LV12209B - HEXEROCYCLES AS CYCLOOKSIGENASES-2 INHIBITORS REFILLED - Google Patents
HEXEROCYCLES AS CYCLOOKSIGENASES-2 INHIBITORS REFILLED Download PDFInfo
- Publication number
- LV12209B LV12209B LVP-98-238A LV980238A LV12209B LV 12209 B LV12209 B LV 12209B LV 980238 A LV980238 A LV 980238A LV 12209 B LV12209 B LV 12209B
- Authority
- LV
- Latvia
- Prior art keywords
- furanone
- phenyl
- methylsulfonyl
- pharmaceutical composition
- fluorophenyl
- Prior art date
Links
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 45
- -1 2,6-difluorophenyl Chemical group 0.000 claims description 33
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000003937 drug carrier Substances 0.000 claims description 17
- 208000027866 inflammatory disease Diseases 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 9
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- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
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- 230000004054 inflammatory process Effects 0.000 claims description 5
- CVLFUMMNMNBFTN-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-4-naphthalen-2-yl-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C3C=CC=CC3=CC=2)C(=O)OC1 CVLFUMMNMNBFTN-UHFFFAOYSA-N 0.000 claims description 4
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- 208000002193 Pain Diseases 0.000 claims description 4
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- FPGNJXJYBXKRBP-UHFFFAOYSA-N 4-(2-chlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C(=O)OC1 FPGNJXJYBXKRBP-UHFFFAOYSA-N 0.000 claims description 3
- DKFBOFPVCWDYHN-UHFFFAOYSA-N 4-(4-bromo-2-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Br)=CC=2)F)C(=O)OC1 DKFBOFPVCWDYHN-UHFFFAOYSA-N 0.000 claims description 3
- ZOZVHIIYFMNPMN-UHFFFAOYSA-N 4-(4-bromo-3-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(Br)=CC=2)C(=O)OC1 ZOZVHIIYFMNPMN-UHFFFAOYSA-N 0.000 claims description 3
- ZRCURVJXQGLLOZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(=O)OC1 ZRCURVJXQGLLOZ-UHFFFAOYSA-N 0.000 claims description 3
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- INRQTVDUZFESAO-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)C(=O)OC1 INRQTVDUZFESAO-UHFFFAOYSA-N 0.000 claims description 2
- GOXAQESCHCROMJ-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(F)=CC=2)C(=O)OC1 GOXAQESCHCROMJ-UHFFFAOYSA-N 0.000 claims description 2
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- NXERGIJHYVUXHM-UHFFFAOYSA-N 3-(3-fluorophenyl)-5,5-dimethyl-4-(4-methylsulfonylphenyl)furan-2-one Chemical compound CC1(C)OC(=O)C(C=2C=C(F)C=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 NXERGIJHYVUXHM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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BR (1) | BR9406979A (de) |
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WO (1) | WO1995000501A2 (de) |
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US5663180A (en) * | 1983-10-29 | 1997-09-02 | G.D. Searle & Co. | Substituted cyclopentenes for the treatment of inflammation |
US6492413B2 (en) | 1993-01-15 | 2002-12-10 | G.D. Searle & Co. | 3.4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
CA2297592A1 (en) * | 1993-01-15 | 1994-07-21 | G.D. Searle & Co. | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
GB9420616D0 (en) * | 1994-10-12 | 1994-11-30 | Merck Sharp & Dohme | Method, compositions and use |
US6090834A (en) * | 1993-05-21 | 2000-07-18 | G.D. Searle & Co. | Substituted oxazoles for the treatment of inflammation |
GB9602877D0 (en) * | 1996-02-13 | 1996-04-10 | Merck Frosst Canada Inc | 3,4-Diaryl-2-hydroxy-2,5- dihydrofurans as prodrugs to cox-2 inhibitors |
US5840746A (en) * | 1993-06-24 | 1998-11-24 | Merck Frosst Canada, Inc. | Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases |
US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
SG43841A1 (en) * | 1994-01-10 | 1997-11-14 | Merck Frosst Canada Inc | Phenyl heterocycles as cox-2 inhibitors |
JPH10504542A (ja) * | 1994-07-27 | 1998-05-06 | ジー.ディー.サール アンド カンパニー | 炎症処置用の置換チアゾール化合物 |
US6426360B1 (en) * | 1994-07-28 | 2002-07-30 | G D Searle & Co. | 4,5-substituted imidazolyl compounds for the treatment of inflammation |
US5616601A (en) * | 1994-07-28 | 1997-04-01 | Gd Searle & Co | 1,2-aryl and heteroaryl substituted imidazolyl compounds for the treatment of inflammation |
US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
US6613789B2 (en) | 1994-07-28 | 2003-09-02 | G. D. Searle & Co. | Heterocyclo-substituted imidazoles for the treatment of inflammation |
US6239172B1 (en) * | 1997-04-10 | 2001-05-29 | Nitrosystems, Inc. | Formulations for treating disease and methods of using same |
GB2294879A (en) * | 1994-10-19 | 1996-05-15 | Merck & Co Inc | Cylcooxygenase-2 Inhibitors |
AU688980B2 (en) * | 1994-10-27 | 1998-03-19 | Merck Frosst Company | Stilbene derivatives useful as cyclooxygenase-2 inhibitors |
JP2636819B2 (ja) | 1994-12-20 | 1997-07-30 | 日本たばこ産業株式会社 | オキサゾール系複素環式芳香族化合物 |
EP0799218B1 (de) * | 1994-12-21 | 2003-02-19 | Merck Frosst Canada & Co. | Diaryl-2(5h)-fuaranone als cox-2-inhibitoren |
DK0809636T3 (da) * | 1995-02-13 | 2003-01-06 | Searle & Co | Substituerede isoxazoler til behandling af inflammation |
US5633272A (en) * | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
US5691374A (en) * | 1995-05-18 | 1997-11-25 | Merck Frosst Canada Inc. | Diaryl-5-oxygenated-2-(5H) -furanones as COX-2 inhibitors |
US6515014B2 (en) | 1995-06-02 | 2003-02-04 | G. D. Searle & Co. | Thiophene substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US5643933A (en) * | 1995-06-02 | 1997-07-01 | G. D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US6512121B2 (en) | 1998-09-14 | 2003-01-28 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
WO1996038418A1 (en) | 1995-06-02 | 1996-12-05 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US6156776A (en) * | 1995-06-08 | 2000-12-05 | Yu; Dingwei Tim | Diaryl substituted thiazoles useful in the treatment of fungal infections |
US5700816A (en) * | 1995-06-12 | 1997-12-23 | Isakson; Peter C. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor |
CA2224517A1 (en) * | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
US6342510B1 (en) | 1995-06-12 | 2002-01-29 | G. D. Searle & Co. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitors and a leukotriene B4 receptor antagonist |
US6593361B2 (en) | 1995-07-19 | 2003-07-15 | Merck & Co Inc | Method of treating colonic adenomas |
US5968974A (en) * | 1995-07-19 | 1999-10-19 | Merck & Co., Inc. | Method of treating colonic adenomas |
US5837719A (en) * | 1995-08-10 | 1998-11-17 | Merck & Co., Inc. | 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use |
US5792778A (en) * | 1995-08-10 | 1998-08-11 | Merck & Co., Inc. | 2-substituted aryl pyrroles, compositions containing such compounds and methods of use |
US5786515A (en) * | 1995-09-15 | 1998-07-28 | Merck & Co., Inc. | Synthesis of α-chloro or fluoro ketones |
WO1997011701A1 (en) * | 1995-09-27 | 1997-04-03 | Merck-Frosst Canada Inc. | Compositions for treating inflammation containing certain prostaglandins and a selective cyclooxygenase-2 inhibitor |
US6083949A (en) * | 1995-10-06 | 2000-07-04 | Merck & Co., Inc. | Substituted imidazoles having anti-cancer and cytokine inhibitory activity |
US5717100A (en) * | 1995-10-06 | 1998-02-10 | Merck & Co., Inc. | Substituted imidazoles having anti-cancer and cytokine inhibitory activity |
US6020343A (en) * | 1995-10-13 | 2000-02-01 | Merck Frosst Canada, Inc. | (Methylsulfonyl)phenyl-2-(5H)-furanones as COX-2 inhibitors |
US5981576A (en) * | 1995-10-13 | 1999-11-09 | Merck Frosst Canada, Inc. | (Methylsulfonyl)phenyl-2-(5H)-furanones as COX-2 inhibitors |
UA57002C2 (uk) * | 1995-10-13 | 2003-06-16 | Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі. | Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування |
CA2234633A1 (en) * | 1995-10-17 | 1997-04-24 | G.D. Searle & Co. | Method of detecting cyclooxygenase-2 |
JP3337477B2 (ja) * | 1995-10-30 | 2002-10-21 | メルク フロスト カナダ アンド カンパニー | Cox−2阻害剤のプロドラッグとしての3,4−ジアリール−2−ヒドロキシ−2,5−ジヒドロフラン |
US6222048B1 (en) * | 1995-12-18 | 2001-04-24 | Merck Frosst Canada & Co. | Diaryl-2-(5H)-furanones as Cox-2 inhibitors |
DK1193265T3 (da) * | 1996-01-26 | 2007-02-19 | Searle Llc | Fremgangsmåde til fremstilling af 4-2-(aryl eller heterocyclo)-1H-imidazol-1-yl-benzensulfonamider |
US5789413A (en) * | 1996-02-01 | 1998-08-04 | Merck Frosst Canada, Inc. | Alkylated styrenes as prodrugs to COX-2 inhibitors |
US5733909A (en) * | 1996-02-01 | 1998-03-31 | Merck Frosst Canada, Inc. | Diphenyl stilbenes as prodrugs to COX-2 inhibitors |
ATE198323T1 (de) * | 1996-02-01 | 2001-01-15 | Merck Frosst Canada Inc | Diphenylstibene als prodrugs zu cox-2-inhibitoren |
ES2147973T3 (es) * | 1996-02-01 | 2000-10-01 | Merck Frosst Canada Inc | Estirenos alquilatados como profarmacos de inhibidores de cox-2. |
