ZA200101186B - Phenyl xanthine derivatives. - Google Patents
Phenyl xanthine derivatives. Download PDFInfo
- Publication number
- ZA200101186B ZA200101186B ZA200101186A ZA200101186A ZA200101186B ZA 200101186 B ZA200101186 B ZA 200101186B ZA 200101186 A ZA200101186 A ZA 200101186A ZA 200101186 A ZA200101186 A ZA 200101186A ZA 200101186 B ZA200101186 B ZA 200101186B
- Authority
- ZA
- South Africa
- Prior art keywords
- purin
- dioxo
- bis
- tetrahydro
- methyl ether
- Prior art date
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- ACCCXSZCOGNLFL-UHFFFAOYSA-N 8-phenyl-3,7-dihydropurine-2,6-dione Chemical class N1C=2C(=O)NC(=O)NC=2N=C1C1=CC=CC=C1 ACCCXSZCOGNLFL-UHFFFAOYSA-N 0.000 title description 2
- 229920000847 nonoxynol Polymers 0.000 claims description 155
- 150000001875 compounds Chemical class 0.000 claims description 142
- 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 132
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 127
- 235000013985 cinnamic acid Nutrition 0.000 claims description 127
- 229930016911 cinnamic acid Natural products 0.000 claims description 127
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 127
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 125
- 239000000203 mixture Substances 0.000 claims description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 54
- -1 said cycloalky! Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 29
- 150000001408 amides Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 208000028169 periodontal disease Diseases 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000004544 purin-8-yl group Chemical group N1=CN=C2N=C(NC2=C1)* 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 208000026278 immune system disease Diseases 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 230000004968 inflammatory condition Effects 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 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 10
- 201000010099 disease Diseases 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 108010067225 Cell Adhesion Molecules Proteins 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 208000035473 Communicable disease Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 4
- XAHJEPPRQOCLMF-KLSJZZFUSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)C)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)C)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O XAHJEPPRQOCLMF-KLSJZZFUSA-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 class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000008506 pathogenesis Effects 0.000 claims description 4
- 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
- OJCFEGKCRWEVSN-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCO OJCFEGKCRWEVSN-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
- 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
- YSTGKSQLLQVZGV-NBYYMMLRSA-N (E)-3-[4-[1,3-bis(cyclobutylmethyl)-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(CC2CCC2)C(=O)N2CC3CCC3)=O)=C2N1 YSTGKSQLLQVZGV-NBYYMMLRSA-N 0.000 claims description 2
- 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 2
- PHPTYNIVTRERGL-CCEZHUSRSA-N (e)-3-[3-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7h-purin-8-yl]phenyl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C=2NC3=C(C(N(CC4CCCCC4)C(=O)N3CC3CCCCC3)=O)N=2)=C1 PHPTYNIVTRERGL-CCEZHUSRSA-N 0.000 claims description 2
