ES2215399T3 - Derivados de fenilxantina. - Google Patents
Derivados de fenilxantina.Info
- Publication number
- ES2215399T3 ES2215399T3 ES99944358T ES99944358T ES2215399T3 ES 2215399 T3 ES2215399 T3 ES 2215399T3 ES 99944358 T ES99944358 T ES 99944358T ES 99944358 T ES99944358 T ES 99944358T ES 2215399 T3 ES2215399 T3 ES 2215399T3
- Authority
- ES
- Spain
- Prior art keywords
- purin
- tetrahydro
- dioxo
- bis
- cinnamic
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 179
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 53
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 259
- -1 1,3-bis (benzyl) -1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl Chemical group 0.000 claims description 243
- 229920000847 nonoxynol Polymers 0.000 claims description 222
- 239000002253 acid Substances 0.000 claims description 215
- 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 213
- 150000002148 esters Chemical class 0.000 claims description 193
- 150000001408 amides Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 45
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 44
- 238000011282 treatment Methods 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 208000028169 periodontal disease Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 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 12
- 210000000265 leukocyte Anatomy 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 11
- 230000004968 inflammatory condition Effects 0.000 claims description 11
- 208000026278 immune system disease Diseases 0.000 claims description 10
- 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 description 9
- 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 9
- 201000010099 disease Diseases 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000021164 cell adhesion Effects 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 4
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 230000003902 lesion Effects 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- 206010061216 Infarction Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000007574 infarction Effects 0.000 claims description 3
- 230000008595 infiltration Effects 0.000 claims description 3
- 238000001764 infiltration Methods 0.000 claims description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
- 230000008506 pathogenesis Effects 0.000 claims description 3
- SLNYBUIEAMRFSZ-UHFFFAOYSA-N 2-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol Chemical compound COCCOCCOCCOCCOCCO SLNYBUIEAMRFSZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- CYJDTNVCSIRSSO-UHFFFAOYSA-N Cl.C1(CCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(CN)C=C1)CC1CCCCC1)=O Chemical compound Cl.C1(CCCCC1)CN1C(N(C=2NC(=NC2C1=O)C1=CC=C(CN)C=C1)CC1CCCCC1)=O CYJDTNVCSIRSSO-UHFFFAOYSA-N 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 206010010741 Conjunctivitis Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- 206010012742 Diarrhoea infectious Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 2
- 206010028116 Mucosal inflammation Diseases 0.000 claims description 2
- 201000010927 Mucositis Diseases 0.000 claims description 2
- 206010030216 Oesophagitis Diseases 0.000 claims description 2
- 206010035664 Pneumonia Diseases 0.000 claims description 2
- 206010036774 Proctitis Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 206010046851 Uveitis Diseases 0.000 claims description 2
- 230000004075 alteration Effects 0.000 claims description 2
- 206010006451 bronchitis Diseases 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
- 238000002512 chemotherapy Methods 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
- 208000006881 esophagitis 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
- 201000008482 osteoarthritis Diseases 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
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 208000001848 dysentery Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 230000003903 intestinal lesions Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 79
- 239000000203 mixture Substances 0.000 description 76
- 238000005160 1H NMR spectroscopy Methods 0.000 description 42
