JP2010516679A5 - - Google Patents
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- JP2010516679A5 JP2010516679A5 JP2009546424A JP2009546424A JP2010516679A5 JP 2010516679 A5 JP2010516679 A5 JP 2010516679A5 JP 2009546424 A JP2009546424 A JP 2009546424A JP 2009546424 A JP2009546424 A JP 2009546424A JP 2010516679 A5 JP2010516679 A5 JP 2010516679A5
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- JP
- Japan
- Prior art keywords
- alkyl
- hydroxyl
- group
- aryl
- nitro
- 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.)
- Pending
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- 239000002184 metal Substances 0.000 claims description 150
- 229910052751 metal Inorganic materials 0.000 claims description 150
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- -1 alkyl carboxylic acid Chemical class 0.000 claims description 110
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 104
- 125000003118 aryl group Chemical group 0.000 claims description 76
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 74
- 125000005843 halogen group Chemical group 0.000 claims description 62
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
- 229910052760 oxygen Inorganic materials 0.000 claims description 54
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 53
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims description 53
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 44
- CISNNLXXANUBPI-UHFFFAOYSA-N cyano(nitro)azanide Chemical compound [O-][N+](=O)[N-]C#N CISNNLXXANUBPI-UHFFFAOYSA-N 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 37
- 229930194542 Keto Natural products 0.000 claims description 33
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims description 32
- 125000000468 ketone group Chemical group 0.000 claims description 32
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 32
- 230000005298 paramagnetic effect Effects 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 32
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 125000005647 linker group Chemical group 0.000 claims description 30
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical compound [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims description 29
- 230000004962 physiological condition Effects 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052702 rhenium Inorganic materials 0.000 claims description 10
- 230000002018 overexpression Effects 0.000 claims description 9
- 150000003180 prostaglandins Chemical class 0.000 claims description 9
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 8
- 229910052693 Europium Inorganic materials 0.000 claims description 8
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 8
- 229910052689 Holmium Inorganic materials 0.000 claims description 8
- 229910052765 Lutetium Inorganic materials 0.000 claims description 8
- 229910052772 Samarium Inorganic materials 0.000 claims description 8
- 229910052775 Thulium Inorganic materials 0.000 claims description 8
- 229910052785 arsenic Inorganic materials 0.000 claims description 8
- 229910052797 bismuth Inorganic materials 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052738 indium Inorganic materials 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 230000002285 radioactive effect Effects 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical compound NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 229940111134 coxibs Drugs 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000014509 gene expression Effects 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- XNTLXAUHLBBEKP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 XNTLXAUHLBBEKP-UHFFFAOYSA-N 0.000 claims description 4
- ULFYMTMZNITFSB-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=C(F)C=2)C(=O)CC1 ULFYMTMZNITFSB-UHFFFAOYSA-N 0.000 claims description 4
- OKGJGFZQNSWNSS-UHFFFAOYSA-N 2-[2-(2,4-dichloro-6-methylanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=C(Cl)C=C1Cl OKGJGFZQNSWNSS-UHFFFAOYSA-N 0.000 claims description 4
