CA2340350A1 - Phenyl yanthine derivatives - Google Patents
Phenyl yanthine derivatives Download PDFInfo
- Publication number
- CA2340350A1 CA2340350A1 CA002340350A CA2340350A CA2340350A1 CA 2340350 A1 CA2340350 A1 CA 2340350A1 CA 002340350 A CA002340350 A CA 002340350A CA 2340350 A CA2340350 A CA 2340350A CA 2340350 A1 CA2340350 A1 CA 2340350A1
- Authority
- CA
- Canada
- Prior art keywords
- purin
- tetrahydro
- dioxo
- bis
- methyl ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 173
- 238000000034 method Methods 0.000 claims abstract description 64
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 208000026278 immune system disease Diseases 0.000 claims abstract description 14
- 230000004968 inflammatory condition Effects 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 229920000847 nonoxynol Polymers 0.000 claims description 117
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 115
- 235000013985 cinnamic acid Nutrition 0.000 claims description 115
- 229930016911 cinnamic acid Natural products 0.000 claims description 115
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 115
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 113
- WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 claims description 101
- -1 C1-12 Chemical group 0.000 claims description 98
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000001408 amides Chemical class 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 208000028169 periodontal disease Diseases 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- OXVWIJJNMKEUMZ-ZUQRMPMESA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC2CCCCC2)C(=O)N2CC3CCCCC3)=O)=C2N1 OXVWIJJNMKEUMZ-ZUQRMPMESA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 108010067225 Cell Adhesion Molecules Proteins 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 208000035473 Communicable disease Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- DNMZJIGSDQVGSA-UHFFFAOYSA-N methoxymethane;hydrochloride Chemical compound Cl.COC DNMZJIGSDQVGSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- ATEQPBZVVKMNFL-FLNCGGNMSA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-7-(2-methylprop-2-enyl)-2,6-dioxopurin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.O=C1N(CC2CCCCC2)C(=O)C=2N(CC(=C)C)C(C=3C=CC(\C=C\C(O)=O)=CC=3)=NC=2N1CC1CCCCC1 ATEQPBZVVKMNFL-FLNCGGNMSA-N 0.000 claims description 4
- UGFQRWMESNXYQT-KLSJZZFUSA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-7-(3-morpholin-4-ylpropyl)-2,6-dioxopurin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)CCCN1CCOCC1)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O UGFQRWMESNXYQT-KLSJZZFUSA-N 0.000 claims description 4
- LERWZBXJAOSNBN-DTQAZKPQSA-N (e)-3-[4-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7h-purin-8-yl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC2CCCCC2)C(=O)N2CC3CCCCC3)=O)=C2N1 LERWZBXJAOSNBN-DTQAZKPQSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- CNGGDAGBSQGQJU-UHFFFAOYSA-N 8-[4-(aminomethyl)phenyl]-1,3-bis(cyclohexylmethyl)-7h-purine-2,6-dione Chemical compound C1=CC(CN)=CC=C1C1=NC(C(N(CC2CCCCC2)C(=O)N2CC3CCCCC3)=O)=C2N1 CNGGDAGBSQGQJU-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 230000008506 pathogenesis Effects 0.000 claims description 4
