NO315369B1 - p-terfenylforbindelser, fremgangsmåter for deres fremstilling, preparat/middel inneholdende en slik forbindelse, samt deres anvendelse - Google Patents
p-terfenylforbindelser, fremgangsmåter for deres fremstilling, preparat/middel inneholdende en slik forbindelse, samt deres anvendelse Download PDFInfo
- Publication number
- NO315369B1 NO315369B1 NO19990415A NO990415A NO315369B1 NO 315369 B1 NO315369 B1 NO 315369B1 NO 19990415 A NO19990415 A NO 19990415A NO 990415 A NO990415 A NO 990415A NO 315369 B1 NO315369 B1 NO 315369B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- optionally substituted
- halogen
- hydrogen
- alkoxycarbonyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 326
- 238000000034 method Methods 0.000 title claims abstract description 68
- 230000008569 process Effects 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 185
- 150000002367 halogens Chemical class 0.000 claims abstract description 185
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 169
- 239000001257 hydrogen Substances 0.000 claims abstract description 169
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 76
- 238000004519 manufacturing process Methods 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims description 158
- -1 hydroxy, carboxy Chemical group 0.000 claims description 95
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 89
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 45
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 37
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 230000009257 reactivity Effects 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 13
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000003018 immunosuppressive agent Substances 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 239000000043 antiallergic agent Substances 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 230000007717 exclusion Effects 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 210000004969 inflammatory cell Anatomy 0.000 claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 239000004305 biphenyl Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
- 210000003979 eosinophil Anatomy 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000005179 haloacetyl group Chemical group 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 210000000440 neutrophil Anatomy 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000001506 immunosuppresive effect Effects 0.000 claims description 5
- 230000001861 immunosuppressant effect Effects 0.000 claims description 5
- 230000008595 infiltration Effects 0.000 claims description 5
- 238000001764 infiltration Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 56
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 210000000628 antibody-producing cell Anatomy 0.000 abstract description 8
- 210000003519 mature b lymphocyte Anatomy 0.000 abstract description 6
- 230000004069 differentiation Effects 0.000 abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 80
- 239000000243 solution Substances 0.000 description 56
- 239000000203 mixture Substances 0.000 description 47
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 43
- 238000003786 synthesis reaction Methods 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- 230000000694 effects Effects 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 24
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 20
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 241000699670 Mus sp. Species 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 16
- 210000004698 lymphocyte Anatomy 0.000 description 16
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- 238000002474 experimental method Methods 0.000 description 15
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- C—CHEMISTRY; METALLURGY
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| PCT/JP1997/002635 WO1998004508A1 (fr) | 1996-07-31 | 1997-07-30 | NOUVEAUX COMPOSES DE p-TERPHENYL |
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Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998042134A1 (fr) | 1997-03-17 | 1998-09-24 | Mitsubishi Denki Kabushiki Kaisha | Codeur et decodeur d'image, methode de codage et de decodage d'image, et systeme de codage/decodage d'image |
