKA-PZORYLMUSA-N 6-amino-9-[2-(2,2-dimethyloxan-4-yl)ethyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCC1CCOC(C)(C)C1 RRBWHCJRNKUDKA-PZORYLMUSA-N 0.000 claims 1
- RRBWHCJRNKUDKA-UEWDXFNNSA-N 6-amino-9-[2-(2,2-dimethyloxan-4-yl)ethyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCC1CCOC(C)(C)C1 RRBWHCJRNKUDKA-UEWDXFNNSA-N 0.000 claims 1
- LAHHOMWMMQYZDM-NFJWQWPMSA-N 6-amino-9-[2-(oxolan-2-yl)ethyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCC1CCCO1 LAHHOMWMMQYZDM-NFJWQWPMSA-N 0.000 claims 1
- LAHHOMWMMQYZDM-VUWPPUDQSA-N 6-amino-9-[2-(oxolan-2-yl)ethyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCC1CCCO1 LAHHOMWMMQYZDM-VUWPPUDQSA-N 0.000 claims 1
- AKSUHWPUXDBBJD-KWCCSABGSA-N 6-amino-9-[3-(2,2-dimethyloxan-4-yl)propyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCCC1CCOC(C)(C)C1 AKSUHWPUXDBBJD-KWCCSABGSA-N 0.000 claims 1
- AKSUHWPUXDBBJD-LSLKUGRBSA-N 6-amino-9-[3-(2,2-dimethyloxan-4-yl)propyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCCC1CCOC(C)(C)C1 AKSUHWPUXDBBJD-LSLKUGRBSA-N 0.000 claims 1
- LIWBHAGYRGDDNZ-JHJMLUEUSA-N 6-amino-9-[3-(oxolan-2-yl)propyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCCC1CCCO1 LIWBHAGYRGDDNZ-JHJMLUEUSA-N 0.000 claims 1
- LIWBHAGYRGDDNZ-PXYINDEMSA-N 6-amino-9-[3-(oxolan-2-yl)propyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCCC1CCCO1 LIWBHAGYRGDDNZ-PXYINDEMSA-N 0.000 claims 1
- IYUJKPDZTKPZFT-JHJMLUEUSA-N 6-amino-9-[3-(oxolan-3-yl)propyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCCC1CCOC1 IYUJKPDZTKPZFT-JHJMLUEUSA-N 0.000 claims 1
- IYUJKPDZTKPZFT-PXYINDEMSA-N 6-amino-9-[3-(oxolan-3-yl)propyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCCC1CCOC1 IYUJKPDZTKPZFT-PXYINDEMSA-N 0.000 claims 1
- TVMPQPYQPJXNSK-GICMACPYSA-N 6-amino-9-[4-(2,2-dimethyloxan-4-yl)butyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC(C)(C)C1 TVMPQPYQPJXNSK-GICMACPYSA-N 0.000 claims 1
- TVMPQPYQPJXNSK-MLCCFXAWSA-N 6-amino-9-[4-(2,2-dimethyloxan-4-yl)butyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC(C)(C)C1 TVMPQPYQPJXNSK-MLCCFXAWSA-N 0.000 claims 1
- GCZGGKFBJGUHFA-PZORYLMUSA-N 6-amino-9-[4-(oxolan-3-yl)butyl]-2-[(2r)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@H](C)CCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC1 GCZGGKFBJGUHFA-PZORYLMUSA-N 0.000 claims 1
- GCZGGKFBJGUHFA-UEWDXFNNSA-N 6-amino-9-[4-(oxolan-3-yl)butyl]-2-[(2s)-pentan-2-yl]oxy-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCCCC1CCOC1 GCZGGKFBJGUHFA-UEWDXFNNSA-N 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 239000012646 vaccine adjuvant Substances 0.000 claims 1
- 229940124931 vaccine adjuvant Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89052307P | 2007-02-19 | 2007-02-19 | |
| US97231307P | 2007-09-14 | 2007-09-14 | |
| US2192108P | 2008-01-18 | 2008-01-18 | |
| PCT/EP2008/051832 WO2008101867A1 (en) | 2007-02-19 | 2008-02-15 | Purine derivatives as immunomodulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110115T1 true HRP20110115T1 (hr) | 2011-03-31 |
Family
ID=39473324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110115T HRP20110115T1 (hr) | 2007-02-19 | 2011-02-16 | Derivati purina kao imunomodulatori |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US7977344B2 (es) |
| EP (1) | EP2125792B1 (es) |
| JP (1) | JP2010519186A (es) |
| AR (1) | AR065372A1 (es) |
| AT (1) | ATE490249T1 (es) |
| CL (1) | CL2008000496A1 (es) |
| CY (1) | CY1111281T1 (es) |
| DE (1) | DE602008003764D1 (es) |
| DK (1) | DK2125792T3 (es) |
| HR (1) | HRP20110115T1 (es) |
| PL (1) | PL2125792T3 (es) |
| PT (1) | PT2125792E (es) |
| SI (1) | SI2125792T1 (es) |
| TW (1) | TW200843779A (es) |
| WO (1) | WO2008101867A1 (es) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0509258A8 (pt) * | 2004-03-26 | 2019-01-22 | Astrazeneca Ab | composto de 8-oxoadenina 9-substituída |
| WO2007034817A1 (ja) * | 2005-09-22 | 2007-03-29 | Dainippon Sumitomo Pharma Co., Ltd. | 新規アデニン化合物 |
| US7989459B2 (en) * | 2006-02-17 | 2011-08-02 | Pharmacopeia, Llc | Purinones and 1H-imidazopyridinones as PKC-theta inhibitors |
| US20090281075A1 (en) * | 2006-02-17 | 2009-11-12 | Pharmacopeia, Inc. | Isomeric purinones and 1h-imidazopyridinones as pkc-theta inhibitors |
