JP2016516050A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016516050A5 JP2016516050A5 JP2016502973A JP2016502973A JP2016516050A5 JP 2016516050 A5 JP2016516050 A5 JP 2016516050A5 JP 2016502973 A JP2016502973 A JP 2016502973A JP 2016502973 A JP2016502973 A JP 2016502973A JP 2016516050 A5 JP2016516050 A5 JP 2016516050A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- methyl
- oxopyrrolidin
- methylnon
- oxopyrrolidine
- 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.)
- Granted
Links
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 128
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 120
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 75
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 50
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 claims description 44
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- -1 C 1 -C 3 alkoxy Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- KPSZWAJWFMFMFF-UHFFFAOYSA-N hept-5-enoic acid Chemical compound CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 239000005711 Benzoic acid Substances 0.000 claims description 17
- 235000010233 benzoic acid Nutrition 0.000 claims description 17
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims description 16
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 16
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004419 alkynylene group Chemical group 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- LSHMGTXEUMQTLQ-DMBFJYOSSA-N 7-[(2r)-2-[(e,3r)-3-hydroxy-3-(1-pent-2-ynylcyclobutyl)prop-1-enyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCC#CCC1([C@H](O)\C=C\[C@@H]2N(C(=O)CC2)CCCCCCC(O)=O)CCC1 LSHMGTXEUMQTLQ-DMBFJYOSSA-N 0.000 claims description 2
- PZTUDMCYRNFKGN-GMIBQGTOSA-N 7-[(2r)-2-[(e,3r)-3-hydroxy-3-(1-pent-2-ynylcyclopropyl)prop-1-enyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCC#CCC1([C@H](O)\C=C\[C@@H]2N(C(=O)CC2)CCCCCCC(O)=O)CC1 PZTUDMCYRNFKGN-GMIBQGTOSA-N 0.000 claims description 2
- 206010065687 Bone loss Diseases 0.000 claims description 2
- 206010017076 Fracture Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005622 butynylene group Chemical group 0.000 claims description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 230000000399 orthopedic effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 208000028169 periodontal disease Diseases 0.000 claims description 2
- 210000002805 bone matrix Anatomy 0.000 claims 1
- 229910000389 calcium phosphate Inorganic materials 0.000 claims 1
- 239000001506 calcium phosphate Substances 0.000 claims 1
- 235000011010 calcium phosphates Nutrition 0.000 claims 1
- 239000004568 cement Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361793736P | 2013-03-15 | 2013-03-15 | |
| US61/793,736 | 2013-03-15 | ||
| PCT/US2014/029057 WO2014144584A2 (en) | 2013-03-15 | 2014-03-14 | Lactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated diseases and conditions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017109178A Division JP6352497B2 (ja) | 2013-03-15 | 2017-06-01 | Ｅｐ４媒介性の疾病及び病態の治療に使用するためのｅｐ４受容体選択性アゴニストとしてのラクタム化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016516050A JP2016516050A (ja) | 2016-06-02 |
| JP2016516050A5 true JP2016516050A5 (enExample) | 2017-04-20 |
| JP6317807B2 JP6317807B2 (ja) | 2018-04-25 |
Family
ID=50897877
