HRP980077A2 - Phenyl xanthine esters and amides - Google Patents
Phenyl xanthine esters and amidesInfo
- Publication number
- HRP980077A2 HRP980077A2 HR9703044.9A HRP980077A HRP980077A2 HR P980077 A2 HRP980077 A2 HR P980077A2 HR P980077 A HRP980077 A HR P980077A HR P980077 A2 HRP980077 A2 HR P980077A2
- Authority
- HR
- Croatia
- Prior art keywords
- bis
- cyclohexylmethyl
- compound
- tetrahydro
- purin
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title description 3
- 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
- 150000001875 compounds Chemical class 0.000 claims description 116
- -1 (E)-4-(1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)cinnamic acid decaethylene glycol methyl ether ester Chemical class 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 20
- 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 claims description 15
- 229920000847 nonoxynol Polymers 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 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 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 230000004968 inflammatory condition Effects 0.000 claims description 12
- 208000026278 immune system disease Diseases 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 58
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 53
- 238000005160 1H NMR spectroscopy Methods 0.000 description 51
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 43
- 235000019256 formaldehyde Nutrition 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 33
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 31
- 239000000843 powder Substances 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 238000009472 formulation Methods 0.000 description 26
- 239000000725 suspension Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 229920001223 polyethylene glycol Polymers 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 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 description 21
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002202 Polyethylene glycol Substances 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- NGGYORCZEQCALY-UHFFFAOYSA-N 2-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7h-purin-8-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(N1)=NC2=C1C(=O)N(CC1CCCCC1)C(=O)N2CC1CCCCC1 NGGYORCZEQCALY-UHFFFAOYSA-N 0.000 description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 206010040070 Septic Shock Diseases 0.000 description 10
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- VVHAVLIDQNWEKF-UHFFFAOYSA-N nonaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO VVHAVLIDQNWEKF-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000036303 septic shock Effects 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000011321 prophylaxis Methods 0.000 description 8
- 239000003039 volatile agent Substances 0.000 description 8
- UTTPFTULPHRGJT-DTQAZKPQSA-N 1,3-bis(cyclohexylmethyl)-8-[4-[(e)-3-imidazol-1-yl-3-oxoprop-1-enyl]phenyl]-7h-purine-2,6-dione Chemical compound C1=CN=CN1C(=O)\C=C\C(C=C1)=CC=C1C(N1)=NC(C(N(CC2CCCCC2)C2=O)=O)=C1N2CC1CCCCC1 UTTPFTULPHRGJT-DTQAZKPQSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 239000002158 endotoxin Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229920006008 lipopolysaccharide Polymers 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VVBQKDDPSXBMMZ-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1 VVBQKDDPSXBMMZ-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000013375 chromatographic separation Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 210000000265 leukocyte Anatomy 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 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 description 3
- SVZORQBLCFZGBK-UHFFFAOYSA-N 1,3-bis(cyclohexylmethyl)urea Chemical compound C1CCCCC1CNC(=O)NCC1CCCCC1 SVZORQBLCFZGBK-UHFFFAOYSA-N 0.000 description 3
- IUDNRKGPFWUYIC-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound COCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 IUDNRKGPFWUYIC-UHFFFAOYSA-N 0.000 description 3
- AAFALUZRMOLETN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxymethylbenzene Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1 AAFALUZRMOLETN-UHFFFAOYSA-N 0.000 description 3
- YMBLPWKGRIGDBP-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO YMBLPWKGRIGDBP-UHFFFAOYSA-N 0.000 description 3
- SKYWUTJNPCCSDO-UHFFFAOYSA-N 6-amino-1,3-bis(cyclohexylmethyl)pyrimidine-2,4-dione Chemical compound O=C1N(CC2CCCCC2)C(N)=CC(=O)N1CC1CCCCC1 SKYWUTJNPCCSDO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000004147 Sorbitan trioleate Substances 0.000 description 3
