JP2016516050A5 - - Google Patents
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- 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 (https=) | 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 (https=) |
| EP (2) | EP3235817B1 (https=) |
| JP (2) | JP6317807B2 (https=) |
| KR (1) | KR20150130326A (https=) |
| CN (1) | CN105143217A (https=) |
| AU (1) | AU2014228973B2 (https=) |
| BR (1) | BR112015023080A2 (https=) |
| CA (1) | CA2906134A1 (https=) |
| DK (1) | DK2989098T3 (https=) |
| EA (1) | EA201591793A1 (https=) |
| ES (1) | ES2635635T3 (https=) |
| IL (2) | IL240988A (https=) |
| PH (1) | PH12015502165A1 (https=) |
| PT (1) | PT2989098T (https=) |
| SG (1) | SG11201507470WA (https=) |
| WO (1) | WO2014144584A2 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014015247A1 (en) | 2012-07-19 | 2014-01-23 | Cayman Chemical Company, Inc. | Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions |
| KR20160048054A (ko) | 2013-07-19 | 2016-05-03 | 카이맨 케미칼 컴파니 인코포레이티드 | 골 성장의 촉진을 위한 방법, 시스템 및 조성물 |
| 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 |
| PT3733665T (pt) * | 2017-12-25 | 2022-10-21 | Asahi Kasei Pharma Corp | Compostos contendo unidade de 2-oxo-1,3,4-tiadiazinan-3-ilo com atividade agonista do recetor ep4 |
| AU2020256166A1 (en) | 2019-04-02 | 2021-10-14 | 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 |
| CA1085859A (en) | 1975-06-27 | 1980-09-16 | Wilhelm Bartmann | Pyrrolidones and process for their manufacture |
| DE2528664A1 (de) | 1975-06-27 | 1977-01-13 | Hoechst Ag | Pyrrolidone und verfahren zu ihrer herstellung |
| 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 |
| GEP20043203B (en) * | 1999-12-22 | 2004-03-25 | Pfizer Prod 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 |
| AU2001290250A1 (en) | 2000-09-21 | 2002-04-02 | Ono Pharmaceutical Co. Ltd. | Ep4 receptor agonists containing 8-azaprostaglandin derivatives as the active ingredient |
| OA12533A (en) | 2000-11-27 | 2006-06-05 | Pfizer Prod Inc | Ep4 receptor selective agonists in the treatment of osteoporosis. |
| CA2451392A1 (en) | 2001-07-16 | 2003-01-30 | F. Hoffmann-La Roche Ag | Prostaglandin analogues as ep4 receptor agonists |
| CN100371322C (zh) | 2001-07-16 | 2008-02-27 | 霍夫曼-拉罗奇有限公司 | 作为前列腺素类化合物激动剂的2-吡咯烷酮衍生物 |
| EP2255829A3 (en) | 2001-07-23 | 2012-03-28 | Ono Pharmaceutical Co., Ltd. | Pharmaceutical composition for treatment of diseases associated with decrease in bone mass comprising EP4 agonist as active ingredient |
| US7410991B2 (en) | 2001-10-23 | 2008-08-12 | Laboratoires Serono S.A. | Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors |
| EP1461026A2 (en) | 2001-12-03 | 2004-09-29 | Merck & Co., Inc. | Method for treating ocular hypertension |
| WO2003047417A2 (en) | 2001-12-03 | 2003-06-12 | Merck & Co., Inc. | Ep4 receptor agonist, compositions and methods thereof |
| AU2003211574A1 (en) | 2002-03-05 | 2003-09-16 | Ono Pharmaceutical Co., Ltd. | 8-azaprostaglandin derivative compounds and drugs containing the compounds as the active ingredient |
| 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 |
| WO2003077910A1 (en) | 2002-03-18 | 2003-09-25 | Pfizer Products Inc. | Methods of treatment with selective ep4 receptor agonists |