- 239000007787 solid Substances 0.000 description 40
- 238000009472 formulation Methods 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 26
- 239000004480 active ingredient Substances 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- 239000000843 powder Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000003039 volatile agent Substances 0.000 description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- GPTPPLBWOXHYIO-UHFFFAOYSA-N 5,6-diamino-1,3-bis(cyclohexylmethyl)pyrimidine-2,4-dione Chemical compound O=C1N(CC2CCCCC2)C(N)=C(N)C(=O)N1CC1CCCCC1 GPTPPLBWOXHYIO-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
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- 239000000463 material Substances 0.000 description 9
- VVHAVLIDQNWEKF-UHFFFAOYSA-N nonaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO VVHAVLIDQNWEKF-UHFFFAOYSA-N 0.000 description 9
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- 238000003756 stirring Methods 0.000 description 9
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- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 7
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- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229940044519 poloxamer 188 Drugs 0.000 description 1
- 229950005134 polycarbophil Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- VILMUCRZVVVJCA-UHFFFAOYSA-M sodium glycolate Chemical compound [Na+].OCC([O-])=O VILMUCRZVVVJCA-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 238000010561 standard procedure 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000011593 sulfur 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
- 239000007916 tablet composition Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 238000011200 topical administration Methods 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9817623 | 1998-08-13 | ||
| GBGB9817623.3A GB9817623D0 (en) | 1998-08-13 | 1998-08-13 | Pharmaceutical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2215399T3 true ES2215399T3 (es) | 2004-10-01 |
Family
ID=10837179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99944358T Expired - Lifetime ES2215399T3 (es) | 1998-08-13 | 1999-08-11 | Derivados de fenilxantina. |
Country Status (36)
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 |
| BR0115474A (pt) * | 2000-11-17 | 2006-01-31 | Idenix Cayman Ltd | Composição e método para inibição da transmissão de hiv que usam 6-benzil-4-oxopirimidinas substituìdas aplicada por via tópica |
| ATE326225T1 (de) * | 2001-02-28 | 2006-06-15 | Smithkline Beecham Corp | Xanthin-glycol-derivate zur behandlung des reizdarmsyndroms |
| WO2003017964A1 (en) | 2001-08-24 | 2003-03-06 | Unilever N.V. | Oral composition comprising an alkylhydroxybenzoate |
| US7317017B2 (en) | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| PT1444233E (pt) | 2001-11-09 | 2011-09-29 | Gilead Palo Alto Inc | Antagonistas de receptor de adenosina a2b |
| US7125993B2 (en) | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US6977300B2 (en) | 2001-11-09 | 2005-12-20 | 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 |
| WO2004009091A1 (en) | 2002-06-17 | 2004-01-29 | Glaxo Group Limited | Purine derivatives as liver x receptor agonists |
| JP4769721B2 (ja) * | 2003-08-25 | 2011-09-07 | トロヴィス ファーマシューティカルズ リミテッド ライアビリティ カンパニー | 置換８−ヘテロアリールキサンチン |
| 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 |
| WO2006091936A2 (en) | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| WO2006091898A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyrazolyl substituted xanthines |
| US7884100B2 (en) * | 2006-06-16 | 2011-02-08 | Pgxhealth, Llc | Substituted 8-[6-amino-3-pyridyl]xanthines |
| WO2009140519A1 (en) * | 2008-05-14 | 2009-11-19 | 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 |
| US8318728B2 (en) | 2008-05-14 | 2012-11-27 | Hydra Biosciences, Inc. | Compounds and compositions for treating chemical warfare agent-induced injuries |
| KR20110042153A (ko) * | 2008-05-30 | 2011-04-25 | 제넨테크, 인크. | 퓨린 ｐｉ３ｋ 억제 화합물 및 사용 방법 |
| 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 |