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- AGZPHKMSWBPKLR-RMKNXTFCSA-N methyl (e)-3-[4-(dimethoxymethyl)phenyl]prop-2-enoate Chemical compound COC(OC)C1=CC=C(\C=C\C(=O)OC)C=C1 AGZPHKMSWBPKLR-RMKNXTFCSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 235000019337 sorbitan trioleate Nutrition 0.000 description 3
- 229960000391 sorbitan trioleate Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- LBOUHDMYVURTMA-AATRIKPKSA-N (e)-3-(4-formylphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(C=O)C=C1 LBOUHDMYVURTMA-AATRIKPKSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- XCJOKVCGRCTLIS-UHFFFAOYSA-N 1-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]propan-2-ol hydrochloride Chemical compound Cl.CC(O)COCCOCCOCCOCCOCCO XCJOKVCGRCTLIS-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 2
- UTAUAPARQSZZSV-UHFFFAOYSA-N 3-[4-[1,3-bis(cyclohexylmethyl)-2,6-dioxo-7h-purin-8-yl]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1C1=NC(C(N(CC2CCCCC2)C(=O)N2CC3CCCCC3)=O)=C2N1 UTAUAPARQSZZSV-UHFFFAOYSA-N 0.000 description 2
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- 230000003448 neutrophilic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
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- 208000037803 restenosis Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 208000005801 spondylosis Diseases 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 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
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
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- 210000003606 umbilical vein Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005550 wet granulation Methods 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9703044.9A GB9703044D0 (en) | 1997-02-14 | 1997-02-14 | Phenyl xanthine esters and amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980077A2 true HRP980077A2 (en) | 1998-12-31 |
Family
ID=10807635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR9703044.9A HRP980077A2 (en) | 1997-02-14 | 1998-02-13 | Phenyl xanthine esters and amides |
Country Status (38)
| Country | Link |
|---|---|
| US (3) | US6355646B1 (uk) |
| EP (1) | EP0970081B1 (uk) |
| JP (1) | JP2001511792A (uk) |
| KR (1) | KR100522639B1 (uk) |
| CN (1) | CN1140527C (uk) |
| AP (1) | AP1000A (uk) |
| AR (1) | AR011441A1 (uk) |
| AT (1) | ATE304542T1 (uk) |
| AU (1) | AU754456B2 (uk) |
| BG (1) | BG103722A (uk) |
| BR (1) | BR9807682B1 (uk) |
| CA (1) | CA2280730C (uk) |
| CO (1) | CO4940444A1 (uk) |
| CZ (1) | CZ298764B6 (uk) |
| DE (1) | DE69831559T2 (uk) |
| DK (1) | DK0970081T3 (uk) |
| EA (1) | EA199900648A1 (uk) |
| EE (1) | EE9900348A (uk) |
| ES (1) | ES2249822T3 (uk) |
| GB (1) | GB9703044D0 (uk) |
| HK (1) | HK1022907A1 (uk) |
| HR (1) | HRP980077A2 (uk) |
| HU (1) | HU225962B1 (uk) |
| ID (1) | ID22770A (uk) |
| IL (1) | IL131179A (uk) |
| IS (1) | IS5144A (uk) |
| MY (1) | MY118545A (uk) |
| NO (1) | NO325685B1 (uk) |
| NZ (1) | NZ336923A (uk) |
| PE (1) | PE58899A1 (uk) |
| PL (1) | PL188018B1 (uk) |
| SK (1) | SK110399A3 (uk) |
| TR (1) | TR199901942T2 (uk) |
| TW (1) | TW520371B (uk) |
| UA (1) | UA57767C2 (uk) |
| WO (1) | WO1998035966A1 (uk) |
| YU (1) | YU38399A (uk) |
| ZA (1) | ZA981175B (uk) |
Families Citing this family (15)
| 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 |
| US6545002B1 (en) * | 1999-06-01 | 2003-04-08 | University Of Virginia Patent Foundation | Substituted 8-phenylxanthines useful as antagonists of A2B adenosine receptors |
| FR2804958B1 (fr) * | 2000-02-15 | 2005-07-08 | Hoechst Marion Roussel Inc | Derives de xanthine, leur procede de preparation et les intermediaires de ce procede, leur application comme medicament et les compositions pharmaceutiques les renfermant |
| WO2002067942A2 (en) * | 2001-02-28 | 2002-09-06 | Smithkline Beecham Corporation | Methods of treating irritable bowel syndrome and functional dyspepsia |
| US20080318983A1 (en) * | 2001-11-09 | 2008-12-25 | Rao Kalla | A2b adenosine receptor antagonists |
| US7125993B2 (en) * | 2001-11-09 | 2006-10-24 | 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 |
| US20060182692A1 (en) | 2003-12-16 | 2006-08-17 | Fishburn C S | Chemically modified small molecules |
| AU2012227249B2 (en) * | 2003-12-16 | 2014-10-02 | Nektar Therapeutics | Chemically modified small molecules |
| CN1925875A (zh) * | 2003-12-16 | 2007-03-07 | 尼克塔治疗亚拉巴马公司 | 化学改性的小分子 |
| WO2005102976A1 (en) * | 2004-04-21 | 2005-11-03 | Smithkline Beecham Corporation | Process for preparing nonaethylene glycol monomethyl ether |