WO1997029776A1 (en) | 1996-02-13 | 1997-08-21 | G.D. Searle & Co. | Combinations having immunosuppressive effects, containing cyclooxygenase-2-inhibitors and 5-lipoxygenase inhibitors |
AU1952597A (en) | 1996-02-13 | 1997-09-02 | G.D. Searle & Co. | Combinations, having immunosuppressive effects, containing cyclooxygenase-2 inhibitor and a leukotriene a4 hydrolase inhibitor |
JP2000505445A (ja) * | 1996-02-13 | 2000-05-09 | ジー.ディー.サール アンド カンパニー | シクロオキシゲナーゼ―2インヒビターとロイコトリエンb▲下4▼受容体アンタゴニストの投与の免疫抑制作用 |
CN1255396C (zh) * | 1996-03-18 | 2006-05-10 | 卫材株式会社 | 含有稠环的羧酸衍生物 |
ATE223376T1 (de) * | 1996-03-29 | 2002-09-15 | Merck Frosst Canada Inc | Bisarylcyclobutenderivate als cyclooxygenasehemmer |
FR2747123B1 (fr) * | 1996-04-04 | 1998-06-26 | Union Pharma Scient Appl | Nouveaux derives diarylmethylidene tetrahydrofurane, leurs procedes de preparation, et leurs utilisations en therapeutique |
US6180651B1 (en) * | 1996-04-04 | 2001-01-30 | Bristol-Myers Squibb | Diarylmethylidenefuran derivatives, processes for their preparation and their uses in therapeutics |
US5807873A (en) * | 1996-04-04 | 1998-09-15 | Laboratories Upsa | Diarylmethylidenefuran derivatives and their uses in therapeutics |
US5908858A (en) * | 1996-04-05 | 1999-06-01 | Sankyo Company, Limited | 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic uses |
CA2249009C (en) * | 1996-04-12 | 2003-09-16 | G.D. Searle & Co. | Substituted benzenesulfonamide derivatives as prodrugs of cox-2 inhibitors |
CA2252401C (en) * | 1996-04-23 | 2004-02-17 | Merck Frosst Canada Inc. | Pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors |
US5922742A (en) * | 1996-04-23 | 1999-07-13 | Merck Frosst Canada | Pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors |
AU775030B2 (en) * | 1996-05-17 | 2004-07-15 | Merck Frosst Company | Compositions for a once a day treatment of cyclooxygenase-2 mediated diseases |
WO1997044027A1 (en) * | 1996-05-17 | 1997-11-27 | Merck & Co., Inc. | Compositions for a once a day treatment of cyclooxygenase-2 mediated diseases |
NZ332670A (en) * | 1996-05-17 | 2000-07-28 | Merck & Co Inc | Compositions for a once a day treatment of cyclooxygenase-2 mediated diseases comprising 3-phenyl-4-(4-methylsulfonyl)phenyl)-2-(5H)-furanone |
US6677364B2 (en) | 1998-04-20 | 2004-01-13 | G.D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US5883267A (en) * | 1996-05-31 | 1999-03-16 | Merck & Co., Inc. | Process for making phenyl heterocycles useful as cox-2 inhibitors |
HRP970289A2 (en) * | 1996-05-31 | 1998-04-30 | Merck & Co Inc | Process for preparing phenyl heterocycles useful as cox-2 inhibitors |
EP0906307B1 (de) * | 1996-06-10 | 2005-04-27 | Merck & Co., Inc. | Substituierte imidazole mit cytokinin-inhibirender wirkung |
GB9615867D0 (en) * | 1996-07-03 | 1996-09-11 | Merck & Co Inc | Process of preparing phenyl heterocycles useful as cox-2 inhibitors |
US5677318A (en) * | 1996-07-11 | 1997-10-14 | Merck Frosst Canada, Inc. | Diphenyl-1,2-3-thiadiazoles as anti-inflammatory agents |
DK0920422T3 (da) * | 1996-08-14 | 2003-03-17 | Searle & Co | Krystallinsk form af 4-[5-methyl-3-phenylisoxazol-4-yl]benzensulfonamid |
US8022095B2 (en) * | 1996-08-16 | 2011-09-20 | Pozen, Inc. | Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs |
US6586458B1 (en) * | 1996-08-16 | 2003-07-01 | Pozen Inc. | Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs |
US5939069A (en) * | 1996-08-23 | 1999-08-17 | University Of Florida | Materials and methods for detection and treatment of immune system dysfunctions |
FR2753449B1 (fr) * | 1996-09-13 | 1998-12-04 | Union Pharma Scient Appl | Nouveaux derives 3,4-diaryloxazolone, leurs procedes de preparation, et leurs utilisations en therapeutique |
JP2001503395A (ja) | 1996-10-15 | 2001-03-13 | ジー.ディー.サール アンド カンパニー | 腫瘍新生の処置および予防にシクロオキシゲナーゼ―2阻害剤を使用する方法 |
US5776954A (en) * | 1996-10-30 | 1998-07-07 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
US5985930A (en) | 1996-11-21 | 1999-11-16 | Pasinetti; Giulio M. | Treatment of neurodegenerative conditions with nimesulide |
WO1998025896A1 (en) * | 1996-12-10 | 1998-06-18 | G.D. Searle & Co. | Substituted pyrrolyl compounds for the treatment of inflammation |
EP0863134A1 (de) * | 1997-03-07 | 1998-09-09 | Merck Frosst Canada Inc. | 2-(3,5-difluorophenyl)-3-(4-methylsulfonylphenyl)-2-cyclopenten-1-on zur Verwendung als Inhibitor der Cyclooxygenase-2 |
US6004960A (en) * | 1997-03-14 | 1999-12-21 | Merck Frosst Canada, Inc. | Pyridazinones as inhibitors of cyclooxygenase-2 |
US6071954A (en) * | 1997-03-14 | 2000-06-06 | Merk Frosst Canada, Inc. | (methylsulfonyl)phenyl-2-(5H)-furanones with oxygen link as COX-2 inhibitors |
WO1998041511A1 (en) * | 1997-03-14 | 1998-09-24 | Merck Frosst Canada & Co. | Pyridazinones as inhibitors of cyclooxygenase-2 |
EP0970067B1 (de) * | 1997-03-14 | 2003-07-02 | Merck Frosst Canada & Co. | (methylsulfonyl)phenyl-2-(5h)-furanone mit sauerstoff-bindung als cox-2-hemmer |
US6127545A (en) * | 1997-04-18 | 2000-10-03 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors |
TW492959B (en) * | 1997-04-18 | 2002-07-01 | Merck & Co Inc | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
US6130334A (en) * | 1998-04-15 | 2000-10-10 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors |
US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
US6307047B1 (en) * | 1997-08-22 | 2001-10-23 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
US6525053B1 (en) | 1997-08-22 | 2003-02-25 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
WO1999012930A1 (en) | 1997-09-05 | 1999-03-18 | Glaxo Group Limited | 2,3-diaryl-pyrazolo[1,5-b]pyridazines derivatives, their prepa ration and their use as cyclooxygenase 2 (cox-2) inhibitors |
ATE293602T1 (de) * | 1997-09-12 | 2005-05-15 | Merck Frosst Canada Inc | 2-aminopyridine als inhibitoren von cyclooxygenase-2 |
US6004950A (en) * | 1997-09-12 | 1999-12-21 | Merck Frosst Canada, Inc. | 2-aminopyridines as inhibitors of cyclooxygenase-2 |
RS49982B (sr) * | 1997-09-17 | 2008-09-29 | Euro-Celtique S.A., | Sinergistička analgetička kombinacija analgetičkog opijata i inhibitora ciklooksigenaze-2 |
US6020339A (en) * | 1997-10-03 | 2000-02-01 | Merck & Co., Inc. | Aryl furan derivatives as PDE IV inhibitors |
US6034089A (en) * | 1997-10-03 | 2000-03-07 | Merck & Co., Inc. | Aryl thiophene derivatives as PDE IV inhibitors |
FR2769311B1 (fr) * | 1997-10-07 | 1999-12-24 | Union Pharma Scient Appl | Nouveaux derives 3,4-diarylthiazolin-2-one ou -2-thione, leurs procedes de preparation et leurs utilisations en therapeutique |
US5972986A (en) * | 1997-10-14 | 1999-10-26 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia |
US6080876A (en) * | 1997-10-29 | 2000-06-27 | Merck & Co., Inc. | Process for making phenyl heterocycles useful as COX-2 inhibitors |
US6133292A (en) * | 1997-10-30 | 2000-10-17 | Merck Frosst Canada & Co. | Diaryl-5-alkyl-5-methyl-2-(5H)-furanones as selective cyclooxygenase-2-inhibitors |
AU741790B2 (en) * | 1997-10-30 | 2001-12-06 | Merck Frosst Canada & Co. | Diaryl-5-alkyl-5-methyl-2(5H)-furanones as selective cyclooxygenase-2 inhibitors |
BR9813164A (pt) * | 1997-10-31 | 2000-08-22 | Searle & Co | Método de uso de inibidores da ciclooxigenase-2 na manutenção do ducto arterial fetal durante o tratamento e prevenção de dores prematuras de parto |
US6025353A (en) * | 1997-11-19 | 2000-02-15 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents |
WO1999030721A1 (en) | 1997-12-17 | 1999-06-24 | Cornell Research Foundation, Inc. | Cyclooxygenase-2 inhibition |
US7041694B1 (en) | 1997-12-17 | 2006-05-09 | Cornell Research Foundation, Inc. | Cyclooxygenase-2 inhibition |
US6375957B1 (en) | 1997-12-22 | 2002-04-23 | Euro-Celtique, S.A. | Opioid agonist/opioid antagonist/acetaminophen combinations |
RS50070B (sr) | 1997-12-22 | 2009-01-22 | Euro-Celtique S.A., | Oralni dozni oblik sa kombinacijom opijatnog agonista i antagonista |
NZ333399A (en) * | 1997-12-24 | 2000-05-26 | Sankyo Co | Cyclooxygenase-2 inhibitors (COX-2) for the prevention and treatment of tumors, cachexia and tumor-metastasis |
FR2775477B1 (fr) * | 1998-02-27 | 2000-05-19 | Union Pharma Scient Appl | Nouveaux derives diarylmethylene heterocycliques, leurs procedes de preparation et leurs utilisations en therapeutique |
US6136804A (en) * | 1998-03-13 | 2000-10-24 | Merck & Co., Inc. | Combination therapy for treating, preventing, or reducing the risks associated with acute coronary ischemic syndrome and related conditions |
US6294558B1 (en) | 1999-05-31 | 2001-09-25 | Pfizer Inc. | Sulfonylbenzene compounds as anti-inflammatory/analgesic agents |
US6727238B2 (en) * | 1998-06-11 | 2004-04-27 | Pfizer Inc. | Sulfonylbenzene compounds as anti-inflammatory/analgesic agents |
TNSN99111A1 (fr) * | 1998-06-11 | 2005-11-10 | Pfizer | Derives de sulfonylbenzene nouveaux, procede pour leur preparation et compositions pharmaceutiques les contenant. |
JP2002523461A (ja) * | 1998-08-31 | 2002-07-30 | メルク エンド カムパニー インコーポレーテッド | 神経変性疾患の治療方法 |