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-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
- 208000015181 infectious disease Diseases 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
- 208000037816 tissue injury Diseases 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 21
- 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 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 3
- 102000008395 cell adhesion mediator activity proteins Human genes 0.000 claims 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 2
- YZFOJTPUQQCGBO-FLNCGGNMSA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-7-ethyl-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=3C=CC(\C=C\C(O)=O)=CC=3)=NC=2N1CC1CCCCC1 YZFOJTPUQQCGBO-FLNCGGNMSA-N 0.000 claims 2
- 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 2
- AGWKUHGLWHMYTG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCO AGWKUHGLWHMYTG-UHFFFAOYSA-N 0.000 claims 2
- PQYIFXMUYXVPMV-FLNCGGNMSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)CC(=O)OCC)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)CC(=O)OCC)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O PQYIFXMUYXVPMV-FLNCGGNMSA-N 0.000 claims 2
- DNMZJIGSDQVGSA-UHFFFAOYSA-N methoxymethane;hydrochloride Chemical compound Cl.COC DNMZJIGSDQVGSA-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- AEAYZIMASHXPSM-FLNCGGNMSA-N (E)-3-[4-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7-propylpurin-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)CCC)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O AEAYZIMASHXPSM-FLNCGGNMSA-N 0.000 claims 1
- LVQICOYOIOOCLP-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-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound C(CCCCCCCCCCC)OCCOCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O LVQICOYOIOOCLP-ZUQRMPMESA-N 0.000 claims 1
- ZEROKSIPULJJLY-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-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCO.C1(CCCCC1)CN1C(N(C=2N=C(N(C2C1=O)C)C1=CC=C(/C=C/C(=O)O)C=C1)CC1CCCCC1)=O ZEROKSIPULJJLY-KLSJZZFUSA-N 0.000 claims 1
- 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 1
- MIAAVIRGNXXYRD-NBYYMMLRSA-N (E)-3-[4-[1-(cyclohexylmethyl)-7-methyl-2,6-dioxo-3H-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.C1CC(CCC1)CN1C(NC=2N=C(N(C2C1=O)C)C1=CC=C(/C=C/C(=O)O)C=C1)=O MIAAVIRGNXXYRD-NBYYMMLRSA-N 0.000 claims 1
- UTMCXVIPFWOWAG-UNGNXWFZSA-N (E)-3-[5-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7H-purin-8-yl]thiophen-2-yl]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(NC2C1=O)C1=CC=C(S1)/C=C/C(=O)O)CC1CCCCC1)=O UTMCXVIPFWOWAG-UNGNXWFZSA-N 0.000 claims 1
- 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 1
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- 208000017520 skin disease Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 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
- C07D473/04—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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9817623.3A GB9817623D0 (en) | 1998-08-13 | 1998-08-13 | Pharmaceutical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200101186B true ZA200101186B (en) | 2002-02-12 |
Family
ID=10837179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200101186A ZA200101186B (en) | 1998-08-13 | 2001-02-12 | Phenyl xanthine derivatives. |
Country Status (37)
| Country | Link |