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| US20030149061A1 (en) * | 2000-04-04 | 2003-08-07 | Yoshitaka Nishihara | Oily compositions containing highly fat-soluble drugs |
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| EP1354877A1 (en) * | 2001-01-22 | 2003-10-22 | Shionogi & Co., Ltd. | Hetero-tricyclic compounds having substituted amino groups |
| US6858600B2 (en) | 2001-05-08 | 2005-02-22 | Yale University | Proteomimetic compounds and methods |
| US6890940B2 (en) | 2001-06-29 | 2005-05-10 | Kowa Co., Ltd. | Bis(2-aryl-5-pyridyl) derivatives |
| US6706703B2 (en) | 2001-06-29 | 2004-03-16 | Kowa Co., Ltd. | Bis(5-aryl-2-pyridyl) derivatives |
| EP2168576A3 (en) * | 2001-09-14 | 2010-05-26 | Shionogi & Co., Ltd. | Tricyclic compounds for treating dyslipidemia and arteriosclerotic diseases |
| US20070105959A1 (en) * | 2003-03-11 | 2007-05-10 | Shinya Kusuda | Cynnamyl alcohol derivative compounds and drugs containing the compounds as active ingredient |
| US7473943B2 (en) * | 2004-10-15 | 2009-01-06 | Nanosys, Inc. | Gate configuration for nanowire electronic devices |
| US20080138635A1 (en) * | 2005-03-02 | 2008-06-12 | Zhikuan Chen | Conjugated Organic Molecules for Molecular Electronic Devices |
| CN101166534B (zh) | 2005-04-28 | 2011-09-21 | 大日本住友制药株式会社 | 用于慢性阻塞性肺部疾病的治疗剂 |
| JP5090368B2 (ja) * | 2005-12-30 | 2012-12-05 | エルジー・ケム・リミテッド | 遷移金属化合物およびその製造方法 |
| KR100684376B1 (ko) * | 2006-01-12 | 2007-02-22 | 광주과학기술원 | 설폰네이트기 함유 터페닐 디할라이드 단량체 및 이의제조방법 |
| JO3598B1 (ar) * | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2008044729A1 (fr) * | 2006-10-12 | 2008-04-17 | Institute Of Medicinal Molecular Design. Inc. | Dérivé d'acide carboxylique |
| US20100249165A1 (en) * | 2007-06-08 | 2010-09-30 | University Of Copenhagen | Pdz domain modulators |
| CA2963784A1 (en) | 2007-06-08 | 2008-12-18 | Mannkind Corporation | Ire-1.alpha. inhibitors |
| JP5408660B2 (ja) * | 2007-09-04 | 2014-02-05 | 学校法人東京農業大学 | パラテルフェニル化合物、その薬理学的に許容される塩、その製造方法及び用途 |
| CN101959404B (zh) | 2008-02-04 | 2015-12-02 | 墨丘瑞医疗有限公司 | 单磷酸腺苷活化蛋白激酶调节剂 |
| CA2721060A1 (en) * | 2008-04-09 | 2009-10-15 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8633245B2 (en) * | 2008-04-11 | 2014-01-21 | Institute Of Medicinal Molecular Design, Inc. | PAI-1 inhibitor |
| JP2012523424A (ja) | 2009-04-07 | 2012-10-04 | インフイニトイ プハルマセウトイカルス インコーポレイテッド | 脂肪酸アミドヒドロラーゼの阻害薬 |
| JP2012523425A (ja) | 2009-04-07 | 2012-10-04 | インフイニトイ プハルマセウトイカルス インコーポレイテッド | 脂肪酸アミドヒドロラーゼの阻害薬 |
| EP2496544B1 (en) * | 2009-11-05 | 2014-08-20 | Fibrostatin, S.L. | Gpbp inhibition using q2 peptidomimetics |
| RU2569061C2 (ru) * | 2010-02-03 | 2015-11-20 | Инфинити Фармасьютикалз, Инк. | Ингибиторы амид-гидролазы жирных кислот |
| US9527807B2 (en) | 2011-04-05 | 2016-12-27 | Takeda Pharmaceutical Company Limited | Sulfonamide derivative and use thereof |
| KR101691873B1 (ko) * | 2013-12-16 | 2017-01-02 | 디아이씨 가부시끼가이샤 | 알케닐에테르 화합물 및 이것을 사용한 액정 조성물 |
| CN104447452B (zh) * | 2014-11-06 | 2016-04-20 | 广东工业大学 | 一种巯基功能化多芳基羧酸化合物的合成方法 |
| KR20170105001A (ko) * | 2015-01-14 | 2017-09-18 | 제이엔씨 주식회사 | 중합성기를 가지는 화합물, 액정 조성물 및 액정 표시 소자 |
| CN105175241B (zh) * | 2015-08-28 | 2017-09-29 | 浙江工业大学 | 三联苯类化合物及其制备方法和应用 |
| US11078528B2 (en) | 2015-10-12 | 2021-08-03 | Advanced Cell Diagnostics, Inc. | In situ detection of nucleotide variants in high noise samples, and compositions and methods related thereto |
| JP2020100564A (ja) * | 2017-04-03 | 2020-07-02 | 京都薬品工業株式会社 | リードスルー誘導剤およびその医薬用途 |
| CN110396415B (zh) * | 2018-04-25 | 2021-01-26 | 北京八亿时空液晶科技股份有限公司 | 一种新型液晶垂直配向剂及其制备方法与应用 |
| CN113214056B (zh) * | 2021-04-16 | 2023-08-29 | 子辰海洋医药科技(上海)有限公司 | 联苯类化合物和二萜类化合物及其制备方法与应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3624142A (en) | 1964-09-10 | 1971-11-30 | Merck & Co Inc | Substituted biphenyl acetic acid derivatives |
| US4495202A (en) | 1983-06-22 | 1985-01-22 | Eli Lilly And Company | Terphenyl derivatives and pharmaceutical uses thereof |
| GB8319849D0 (en) * | 1983-07-22 | 1983-08-24 | Secr Defence | Compounds containing fluorobiphenyl group |
| US4728670A (en) | 1986-06-04 | 1988-03-01 | E. R. Squibb & Sons, Inc. | Biphenyl hydroxamic acids |
| GB8627107D0 (en) * | 1986-11-13 | 1986-12-10 | Secr Defence | Ferroelectric smectic liquid crystal mixtures |