DE19842833B4 (de) * | 1998-09-18 | 2005-04-14 | Merckle Gmbh | 2-Arylalkylthio-imidazole, 2-Arylalkenylthio-imidazole und 2-Arylalkinylthio-imidazole als Entzündungs-Hemmstoffe und Hemmstoffe der Cytokin-Freisetzung |
JP2002528435A (ja) * | 1998-10-27 | 2002-09-03 | メルク エンド カムパニー インコーポレーテッド | メチルチオフェニルヒドロキシケトンの合成 |
ES2234324T3 (es) * | 1998-11-02 | 2005-06-16 | MERCK & CO., INC. | Combinaciones de un agonista 5ht1b/1d y un inhibidor selectivo de cox-2 para el tratamiento de la migraña. |
PL348208A1 (en) | 1998-11-03 | 2002-05-06 | Glaxo Group Ltd | Pyrazolopyridine derivatives as selective cox-2 inhibitors |
SA99191255B1 (ar) | 1998-11-30 | 2006-11-25 | جي دي سيرل اند كو | مركبات سيليكوكسيب celecoxib |
US20030013739A1 (en) * | 1998-12-23 | 2003-01-16 | Pharmacia Corporation | Methods of using a combination of cyclooxygenase-2 selective inhibitors and thalidomide for the treatment of neoplasia |
US20040122011A1 (en) * | 1998-12-23 | 2004-06-24 | Pharmacia Corporation | Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy |
US6649645B1 (en) | 1998-12-23 | 2003-11-18 | Pharmacia Corporation | Combination therapy of radiation and a COX-2 inhibitor for treatment of neoplasia |
US6155267A (en) * | 1998-12-31 | 2000-12-05 | Medtronic, Inc. | Implantable medical device monitoring method and system regarding same |
ATE425749T1 (de) * | 1999-01-27 | 2009-04-15 | Cornell Res Foundation Inc | Behandlung von mit her-2/neu-uberexprimierung einhergehendem krebs |
AU2661400A (en) | 1999-02-27 | 2000-09-21 | Glaxo Group Limited | Pyrazolopyridines |
US20010000178A1 (en) | 1999-03-25 | 2001-04-05 | Yu Dingwei Tim | Pyridyl substituted thiazoles |
KR20010094161A (ko) * | 2000-04-04 | 2001-10-31 | 서경배 | 2,2-디메틸-4,5-디아릴-3(2h)퓨라논의 유도체 및 이를함유하는 선택적인 시클로옥시게네이즈-2 저해제로서약제학적 조성물 |
KR20010111584A (ko) | 1999-04-14 | 2001-12-19 | 서경배 | 시클로옥시게네이즈-2 저해제로서의4,5-디아릴-3(2h)-퓨라논 유도체 |
CO5261541A1 (es) * | 1999-05-14 | 2003-03-31 | Pfizer Prod Inc | Terapia de combinacion para el tratamiento de la migrana |
CO5190664A1 (es) | 1999-06-30 | 2002-08-29 | Pfizer Prod Inc | Terapia de combinacion para el tratamiento de migrana administracion de un receptor 5ht, cafeina y un inhibidor de ciclooxigenasa-2 |
US6066667A (en) * | 1999-08-17 | 2000-05-23 | Ashbrook; Charles D. | Substituted furanones, compositions and antiarthritic use |
WO2001017996A1 (en) * | 1999-09-08 | 2001-03-15 | Merck Frosst Canada & Co. | 1,2,3-thiadiazoles and their use as cox-2 inhibitors |
WO2001021259A2 (en) * | 1999-09-21 | 2001-03-29 | Emory University | Use and compositions for treating platelet-related disorders using anagrelide |
ES2326849T3 (es) * | 1999-10-08 | 2009-10-20 | Merial | sin titulo. |
EP1099695A1 (de) | 1999-11-09 | 2001-05-16 | Laboratoire Theramex S.A. | 5-Aryl-1H-1,2,4-triazolverbindungen als Cyclooxygenase-2 Inhibitoren und diese enthaltende pharmazeutische Zusammensetzungen |
ATE252576T1 (de) | 1999-12-03 | 2003-11-15 | Pfizer Prod Inc | Heteroarylphenylpyrazolverbindungen zur verwendung als analgetisches/entzündungshemmendes mittel |
PT1104760E (pt) | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios |
JP2003517475A (ja) | 1999-12-03 | 2003-05-27 | ファイザー・プロダクツ・インク | 抗炎症/鎮痛薬としてのヘテロシクロ−アルキルスルホニルピラゾール誘導体 |
CA2326970C (en) | 1999-12-03 | 2004-11-23 | Pfizer Products Inc. | Acetylene derivatives as anti-inflammatory/analgesic agents |
AU784490B2 (en) * | 1999-12-08 | 2006-04-13 | Pharmacia Corporation | Cyclooxygenase-2 inhibitor compositions having rapid onset of therapeutic effect |
HUP0200580A3 (en) * | 1999-12-08 | 2002-12-28 | Pharmacia Corp Chicago | Polymorphic crystalline forms of celecoxib, process their preparation and pharmaceutical compositions containing them |
UA74539C2 (en) | 1999-12-08 | 2006-01-16 | Pharmacia Corp | Crystalline polymorphous forms of celecoxib (variants), a method for the preparation thereof (variants), a pharmaceutical composition (variants) |
GB9930358D0 (en) | 1999-12-22 | 2000-02-09 | Glaxo Group Ltd | Process for the preparation of chemical compounds |
EP1246621A4 (de) | 1999-12-23 | 2004-11-24 | Nitromed Inc | Nitrosierte und nitrosylierte cyclooxygenase-2-inhibitoren, zusammensetzungen und methoden für deren verwendung |
DE10001166A1 (de) | 2000-01-13 | 2001-07-19 | Merckle Gmbh | Anellierte Pyrrolverbindungen, diese enthaltende pharmazeutische Mittel und deren Verwendung |
JP2003523330A (ja) | 2000-02-04 | 2003-08-05 | チルドレンズ・ホスピタル・リサーチ・ファウンデイション | アテローム性動脈硬化症および関連疾患のための脂質加水分解治療 |
EA200200839A1 (ru) | 2000-02-08 | 2003-04-24 | Эро-Селтик, С.А. | Композиции с контролируемым высвобождением, содержащие агонист и антагонист опиоидов |
JP2003522146A (ja) | 2000-02-08 | 2003-07-22 | ユーロ−セルティーク,エス.エイ. | 外圧に抵抗性の経口オピオイドアゴニスト製剤 |
ES2166710B1 (es) * | 2000-04-25 | 2004-10-16 | J. URIACH & CIA, S.A. | Nuevos compuestos heterociclicos con actividad antiinflamatoria. |
US20020183362A1 (en) | 2000-04-25 | 2002-12-05 | Pharmacia Corporation | 2-Fluorobenzenesulfonyl compounds for the treatment of inflammation |
MXPA03000161A (es) * | 2000-05-22 | 2004-02-26 | Reddy Research Foundation | Compuestos novedosos los cuales tienen actividad antiinflamatoria, proceso para su preparacion y composiciones farmaceuticas que las contienen. |
KR20030019422A (ko) * | 2000-06-13 | 2003-03-06 | 와이어쓰 | Cox-2저해제를 함유하는 진통성 및 항-염증성 조성물 |
US6465509B2 (en) | 2000-06-30 | 2002-10-15 | Merck Frosst Canada & Co. | Pyrones as inhibitors of cyclooxygenase-2 |
AU5754701A (en) * | 2000-07-13 | 2002-01-30 | Pharmacia Corp | Method of using cox-2 inhibitors in the treatment and prevention of ocular cox-2mediated disorders |
PE20020146A1 (es) * | 2000-07-13 | 2002-03-31 | Upjohn Co | Formulacion oftalmica que comprende un inhibidor de ciclooxigenasa-2 (cox-2) |
EP1303265B1 (de) * | 2000-07-20 | 2007-07-11 | Lauras AS | Verwendung von cox-2 inhibitoren als immunostimulantien zur behandlung von hiv oder aids |
US6716829B2 (en) | 2000-07-27 | 2004-04-06 | Pharmacia Corporation | Aldosterone antagonist and cyclooxygenase-2 inhibitor combination therapy to prevent or treat inflammation-related cardiovascular disorders |
PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
US8680081B2 (en) * | 2000-08-29 | 2014-03-25 | Peter Van Patten | Prophylactic treatment of migraine |
GB0021494D0 (en) * | 2000-09-01 | 2000-10-18 | Glaxo Group Ltd | Chemical comkpounds |
US20030219461A1 (en) * | 2000-09-12 | 2003-11-27 | Britten Nancy J. | Parenteral combination therapy for infective conditions |
CA2422064A1 (en) * | 2000-09-18 | 2002-03-21 | Merck & Co., Inc. | Treatment of inflammation with a combination of a cyclooxygenase-2 inhibitor and an integrin alpha-v antagonist |
DE10057366A1 (de) * | 2000-11-18 | 2002-05-23 | Mahle Gmbh | Verfahren zur gießtechnischen Herstellung eines Kolbens mit einem gekühlten Ringträger |
DE60112330T2 (de) | 2000-12-15 | 2006-04-13 | Glaxo Group Ltd., Greenford | Pyrazolopyridinderivate |
US6919352B2 (en) | 2000-12-15 | 2005-07-19 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyridine and pyrimidine therapeutic compounds |
CA2432642A1 (en) | 2000-12-21 | 2002-08-08 | Subhash P. Khanapure | Substituted aryl compounds as novel cyclooxygenase-2 selective inhibitors, compositions and methods of use |
US7115565B2 (en) * | 2001-01-18 | 2006-10-03 | Pharmacia & Upjohn Company | Chemotherapeutic microemulsion compositions of paclitaxel with improved oral bioavailability |
AUPR283801A0 (en) * | 2001-02-01 | 2001-03-01 | Australian National University, The | Chemical compounds and methods |
WO2002062391A2 (en) * | 2001-02-02 | 2002-08-15 | Pharmacia Corporation | Method of using a cyclooxygenase-2 inhibitor and sex steroids as a combination therapy for the treatment and prevention of dismenorrhea |
DE10107683A1 (de) | 2001-02-19 | 2002-08-29 | Merckle Gmbh Chem Pharm Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
WO2002072581A2 (en) | 2001-03-08 | 2002-09-19 | Smithkline Beecham Corporation | Pyrazolopyriadine derivatives |
US7034030B2 (en) | 2001-03-30 | 2006-04-25 | Smithkline Beecham Corporation | Pyralopyridines, process for their preparation and use as therapeutic compounds |
MY137736A (en) | 2001-04-03 | 2009-03-31 | Pharmacia Corp | Reconstitutable parenteral composition |
DE60212949T2 (de) | 2001-04-10 | 2007-01-04 | Smithkline Beecham Corp. | Antivirale pyrazolopyridin verbindungen |
US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
US6673818B2 (en) | 2001-04-20 | 2004-01-06 | Pharmacia Corporation | Fluoro-substituted benzenesulfonyl compounds for the treatment of inflammation |
US6756498B2 (en) | 2001-04-27 | 2004-06-29 | Smithkline Beecham Corporation | Process for the preparation of chemical compounds |
ES2242028T3 (es) | 2001-04-27 | 2005-11-01 | Smithkline Beecham Corporation | Derivados de pirazolo(1,5-a)piridina. |
UA81224C2 (uk) | 2001-05-02 | 2007-12-25 | Euro Celtic S A | Дозована форма оксикодону та її застосування |
WO2002089798A2 (en) * | 2001-05-04 | 2002-11-14 | Merck & Co., Inc. | Method and compositions for treating migraines |