| WO2014182945A1 (en) | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Acc inhibitors and uses thereof |
| AU2014262636A1 (en) * | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| US10208044B2 (en) | 2013-05-10 | 2019-02-19 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| MX2015015421A (es) * | 2013-05-10 | 2016-06-21 | Nimbus Apollo Inc | Inhibidores de acetil-coa carboxilasa (acc) y usos de los mismos. |
| CN120435477A (zh) | 2022-12-20 | 2025-08-05 | 英威欧斯有限公司 | 被取代的3,7-二氢-1h-嘌呤-2,6-二酮及其用途 |
| 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 |
| NZ240644A (en) | 1990-11-21 | 1994-08-26 | Smithkline Beecham Corp | Use of xanthine derivatives to inhibit the production of tumour necrosis factor (tnf) |
| GB9210839D0 (en) | 1992-05-21 | 1992-07-08 | Smithkline Beecham Plc | Novel compounds |
| TW252044B (enExample) | 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 |
| JPH09511220A (ja) * | 1993-11-10 | 1997-11-11 | ブリストル‐マイヤーズ スクイブ カンパニー | バクテリアによって誘発される炎症性疾患の治療 |
| 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 |
| EP0812844B1 (de) | 1996-06-07 | 2002-10-23 | Hoechst Aktiengesellschaft | 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 |
| WO1999043673A1 (en) | 1998-02-26 | 1999-09-02 | Zenyaku Kogyo Kabushiki Kaisha | 1-azaindolizine derivatives |
| GB9817623D0 (en) * | 1998-08-13 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| CA2393724A1 (en) | 1999-12-23 | 2001-06-28 | Nitromed, Inc. | Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use |
| 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 AR ARP990103999A patent/AR020154A1/es not_active Application Discontinuation
- 1999-08-10 CO CO99050691A patent/CO5130007A1/es unknown
- 1999-08-11 US US09/762,559 patent/US6608069B1/en not_active Expired - Fee Related
- 1999-08-11 EP EP99944358A patent/EP1104422B1/en not_active Expired - Lifetime
- 1999-08-11 CA CA002340350A patent/CA2340350A1/en not_active Abandoned
- 1999-08-11 EE EEP200100083A patent/EE04721B1/xx not_active IP Right Cessation
- 1999-08-11 JP JP2000564958A patent/JP3631961B2/ja not_active Expired - Fee Related
- 1999-08-11 DK DK99944358T patent/DK1104422T3/da active
- 1999-08-11 AU AU57323/99A patent/AU775819B2/en not_active Ceased
- 1999-08-11 CN CNB031104673A patent/CN1251676C/zh not_active Expired - Fee Related
- 1999-08-11 MY MYPI99003429A patent/MY133393A/en unknown
- 1999-08-11 WO PCT/EP1999/005814 patent/WO2000009507A1/en not_active Ceased
- 1999-08-11 HU HU0103637A patent/HUP0103637A3/hu unknown
- 1999-08-11 TR TR2001/00448T patent/TR200100448T2/xx unknown
- 1999-08-11 CN CNB998119695A patent/CN1149215C/zh not_active Expired - Fee Related
- 1999-08-11 EA EA200100127A patent/EA004139B1/ru unknown
- 1999-08-11 ID IDW20010591A patent/ID28723A/id unknown
- 1999-08-11 SI SI9930545T patent/SI1104422T1/xx unknown
- 1999-08-11 AP APAP/P/2001/002071A patent/AP1408A/en active
- 1999-08-11 MA MA25728A patent/MA26673A1/fr unknown
- 1999-08-11 YU YU11601A patent/YU11601A/sh unknown
- 1999-08-11 NZ NZ509778A patent/NZ509778A/en unknown
- 1999-08-11 PL PL99346055A patent/PL346055A1/xx not_active Application Discontinuation
- 1999-08-11 DE DE69914921T patent/DE69914921T2/de not_active Expired - Fee Related
- 1999-08-11 BR BR9913020-3A patent/BR9913020A/pt not_active IP Right Cessation
- 1999-08-11 IL IL14131899A patent/IL141318A0/xx unknown
- 1999-08-11 ES ES99944358T patent/ES2215399T3/es not_active Expired - Lifetime
- 1999-08-11 KR KR1020017001799A patent/KR20010085369A/ko not_active Abandoned
- 1999-08-11 SK SK222-2001A patent/SK2222001A3/sk unknown
- 1999-08-11 PT PT99944358T patent/PT1104422E/pt unknown
- 1999-08-11 AT AT99944358T patent/ATE259810T1/de not_active IP Right Cessation
- 1999-08-11 PE PE1999000814A patent/PE20000952A1/es not_active Application Discontinuation
- 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
-
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
Also Published As
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| Publication | Publication Date | Title |
|---|---|---|
| ES2215399T3 (es) | Derivados de fenilxantina. | |
| CA2094270C (en) | Xanthine derivatives | |
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