- JHALWMSZGCVVEM-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7-triazonan-1-yl]acetic acid Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CC1 JHALWMSZGCVVEM-UHFFFAOYSA-N 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 4
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims description 4
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 4
- KTDZCOWXCWUPEO-UHFFFAOYSA-N NS-398 Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1CCCCC1 KTDZCOWXCWUPEO-UHFFFAOYSA-N 0.000 claims description 4
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229960000590 celecoxib Drugs 0.000 claims description 4
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 4
- 229950010851 cimicoxib Drugs 0.000 claims description 4
- KYXDNECMRLFQMZ-UHFFFAOYSA-N cimicoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=C(Cl)N=CN1C1=CC=C(S(N)(=O)=O)C=C1 KYXDNECMRLFQMZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 4
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 claims description 4
- 229960000994 lumiracoxib Drugs 0.000 claims description 4
- 229960001929 meloxicam Drugs 0.000 claims description 4
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960004662 parecoxib Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 229960000371 rofecoxib Drugs 0.000 claims description 4
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229960002004 valdecoxib Drugs 0.000 claims description 4
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 4
- 230000008728 vascular permeability Effects 0.000 claims description 4
- 238000005549 size reduction Methods 0.000 claims description 3
- OFOFOZKUGISWRT-WUKNDPDISA-N (3z)-3-[(4-chlorophenyl)-(4-methylsulfonylphenyl)methylidene]oxolan-2-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/1C(=O)OCC\1 OFOFOZKUGISWRT-WUKNDPDISA-N 0.000 claims description 2
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 claims description 2
- 206010005949 Bone cancer Diseases 0.000 claims description 2
- 208000018084 Bone neoplasm Diseases 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 230000033115 angiogenesis Effects 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 238000002648 combination therapy Methods 0.000 claims description 2
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000011347 external beam therapy Methods 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000003368 amide group Chemical group 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 3
- 239000013522 chelant Substances 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 29
- 0 *N(*)S(c1ccc(*(c2ccccc2)I*)cc1)(=O)=O Chemical compound *N(*)S(c1ccc(*(c2ccccc2)I*)cc1)(=O)=O 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 2
- DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 description 1
- KFGOFTHODYBSGM-IJCBKZNRSA-N 6-Keto-prostaglandin F1a Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O KFGOFTHODYBSGM-IJCBKZNRSA-N 0.000 description 1
- GGYIQYGLFMZSTG-UHFFFAOYSA-N CC(CI)c1ccccc1S Chemical compound CC(CI)c1ccccc1S GGYIQYGLFMZSTG-UHFFFAOYSA-N 0.000 description 1
- XQTJMFWCZRJYPC-UHFFFAOYSA-N Oc1cccc(S)c1I Chemical compound Oc1cccc(S)c1I XQTJMFWCZRJYPC-UHFFFAOYSA-N 0.000 description 1
- VWXBGHWQKMLUAP-UHFFFAOYSA-N Sc(cccc1S)c1I Chemical compound Sc(cccc1S)c1I VWXBGHWQKMLUAP-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88569007P | 2007-01-19 | 2007-01-19 | |
| PCT/US2008/000631 WO2008091530A2 (en) | 2007-01-19 | 2008-01-17 | Diagnostic and therapeutic cyclooxygenase-2 binding ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010516679A JP2010516679A (ja) | 2010-05-20 |
| JP2010516679A5 true JP2010516679A5 (enExample) | 2012-02-02 |
Family
ID=39567925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009546424A Pending JP2010516679A (ja) | 2007-01-19 | 2008-01-17 | 診断用および治療用シクロオキシゲナーゼ−２結合リガンド |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100111858A1 (enExample) |
| EP (1) | EP2114461A2 (enExample) |
| JP (1) | JP2010516679A (enExample) |
| CN (1) | CN101626787A (enExample) |
| CA (1) | CA2676413A1 (enExample) |