ATE493130T1 (de) | 2001-05-11 | 2011-01-15 | Endo Pharmaceuticals Inc | Opioid enthaltende arzneiform gegen missbrauch |
GB0112810D0 (en) * | 2001-05-25 | 2001-07-18 | Glaxo Group Ltd | Pyrimidine derivatives |
GB0112802D0 (en) * | 2001-05-25 | 2001-07-18 | Glaxo Group Ltd | Pyrimidine derivatives |
US20030153801A1 (en) * | 2001-05-29 | 2003-08-14 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease |
SK14762003A3 (sk) * | 2001-05-31 | 2004-08-03 | Pharmacia Corporation | Kožou prestupujúci prípravok obsahujúci selektívne inhibujúcu cyklooxygenázu-2 a jednosýtny alkohol |
DE10129320A1 (de) * | 2001-06-19 | 2003-04-10 | Norbert Mueller | Verwendung von COX-2 Inhibitoren zur Behandlung von Schizophrenie, wahnhaften Störungen, affektiven Störungen oder Ticstörungen |
US20060167074A1 (en) * | 2001-06-19 | 2006-07-27 | Norbert Muller | Methods and compositions for the treatment of psychiatric disorders |
CN1518550A (zh) | 2001-06-21 | 2004-08-04 | ʷ��˿�������ȳ�ķ����˾ | 用于预防和治疗疱疹病毒感染的咪唑并[1,2-a]吡啶衍生物 |
DE60204823T2 (de) | 2001-07-05 | 2005-12-29 | Pfizer Products Inc., Groton | Heterocyclo-alkylsulfonyl Pyrazole als entzündungshemmende/analgetische Mittel |
DK1416842T3 (da) | 2001-07-18 | 2009-03-16 | Euro Celtique Sa | Farmaceutiske kombinationer af oxycodon og naloxon |
NZ530971A (en) | 2001-08-06 | 2004-08-27 | Euro Celtique S | Oral dosage forms comprising an opioid agonist with releasable and sequestered opioid antagonists |
US20030044458A1 (en) | 2001-08-06 | 2003-03-06 | Curtis Wright | Oral dosage form comprising a therapeutic agent and an adverse-effect agent |
US20030068375A1 (en) | 2001-08-06 | 2003-04-10 | Curtis Wright | Pharmaceutical formulation containing gelling agent |
UA80682C2 (en) * | 2001-08-06 | 2007-10-25 | Pharmacia Corp | Orally deliverable stabilized oral suspension formulation and process for the incresaing physical stability of thixotropic pharmaceutical composition |
US20030157168A1 (en) | 2001-08-06 | 2003-08-21 | Christopher Breder | Sequestered antagonist formulations |
GB0119477D0 (en) * | 2001-08-09 | 2001-10-03 | Glaxo Group Ltd | Pyrimidine derivatives |
AR038957A1 (es) | 2001-08-15 | 2005-02-02 | Pharmacia Corp | Terapia de combinacion para el tratamiento del cancer |
WO2003018575A1 (en) * | 2001-08-24 | 2003-03-06 | Wyeth Holdings Corporation | 5-substituted-3(2h)-furanones useful for inhibition of farnesyl-protein transferase |
US20030114483A1 (en) * | 2001-09-18 | 2003-06-19 | Pharmacia Corporation | Compositions of chromene cyclooxygenase-2 selective inhibitors and acetaminophen for treatment and prevention of inflammation, inflammation-mediated disorders and pain |
US20030236308A1 (en) * | 2001-09-18 | 2003-12-25 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and acetaminophen for treatment and prevention of inflammation, inflammation-mediated disorders and pain |
PL369298A1 (en) * | 2001-09-26 | 2005-04-18 | Pharmacia Corporation | Intraorally disintegrating valdecoxib compositions |
GT200200183A (es) | 2001-09-28 | 2003-05-23 | Procedimiento para preparar derivados de heterocicloalquilsulfonil pirazol | |
ATE326466T1 (de) | 2001-10-05 | 2006-06-15 | Smithkline Beecham Corp | Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion |
KR100810468B1 (ko) | 2001-10-10 | 2008-03-07 | 씨제이제일제당 (주) | 사이클로옥시게나제-2의 저해제로서 선택성이 뛰어난1h-인돌 유도체 |
KR100824233B1 (ko) | 2001-10-10 | 2008-04-24 | 씨제이제일제당 (주) | 사이클로옥시게나제-2의 저해제로서 선택성이 뛰어난3,4-디하이드로-1h-나프탈렌 유도체 |
WO2003037336A1 (en) | 2001-11-02 | 2003-05-08 | Pfizer Products Inc. | 1-(5-sulfonyl-pyridin-2-yl)-5-(methylidene-cycloalkylmethoxy)-1h-pyrazole-4-carbonitrile derivatives and other compounds as cyclooxygenase inhibitors for the treatment of arthritis, neurodegeneration and colon cancer |
EP1551812B1 (de) | 2001-12-06 | 2009-03-04 | Merck & Co., Inc. | Mitotische kinesinhemmer |
FR2833164B1 (fr) * | 2001-12-07 | 2004-07-16 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
JP2005516916A (ja) | 2001-12-11 | 2005-06-09 | スミスクライン ビーチャム コーポレーション | 抗ヘルペス薬としてのピラゾロ−ピリジン誘導体 |
US20040082940A1 (en) * | 2002-10-22 | 2004-04-29 | Michael Black | Dermatological apparatus and method |
DE10162120A1 (de) * | 2001-12-12 | 2003-06-18 | Berolina Drug Dev Ab Svedala | Deuterierte substituierte Dihydrofuranone sowie diese Verbindungen enthaltende Arzneimittel |
US20030220374A1 (en) * | 2002-01-14 | 2003-11-27 | Pharmacia Corporation | Compositions and methods of treatment involving peroxisome proliferator-activated receptor-gamma agonists and cyclooxygenase-2 selective inhibitors |
US20030212138A1 (en) * | 2002-01-14 | 2003-11-13 | Pharmacia Corporation | Combinations of peroxisome proliferator-activated receptor-alpha agonists and cyclooxygenase-2 selective inhibitors and therapeutic uses therefor |
US7985771B2 (en) * | 2002-01-31 | 2011-07-26 | Monsanto Technology Llc | Furanone derivatives |
US6667330B2 (en) | 2002-01-31 | 2003-12-23 | Galileo Pharmaceuticals, Inc. | Furanone derivatives |
EP1492505B1 (de) | 2002-04-05 | 2015-06-03 | Euro-Celtique S.A. | Pharmazeutische zubereitung enthaltend oxycodon und naloxon |
MXPA04009800A (es) * | 2002-04-08 | 2004-12-13 | Glaxo Group Ltd | Acido (2-((2-alcoxi)-fenil)-ciclopent-1-enil) carbociclico y heterociclico aromatico y derivados. |
IL164163A0 (en) * | 2002-04-09 | 2005-12-18 | Pharmacia Corp | Process for preparing a finely self-emulsifiable pharmaceutical composition |
US7329401B2 (en) | 2002-04-15 | 2008-02-12 | The Regents Of The University Of California | Cyclooxygenase-2 selective agents useful as imaging probes and related methods |
CA2481941A1 (en) | 2002-04-17 | 2003-10-30 | The Cleveland Clinic Foundation | Systemic marker for monitoring anti-inflammatory and antioxidant actions of therapeutic agents |
BR0309412A (pt) * | 2002-04-22 | 2005-02-01 | Pfizer Prod Inc | Indol-2-onas como inibidores seletivos da ciclooxigenase-2 |
GB0210121D0 (en) | 2002-05-02 | 2002-06-12 | Celltech R&D Ltd | Biological products |
DK2336359T3 (en) | 2002-05-09 | 2016-05-30 | Brigham & Womens Hospital | 1L1RL-1 as cardiovascular disease marker |
AU2003229016A1 (en) * | 2002-05-10 | 2003-11-11 | The Trustees Of Columbia University In The City Of New York | Genetically engineered cell lines and systems for propagatingvaricella zoster virus and methods of use thereof |
KR100804827B1 (ko) * | 2002-05-17 | 2008-02-20 | 씨제이제일제당 (주) | 티아졸리딘-4-온 유도체, 그 제조방법 및 약제학적 조성물 |
US20030225054A1 (en) * | 2002-06-03 | 2003-12-04 | Jingwu Duan | Combined use of tace inhibitors and COX2 inhibitors as anti-inflammatory agents |
KR100478467B1 (ko) | 2002-06-24 | 2005-03-23 | 씨제이 주식회사 | 피라졸-3-온 유도체, 그 제조방법 및 약제학적 조성물 |
KR100465455B1 (ko) | 2002-06-24 | 2005-01-13 | 씨제이 주식회사 | 2-티옥소티아졸 유도체, 그 제조방법 및 약제학적 조성물 |
JP2006501179A (ja) * | 2002-06-27 | 2006-01-12 | ニトロメッド インコーポレーティッド | シクロオキシゲナーゼ−2選択的阻害剤、組成物、および使用方法 |
AU2003279622A1 (en) * | 2002-06-28 | 2004-01-19 | Nitromed, Inc. | Oxime and/or hydrazone containing nitrosated and/or nitrosylated cyclooxigenase-2 selective inhibitors, compositions and methods of use |
JP2005535657A (ja) * | 2002-07-02 | 2005-11-24 | ファルマシア・コーポレーション | シクロオキシゲナーゼ−2選択阻害剤及び血栓溶解剤の血管閉塞イベントの治療又は予防への使用 |
US7771707B2 (en) | 2004-06-12 | 2010-08-10 | Collegium Pharmaceutical, Inc. | Abuse-deterrent drug formulations |
KR100467668B1 (ko) * | 2002-08-07 | 2005-01-24 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
DE60305053T2 (de) * | 2002-08-19 | 2006-08-31 | Glaxo Group Ltd., Greenford | Pyrimidinderivate als selektive cox-2-inhibitoren |
DE10238045A1 (de) | 2002-08-20 | 2004-03-04 | Merckle Gmbh Chem.-Pharm. Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
GB0221443D0 (en) | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
AU2003270778B2 (en) | 2002-09-20 | 2009-10-08 | Alpharma Pharmaceuticals, Llc | Sequestering subunit and related compositions and methods |
US8303511B2 (en) * | 2002-09-26 | 2012-11-06 | Pacesetter, Inc. | Implantable pressure transducer system optimized for reduced thrombosis effect |
US7153863B2 (en) | 2002-10-03 | 2006-12-26 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridline derivatives |
AU2003304238A1 (en) | 2002-10-08 | 2005-01-13 | Rinat Neuroscience Corp. | Methods for treating post-surgical pain by administering an anti-nerve growth factor antagonist antibody and compositions containing the same |
DK1556083T3 (da) * | 2002-10-08 | 2011-04-04 | Rinat Neuroscience Corp | Fremgangsmåde til behandling af post-operative smerter ved indgivelse af en antistof mod nervevækstfaktor og sammensætning indeholdende samme |
KR100484525B1 (ko) * | 2002-10-15 | 2005-04-20 | 씨제이 주식회사 | 이소티아졸 유도체, 그 제조방법 및 약제학적 조성물 |
US20040082543A1 (en) * | 2002-10-29 | 2004-04-29 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and NMDA receptor antagonists for the treatment or prevention of neuropathic pain |
DE60336576D1 (de) * | 2002-10-30 | 2011-05-12 | Merck Sharp & Dohme | Hemmer der akt aktivität |
GB0225548D0 (en) * | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