| MX2007002437A (es) * | 2004-09-01 | 2007-08-14 | Cv Therapeutics Inc | Metodo para el sanado de heridas utilizando antagonistas del receptor de adenosina a2b. |
| US20070059740A1 (en) * | 2005-08-26 | 2007-03-15 | Linden Joel M | Method of targeting a2b adenosine receptor antagonist therapy |
| US8193200B2 (en) * | 2007-01-04 | 2012-06-05 | University Of Virginia Patent Foundation | Antagonists of A2B adenosine receptors for treatment of inflammatory bowel disease |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (uk) * | 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 |
| 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 |
| DK0812844T3 (da) | 1996-06-07 | 2003-02-17 | Hoechst Ag | Anvendelse af theophyllinderivater til behandling og profylakse af choktilstande, nye xanthinforbindelser og fremgangsmåder til deres fremstilling |
| GB9703044D0 (en) * | 1997-02-14 | 1997-04-02 | Glaxo Group Ltd | Phenyl xanthine esters and amides |
| 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 |
| EP1246621A4 (en) | 1999-12-23 | 2004-11-24 | Nitromed Inc | NITROSED AND NITROSYLATED CYCLOOXYGENASE-2 INHIBITORS, COMPOSITIONS AND METHODS FOR THEIR USE |
| US6751206B1 (en) * | 2000-06-29 | 2004-06-15 | Qualcomm Incorporated | Method and apparatus for beam switching in a wireless communication system |
-
1997
- 1997-02-14 GB GBGB9703044.9A patent/GB9703044D0/en active Pending
-
1998
- 1998-02-11 CO CO98007044A patent/CO4940444A1/es unknown
- 1998-02-11 MY MYPI98000546A patent/MY118545A/en unknown
- 1998-02-11 PE PE1998000099A patent/PE58899A1/es not_active Application Discontinuation
- 1998-02-12 NZ NZ336923A patent/NZ336923A/en unknown
- 1998-02-12 PL PL98335135A patent/PL188018B1/pl unknown
- 1998-02-12 ES ES98908090T patent/ES2249822T3/es not_active Expired - Lifetime
- 1998-02-12 JP JP53534098A patent/JP2001511792A/ja not_active Ceased
- 1998-02-12 ZA ZA9801175A patent/ZA981175B/xx unknown
- 1998-02-12 AU AU66221/98A patent/AU754456B2/en not_active Ceased
- 1998-02-12 WO PCT/EP1998/000784 patent/WO1998035966A1/en active IP Right Grant
- 1998-02-12 ID IDW990879A patent/ID22770A/id unknown
- 1998-02-12 CN CNB988039419A patent/CN1140527C/zh not_active Expired - Fee Related
- 1998-02-12 EA EA199900648A patent/EA199900648A1/ru unknown
- 1998-02-12 BR BRPI9807682-5A patent/BR9807682B1/pt not_active IP Right Cessation
- 1998-02-12 EP EP98908090A patent/EP0970081B1/en not_active Expired - Lifetime
- 1998-02-12 YU YU38399A patent/YU38399A/sh unknown
- 1998-02-12 EE EEP199900348A patent/EE9900348A/xx unknown
- 1998-02-12 CZ CZ0288799A patent/CZ298764B6/cs not_active IP Right Cessation
- 1998-02-12 DE DE69831559T patent/DE69831559T2/de not_active Expired - Lifetime
- 1998-02-12 SK SK1103-99A patent/SK110399A3/sk unknown
- 1998-02-12 CA CA002280730A patent/CA2280730C/en not_active Expired - Fee Related
- 1998-02-12 AT AT98908090T patent/ATE304542T1/de active
- 1998-02-12 IL IL13117998A patent/IL131179A/en not_active IP Right Cessation
- 1998-02-12 HU HU0000894A patent/HU225962B1/hu not_active IP Right Cessation
- 1998-02-12 TR TR1999/01942T patent/TR199901942T2/xx unknown
- 1998-02-12 DK DK98908090T patent/DK0970081T3/da active
- 1998-02-12 AP APAP/P/1999/001622A patent/AP1000A/en active
- 1998-02-12 US US09/367,313 patent/US6355646B1/en not_active Expired - Lifetime
- 1998-02-12 KR KR10-1999-7007276A patent/KR100522639B1/ko not_active IP Right Cessation
- 1998-02-13 AR ARP980100664A patent/AR011441A1/es active IP Right Grant
- 1998-02-13 HR HR9703044.9A patent/HRP980077A2/hr not_active Application Discontinuation
- 1998-02-24 TW TW087102632A patent/TW520371B/zh not_active IP Right Cessation
- 1998-12-02 UA UA99084601A patent/UA57767C2/uk unknown
-
1999
- 1999-07-30 IS IS5144A patent/IS5144A/is unknown
- 1999-08-13 NO NO19993915A patent/NO325685B1/no not_active IP Right Cessation
- 1999-09-09 BG BG103722A patent/BG103722A/xx unknown
-
2000
- 2000-03-29 HK HK00101936A patent/HK1022907A1/xx not_active IP Right Cessation
-
2001
- 2001-06-01 US US09/872,546 patent/US6437124B1/en not_active Expired - Fee Related
-
2002
- 2002-06-17 US US10/174,414 patent/US7002012B2/en not_active Expired - Fee Related
Also Published As
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| JP3631961B2 (ja) | フェニルキサンチン誘導体 | |
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| JPH10503767A (ja) | フェニルキサンチン誘導体 | |
| MXPA99007508A (en) | Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders | |
| MXPA01001632A (en) | Phenyl yanthine derivatives | |
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