- ZHTRGSHEPHAUHM-WPDLWGESSA-N (E)-3-[3-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.OC(=O)\C=C\C1=CC=CC(C=2NC3=C(C(N(CC4CCCCC4)C(=O)N3CC3CCCCC3)=O)N=2)=C1 ZHTRGSHEPHAUHM-WPDLWGESSA-N 0.000 claims description 3
- ACGQHWSXTHERRV-OAZHBLANSA-N (E)-3-[4-[1,3-bis(2-bicyclo[2.2.1]heptanylmethyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC2C3CCC(C3)C2)C(=O)N2CC3C4CCC(C4)C3)=O)=C2N1 ACGQHWSXTHERRV-OAZHBLANSA-N 0.000 claims description 3
- ZBIJJUUYDGLZEB-ZUQRMPMESA-N (E)-3-[4-[1,3-bis(2-cyclohexylethyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CCN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CCC1CCCCC1)=O ZBIJJUUYDGLZEB-ZUQRMPMESA-N 0.000 claims description 3
- MDKAVMDZSXHFFF-HCUGZAAXSA-N (E)-3-[4-[1,3-bis(2-methylpropyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.CC(CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CC(C)C)=O)C MDKAVMDZSXHFFF-HCUGZAAXSA-N 0.000 claims description 3
- VDMRAQAKUUUKET-FLNCGGNMSA-N (E)-3-[4-[1,3-bis(cycloheptylmethyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCCC1)=O VDMRAQAKUUUKET-FLNCGGNMSA-N 0.000 claims description 3
- IALGNTFRVIHOSL-FLNCGGNMSA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7-prop-2-ynylpurin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C(N1CC#C)=NC2=C1C(=O)N(CC1CCCCC1)C(=O)N2CC1CCCCC1 IALGNTFRVIHOSL-FLNCGGNMSA-N 0.000 claims description 3
- HLPJNSYWIJBWEJ-GOSREXKOSA-N (E)-3-[4-[7-benzyl-1,3-bis(cyclohexylmethyl)-2,6-dioxopurin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C(N1CC=2C=CC=CC=2)=NC2=C1C(=O)N(CC1CCCCC1)C(=O)N2CC1CCCCC1 HLPJNSYWIJBWEJ-GOSREXKOSA-N 0.000 claims description 3
- RRYZDZAZAKEOCI-UHFFFAOYSA-N 1,3-bis(cyclohexylmethyl)-8-[3-[2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethyl]phenyl]-7h-purine-2,6-dione Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC(C=2NC=3C(=O)N(CC4CCCCC4)C(=O)N(CC4CCCCC4)C=3N=2)=C1 RRYZDZAZAKEOCI-UHFFFAOYSA-N 0.000 claims description 3
- PPYQHXUMMPHXFC-UHFFFAOYSA-N 1,3-bis(cyclohexylmethyl)-8-[4-[2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethyl]phenyl]-7h-purine-2,6-dione Chemical compound C1=CC(COCCOCCOCCOCCOCCOCCOCCOCCOCCOC)=CC=C1C(N1)=NC2=C1C(=O)N(CC1CCCCC1)C(=O)N2CC1CCCCC1 PPYQHXUMMPHXFC-UHFFFAOYSA-N 0.000 claims description 3
- YCWPSAYEVQPQTA-NBYYMMLRSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C(CC)C1CC(CCC1)CN1C(NC=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C(CC)C1CC(CCC1)CN1C(NC=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)=O YCWPSAYEVQPQTA-NBYYMMLRSA-N 0.000 claims description 3
- OESFJCZLLCTOJF-UHFFFAOYSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)CC1=CC=CC=C1)C1=CC=C(C(=O)O)C=C1)CC1CCCCC1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)CC1=CC=CC=C1)C1=CC=C(C(=O)O)C=C1)CC1CCCCC1)=O OESFJCZLLCTOJF-UHFFFAOYSA-N 0.000 claims description 3
- CTADGRFDLKZNKA-ZUQRMPMESA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C(N1CC#N)=NC2=C1C(=O)N(CC1CCCCC1)C(=O)N2CC1CCCCC1 Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C(N1CC#N)=NC2=C1C(=O)N(CC1CCCCC1)C(=O)N2CC1CCCCC1 CTADGRFDLKZNKA-ZUQRMPMESA-N 0.000 claims description 3