AU2003283096A1 (en) * | 2002-11-05 | 2004-06-07 | Merck Frosst Canada And Co. | Nitric oxide releasing prodrugs of diaryl-2-(5h)-furanones as cyclooxygenase-2 inhibitors |
US20040185110A1 (en) * | 2002-11-08 | 2004-09-23 | Ronald Harland | Formulations of low solubility bioactive agents and processes for making the same |
US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
KR100470075B1 (ko) | 2002-11-21 | 2005-02-05 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
GB0227443D0 (en) * | 2002-11-25 | 2002-12-31 | Glaxo Group Ltd | Pyrimidine derivatives |
KR100491317B1 (ko) | 2002-11-26 | 2005-05-24 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
KR100470076B1 (ko) | 2002-11-27 | 2005-02-05 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
WO2004054560A1 (en) | 2002-12-13 | 2004-07-01 | Warner-Lambert Company Llc | Alpha-2-delta ligand to treat lower urinary tract symptoms |
BR0317539A (pt) * | 2002-12-19 | 2005-11-22 | Pharmacia Corp | Métodos e composições para o tratamento de infecções por vìrus da herpes usando inibidores seletivos da ou ciclooxigenase-2 ou inibidores da ciclooxigenase-2 em combinação com agentes antivirais |
US20040171664A1 (en) * | 2002-12-20 | 2004-09-02 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and selective serotonin reuptake inhibitors for the treatment or prevention of a vaso-occlusive event |
US7569364B2 (en) * | 2002-12-24 | 2009-08-04 | Pfizer Inc. | Anti-NGF antibodies and methods using same |
ES2215474B1 (es) | 2002-12-24 | 2005-12-16 | J. URIACH & CIA S.A. | Nuevos derivados de fosforamida. |
US9498530B2 (en) | 2002-12-24 | 2016-11-22 | Rinat Neuroscience Corp. | Methods for treating osteoarthritis pain by administering a nerve growth factor antagonist and compositions containing the same |
KR101250818B1 (ko) | 2002-12-24 | 2013-04-15 | 리나트 뉴로사이언스 코프. | 항-ngf 항체 및 그것을 이용하는 방법 |
MXPA05006954A (es) * | 2002-12-26 | 2005-09-22 | Pozen Inc | Formas de dosificacion de capas multiples que contienen nsaids y triptanos. |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
US20070265606A1 (en) * | 2003-02-14 | 2007-11-15 | Reliant Technologies, Inc. | Method and Apparatus for Fractional Light-based Treatment of Obstructive Sleep Apnea |
MXPA05008815A (es) * | 2003-02-19 | 2006-05-25 | Rinat Neuroscience Corp | Metodos para tratar el dolor al administrar un antagonista del factor de crecimiento de nervios y un farmaco antiinflamatorio no esteroidal y composiciones que contienen los mismos. |
US20050009931A1 (en) * | 2003-03-20 | 2005-01-13 | Britten Nancy Jean | Dispersible pharmaceutical composition for treatment of mastitis and otic disorders |
US20050004098A1 (en) * | 2003-03-20 | 2005-01-06 | Britten Nancy Jean | Dispersible formulation of an anti-inflammatory agent |
BRPI0408556A (pt) * | 2003-03-20 | 2006-03-21 | Pharmacia Corp | formulações dispersìvel de um agente antiinflamatório |
US20040214753A1 (en) * | 2003-03-20 | 2004-10-28 | Britten Nancy Jean | Dispersible pharmaceutical composition for treatment of mastitis and otic disorders |
US20040220155A1 (en) * | 2003-03-28 | 2004-11-04 | Pharmacia Corporation | Method of providing a steroid-sparing benefit with a cyclooxygenase-2 inhibitor and compositions therewith |
TWI347201B (en) | 2003-04-21 | 2011-08-21 | Euro Celtique Sa | Pharmaceutical products,uses thereof and methods for preparing the same |
WO2004093813A2 (en) * | 2003-04-22 | 2004-11-04 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a calcium modulating agent for the treatment of pain, inflammation or inflammation mediated disorders |
WO2004093816A2 (en) * | 2003-04-22 | 2004-11-04 | Pharmacia Corporation | Compositions comprising a selective cox-2 inhibitor and a calcium modulating agent |
WO2004093895A1 (en) * | 2003-04-22 | 2004-11-04 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a potassium ion channel modulator for the treatment of pain, inflammation or inflammation mediated disorders |
US20040220187A1 (en) * | 2003-04-22 | 2004-11-04 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a sodium ion channel blocker for the treatment of pain, inflammation or inflammation mediated disorders |
WO2004100895A2 (en) * | 2003-05-13 | 2004-11-25 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a peroxisome proliferator activated receptor agonist for the treatment of ischemic mediated central nervous system disorders |
US20060160776A1 (en) * | 2003-05-28 | 2006-07-20 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a cannabinoid agent for the treatment of central nervous system damage |
NZ543741A (en) | 2003-05-30 | 2009-10-30 | Ranbaxy Lab Ltd | Substituted pyrrole derivatives and their use as HMG-Co inhibitors |
CN1309717C (zh) * | 2003-06-03 | 2007-04-11 | 李小虎 | 4-芳基-5h-噻吩-2-酮衍生物、其制法和用途 |
AU2004247076A1 (en) * | 2003-06-06 | 2004-12-23 | Glaxo Group Limited | Composition comprising triptans and NSAIDs |
EP1638573A4 (de) * | 2003-06-20 | 2009-12-02 | Merck & Co Inc | Verwendung von selektiven cyclooxygenase-2-hemmern zur behandlung von endometriose |
MXPA05013624A (es) * | 2003-06-24 | 2006-02-24 | Pharmacia Corp | Tratamiento de migrana acompanada de nauseas. |
WO2005007106A2 (en) * | 2003-07-10 | 2005-01-27 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a non-nmda glutamate modulator for the treatment of central nervous system damage |
US20050014729A1 (en) * | 2003-07-16 | 2005-01-20 | Pharmacia Corporation | Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith |
WO2005009354A2 (en) * | 2003-07-17 | 2005-02-03 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and an ikk inhibitor for the treatment of ischemic-mediated central nervous system disorders or injury |
AU2004266705A1 (en) * | 2003-08-20 | 2005-03-03 | Nitromed, Inc. | Nitrosated and nitrosylated cardiovascular compounds, compositions and methods of use |
US20050119262A1 (en) * | 2003-08-21 | 2005-06-02 | Pharmacia Corporation | Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent |
US20050107350A1 (en) * | 2003-08-22 | 2005-05-19 | Pharmacia Corporation | Method for the treatment or prevention of bone disorders with a cyclooxygenase-2 inhibitor alone and in combination with a bone disorder treatment agent and compositions therewith |
US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
AU2004270162B2 (en) * | 2003-08-28 | 2010-05-13 | Nicox S.A. | Nitrosated ad nitrosylated diuretic compouds, compositions and methods of use |
CA2536622C (en) | 2003-08-29 | 2014-02-11 | The Brigham And Women's Hospital, Inc. | Inhibitors of cellular necrosis |
WO2005023189A2 (en) * | 2003-09-03 | 2005-03-17 | Pharmacia Corporation | Method of cox-2 selective inhibitor and nitric oxide-donating agent |
US20050131028A1 (en) * | 2003-09-11 | 2005-06-16 | Pharmacia Corporation | Methods and compositions for the extended duration treatment of pain, inflammation and inflammation-related disorders |
SI1663229T1 (sl) | 2003-09-25 | 2010-08-31 | Euro Celtique Sa | Farmacevtske kombinacije hidrokodona in naltreksona |
GB0323584D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Compounds |
GB0323581D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Novel compounds |
GB0323585D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Compounds |
FR2860792B1 (fr) * | 2003-10-10 | 2006-02-24 | Sanofi Synthelabo | Derives de thiophene-2-carboxamide, leur preparation et leur application en therapeutique |
WO2005044227A1 (en) * | 2003-11-05 | 2005-05-19 | Glenmark Pharmaceuticals Limited | Topical pharmaceutical compositions |
US20050100594A1 (en) * | 2003-11-12 | 2005-05-12 | Nilendu Sen | Pharmaceutical formulation containing muscle relaxant and COX-II inhibitor |
DK1689721T3 (da) * | 2003-11-26 | 2010-09-20 | Pfizer Prod Inc | Aminopyrazolderivater som GSK-3-ihibitorer |
ES2381551T3 (es) | 2003-12-05 | 2012-05-29 | The Cleveland Clinic Foundation | Marcadores de riesgo para enfermedad cardiovascular |
US7070816B2 (en) * | 2003-12-05 | 2006-07-04 | New Chapter, Inc. | Methods for treating prostatic intraepithelial neoplasia with herbal compositions |
US7067159B2 (en) * | 2003-12-05 | 2006-06-27 | New Chapter, Inc. | Methods for treating prostate cancer with herbal compositions |
EP1708718A1 (de) | 2004-01-22 | 2006-10-11 | Pfizer Limited | Triazol-derivate zur hemmung der vasopressing-antagonistischen aktivität |
AU2005207037A1 (en) * | 2004-01-22 | 2005-08-04 | Nitromed, Inc. | Nitrosated and/or nitrosylated compounds, compositions and methods of use |
US20050203081A1 (en) * | 2004-02-25 | 2005-09-15 | Jinbo Lee | Inhibitors of protein tyrosine phosphatase 1B |
WO2005081954A2 (en) * | 2004-02-25 | 2005-09-09 | Wyeth | Inhibitors of protein tyrosine phosphatase 1b |
MXPA06011463A (es) | 2004-04-07 | 2007-04-25 | Rinat Neuroscience Corp | Metodos para tratar dolor por cancer de hueso al administrar un antagonista de factor de crecimiento de nervio. |
BRPI0510340A (pt) * | 2004-04-28 | 2007-10-30 | Pfizer | derivados de 3-heterociclil-4-feniltriazol como inibidores do receptor via da vasopressina |