|---|---|
| US (3) | US6608069B1 (ja) |
| EP (1) | EP1104422B1 (ja) |
| JP (3) | JP3631961B2 (ja) |
| KR (1) | KR20010085369A (ja) |
| CN (2) | CN1251676C (ja) |
| AP (1) | AP1408A (ja) |
| AR (1) | AR020154A1 (ja) |
| AT (1) | ATE259810T1 (ja) |
| AU (1) | AU775819B2 (ja) |
| BR (1) | BR9913020A (ja) |
| CA (1) | CA2340350A1 (ja) |
| CO (1) | CO5130007A1 (ja) |
| DE (1) | DE69914921T2 (ja) |
| DK (1) | DK1104422T3 (ja) |
| EA (1) | EA004139B1 (ja) |
| EE (1) | EE04721B1 (ja) |
| ES (1) | ES2215399T3 (ja) |
| GB (1) | GB9817623D0 (ja) |
| HK (1) | HK1035195A1 (ja) |
| HU (1) | HUP0103637A3 (ja) |
| ID (1) | ID28723A (ja) |
| IL (1) | IL141318A0 (ja) |
| IS (1) | IS5843A (ja) |
| MA (1) | MA26673A1 (ja) |
| MY (1) | MY133393A (ja) |
| NO (1) | NO20010715L (ja) |
| NZ (1) | NZ509778A (ja) |
| PE (1) | PE20000952A1 (ja) |
| PL (1) | PL346055A1 (ja) |
| PT (1) | PT1104422E (ja) |
| SI (1) | SI1104422T1 (ja) |
| SK (1) | SK2222001A3 (ja) |
| TR (1) | TR200100448T2 (ja) |
| TW (1) | TWI224598B (ja) |
| WO (1) | WO2000009507A1 (ja) |
| YU (1) | YU11601A (ja) |
| ZA (1) | ZA200101186B (ja) |
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 |
| US6545007B2 (en) * | 2000-11-17 | 2003-04-08 | Idenix (Cayman) Limited | Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4-oxopyrimidines |
| WO2002067942A2 (en) * | 2001-02-28 | 2002-09-06 | Smithkline Beecham Corporation | Methods of treating irritable bowel syndrome and functional dyspepsia |
| WO2003017964A1 (en) | 2001-08-24 | 2003-03-06 | Unilever N.V. | Oral composition comprising an alkylhydroxybenzoate |
| US6977300B2 (en) | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US7125993B2 (en) | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| IL161867A0 (en) | 2001-11-09 | 2005-11-20 | Cv Therapeutics Inc | A2b adenosine receptor antagonists |
| US7317017B2 (en) | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US20040072848A1 (en) * | 2002-02-26 | 2004-04-15 | Huber Brian E | Methods of treating irritable bowel syndrome and functional dyspepsia |
| EP1521584A1 (en) | 2002-06-17 | 2005-04-13 | Glaxo Group Limited | Purine derivatives as liver x receptor agonists |
| CN1894250B (zh) * | 2003-08-25 | 2010-06-09 | PGx健康有限责任公司 | 取代的8-杂芳基黄嘌呤 |
| GB0324086D0 (en) * | 2003-10-14 | 2003-11-19 | Glaxo Group Ltd | Process for preparing a co-precipitate of a non-crystalline solid drug substance |
| WO2006004903A2 (en) * | 2004-06-28 | 2006-01-12 | Atherogenics, Inc. | 1,2-bis-(substituted-phenyl)-2-propen-1-ones and pharmaceutical compositions thereof |
| WO2006091898A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyrazolyl substituted xanthines |
| WO2006091936A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| US7884100B2 (en) * | 2006-06-16 | 2011-02-08 | Pgxhealth, Llc | Substituted 8-[6-amino-3-pyridyl]xanthines |
| US20120108614A1 (en) * | 2008-05-14 | 2012-05-03 | Chong Jayhong A | Compounds and compositions for treating chemical warfare agent-induced injuries |
| US8318728B2 (en) | 2008-05-14 | 2012-11-27 | Hydra Biosciences, Inc. | Compounds and compositions for treating chemical warfare agent-induced injuries |
| WO2009140517A1 (en) | 2008-05-14 | 2009-11-19 | Hydra Biosciences, Inc. | Compounds and compositions for treating chemical warfare agent-induced injuries |
| JP2011521968A (ja) * | 2008-05-30 | 2011-07-28 | ジェネンテック， インコーポレイテッド | プリンｐｉ３ｋ阻害剤化合物および使用方法 |