- CLUAKXQDMMMMOS-JHGYPSGKSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC2CCCC2)C(=O)N2CC3CCCC3)=O)=C2N1 Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC2CCCC2)C(=O)N2CC3CCCC3)=O)=C2N1 CLUAKXQDMMMMOS-JHGYPSGKSA-N 0.000 claims description 3
- QCUBNJRDIIZPEL-ZUQRMPMESA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC=2C=CC=CC=2)C(=O)N2CC=3C=CC=CC=3)=O)=C2N1 Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CC=2C=CC=CC=2)C(=O)N2CC=3C=CC=CC=3)=O)=C2N1 QCUBNJRDIIZPEL-ZUQRMPMESA-N 0.000 claims description 3
- JOHVQYKKMGGVMA-ZUQRMPMESA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CCC=2C=CC=CC=2)C(=O)N2CCC=3C=CC=CC=3)=O)=C2N1 Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1=CC(/C=C/C(=O)O)=CC=C1C1=NC(C(N(CCC=2C=CC=CC=2)C(=O)N2CCC=3C=CC=CC=3)=O)=C2N1 JOHVQYKKMGGVMA-ZUQRMPMESA-N 0.000 claims description 3
- XBROICKYXLMJHU-FJUODKGNSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.FC1=CC=C(CN2C(N(C=3NC(=NC3C2=O)C2=CC=C(/C=C/C(=O)O)C=C2)CC2=CC=C(C=C2)F)=O)C=C1 Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.FC1=CC=C(CN2C(N(C=3NC(=NC3C2=O)C2=CC=C(/C=C/C(=O)O)C=C2)CC2=CC=C(C=C2)F)=O)C=C1 XBROICKYXLMJHU-FJUODKGNSA-N 0.000 claims description 3
- SRPKLPVNEDFBCF-GOSREXKOSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.c1cc(/C=C/C(=O)O)ccc1-c1nc2n(CC3CCCCC3)c(=O)n(CC3CCCCC3)c(=O)c2n1CC(=O)c1ccccc1 Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.c1cc(/C=C/C(=O)O)ccc1-c1nc2n(CC3CCCCC3)c(=O)n(CC3CCCCC3)c(=O)c2n1CC(=O)c1ccccc1 SRPKLPVNEDFBCF-GOSREXKOSA-N 0.000 claims description 3
- DBASZNTZKLRXSI-ZUQRMPMESA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O DBASZNTZKLRXSI-ZUQRMPMESA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 208000037816 tissue injury Diseases 0.000 claims description 3
- LKZNIQKJUAZOJG-KLSJZZFUSA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-7-methyl-2,6-dioxopurin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCO.O=C1N(CC2CCCCC2)C(=O)C=2N(C)C(C=3C=CC(\C=C\C(O)=O)=CC=3)=NC=2N1CC1CCCCC1 LKZNIQKJUAZOJG-KLSJZZFUSA-N 0.000 claims description 2
- VJDJXZZZVCRNQB-HCUGZAAXSA-N (E)-3-[4-[1,3-bis(cyclopropylmethyl)-2,6-dioxo-7H-purin-8-yl]phenyl]prop-2-enoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CC1)=O VJDJXZZZVCRNQB-HCUGZAAXSA-N 0.000 claims description 2
- IJVFPDHKTFXORE-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol propanoic acid Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C(CC)(=O)O IJVFPDHKTFXORE-UHFFFAOYSA-N 0.000 claims description 2
- ZWIOCMDKOKPNBC-UHFFFAOYSA-N 4-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7H-purin-8-yl]benzoic acid 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(C(=O)O)C=C1)CC1CCCCC1)=O ZWIOCMDKOKPNBC-UHFFFAOYSA-N 0.000 claims description 2
- JIWOCBLHVIQNPZ-NBYYMMLRSA-N COCCOCCOCCOCCOCCOCCOCCO.C1CC(CCC1)CN1C(NC=2N=C(N(C2C1=O)C)C1=CC=C(/C=C/C(=O)O)C=C1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCO.C1CC(CCC1)CN1C(NC=2N=C(N(C2C1=O)C)C1=CC=C(/C=C/C(=O)O)C=C1)=O JIWOCBLHVIQNPZ-NBYYMMLRSA-N 0.000 claims description 2