| WO (1) | WO2008091530A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012511024A (ja) * | 2008-12-05 | 2012-05-17 | モレキュラ インサイト ファーマシューティカルズ インコーポレイテッド | 癌の治療及び撮像用のｃａ−ｉｘ特異性放射性医薬品 |
| EP2740726A1 (en) * | 2012-12-07 | 2014-06-11 | 3B Pharmaceuticals GmbH | Neurotensin receptor ligands |
| US9850183B2 (en) | 2014-06-27 | 2017-12-26 | Reiley Pharmaceuticals, Inc. | Conjugates derived from non-steroidal anti-inflammatory drugs and methods of use thereof in imaging |
| EP3242688B1 (en) | 2015-01-09 | 2020-01-29 | Reiley Pharmaceuticals, Inc. | Cox-2-targeting, platinum-containing conjugates and their use in the treatment of tumors and cancers |
| CN107007571B (zh) * | 2017-02-24 | 2020-08-21 | 福州市传染病医院 | 肿瘤微酸性敏感的铜-药物共配位自组装纳米粒及应用 |
| WO2018204872A2 (en) | 2017-05-05 | 2018-11-08 | Fusion Pharmaceuticals Inc. | Igf-1r monoclonal antibodies and uses thereof |
| MA48861A (fr) | 2017-05-05 | 2020-04-01 | Fusion Pharmaceuticals Inc | Améliorations pharmacocinétiques de chélates bifonctionnels et leurs utilisations |
| WO2019182395A1 (ko) * | 2018-03-22 | 2019-09-26 | 장용민 | 신규한 구조를 갖는 화합물, 이를 포함하는 항염증제 및 시클로옥시게나아제-2 억제제 |
| KR102232979B1 (ko) | 2018-03-22 | 2021-03-29 | 경북대학교 산학협력단 | Do3a 가돌리늄 착물의 신규한 구조를 갖는 화합물, 이를 포함하는 항염증제 및 조영제 |
| WO2019235824A1 (ko) * | 2018-06-08 | 2019-12-12 | 경북대학교 산학협력단 | Cox2 과발현 질환 진단용 조성물 및 이의 스크리닝 방법 |
| WO2022076741A1 (en) * | 2020-10-07 | 2022-04-14 | Reiley Pharmaceuticals, Inc. | Coxib-derived conjugate compounds and methods of use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2893191B2 (ja) * | 1988-11-08 | 1999-05-17 | 武田薬品工業株式会社 | 放出制御性マトリックス剤 |
| US6884418B1 (en) * | 1989-08-04 | 2005-04-26 | Berlex Laboratories, Inc. | Use of ligand-mimicking agents and anti-neoplastic drugs in cancer therapy |
| PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| US5821260A (en) * | 1992-10-30 | 1998-10-13 | Emory University | Treatment for atherosclerosis and other cardiovascular and inflammatory diseases |
| US5604260A (en) * | 1992-12-11 | 1997-02-18 | Merck Frosst Canada Inc. | 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2 |
| EP0679157B1 (en) * | 1993-01-15 | 1997-11-19 | G.D. Searle & Co. | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
| US5409944A (en) * | 1993-03-12 | 1995-04-25 | Merck Frosst Canada, Inc. | Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase |
| US6090834A (en) * | 1993-05-21 | 2000-07-18 | G.D. Searle & Co. | Substituted oxazoles for the treatment of inflammation |
| US5380738A (en) * | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5436265A (en) * | 1993-11-12 | 1995-07-25 | Merck Frosst Canada, Inc. | 1-aroyl-3-indolyl alkanoic acids and derivatives thereof useful as anti-inflammatory agents |
| DE69422306T4 (de) * | 1993-11-30 | 2000-09-07 | G.D. Searle & Co., Chicago | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
| US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| US5401765A (en) * | 1993-11-30 | 1995-03-28 | G. D. Searle | 1,4,5-triphenyl pyrazolyl compounds for the treatment of inflammation and inflammation-related disorders |
| US5434178A (en) * | 1993-11-30 | 1995-07-18 | G.D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
| US5393790A (en) * | 1994-02-10 | 1995-02-28 | G.D. Searle & Co. | Substituted spiro compounds for the treatment of inflammation |
| US5418254A (en) * | 1994-05-04 | 1995-05-23 | G. D. Searle & Co. | Substituted cyclopentadienyl compounds for the treatment of inflammation |
| US5486534A (en) * | 1994-07-21 | 1996-01-23 | G. D. Searle & Co. | 3,4-substituted pyrazoles 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 |
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-
2008
- 2008-01-17 EP EP08724592A patent/EP2114461A2/en not_active Ceased
- 2008-01-17 CA CA002676413A patent/CA2676413A1/en not_active Abandoned
- 2008-01-17 WO PCT/US2008/000631 patent/WO2008091530A2/en not_active Ceased
- 2008-01-17 CN CN200880002675A patent/CN101626787A/zh active Pending
- 2008-01-17 US US12/523,402 patent/US20100111858A1/en not_active Abandoned
- 2008-01-17 JP JP2009546424A patent/JP2010516679A/ja active Pending
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