| WO2008004948A1 (en) * | 2006-07-05 | 2008-01-10 | Astrazeneca Ab | 8-oxoadenine derivatives acting as modulators of tlr7 |
| TW200831105A (en) * | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| TW200843779A (en) * | 2007-02-19 | 2008-11-16 | Smithkline Beecham Corp | Compounds |
| ATE530549T1 (de) * | 2007-03-19 | 2011-11-15 | Astrazeneca Ab | 9-substituierte 8-oxoadeninverbindungen als modulatoren des toll-like-receptor (tlr7) |
| US8067413B2 (en) * | 2007-03-19 | 2011-11-29 | Astrazeneca Ab | 9-substituted-8-oxo-adenine compounds as toll-like receptor (TLR7 ) modulators |
| AR065784A1 (es) * | 2007-03-20 | 2009-07-01 | Dainippon Sumitomo Pharma Co | Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas. |
| WO2008114819A1 (ja) * | 2007-03-20 | 2008-09-25 | Dainippon Sumitomo Pharma Co., Ltd. | 新規アデニン化合物 |
| EP2155743B1 (en) * | 2007-05-08 | 2012-08-29 | AstraZeneca AB | Imidazoquinolines with immuno-modulating properties |
| PT2170888E (pt) * | 2007-06-29 | 2015-08-21 | Gilead Sciences Inc | Purina derivados e sua utilização como moduladores de recetor de tipo toll 7 |
| UY31531A1 (es) | 2007-12-17 | 2009-08-03 | Sales derivadas de 8-oxoadenina composiciones farmacéuticas que las contienen y su uso en terapia como moduladores de receptor tipo toll (tlr) | |
| JPWO2009091031A1 (ja) * | 2008-01-17 | 2011-05-26 | 大日本住友製薬株式会社 | アデニン化合物の製造方法 |
| EP2246353A4 (en) | 2008-01-17 | 2011-04-20 | Dainippon Sumitomo Pharma Co | PROCESS FOR PREPARING AN ADENINE COMPOUND |
| US8802684B2 (en) | 2008-08-11 | 2014-08-12 | Glaxosmithkline Llc | Adenine derivatives |
| PT2320905T (pt) * | 2008-08-11 | 2017-09-19 | Glaxosmithkline Llc | Novos derivados de adenina |
| WO2010018132A1 (en) * | 2008-08-11 | 2010-02-18 | Smithkline Beecham Corporation | Compounds |
| WO2010018130A1 (en) * | 2008-08-11 | 2010-02-18 | Smithkline Beecham Corporation | Purine derivatives for use in the treatment of allergic, inflammatory and infectious diseases |
| JP2011530562A (ja) * | 2008-08-11 | 2011-12-22 | グラクソスミスクライン エルエルシー | アレルギー性、炎症性及び感染性疾患治療用のプリン誘導体 |
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-
2008
- 2008-02-15 TW TW097105460A patent/TW200843779A/zh unknown
- 2008-02-15 AR ARP080100658A patent/AR065372A1/es not_active Application Discontinuation
- 2008-02-15 JP JP2009549421A patent/JP2010519186A/ja active Pending
- 2008-02-15 PT PT08716859T patent/PT2125792E/pt unknown
- 2008-02-15 PL PL08716859T patent/PL2125792T3/pl unknown
- 2008-02-15 DE DE602008003764T patent/DE602008003764D1/de active Active
- 2008-02-15 CL CL200800496A patent/CL2008000496A1/es unknown
- 2008-02-15 SI SI200830160T patent/SI2125792T1/sl unknown
- 2008-02-15 DK DK08716859.7T patent/DK2125792T3/da active
- 2008-02-15 US US12/031,764 patent/US7977344B2/en active Active
- 2008-02-15 US US12/527,820 patent/US20100120799A1/en not_active Abandoned
- 2008-02-15 AT AT08716859T patent/ATE490249T1/de active
- 2008-02-15 WO PCT/EP2008/051832 patent/WO2008101867A1/en active Application Filing
- 2008-02-15 EP EP08716859A patent/EP2125792B1/en active Active
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2011
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- 2011-06-07 US US13/154,818 patent/US20110269781A1/en not_active Abandoned
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2012
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| Publication number | Publication date |
|---|---|
| EP2125792B1 (en) | 2010-12-01 |
| WO2008101867A1 (en) | 2008-08-28 |
| SI2125792T1 (sl) | 2011-03-31 |
| ATE490249T1 (de) | 2010-12-15 |
| US20120283438A1 (en) | 2012-11-08 |
| PL2125792T3 (pl) | 2011-05-31 |
| DK2125792T3 (da) | 2011-03-07 |
| PT2125792E (pt) | 2011-03-01 |
| EP2125792A1 (en) | 2009-12-02 |
| DE602008003764D1 (de) | 2011-01-13 |
| US20100120799A1 (en) | 2010-05-13 |
| US7977344B2 (en) | 2011-07-12 |
| CL2008000496A1 (es) | 2008-09-22 |
| TW200843779A (en) | 2008-11-16 |
| AR065372A1 (es) | 2009-06-03 |
| JP2010519186A (ja) | 2010-06-03 |
| US20110269781A1 (en) | 2011-11-03 |
| US20090131458A1 (en) | 2009-05-21 |
| CY1111281T1 (el) | 2015-08-05 |
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