- BFMYHGHIDJNQAX-ZUQRMPMESA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)N1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)C1CCCCC1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)N1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)C1CCCCC1)=O BFMYHGHIDJNQAX-ZUQRMPMESA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
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Classifications
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- 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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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)
- Oncology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9817623.3A GB9817623D0 (en) | 1998-08-13 | 1998-08-13 | Pharmaceutical compounds |
| GB9817623.3 | 1998-08-13 | ||
| PCT/EP1999/005814 WO2000009507A1 (en) | 1998-08-13 | 1999-08-11 | Phenyl yanthine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2340350A1 true CA2340350A1 (en) | 2000-02-24 |
Family
ID=10837179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002340350A Abandoned CA2340350A1 (en) | 1998-08-13 | 1999-08-11 | Phenyl yanthine derivatives |
Country Status (36)
| Country | Link |
|---|---|
| US (3) | US6608069B1 (OSRAM) |
| EP (1) | EP1104422B1 (OSRAM) |
| JP (3) | JP3631961B2 (OSRAM) |
| KR (1) | KR20010085369A (OSRAM) |
| CN (2) | CN1251676C (OSRAM) |
| AP (1) | AP1408A (OSRAM) |
| AR (1) | AR020154A1 (OSRAM) |
| AT (1) | ATE259810T1 (OSRAM) |
| AU (1) | AU775819B2 (OSRAM) |
| BR (1) | BR9913020A (OSRAM) |
| CA (1) | CA2340350A1 (OSRAM) |
| CO (1) | CO5130007A1 (OSRAM) |
| DE (1) | DE69914921T2 (OSRAM) |
| DK (1) | DK1104422T3 (OSRAM) |
| EA (1) | EA004139B1 (OSRAM) |
| EE (1) | EE04721B1 (OSRAM) |
| ES (1) | ES2215399T3 (OSRAM) |
| GB (1) | GB9817623D0 (OSRAM) |
| HU (1) | HUP0103637A3 (OSRAM) |
| ID (1) | ID28723A (OSRAM) |
| IL (1) | IL141318A0 (OSRAM) |
| IS (1) | IS5843A (OSRAM) |
| MA (1) | MA26673A1 (OSRAM) |
| MY (1) | MY133393A (OSRAM) |
| NO (1) | NO20010715L (OSRAM) |
| NZ (1) | NZ509778A (OSRAM) |
| PE (1) | PE20000952A1 (OSRAM) |
| PL (1) | PL346055A1 (OSRAM) |
| PT (1) | PT1104422E (OSRAM) |
| SI (1) | SI1104422T1 (OSRAM) |
| SK (1) | SK2222001A3 (OSRAM) |
| TR (1) | TR200100448T2 (OSRAM) |
| TW (1) | TWI224598B (OSRAM) |
| WO (1) | WO2000009507A1 (OSRAM) |
| YU (1) | YU11601A (OSRAM) |
| ZA (1) | ZA200101186B (OSRAM) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9703044D0 (en) | 1997-02-14 | 1997-04-02 | Glaxo Group Ltd | Phenyl xanthine esters and amides |
| GB9817623D0 (en) | 1998-08-13 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| AU2002248910A1 (en) * | 2000-11-17 | 2002-05-27 | Idenix (Cayman) Limited | Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4-oxopyrmidines |
| JP2004523559A (ja) * | 2001-02-28 | 2004-08-05 | スミスクライン ビーチャム コーポレーション | 過敏性腸症候群および機能性胃腸症の治療方法 |
| EP1418882A1 (en) | 2001-08-24 | 2004-05-19 | Unilever N.V. | Oral composition comprising an alkylhydroxybenzoate |
| CN100467469C (zh) | 2001-11-09 | 2009-03-11 | Cv医药有限公司 | A2b腺苷受体拮抗剂 |
| US7125993B2 (en) | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
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