| US6573294B1 (en) | 2002-05-14 | 2003-06-03 | Allergan, Inc. | 8-azaprostaglandin analogs as agents for lowering intraocular pressure |
| JP4754820B2 (ja) * | 2002-06-10 | 2011-08-24 | メルク セローノ ソシエテ アノニム | プロスタグランジン作動薬としてのγラクタムおよびその使用 |
| US20060167081A1 (en) | 2002-10-25 | 2006-07-27 | Xavier Billot | Ep4 receptor agonists |
| US7256211B1 (en) | 2003-01-21 | 2007-08-14 | Ono Pharmaceutical Co., Ltd. | 8-azaprostaglandin derivatives and medical use thereof |
| ES2305779T3 (es) * | 2003-03-03 | 2008-11-01 | Laboratoires Serono Sa | Derivados de g-lactama como agonistas de prostaglandinas. |
| US7169807B2 (en) | 2004-04-09 | 2007-01-30 | Allergan, Inc. | 10-Hydroxy-11-dihydroprostaglandin analogs as selective EP4 agonists |
| WO2006016695A1 (ja) | 2004-08-10 | 2006-02-16 | Ono Pharmaceutical Co., Ltd. | 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 |
| US7858610B2 (en) | 2004-08-10 | 2010-12-28 | Ono Pharmaceutical Co., Ltd. | Preventive and/or remedy for lower urinary tract diseases containing EP4 agonist |
| AU2006253356B2 (en) * | 2005-06-03 | 2011-12-01 | Ono Pharmaceutical Co., Ltd. | Agent for regeneration and/or protection of nerves |
| US20070232660A1 (en) | 2006-04-04 | 2007-10-04 | Allergan, Inc. | Therapeutic and delivery methods of prostaglandin ep4 agonists |
| EP2147672A4 (en) | 2007-05-08 | 2011-11-02 | Nat University Corp Hamamatsu University School Of Medicine | CYTOTOXIC T CELL ACTIVATOR WITH AN EP4 AGONIST |
| WO2009055289A2 (en) | 2007-10-23 | 2009-04-30 | Allergan, Inc. | Therapeutic substituted lactams |
| US20120270934A1 (en) * | 2009-07-03 | 2012-10-25 | Concert Pharmaceuticals, Inc. | Prostacyclin derivatives |
| CN103201261A (zh) | 2010-11-10 | 2013-07-10 | 埃科特莱茵药品有限公司 | 用作为食欲素受体拮抗剂的内酰胺衍生物 |
| 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 |
| WO2013018837A1 (ja) | 2011-08-02 | 2013-02-07 | 小野薬品工業株式会社 | 左室拡張機能改善剤 |
| WO2014015247A1 (en) | 2012-07-19 | 2014-01-23 | Cayman Chemical Company, Inc. | Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions |
-
2014
- 2014-03-14 PT PT147291066T patent/PT2989098T/pt unknown
- 2014-03-14 BR BR112015023080A patent/BR112015023080A2/pt not_active IP Right Cessation
- 2014-03-14 EP EP17169751.9A patent/EP3235817B1/en not_active Not-in-force
- 2014-03-14 CN CN201480015554.7A patent/CN105143217A/zh active Pending
- 2014-03-14 KR KR1020157026225A patent/KR20150130326A/ko not_active Withdrawn
- 2014-03-14 US US14/775,427 patent/US9688627B2/en active Active
- 2014-03-14 EP EP14729106.6A patent/EP2989098B1/en active Active
- 2014-03-14 WO PCT/US2014/029057 patent/WO2014144584A2/en not_active Ceased
- 2014-03-14 AU AU2014228973A patent/AU2014228973B2/en not_active Expired - Fee Related
- 2014-03-14 ES ES14729106.6T patent/ES2635635T3/es active Active
- 2014-03-14 SG SG11201507470WA patent/SG11201507470WA/en unknown
- 2014-03-14 DK DK14729106.6T patent/DK2989098T3/en active
- 2014-03-14 JP JP2016502973A patent/JP6317807B2/ja active Active
- 2014-03-14 CA CA2906134A patent/CA2906134A1/en active Pending
- 2014-03-14 EA EA201591793A patent/EA201591793A1/ru unknown
-
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
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