US7507823B2 (en) * | 2004-05-06 | 2009-03-24 | Bristol-Myers Squibb Company | Process of making aripiprazole particles |
GB0410121D0 (en) * | 2004-05-06 | 2004-06-09 | Glaxo Group Ltd | Compounds |
US20080138282A1 (en) * | 2004-06-03 | 2008-06-12 | The Trustees Of Columbia University In The City Of New York | Radiolabeled Arylsulfonyl Compounds and Uses Thereof |
EP1604666A1 (de) | 2004-06-08 | 2005-12-14 | Euro-Celtique S.A. | Opioide zur Behandlung der chronischen obstruktiven Lungenkrankheit |
JP2008505085A (ja) | 2004-07-01 | 2008-02-21 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
ES2257929B1 (es) * | 2004-07-16 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de pirazolina, procedimiento para su obtencion y utilizacion de los mismos como agentes terapeuticos. |
AU2005266088A1 (en) * | 2004-07-22 | 2006-02-02 | Pharmacia Corporation | Compositions for treatment of inflammation and pain using a combination of a COX-2 selective inhibitor and a LTB4 receptor antagonist |
EP1784179A4 (de) | 2004-08-24 | 2010-03-31 | Merck Sharp & Dohme | Kombinationstherapie zur behandlung von cyclooxygenase-2-vermittelten krankheiten oder zuständen bei patienten mit risiko auf thrombotische kardiovaskuläre ereignisse |
US7622142B2 (en) * | 2004-09-14 | 2009-11-24 | New Chapter Inc. | Methods for treating glioblastoma with herbal compositions |
US20060064133A1 (en) * | 2004-09-17 | 2006-03-23 | Cardiac Pacemakers, Inc. | System and method for deriving relative physiologic measurements using an external computing device |
US8067464B2 (en) | 2004-10-04 | 2011-11-29 | Nitromed, Inc. | Compositions and methods using apocynin compounds and nitric oxide donors |
CA2624601C (en) | 2004-10-06 | 2018-07-03 | The Brigham And Women's Hospital, Inc. | Relevance of achieved levels of markers of systemic inflammation following treatment |
US20080300292A1 (en) * | 2004-11-08 | 2008-12-04 | Nitromed, Inc | Nitrosated and Nitrosylated Compounds, Compositions and Methods for the Treatment of Ophthalmic Disorders |
JP2008520578A (ja) * | 2004-11-15 | 2008-06-19 | ニトロメッド インコーポレーティッド | 複素環式の酸化窒素供与体基を含む利尿化合物、組成物および使用方法 |
TW200640865A (en) | 2004-12-23 | 2006-12-01 | Glaxo Group Ltd | Compounds |
AU2005320547B2 (en) | 2004-12-27 | 2009-02-05 | Eisai R & D Management Co., Ltd. | Method for stabilizing anti-dementia drug |
AU2006206249A1 (en) * | 2005-01-21 | 2006-07-27 | Nicox S.A. | Cardiovascular compounds comprising heterocyclic nitric oxide donor group compositions and methods of use |
KR20080016527A (ko) * | 2005-01-31 | 2008-02-21 | 밀란 래보러토리즈, 인크. | 하이드록시화된 네비볼롤을 함유하는 약학적 조성물 |
WO2007086884A2 (en) * | 2005-02-16 | 2007-08-02 | Nitromed, Inc. | Organic nitric oxide donor salts of antimicrobial compounds, compositions and methods of use |
US7521435B2 (en) * | 2005-02-18 | 2009-04-21 | Pharma Diagnostics, N.V. | Silicon containing compounds having selective COX-2 inhibitory activity and methods of making and using the same |
EP1702558A1 (de) | 2005-02-28 | 2006-09-20 | Euro-Celtique S.A. | Verfahren und Vorrichtung zur Darmtätigkeitserfassung |
JP2008531697A (ja) * | 2005-02-28 | 2008-08-14 | ニトロメッド インコーポレーティッド | 酸化窒素増強基を含む心血管化合物、組成物および使用法 |
JP2008533031A (ja) * | 2005-03-09 | 2008-08-21 | ニトロメッド インコーポレーティッド | アンギオテンシンiiアンタゴニストの有機酸化窒素増強塩、組成物および使用法 |
WO2006110918A1 (en) * | 2005-04-13 | 2006-10-19 | Ambit Biosciences Corporation | Pyrrole compounds and uses thereof |
US20090023778A1 (en) * | 2005-04-28 | 2009-01-22 | Eisai R&D Management Co., Ltd. | Composition Containing Anti-Dementia Drug |
WO2006121887A2 (en) * | 2005-05-05 | 2006-11-16 | Cook Biotech Incorporated | Implantable materials and methods for inhibiting tissue adhesion formation |
WO2006123182A2 (en) | 2005-05-17 | 2006-11-23 | Merck Sharp & Dohme Limited | Cyclohexyl sulphones for treatment of cancer |
JP2008540633A (ja) * | 2005-05-18 | 2008-11-20 | ファイザー・リミテッド | バソプレッシン拮抗薬としての1,2,4−トリアゾール誘導体 |
WO2006127591A2 (en) * | 2005-05-23 | 2006-11-30 | Nitromed, Inc. | Organic nitric oxide enhancing salts of nonsteroidal antiinflammatory compounds, compositions and methods of use |
EP1890691A2 (de) | 2005-05-31 | 2008-02-27 | Mylan Laboratories, Inc | Zusammensetzungen mit nebivolol |
WO2007016677A2 (en) | 2005-08-02 | 2007-02-08 | Nitromed, Inc. | Nitric oxide enhancing antimicrobial compounds, compositions and methods of use |
PE20070335A1 (es) * | 2005-08-30 | 2007-04-21 | Novartis Ag | Benzimidazoles sustituidos y metodos para su preparacion |
EP1942909A4 (de) * | 2005-10-04 | 2010-01-06 | Nitromed Inc | Verfahren zur behandlung von atemwegserkrankungen |
US8119358B2 (en) | 2005-10-11 | 2012-02-21 | Tethys Bioscience, Inc. | Diabetes-related biomarkers and methods of use thereof |
JP2009514851A (ja) | 2005-11-08 | 2009-04-09 | ランバクシー ラボラトリーズ リミテッド | (3r,5r)−7−[2−(4−フルオロフェニル)−5−イソプロピル−3−フェニル−4−[(4−ヒドロキシメチルフェニルアミノ)カルボニル]−ピロール−1−イル]−3,5−ジヒドロキシ−ヘプタン酸ヘミカルシウム塩の製法 |
WO2007059311A2 (en) * | 2005-11-16 | 2007-05-24 | Nitromed, Inc. | Furoxan compounds, compositions and methods of use |
TW200735866A (en) | 2005-11-18 | 2007-10-01 | Synta Pharmaceuticals Corp | Compounds for the treatment of proliferative disorders |
EP1968584A2 (de) * | 2005-12-20 | 2008-09-17 | Nitromed, Inc. | Stickoxid-verstärkende glutaminsäure-verbindungen, zusammensetzungen und anwendungsverfahren |
US20080293702A1 (en) * | 2005-12-22 | 2008-11-27 | Nitromed, Inc. | Nitric Oxide Enhancing Pyruvate Compounds, Compositions and Methods of Use |
WO2007087246A2 (en) | 2006-01-24 | 2007-08-02 | Merck & Co., Inc. | Jak2 tyrosine kinase inhibition |
GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
PL3279663T3 (pl) | 2006-03-15 | 2022-01-10 | The Brigham And Women's Hospital, Inc. | Zastosowanie gelsoliny do diagnozowania i leczenia chorób zapalnych |
AU2007243765A1 (en) | 2006-03-29 | 2007-11-08 | Nicox S.A. | Nitric oxide enhancing prostaglandin compounds, compositions and methods of use |
DK2010528T3 (en) | 2006-04-19 | 2018-01-15 | Novartis Ag | 6-O-Substituted Benzoxazole and Benzothiazole Compounds and Methods for Inhibiting CSF-1R Signaling |
CA2659082A1 (en) | 2006-06-07 | 2007-12-21 | Tethys Bioscience, Inc. | Markers associated with arteriovascular events and methods of use thereof |
PT2034975E (pt) | 2006-06-19 | 2012-06-25 | Alpharma Pharmaceuticals Llc | Composições farmacêuticas |
US8128460B2 (en) * | 2006-09-14 | 2012-03-06 | The Material Works, Ltd. | Method of producing rust inhibitive sheet metal through scale removal with a slurry blasting descaling cell |
JP5489333B2 (ja) | 2006-09-22 | 2014-05-14 | メルク・シャープ・アンド・ドーム・コーポレーション | 脂肪酸合成阻害剤を用いた治療の方法 |
WO2008052198A2 (en) * | 2006-10-26 | 2008-05-02 | Reliant Technologies, Inc. | Methods of increasing skin permeability by treatment with electromagnetic radiation |
CN103865288B (zh) | 2006-10-31 | 2017-05-31 | 生物科技环境公司 | 用于使聚合物材料生物可降解的化学添加剂 |
US8513329B2 (en) | 2006-10-31 | 2013-08-20 | Bio-Tec Environmental, Llc | Chemical additives to make polymeric materials biodegradable |
US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
DK2125021T3 (da) | 2006-12-22 | 2011-09-19 | Recordati Ireland Ltd | Kombinationsterapi af sygdomme i de nedre urinveje med alfa2delta-ligander og NSAID'er |
PL2336120T3 (pl) | 2007-01-10 | 2014-12-31 | Msd Italia Srl | Kombinacje zawierające indazole podstawione grupą amidową jako inhibitory polimerazy poli(ADP-rybozy) (PARP) |
CN101626787A (zh) * | 2007-01-19 | 2010-01-13 | 马林克罗特公司 | 诊断的和治疗的环氧合酶-2结合配体 |
MX2009009304A (es) | 2007-03-01 | 2009-11-18 | Novartis Ag | Inhibidores de cinasa pim y metodos para su uso. |
GB0704407D0 (en) | 2007-03-07 | 2007-04-18 | Glaxo Group Ltd | Compounds |
EP2147315B1 (de) | 2007-04-18 | 2013-06-26 | Tethys Bioscience, Inc. | Biomarker in verbindung mit diabetes und verwendungsverfahren dafür |
KR20100017866A (ko) | 2007-05-21 | 2010-02-16 | 노파르티스 아게 | Csf-1r 억제제, 조성물 및 사용 방법 |
AU2008269154B2 (en) | 2007-06-27 | 2014-06-12 | Merck Sharp & Dohme Llc | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
MX2010000465A (es) | 2007-07-12 | 2010-08-30 | Tragara Pharmaceuticals Inc | Metodos y composiciones para el tratamiento de cancer, tumores y alteraciones relacionadas con tumores. |
US7943658B2 (en) * | 2007-07-23 | 2011-05-17 | Bristol-Myers Squibb Company | Indole indane amide compounds useful as CB2 agonists and method |
AU2008299220B2 (en) | 2007-09-10 | 2011-07-21 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
US8623418B2 (en) | 2007-12-17 | 2014-01-07 | Alpharma Pharmaceuticals Llc | Pharmaceutical composition |
JP2011515343A (ja) | 2008-03-03 | 2011-05-19 | タイガー ファーマテック | チロシンキナーゼ阻害薬 |
GB2460915B (en) * | 2008-06-16 | 2011-05-25 | Biovascular Inc | Controlled release compositions of agents that reduce circulating levels of platelets and methods therefor |
GB0813144D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
GB0813142D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
US7981925B2 (en) | 2008-08-27 | 2011-07-19 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