| GB8703103D0 (en) * | 1987-02-11 | 1987-03-18 | Secr Defence | Terphenyl derivatives |
| JP2655333B2 (ja) * | 1988-09-01 | 1997-09-17 | 関東化学 株式会社 | 新規なp‐ターフエニル誘導体並びに液晶組成物 |
| BR9006906A (pt) * | 1989-09-06 | 1991-11-12 | Merck Patent Gmbh | Derivados de fluorbenzeno e meio cristalino liquido |
| GB2240778B (en) * | 1990-02-07 | 1993-09-01 | Merck Patent Gmbh | Fluorinated terphenyls |
| JPH0525145A (ja) * | 1991-07-15 | 1993-02-02 | Mochida Pharmaceut Co Ltd | アレルギー性疾患治療剤 |
| US5871665A (en) * | 1992-04-27 | 1999-02-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Electrooptical liquid crystal system |
| US5417885A (en) * | 1993-08-03 | 1995-05-23 | Showa Shell Sekiyu Kabushiki Kaisha | Antiferroelectric liquid crystal compound |
| DE19504224A1 (de) * | 1994-02-23 | 1995-08-24 | Merck Patent Gmbh | Flüssigkristallines Material |
| US5593994A (en) | 1994-09-29 | 1997-01-14 | The Dupont Merck Pharmaceutical Company | Prostaglandin synthase inhibitors |
| EP0798291B1 (en) | 1994-12-14 | 2002-09-11 | Santen Pharmaceutical Co., Ltd. | Novel 1,3-dialkylurea derivatives |
| GB2299333B (en) | 1995-03-29 | 1998-11-25 | Merck Patent Gmbh | Reactive terphenyls |
| EP0769299A4 (en) | 1995-04-24 | 2000-08-09 | Taiho Pharmaceutical Co Ltd | AGAINST ALLERGIC DISEASES IN THE NOSE |
| ATE199083T1 (de) * | 1996-04-22 | 2001-02-15 | Shionogi & Co | Terphenylverbindungen und sie enthaltende arzneimittel |
-
1997
- 1997-07-30 AT AT97933837T patent/ATE256092T1/de not_active IP Right Cessation
- 1997-07-30 BR BR9710780A patent/BR9710780A/pt not_active IP Right Cessation
- 1997-07-30 JP JP50869898A patent/JP4008498B2/ja not_active Expired - Fee Related
- 1997-07-30 CZ CZ99303A patent/CZ30399A3/cs unknown
- 1997-07-30 EP EP97933837A patent/EP0933346B1/en not_active Expired - Lifetime
- 1997-07-30 ES ES97933837T patent/ES2212119T3/es not_active Expired - Lifetime
- 1997-07-30 RU RU99103617/04A patent/RU2200730C2/ru not_active IP Right Cessation
- 1997-07-30 DE DE69726745T patent/DE69726745T2/de not_active Expired - Fee Related
- 1997-07-30 PT PT97933837T patent/PT933346E/pt unknown
- 1997-07-30 CN CN97198341A patent/CN1232443A/zh active Pending
- 1997-07-30 AU AU37067/97A patent/AU729320B2/en not_active Ceased
- 1997-07-30 PL PL97331497A patent/PL331497A1/xx unknown
- 1997-07-30 IL IL12819097A patent/IL128190A0/xx unknown
- 1997-07-30 US US09/214,277 patent/US7101915B1/en not_active Expired - Fee Related
- 1997-07-30 NZ NZ333688A patent/NZ333688A/en unknown
- 1997-07-30 WO PCT/JP1997/002635 patent/WO1998004508A1/ja not_active Ceased
- 1997-07-30 KR KR1019997000747A patent/KR100338855B1/ko not_active Expired - Fee Related
- 1997-07-30 CA CA002261339A patent/CA2261339A1/en not_active Abandoned
- 1997-07-30 DK DK97933837T patent/DK0933346T3/da active
- 1997-07-31 TW TW086110933A patent/TW510895B/zh not_active IP Right Cessation
-
1999
- 1999-01-28 NO NO19990415A patent/NO315369B1/no not_active IP Right Cessation
-
2003
- 2003-11-12 US US10/704,876 patent/US7220783B2/en not_active Expired - Fee Related
- 2003-11-12 US US10/705,505 patent/US7074836B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CZ30399A3 (cs) | 1999-07-14 |
| BR9710780A (pt) | 1999-08-17 |
| EP0933346A1 (en) | 1999-08-04 |
| US7220783B2 (en) | 2007-05-22 |
| RU2200730C2 (ru) | 2003-03-20 |
| KR100338855B1 (ko) | 2002-12-28 |
| NO990415L (no) | 1999-03-26 |
| WO1998004508A1 (fr) | 1998-02-05 |
| US7101915B1 (en) | 2006-09-05 |
| EP0933346B1 (en) | 2003-12-10 |
| US20040127495A1 (en) | 2004-07-01 |
| DE69726745T2 (de) | 2004-09-30 |
| AU3706797A (en) | 1998-02-20 |
| PT933346E (pt) | 2004-03-31 |
| PL331497A1 (en) | 1999-07-19 |
| KR20000029669A (ko) | 2000-05-25 |
| NO990415D0 (no) | 1999-01-28 |
| JP4008498B2 (ja) | 2007-11-14 |
| ES2212119T3 (es) | 2004-07-16 |
| CA2261339A1 (en) | 1998-02-05 |
| US7074836B1 (en) | 2006-07-11 |
| CN1232443A (zh) | 1999-10-20 |
| ATE256092T1 (de) | 2003-12-15 |
| TW510895B (en) | 2002-11-21 |
| NZ333688A (en) | 2001-06-29 |
| IL128190A0 (en) | 1999-11-30 |
| AU729320B2 (en) | 2001-02-01 |
| DE69726745D1 (de) | 2004-01-22 |
| DK0933346T3 (da) | 2004-03-29 |
| EP0933346A4 (en) | 2000-12-06 |
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| MM1K | Lapsed by not paying the annual fees |