CN1251676C - 苯基黄嘌呤衍生物 - Google Patents
苯基黄嘌呤衍生物 Download PDFInfo
- Publication number
- CN1251676C CN1251676C CNB031104673A CN03110467A CN1251676C CN 1251676 C CN1251676 C CN 1251676C CN B031104673 A CNB031104673 A CN B031104673A CN 03110467 A CN03110467 A CN 03110467A CN 1251676 C CN1251676 C CN 1251676C
- Authority
- CN
- China
- Prior art keywords
- purine
- tetrahydrochysene
- dioxo
- ethylene glycol
- cinnamic acid
- 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 - Fee Related
Links
- 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 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 150
- 239000003814 drug Substances 0.000 claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 334
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 206
- 229930016911 cinnamic acid Natural products 0.000 claims description 206
- 235000013985 cinnamic acid Nutrition 0.000 claims description 206
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 206
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 205
- -1 Ethylene Glycol Methyl ether amide Chemical class 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 208000028169 periodontal disease Diseases 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 62
- 238000002360 preparation method Methods 0.000 abstract description 58
- 238000011282 treatment Methods 0.000 abstract description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 15
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- 239000008194 pharmaceutical composition Substances 0.000 abstract description 7
- 206010064147 Gastrointestinal inflammation Diseases 0.000 abstract description 3
- 208000035475 disorder Diseases 0.000 abstract description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract 1
- 230000004968 inflammatory condition Effects 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 238000004364 calculation method Methods 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- 239000000203 mixture Substances 0.000 description 81
- 239000000243 solution Substances 0.000 description 76
- 238000010265 fast atom bombardment Methods 0.000 description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 45
- 238000005160 1H NMR spectroscopy Methods 0.000 description 42
- 239000007787 solid Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 125000003118 aryl group Chemical group 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000004615 ingredient Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 30
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 28
- 239000000376 reactant Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 239000002585 base Substances 0.000 description 23
- 239000000843 powder Substances 0.000 description 22
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical class COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 206010061218 Inflammation Diseases 0.000 description 14
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 230000004054 inflammatory process Effects 0.000 description 14
- 229940035893 uracil Drugs 0.000 description 14
- 201000010099 disease Diseases 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229960001866 silicon dioxide Drugs 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000004519 grease Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229960004756 ethanol Drugs 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 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 8
- 238000010790 dilution Methods 0.000 description 8
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- 210000000265 leukocyte Anatomy 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 210000003725 endotheliocyte Anatomy 0.000 description 7
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- 235000001968 nicotinic acid Nutrition 0.000 description 7
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
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- 238000000605 extraction Methods 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
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- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 108010067225 Cell Adhesion Molecules Proteins 0.000 description 5
- 102000016289 Cell Adhesion Molecules Human genes 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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- WOGITNXCNOTRLK-UHFFFAOYSA-N 3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)C=CC1=CC=CC=C1 WOGITNXCNOTRLK-UHFFFAOYSA-N 0.000 description 4
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- 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
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- 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
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- A61P11/06—Antiasthmatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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| GB9817623.3 | 1998-08-13 | ||
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| 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 |
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| US4442125A (en) * | 1978-06-26 | 1984-04-10 | Oxford Hill, Ltd. | Process for detaching or preventing attachment of microorganisms to a surface |
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| 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 |
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| 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) |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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1999
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