EP2177215A1 (de) | 2008-10-17 | 2010-04-21 | Laboratorios Del. Dr. Esteve, S.A. | Co-Kristalle von Tramadol und NSARs |
CN101429181A (zh) * | 2008-12-18 | 2009-05-13 | 毛近隆 | 对羟基苯丙烯酸衍生物及其应用 |
WO2010071865A1 (en) | 2008-12-19 | 2010-06-24 | Nuon Therapeutics, Inc. | Pharmaceutical compositions and methods for treating hyperuricemia and related disorders |
US20100160351A1 (en) * | 2008-12-19 | 2010-06-24 | Nuon Therapeutics, Inc. | Pharmaceutical compositions and methods for treating hyperuricemia and related disorders |
GB0903493D0 (en) | 2009-02-27 | 2009-04-08 | Vantia Ltd | New compounds |
LT2405915T (lt) | 2009-03-10 | 2019-03-12 | Euro-Celtique S.A. | Greito atpalaidavimo farmacinė kompozicija, apimanti oksikodoną ir naloksoną |
WO2011012622A1 (en) | 2009-07-30 | 2011-02-03 | Glaxo Group Limited | Benzoxazinone derivatives for the treatment of glytl mediated disorders |
WO2011023753A1 (en) | 2009-08-27 | 2011-03-03 | Glaxo Group Limited | Benzoxazine derivatives as glycine transport inhibitors |
WO2011032175A1 (en) | 2009-09-14 | 2011-03-17 | Nuon Therapeutics, Inc. | Combination formulations of tranilast and allopurinol and methods related thereto |
WO2011046771A1 (en) | 2009-10-14 | 2011-04-21 | Schering Corporation | SUBSTITUTED PIPERIDINES THAT INCREASE p53 ACTIVITY AND THE USES THEREOF |
US10668060B2 (en) | 2009-12-10 | 2020-06-02 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
EP2512247B1 (de) | 2009-12-16 | 2014-06-04 | N30 Pharmaceuticals, Inc. | Neue thiopheninhemmer der s-nitrosoglutathion-reduktase |
GB201000685D0 (en) | 2010-01-15 | 2010-03-03 | Glaxo Group Ltd | Novel compounds |
SG182821A1 (en) | 2010-02-01 | 2012-08-30 | Hospital For Sick Children | Remote ischemic conditioning for treatment and prevention of restenosis |
US20110240043A1 (en) | 2010-03-31 | 2011-10-06 | The Hospital For Sick Children | Use of remote ischemic conditioning to improve outcome after myocardial infarction |
WO2011139489A2 (en) | 2010-04-27 | 2011-11-10 | Calcimedica Inc. | Compounds that modulate intracellular calcium |
AU2011248579A1 (en) | 2010-04-27 | 2012-11-29 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
GB201007791D0 (en) | 2010-05-10 | 2010-06-23 | Glaxo Group Ltd | Novel compounds |
GB201007789D0 (en) | 2010-05-10 | 2010-06-23 | Glaxo Group Ltd | Novel Compound |
WO2011163330A1 (en) | 2010-06-24 | 2011-12-29 | Merck Sharp & Dohme Corp. | Novel heterocyclic compounds as erk inhibitors |
WO2012004604A1 (en) | 2010-07-09 | 2012-01-12 | Convergence Pharmaceuticals Limited | Tetrazole compounds as calcium channel blockers |
CA2805265A1 (en) | 2010-08-02 | 2012-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (ctnnb1) gene expression using short interfering nucleic acid (sina) |
CA2807307C (en) | 2010-08-17 | 2021-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of hepatitis b virus (hbv) gene expression using short interfering nucleic acid (sina) |
LT3333188T (lt) | 2010-08-19 | 2022-06-10 | Zoetis Belgium S.A. | Anti-ngf antikūnai ir jų panaudojimas |
EP2608669B1 (de) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | Neue pyrazolo-[1,5-a-]pyrimidinderivate als mtor-hemmer |
MX337711B (es) | 2010-08-27 | 2016-03-15 | Calcimedica Inc | Compuestos que modulan el calcio intracelular. |
WO2012030685A2 (en) | 2010-09-01 | 2012-03-08 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
EP2615916B1 (de) | 2010-09-16 | 2017-01-04 | Merck Sharp & Dohme Corp. | Kondensierte pyrazolderivate als neue erk-hemmer |
ES2663009T3 (es) | 2010-10-29 | 2018-04-10 | Sirna Therapeutics, Inc. | Inhibición de la expresión génica mediada por interferencia por ARN utilizando ácidos nucleicos de interferencia cortos (ANic) |
EP2654748B1 (de) | 2010-12-21 | 2016-07-27 | Merck Sharp & Dohme Corp. | Indazolderivate als erk-hemmer |
CN104873455B (zh) | 2010-12-22 | 2023-09-12 | 普渡制药公司 | 包覆的抗篡改控制释放剂型 |
CN103327969A (zh) | 2010-12-23 | 2013-09-25 | 普渡制药公司 | 抗篡改固体口服剂型 |
ES2541416T3 (es) | 2011-01-19 | 2015-07-20 | Convergence Pharmaceuticals Limited | Derivados de piperazina como bloqueadores de los canales de calcio Cav2.2 |
JP2014514321A (ja) | 2011-04-21 | 2014-06-19 | メルク・シャープ・アンド・ドーム・コーポレーション | インスリン様増殖因子1受容体阻害剤 |
EP3662932B1 (de) | 2011-05-20 | 2021-04-07 | H. Lundbeck A/S | Anti-cgrp-zusammensetzungen und verwendung davon |
US9023865B2 (en) | 2011-10-27 | 2015-05-05 | Merck Sharp & Dohme Corp. | Compounds that are ERK inhibitors |
US9221809B2 (en) | 2011-10-31 | 2015-12-29 | Merck Sharp & Dohme Corp. | Aminopyrimidinones as interleukin receptor-associated kinase inhibitors |
GB201122113D0 (en) | 2011-12-22 | 2012-02-01 | Convergence Pharmaceuticals | Novel compounds |
EP3358013B1 (de) | 2012-05-02 | 2020-06-24 | Sirna Therapeutics, Inc. | Sina-zusammensetzungen |
JP6377054B2 (ja) | 2012-05-11 | 2018-08-22 | リセット セラピューティークス, インコーポレイテッド | クリプトクロム調節薬としてのカルバゾール含有スルホンアミド |
US9617334B2 (en) | 2012-06-06 | 2017-04-11 | Zoetis Services Llc | Caninized anti-NGF antibodies and methods thereof |
JP6280554B2 (ja) | 2012-09-28 | 2018-02-14 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | Erk阻害剤である新規化合物 |
WO2014059333A1 (en) | 2012-10-12 | 2014-04-17 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
BR112015012295A8 (pt) | 2012-11-28 | 2023-03-14 | Merck Sharp & Dohme | Uso de um inibidor de wee1, e, kit para identificar um paciente com câncer |
MX2015008196A (es) | 2012-12-20 | 2015-09-16 | Merck Sharp & Dohme | Imidazopiridinas sustituidas como inhibidores de doble minuto 2 humana. |
WO2014120748A1 (en) | 2013-01-30 | 2014-08-07 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
WO2014123899A1 (en) | 2013-02-05 | 2014-08-14 | Purdue Pharma L.P. | Tamper resistant pharmaceutical formulations |
EP2968276A4 (de) | 2013-03-15 | 2017-02-15 | President and Fellows of Harvard College | Hybride nekroptoseinhibitoren |
US10751287B2 (en) | 2013-03-15 | 2020-08-25 | Purdue Pharma L.P. | Tamper resistant pharmaceutical formulations |
TWI634114B (zh) | 2013-05-08 | 2018-09-01 | 永恒生物科技公司 | 作為激酶抑制劑之呋喃酮化合物 |
WO2015006181A1 (en) | 2013-07-11 | 2015-01-15 | Merck Sharp & Dohme Corp. | Substituted amidopyrazole inhibitors of interleukin receptor-associated kinases (irak-4) |
AU2014295042B2 (en) | 2013-07-23 | 2017-03-30 | Mundipharma Pty Limited | A combination of oxycodone and naloxone for use in treating pain in patients suffering from pain and a disease resulting in intestinal dysbiosis and/or increasing the risk for intestinal bacterial translocation |
EP3041938A1 (de) | 2013-09-03 | 2016-07-13 | Moderna Therapeutics, Inc. | Kreisförmige polynukleotide |
WO2015054283A1 (en) | 2013-10-08 | 2015-04-16 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
US10413520B2 (en) | 2014-01-29 | 2019-09-17 | Crystalgenomics, Inc. | Oral pharmacological composition including 5-{4-(amino sulfonyl)phenyl}-2,2-dimethyl-4-(3-fluorophenyl)-3(2H)-furanone having crystalline structure with excellent stability |
KR101446601B1 (ko) * | 2014-01-29 | 2014-10-07 | 크리스탈지노믹스(주) | 5-(4-(아미노설포닐)페닐)-2,2-디메틸-4-(3-플루오로페닐)-3(2h)-퓨라논을 포함하는 약학적 조성물 및 캡슐 제형 |
TWI690521B (zh) | 2014-04-07 | 2020-04-11 | 美商同步製藥公司 | 作為隱花色素調節劑之含有咔唑之醯胺類、胺基甲酸酯類及脲類 |
JO3589B1 (ar) | 2014-08-06 | 2020-07-05 | Novartis Ag | مثبطات كيناز البروتين c وطرق استخداماتها |
GB201417500D0 (en) | 2014-10-03 | 2014-11-19 | Convergence Pharmaceuticals | Novel use |
GB201417499D0 (en) | 2014-10-03 | 2014-11-19 | Convergence Pharmaceuticals | Novel use |
GB201417497D0 (en) | 2014-10-03 | 2014-11-19 | Convergence Pharmaceuticals | Novel use |
RU2563876C1 (ru) * | 2014-11-11 | 2015-09-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Санкт-Петербургский государственный университет" (СПбГУ) | Способ получения 2,2-диалкил-4,5-диарилфуран-3(2н)-онов |
EP3268367B8 (de) | 2015-03-12 | 2022-11-16 | Merck Sharp & Dohme LLC | Carboxamidinhibitoren der irak4-aktivität |
US10040802B2 (en) | 2015-03-12 | 2018-08-07 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of IRAK4 activity |
EP3267996B1 (de) | 2015-03-12 | 2020-11-11 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidinhibitoren der irak4-aktivität |
WO2016177776A1 (en) | 2015-05-04 | 2016-11-10 | Academisch Medisch Centrum | Biomarkers for the detection of aspirin insensitivity |
SG10202109689QA (en) | 2016-04-15 | 2021-10-28 | Alder Biopharmaceuticals Inc | Humanized anti-pacap antibodies and uses thereof |
US9737530B1 (en) | 2016-06-23 | 2017-08-22 | Collegium Pharmaceutical, Inc. | Process of making stable abuse-deterrent oral formulations |
CN117224534A (zh) | 2016-07-21 | 2023-12-15 | 联合利华知识产权控股有限公司 | 用于治疗皮肤损伤的内酰胺 |
US11160787B2 (en) | 2016-07-21 | 2021-11-02 | Conopco, Inc. | 4-(4-chlorophenyl)-5-methylene-pyrrol-2-one and 5-methylene-4-(p-tolyl)pyrrol-2-one for use in the treatment of gram negative bacterial infections |
US10875830B2 (en) | 2016-07-21 | 2020-12-29 | Conopeo, Inc. | Method of treatment |
WO2018071283A1 (en) | 2016-10-12 | 2018-04-19 | Merck Sharp & Dohme Corp. | Kdm5 inhibitors |
WO2019094311A1 (en) | 2017-11-08 | 2019-05-16 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