| CN102260260B (zh) * | 2010-05-24 | 2014-08-06 | 中国科学院上海药物研究所 | 8-苯基黄嘌呤类化合物、其制备方法、包含该化合物的药物组合物及其用途 |
| CN102993203B (zh) * | 2011-09-09 | 2015-11-25 | 温州医学院 | 8-苯基黄嘌呤类衍生物的制备及应用 |
| US9502952B2 (en) | 2012-10-12 | 2016-11-22 | Persimmon Technologies, Corp. | Hybrid motor |
| AU2014262546B2 (en) | 2013-05-10 | 2018-11-08 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| CN105358154A (zh) | 2013-05-10 | 2016-02-24 | 尼普斯阿波罗有限公司 | Acc抑制剂和其用途 |
| BR112015028214A2 (pt) | 2013-05-10 | 2017-07-25 | Nimbus Apollo Inc | inibidores de acc e usos dos mesmos |
| JP6417401B2 (ja) * | 2013-05-10 | 2018-11-07 | ギリアド アポロ， エルエルシー | Ａｃｃ阻害剤及びその使用 |
| WO2024133605A1 (en) | 2022-12-20 | 2024-06-27 | Invios Gmbh | Substituted 3,7-dihydro-1 h-purine-2,6-diones and use thereof |
| EP4389749A1 (en) * | 2022-12-20 | 2024-06-26 | invIOs GmbH | Substituted 3,7-dihydro-1h-purine-2,6-diones and use thereof |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442125A (en) * | 1978-06-26 | 1984-04-10 | Oxford Hill, Ltd. | Process for detaching or preventing attachment of microorganisms to a surface |
| GB8510758D0 (en) | 1985-04-27 | 1985-06-05 | Wellcome Found | Compounds |
| US4968672A (en) * | 1987-01-02 | 1990-11-06 | The United States Of America As Represented By The Department Of Health And Human Services | Adenosine receptor prodrugs |
| US5015647A (en) | 1987-04-24 | 1991-05-14 | Burroughs Wellcome Co. | Method for treating viral infections |
| GB8826595D0 (en) | 1988-11-14 | 1988-12-21 | Beecham Wuelfing Gmbh & Co Kg | Active compounds |
| GB8906792D0 (en) | 1989-03-23 | 1989-05-10 | Beecham Wuelfing Gmbh & Co Kg | Treatment and compounds |
| IL100088A (en) | 1990-11-21 | 1995-07-31 | Smithkline Beecham Corp | FNT inhibitor preparations containing histogenic transducts converted at positions 1, 3, and 8 |
| GB9210839D0 (en) | 1992-05-21 | 1992-07-08 | Smithkline Beecham Plc | Novel compounds |
| TW252044B (ja) | 1992-08-10 | 1995-07-21 | Boehringer Ingelheim Kg | |
| JP2613355B2 (ja) | 1992-09-28 | 1997-05-28 | 協和醗酵工業株式会社 | パーキンソン氏病治療剤 |
| CA2176237A1 (en) * | 1993-11-10 | 1995-05-18 | Richard P. Darveau | Treatment of bacterially-induced inflammatory diseases |
| US5395831A (en) | 1994-04-08 | 1995-03-07 | American Home Products Corporation | Treating cardiac disorders with Δ9(11)-dehydro-8-isoestrone |
| GB9415529D0 (en) | 1994-08-01 | 1994-09-21 | Wellcome Found | Phenyl xanthine derivatives |
| DE19535504A1 (de) | 1995-09-25 | 1997-03-27 | Bayer Ag | Substituierte Xanthine |
| WO1997034616A1 (en) | 1996-03-18 | 1997-09-25 | Medical Science Systems, Inc. | A method for periodontal disease treatment |
| ATE226583T1 (de) | 1996-06-07 | 2002-11-15 | Hoechst Ag | Verwendung von theophyllinderivaten zur behandlung und propylaxe von schockzuständen, neue xanthinverbindungen und verfahren zu deren herstellung |
| GB9703044D0 (en) * | 1997-02-14 | 1997-04-02 | Glaxo Group Ltd | Phenyl xanthine esters and amides |
| US6096707A (en) * | 1997-07-11 | 2000-08-01 | Biotie Therapies Ltd. | Integrin binding peptide and use thereof |
| US6117878A (en) * | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| AU2640999A (en) | 1998-02-26 | 1999-09-15 | Zenyaku Kogyo Kabushiki Kaisha | 1-azaindolizine derivatives |
| GB9817623D0 (en) | 1998-08-13 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| JP2003523958A (ja) | 1999-12-23 | 2003-08-12 | ニトロメド インコーポレーテッド | ニトロソ化およびニトロシル化されたシクロオキシゲナーゼ−２の阻害剤、組成物ならびに使用法 |