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016502973A Active JP6317807B2 (ja) | 2013-03-15 | 2014-03-14 | Ｅｐ４媒介性の疾病及び病態の治療に使用するためのｅｐ４受容体選択性アゴニストとしてのラクタム化合物 |
| JP2017109178A Expired - Fee Related JP6352497B2 (ja) | 2013-03-15 | 2017-06-01 | Ｅｐ４媒介性の疾病及び病態の治療に使用するためのｅｐ４受容体選択性アゴニストとしてのラクタム化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017109178A Expired - Fee Related JP6352497B2 (ja) | 2013-03-15 | 2017-06-01 | Ｅｐ４媒介性の疾病及び病態の治療に使用するためのｅｐ４受容体選択性アゴニストとしてのラクタム化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9688627B2 (enExample) |
| EP (2) | EP2989098B1 (enExample) |
| JP (2) | JP6317807B2 (enExample) |
| KR (1) | KR20150130326A (enExample) |
| CN (1) | CN105143217A (enExample) |
| AU (1) | AU2014228973B2 (enExample) |
| BR (1) | BR112015023080A2 (enExample) |
| CA (1) | CA2906134A1 (enExample) |
| DK (1) | DK2989098T3 (enExample) |
| EA (1) | EA201591793A1 (enExample) |
| ES (1) | ES2635635T3 (enExample) |
| IL (2) | IL240988A (enExample) |
| PH (1) | PH12015502165A1 (enExample) |
| PT (1) | PT2989098T (enExample) |
| SG (1) | SG11201507470WA (enExample) |
| WO (1) | WO2014144584A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2879506C (en) | 2012-07-19 | 2020-10-27 | Cayman Chemical Company, Inc. | Difluorolactam compositions for ep4-mediated osteo related diseases and conditions |
| AU2014290512A1 (en) | 2013-07-19 | 2015-11-12 | Cayman Chemical Company, Inc. | Methods, systems, and compositions for promoting bone growth |
| CN107365329B (zh) * | 2016-05-12 | 2019-02-01 | 华东师范大学 | 一种3-甲基-2-氧代-5-庚炔基磷酸二甲酯的制备方法 |
| ES2929799T3 (es) | 2017-12-25 | 2022-12-01 | Asahi Kasei Pharma Corp | Compuestos que contienen resto de 2-oxo-1,3,4-tiadiazinan-3-ilo con actividad agonista del receptor EP4 |
| SG11202110742TA (en) | 2019-04-02 | 2021-10-28 | Aligos Therapeutics Inc | Compounds targeting prmt5 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975399A (en) | 1974-08-06 | 1976-08-17 | E. I. Du Pont De Nemours And Company | 1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones |
| DE2517771A1 (de) | 1975-04-18 | 1976-10-28 | Schering Ag | Neue prostaglandin-acetylen-analoga und verfahren zu ihrer herstellung |
| DE2528664A1 (de) | 1975-06-27 | 1977-01-13 | Hoechst Ag | Pyrrolidone und verfahren zu ihrer herstellung |
| CA1085859A (en) | 1975-06-27 | 1980-09-16 | Wilhelm Bartmann | Pyrrolidones and process for their manufacture |
| DE2619638A1 (de) | 1976-05-04 | 1977-11-17 | Hoechst Ag | Pyrrolidone und verfahren zu ihrer herstellung |
| US4268522A (en) | 1976-06-14 | 1981-05-19 | Pfizer Inc. | 13,14-Dihydro-15-alkenyl- and 13,14-dihydro-15-alkynyl prostaglandins and analogs thereof |
| US4320136A (en) | 1980-08-11 | 1982-03-16 | E. I. Du Pont De Nemours And Company | 8-Aza-16,16-difluoroprostanoids |
| US6043275A (en) | 1998-04-16 | 2000-03-28 | Ono Pharmaceutical Co., Ltd. | 3,7-dithiaprostanoic acid derivative |
| US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
| TWI247606B (en) | 1999-11-24 | 2006-01-21 | Ono Pharmaceutical Co | Treating agent for osteopenic diseases |
| WO2001046140A1 (en) | 1999-12-22 | 2001-06-28 | Pfizer Products Inc. | Ep4 receptor selective agonists in the treatment of osteoporosis |
| US20010056060A1 (en) | 2000-02-07 | 2001-12-27 | Cameron Kimberly O. | Treatment of osteoporsis with EP2/EP4 receptor selective agonists |