EP3706747A4 (de) | 2017-11-08 | 2021-08-04 | Merck Sharp & Dohme Corp. | Prmt5-inhibitoren |
KR20200130696A (ko) | 2018-03-12 | 2020-11-19 | 조에티스 서비시즈 엘엘씨 | 항-ngf 항체 및 이의 방법 |
EP3833667B1 (de) | 2018-08-07 | 2024-03-13 | Merck Sharp & Dohme LLC | Prmt5-inhibitoren |
EP3833668A4 (de) | 2018-08-07 | 2022-05-11 | Merck Sharp & Dohme Corp. | Prmt5-inhibitoren |
EP3853305B1 (de) | 2018-09-19 | 2024-10-02 | ModernaTX, Inc. | Hochreine peg-lipide und verwendungen davon |
MA53650A (fr) | 2018-09-19 | 2021-07-28 | Modernatx Inc | Lipides peg et leurs utilisations |
CN113660934A (zh) | 2018-11-21 | 2021-11-16 | 特默罗制药股份有限公司 | 罗非昔布的纯化形式、制备方法和用途 |
CN110452198B (zh) * | 2019-09-03 | 2021-03-26 | 山东鲁抗舍里乐药业有限公司 | 一种非罗考昔的制备方法 |
CN110452199B (zh) * | 2019-09-03 | 2021-03-30 | 山东鲁抗舍里乐药业有限公司 | 一种非罗考昔的制备方法 |
US10945992B1 (en) | 2019-11-13 | 2021-03-16 | Tremeau Pharmaceuticals, Inc. | Dosage forms of rofecoxib and related methods |
BR112022012032A2 (pt) | 2019-12-17 | 2022-09-06 | Merck Sharp & Dohme Llc | Inibidores de prmt5 |
CN114014824B (zh) * | 2020-12-09 | 2023-06-13 | 上海科技大学 | 一种杂环化合物的应用 |
US20240199571A1 (en) * | 2021-03-11 | 2024-06-20 | Medshine Discovery Inc. | Thiophene compound and application thereof |
US20240165148A1 (en) | 2021-03-15 | 2024-05-23 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory diseases |
US11161833B1 (en) | 2021-04-09 | 2021-11-02 | Tremeau Pharmaceuticals, Inc. | Deuterated etoricoxib, methods of manufacture, and use thereof |
IL310885A (en) | 2021-08-27 | 2024-04-01 | H Lundbeck As | Treatment of cluster headache using anti-CGRP antibodies |
Family Cites Families (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH423473A (de) * | 1963-01-19 | 1966-10-31 | Ciba Geigy | Verfahren zur Herstellung eines photographischen Farbenbildes unter Verwendung neuer Thiophenverbindungen als Farbstoffbildner für Purpurfarbstoffe |
GB1263940A (en) * | 1968-08-02 | 1972-02-16 | Innothera Lab Sa | 0-phenyl-pyrroles |
US3743656A (en) * | 1969-05-01 | 1973-07-03 | Wyeth John & Brother Ltd | Thiophene and furan lower alkanoic acids and derivatives |
GB1381860A (en) * | 1971-06-03 | 1975-01-29 | Wyeth John & Brother Ltd | Tetrazole derivatives |
JPS4891061A (de) * | 1972-03-10 | 1973-11-27 | ||
JPS4891058A (de) * | 1972-03-10 | 1973-11-27 | ||
US3957791A (en) * | 1972-09-25 | 1976-05-18 | Sandoz, Inc. | Hydroxyalkyl-piperazino-quinoline nitrates |
JPS50121261A (de) * | 1974-03-12 | 1975-09-23 | ||
GB1479297A (en) * | 1974-07-04 | 1977-07-13 | Beecham Group Ltd | 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them |
US4229207A (en) * | 1975-08-15 | 1980-10-21 | Ciba-Geigy Corporation | Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic acid |
GB2000170B (en) * | 1977-06-06 | 1982-02-24 | Eastman Kodak Co | Electrophoretic migration imaging materials and process |
EP0003002B1 (de) * | 1977-12-22 | 1984-06-13 | Ciba-Geigy Ag | Verwendung von aromatisch-aliphatischen Ketonen als Photoinitiatoren, photopolymerisierbare Systeme enthaltend solche Ketone und neue aromatisch-aliphatische Ketone |
US4206220A (en) * | 1978-07-13 | 1980-06-03 | Interx Research Corporation | Prodrugs for the improved delivery of non-steroidal anti-inflammatory agents |
US4302461A (en) * | 1979-08-09 | 1981-11-24 | E. I. Du Pont De Nemours And Company | Antiinflammatory 5-substituted-2,3-diarylthiophenes |
US4381311A (en) * | 1980-12-29 | 1983-04-26 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-α-(polyhalomethyl)-2-thiophenemethanols |
US4427693A (en) * | 1981-08-05 | 1984-01-24 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-α,α-bis (polyhalomethyl)-2-thiophenemethanamines |
US4820827A (en) * | 1982-03-03 | 1989-04-11 | E. I. Du Pont De Nemours And Company | 2,3-diaryl-5-bromothiophene compounds of use for the treatment of inflammaton and dysmenorrhea |
EP0087629B1 (de) * | 1982-03-03 | 1986-01-15 | E.I. Du Pont De Nemours And Company | Entzündungshemmende und/oder Schmerzstillende 2,3-Diaryl-5-halo thiophene |
US4432974A (en) * | 1982-03-04 | 1984-02-21 | E. I. Du Pont De Nemours And Company | Antiinflammatory and/or analgesic 2,3-diaryl-5-silyl thiophenes |
US4477463A (en) * | 1982-05-10 | 1984-10-16 | E. I. Du Pont De Nemours And Company | Antiinflammatory and/or analgesic 1-alkyl-4,5-diaryl-2-fluoroalkyl-1H-pyrroles |
JPS5916884A (ja) * | 1982-07-19 | 1984-01-28 | Fujisawa Pharmaceut Co Ltd | 新規フラン化合物 |
US4543207A (en) * | 1982-12-25 | 1985-09-24 | Nippon Petrochemicals Company, Limited | Electrical insulating oil and oil-filled electrical appliances |
US4539332A (en) * | 1983-11-14 | 1985-09-03 | Merck & Co., Inc. | 2,5-Diaryl tetrahydrofurans and analogs thereof as PAF-antagonists |
US4968817A (en) * | 1984-07-27 | 1990-11-06 | National Distillers And Chemical Corporation | Manufacture of gamma-crotonolactone by carbonylation of glycidol |
US4652582A (en) * | 1985-01-09 | 1987-03-24 | E. I. Du Pont De Nemours And Company | Antiinflammatory-2-halo-4,5-diarylpyrroles |
DE3615157A1 (de) * | 1986-05-05 | 1987-11-12 | Schwabe Willmar Gmbh & Co | 5-arylalkyl-4-alkoxy-2(5h)-furanone, zwischenprodukte und verfahren zu ihrer herstellung sowie ihre anwendung als therapeutische wirkstoffe |
JPS6368581A (ja) * | 1986-09-11 | 1988-03-28 | Sekisui Chem Co Ltd | α,β−不飽和γ−ブチロラクトンの製造方法 |
US4851423A (en) * | 1986-12-10 | 1989-07-25 | Schering Corporation | Pharmaceutically active compounds |
DE3718527A1 (de) * | 1987-06-03 | 1988-12-15 | Basf Ag | Verfahren zur herstellung von 2(5h)-furanonen |
EP0300688A1 (de) * | 1987-07-21 | 1989-01-25 | FISONS plc | Pyrrol-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammenstellungen, die sie enthalten |
DE3817808A1 (de) * | 1987-07-21 | 1989-02-02 | Bayer Ag | Verfahren zur herstellung von 2-substituierten pyrrolen |
DE3739882A1 (de) * | 1987-11-25 | 1989-06-08 | Bayer Ag | Substituierte hydroxylamine |
US4929525A (en) * | 1987-12-08 | 1990-05-29 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography containing azo or disazo compound |
US5217971A (en) * | 1989-01-05 | 1993-06-08 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds and pharmaceutical composition comprising the same |
US5145860A (en) * | 1989-01-05 | 1992-09-08 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds and pharmaceutical composition comprising the same |
US5229386A (en) * | 1989-01-05 | 1993-07-20 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
US5196532A (en) * | 1989-02-08 | 1993-03-23 | Basf Aktiengesellschaft | Diaryl-substituted heterocyclic compounds, their preparation and drugs and cosmetics obtained therefrom |
EP0388909A3 (de) * | 1989-03-22 | 1991-05-08 | Fujisawa Pharmaceutical Co., Ltd. | Thiazolderivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten |
DE3915450A1 (de) * | 1989-05-11 | 1990-11-15 | Gerd Prof Dr Dannhardt | Substituierte pyrrolverbindungen und deren anwendung in der pharmazie |
AU6062590A (en) * | 1989-07-07 | 1991-02-06 | Schering Corporation | Pharmaceutically active compounds |
PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
DE4014420A1 (de) * | 1989-09-23 | 1991-04-04 | Bayer Ag | 5h-furan-2-on-derivate |
US5207817A (en) * | 1989-09-23 | 1993-05-04 | Bayer Aktiengesellschaft | Herbicidal 5H-furan-2-one derivatives |
CA2078771A1 (en) * | 1990-04-17 | 1991-10-18 | Gary C. M. Lee | 2(5h)-furanones substituted in the 5 and or in the 4 position, as anti-inflammatory agents |
GB9012936D0 (en) * | 1990-06-11 | 1990-08-01 | Fujisawa Pharmaceutical Co | Thiophene derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
JPH04279672A (ja) * | 1991-03-06 | 1992-10-05 | Mita Ind Co Ltd | フェニレンジアミン系化合物およびそれを用いた電子写真感光体 |
JP3014162B2 (ja) * | 1991-04-24 | 2000-02-28 | 積水化学工業株式会社 | α,β−不飽和γ−ブチロラクトンの製造方法 |
IT1254558B (it) * | 1992-03-26 | 1995-09-25 | Mini Ricerca Scient Tecnolog | Composti a base di 3,4-diaril-(5h)-furan-2-one ad attivita' fungicida 3 |
US5274072A (en) * | 1992-05-04 | 1993-12-28 | Eastman Kodak Company | Polyester composition having copolymerized therein a light absorbing compound |
CA2297592A1 (en) * | 1993-01-15 | 1994-07-21 | G.D. Searle & Co. | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
CA2165567A1 (en) * | 1993-08-19 | 1995-02-23 | Kent Alan Berryman | Substituted 2(5h)furanone, 2(5h)thiophenone and 2(5h)pyrrolone derivatives, their preparation and their use as endothelien antagonists |
SG43841A1 (en) | 1994-01-10 | 1997-11-14 | Merck Frosst Canada Inc | Phenyl heterocycles as cox-2 inhibitors |
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- 1994-06-09 EP EP94918259A patent/EP0705254B1/de not_active Expired - Lifetime
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- 1994-06-09 AT AT94918259T patent/ATE165825T1/de active
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- 1994-06-09 CA CA002163888A patent/CA2163888A1/en not_active Abandoned
- 1994-06-09 EP EP96202573A patent/EP0754687A1/de not_active Ceased
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