| US20020006915A1 (en) * | 2000-02-15 | 2002-01-17 | Mack Strong Vivian E. | Use of COX-2 inhibitors to treat sepsis, complications thereof, and EP receptor modulation |
| US6751206B1 (en) | 2000-06-29 | 2004-06-15 | Qualcomm Incorporated | Method and apparatus for beam switching in a wireless communication system |
-
1998
- 1998-08-13 GB GBGB9817623.3A patent/GB9817623D0/en not_active Ceased
-
1999
- 1999-08-10 CO CO99050691A patent/CO5130007A1/es unknown
- 1999-08-10 AR ARP990103999A patent/AR020154A1/es not_active Application Discontinuation
- 1999-08-11 SI SI9930545T patent/SI1104422T1/xx unknown
- 1999-08-11 HU HU0103637A patent/HUP0103637A3/hu unknown
- 1999-08-11 WO PCT/EP1999/005814 patent/WO2000009507A1/en active IP Right Grant
- 1999-08-11 AP APAP/P/2001/002071A patent/AP1408A/en active
- 1999-08-11 DK DK99944358T patent/DK1104422T3/da active
- 1999-08-11 BR BR9913020-3A patent/BR9913020A/pt not_active IP Right Cessation
- 1999-08-11 CN CNB031104673A patent/CN1251676C/zh not_active Expired - Fee Related
- 1999-08-11 EE EEP200100083A patent/EE04721B1/xx not_active IP Right Cessation
- 1999-08-11 PE PE1999000814A patent/PE20000952A1/es not_active Application Discontinuation
- 1999-08-11 PL PL99346055A patent/PL346055A1/xx not_active Application Discontinuation
- 1999-08-11 TR TR2001/00448T patent/TR200100448T2/xx unknown
- 1999-08-11 MY MYPI99003429A patent/MY133393A/en unknown
- 1999-08-11 MA MA25728A patent/MA26673A1/fr unknown
- 1999-08-11 CA CA002340350A patent/CA2340350A1/en not_active Abandoned
- 1999-08-11 DE DE69914921T patent/DE69914921T2/de not_active Expired - Fee Related
- 1999-08-11 KR KR1020017001799A patent/KR20010085369A/ko active IP Right Grant
- 1999-08-11 US US09/762,559 patent/US6608069B1/en not_active Expired - Fee Related
- 1999-08-11 YU YU11601A patent/YU11601A/sh unknown
- 1999-08-11 EP EP99944358A patent/EP1104422B1/en not_active Expired - Lifetime
- 1999-08-11 ES ES99944358T patent/ES2215399T3/es not_active Expired - Lifetime
- 1999-08-11 SK SK222-2001A patent/SK2222001A3/sk unknown
- 1999-08-11 PT PT99944358T patent/PT1104422E/pt unknown
- 1999-08-11 AU AU57323/99A patent/AU775819B2/en not_active Ceased
- 1999-08-11 JP JP2000564958A patent/JP3631961B2/ja not_active Expired - Fee Related
- 1999-08-11 CN CNB998119695A patent/CN1149215C/zh not_active Expired - Fee Related
- 1999-08-11 NZ NZ509778A patent/NZ509778A/en unknown
- 1999-08-11 ID IDW20010591A patent/ID28723A/id unknown
- 1999-08-11 IL IL14131899A patent/IL141318A0/xx unknown
- 1999-08-11 AT AT99944358T patent/ATE259810T1/de not_active IP Right Cessation
- 1999-08-11 EA EA200100127A patent/EA004139B1/ru unknown
- 1999-08-12 TW TW088113815A patent/TWI224598B/zh not_active IP Right Cessation
-
2001
- 2001-02-09 IS IS5843A patent/IS5843A/is unknown
- 2001-02-12 NO NO20010715A patent/NO20010715L/no not_active Application Discontinuation
- 2001-02-12 ZA ZA200101186A patent/ZA200101186B/en unknown
- 2001-08-22 HK HK01105939A patent/HK1035195A1/xx not_active IP Right Cessation
-
2002
- 2002-03-26 US US10/106,772 patent/US6770267B2/en not_active Expired - Fee Related
-
2003
- 2003-02-03 US US10/357,751 patent/US20040034020A1/en not_active Abandoned
- 2003-06-09 JP JP2003164252A patent/JP2004137251A/ja not_active Withdrawn
- 2003-11-25 JP JP2003394308A patent/JP2004115534A/ja active Pending
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