| WO2002024647A1 (en) | 2000-09-21 | 2002-03-28 | Ono Pharmaceutical Co., Ltd. | Ep4 receptor agonists containing 8-azaprostaglandin derivatives as the active ingredient |
| SI1339678T1 (sl) * | 2000-11-27 | 2007-12-31 | Pfizer Prod Inc | Selektivni agonisti EP4 receptorja pri zdravljenju osteoporoze |
| AU2002328338C1 (en) | 2001-07-16 | 2009-01-08 | Ono Pharmaceutical Co., Ltd | 2 pyrrolidone derivatives as prostanoid agonists |
| AU2002328855B2 (en) | 2001-07-16 | 2005-11-24 | F. Hoffmann-La Roche Ag | Prostaglandin Analogues As EP4 Receptor Agonists |
| KR100826866B1 (ko) | 2001-07-23 | 2008-05-06 | 오노 야꾸힝 고교 가부시키가이샤 | Ｅｐ４ 아고니스트를 유효 성분으로 하는 골량 저하질환의 치료제 |
| US7410991B2 (en) | 2001-10-23 | 2008-08-12 | Laboratoires Serono S.A. | Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors |
| AU2002346562A1 (en) | 2001-12-03 | 2003-06-17 | Merck & Co., Inc. | Method for treating ocular hypertension |
| CA2466751A1 (en) | 2001-12-03 | 2003-06-12 | Merck And Co., Inc. | Ep4 receptor agonist, compositions and methods thereof |
| JP4547912B2 (ja) | 2002-03-05 | 2010-09-22 | 小野薬品工業株式会社 | ８−アザプロスタグランジン誘導体化合物およびその化合物を有効成分として含有する薬剤 |
| EP1490055A1 (en) | 2002-03-18 | 2004-12-29 | Pfizer Products Inc. | Use of selective ep4 receptor agonists for the treatment of liver failure, loss of patency of the ductus arteriosus, glaucoma or ocular hypertension |
| ATE336247T1 (de) | 2002-03-18 | 2006-09-15 | Pfizer Prod Inc | Verwendung von selektiven ep4 rezeptor agonisten zur behandlung von krankheiten |
| US6573294B1 (en) | 2002-05-14 | 2003-06-03 | Allergan, Inc. | 8-azaprostaglandin analogs as agents for lowering intraocular pressure |
| WO2003103604A2 (en) * | 2002-06-01 | 2003-12-18 | Applied Research Systems Ars Holding N.V | Gamma lactams as prostaglandin agonists and use thereof |
| JP2006505572A (ja) | 2002-10-25 | 2006-02-16 | メルク フロスト カナダ アンド カンパニー | Ｅｐ４受容体アゴニストとしての２−ピロリドン |
| EP1586564B1 (en) | 2003-01-21 | 2012-11-28 | Ono Pharmaceutical Co., Ltd. | 8-azaprostaglandin derivatives and medicinal uses thereof |
| WO2004078103A2 (en) * | 2003-03-03 | 2004-09-16 | Applied Research Systems Ars Holding N.V. | G-lactam derivatives as prostaglandin agonists |
| US7169807B2 (en) | 2004-04-09 | 2007-01-30 | Allergan, Inc. | 10-Hydroxy-11-dihydroprostaglandin analogs as selective EP4 agonists |
| EP1782830A4 (en) | 2004-08-10 | 2009-07-29 | Ono Pharmaceutical Co | PREVENTION AND / OR REMEDY FOR LOWER URINARY TRACT DISEASES CONTAINING AN EP4 AGONIST |
| JPWO2006016695A1 (ja) | 2004-08-10 | 2008-05-01 | 小野薬品工業株式会社 | Ｅｐ４アゴニストを含有してなる高カリウム血症の予防および／または治療剤 |
| TWI404529B (zh) * | 2005-06-03 | 2013-08-11 | Ono Pharmaceutical Co | 神經再生及／或保護劑 |
| US20070232660A1 (en) | 2006-04-04 | 2007-10-04 | Allergan, Inc. | Therapeutic and delivery methods of prostaglandin ep4 agonists |
| US8507545B2 (en) | 2007-05-08 | 2013-08-13 | National University Corporation, Hamamatsu University School Of Medicine | Cytotoxic T cell activator comprising EP4 agonist |
| EP2215084B1 (en) | 2007-10-23 | 2016-09-28 | Allergan, Inc. | Therapeutic substituted lactams |
| WO2011003058A1 (en) * | 2009-07-03 | 2011-01-06 | Concert Pharmaceuticals, Inc. | Prostacyclin derivatives |
| JP5847830B2 (ja) | 2010-11-10 | 2016-01-27 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | オレキシン受容体拮抗薬として有用なラクタム誘導体 |
| US20120283293A1 (en) | 2011-05-06 | 2012-11-08 | The Board Of Trustees Of The Leland Stanford Junior University | Methods of neuroprotection involving Prostaglandin E2 EP4 (PGE2 EP4) receptor activation |
| BR112014002377A2 (pt) | 2011-08-02 | 2017-02-21 | Ono Pharmaceutical Co | agente intensificador da função diastólica do ventrículo esquerdo |
| CA2879506C (en) | 2012-07-19 | 2020-10-27 | Cayman Chemical Company, Inc. | Difluorolactam compositions for ep4-mediated osteo related diseases and conditions |
-
2014
- 2014-03-14 BR BR112015023080A patent/BR112015023080A2/pt not_active IP Right Cessation
- 2014-03-14 SG SG11201507470WA patent/SG11201507470WA/en unknown
- 2014-03-14 DK DK14729106.6T patent/DK2989098T3/en active
- 2014-03-14 EP EP14729106.6A patent/EP2989098B1/en active Active
- 2014-03-14 PT PT147291066T patent/PT2989098T/pt unknown
- 2014-03-14 JP JP2016502973A patent/JP6317807B2/ja active Active
- 2014-03-14 US US14/775,427 patent/US9688627B2/en active Active
- 2014-03-14 EA EA201591793A patent/EA201591793A1/ru unknown
- 2014-03-14 CN CN201480015554.7A patent/CN105143217A/zh active Pending
- 2014-03-14 ES ES14729106.6T patent/ES2635635T3/es active Active
- 2014-03-14 AU AU2014228973A patent/AU2014228973B2/en not_active Expired - Fee Related
- 2014-03-14 EP EP17169751.9A patent/EP3235817B1/en not_active Not-in-force
- 2014-03-14 KR KR1020157026225A patent/KR20150130326A/ko not_active Withdrawn
- 2014-03-14 CA CA2906134A patent/CA2906134A1/en active Pending
- 2014-03-14 WO PCT/US2014/029057 patent/WO2014144584A2/en not_active Ceased
-
2015
- 2015-09-01 IL IL240988A patent/IL240988A/en active IP Right Grant
- 2015-09-15 PH PH12015502165A patent/PH12015502165A1/en unknown
-
2017
- 2017-01-12 IL IL250077A patent/IL250077A0/en unknown
- 2017-06-01 JP JP2017109178A patent/JP6352497B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015522623A5 (enExample) | ||
| JP2016516050A5 (enExample) | ||
| HRP20130143T1 (hr) | Derivati pirazolo piridina kao inhibitori nadph oksidaze | |
| JP2016527006A5 (enExample) | ||
| JP2005536475A5 (enExample) | ||
| HRP20150082T1 (hr) | Derivati pirazolo piridina kao inhibitori nadph oksidaze | |
| HRP20150864T1 (hr) | Novi receptorski ligandi estrogena | |
| HRP20170045T1 (hr) | Difluorlaktamski spojevi kao selektivni agonisti ep4 receptora za uporabu za liječenje bolesti i stanja posredovanih s ep4 receptorom | |
| JP2006515604A5 (enExample) | ||
| JP2014507443A5 (enExample) | ||
| JP2009506039A5 (enExample) | ||
| ME02113B (me) | Parazitocidni spojevi dihidroizoksazola | |
| JP2017160233A5 (enExample) | ||
| WO2015009991A2 (en) | Methods, systems, and compositions for promoting bone growth | |
| JP2008523041A5 (enExample) | ||
| JP2017522374A5 (enExample) | ||
| CA2565813A1 (en) | Substituted methyl aryl or heteroaryl amide compounds | |
| JP2016505619A5 (enExample) | ||
| JP2009504792A5 (enExample) | ||
| PE20100152A1 (es) | {5-[4-(6-CIANO-PIRIDIN-3-ILMETOXI)-FENIL]-[1,2,4]TRIAZOL[1,5-a]PIRIDIN-2-IL}-AMIDA DEL ACIDO CICLOPROPANCARBOXILICO Y COMPOSICIONES QUE LO COMPRENDEN | |
| RU2017134973A (ru) | Бутиролактоны в качестве гербицидов | |
| EP2682387A3 (en) | C7-fluoro substituted tetracycline compounds | |
| JP2013507336A5 (enExample) | ||
| CA2569124A1 (en) | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators | |
| JP2014502979A5 (enExample) |