JP2016525113A5 - - Google Patents
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- Publication number
- JP2016525113A5 JP2016525113A5 JP2016527007A JP2016527007A JP2016525113A5 JP 2016525113 A5 JP2016525113 A5 JP 2016525113A5 JP 2016527007 A JP2016527007 A JP 2016527007A JP 2016527007 A JP2016527007 A JP 2016527007A JP 2016525113 A5 JP2016525113 A5 JP 2016525113A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- yloxy
- pyrazol
- ylmethyl
- 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 31
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002617 leukotrienes Chemical class 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- -1 pyrrolidinonyl Chemical group 0.000 claims 2
- GMMIFPKQJYIPCZ-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 GMMIFPKQJYIPCZ-KRWDZBQOSA-N 0.000 claims 1
- SGFUUDAUBFRRPH-GOSISDBHSA-N (3r)-1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]pyrrolidin-3-ol Chemical compound C1[C@H](O)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 SGFUUDAUBFRRPH-GOSISDBHSA-N 0.000 claims 1
- SGFUUDAUBFRRPH-SFHVURJKSA-N (3s)-1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 SGFUUDAUBFRRPH-SFHVURJKSA-N 0.000 claims 1
- VRNHRFCAVNZHII-VWLOTQADSA-N (3s)-3-hydroxy-1-[1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1[C@@H](O)CCN1C1CCN(CC=2C=C3C=CC(OC=4N=CC(=CC=4)C=4NN=CC=4)=CC3=NC=2)CC1 VRNHRFCAVNZHII-VWLOTQADSA-N 0.000 claims 1
- BQMOHLGGHREEOB-UHFFFAOYSA-N 1-[3-[[methyl-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]amino]methyl]azetidin-1-yl]ethanone Chemical compound C=1N=C2C=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=CC2=CC=1CN(C)CC1CN(C(C)=O)C1 BQMOHLGGHREEOB-UHFFFAOYSA-N 0.000 claims 1
- HQDICABEXSAXJK-UHFFFAOYSA-N 1-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 HQDICABEXSAXJK-UHFFFAOYSA-N 0.000 claims 1
- OKCQFTWHXBDEDJ-UHFFFAOYSA-N 1-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 OKCQFTWHXBDEDJ-UHFFFAOYSA-N 0.000 claims 1
- BPZOKXWKXHSEOJ-UHFFFAOYSA-N 1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 BPZOKXWKXHSEOJ-UHFFFAOYSA-N 0.000 claims 1
- WVYXHIHDEUSURN-UHFFFAOYSA-N 2,2-dimethyl-1-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)(C)C)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 WVYXHIHDEUSURN-UHFFFAOYSA-N 0.000 claims 1
- ZTWXFZSEBOQTMV-HXUWFJFHSA-N 2-hydroxy-1-[(3r)-3-[methyl-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN([C@H]1CN(CC1)C(=O)CO)CC(C=C1C=C2)=CN=C1C=C2OC(N=C1)=CC=C1C1=CC=NN1 ZTWXFZSEBOQTMV-HXUWFJFHSA-N 0.000 claims 1
- ZTWXFZSEBOQTMV-FQEVSTJZSA-N 2-hydroxy-1-[(3s)-3-[methyl-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN([C@@H]1CN(CC1)C(=O)CO)CC(C=C1C=C2)=CN=C1C=C2OC(N=C1)=CC=C1C1=CC=NN1 ZTWXFZSEBOQTMV-FQEVSTJZSA-N 0.000 claims 1
- KAYMQWUWXUHUGU-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 KAYMQWUWXUHUGU-UHFFFAOYSA-N 0.000 claims 1
- GCZZTAIYOQHIMB-HXUWFJFHSA-N 2-hydroxy-n-methyl-n-[(3r)-1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]pyrrolidin-3-yl]acetamide Chemical compound C1[C@H](N(C)C(=O)CO)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 GCZZTAIYOQHIMB-HXUWFJFHSA-N 0.000 claims 1
- GCZZTAIYOQHIMB-FQEVSTJZSA-N 2-hydroxy-n-methyl-n-[(3s)-1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]pyrrolidin-3-yl]acetamide Chemical compound C1[C@@H](N(C)C(=O)CO)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 GCZZTAIYOQHIMB-FQEVSTJZSA-N 0.000 claims 1
- MMDQTGNLXQXGGN-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-[1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperidin-4-yl]acetamide Chemical compound C1CC(N(C)C(=O)CO)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 MMDQTGNLXQXGGN-UHFFFAOYSA-N 0.000 claims 1
- TVJFWQGNCRMXTQ-UHFFFAOYSA-N 2-methoxy-1-[4-[[7-[5-(1H-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]ethanone 1-[[7-[5-(1H-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]azetidin-3-ol Chemical compound OC1CN(Cc2cnc3cc(Oc4ccc(cn4)-c4ccn[nH]4)ccc3c2)C1.COCC(=O)N1CCN(Cc2cnc3cc(Oc4ccc(cn4)-c4ccn[nH]4)ccc3c2)CC1 TVJFWQGNCRMXTQ-UHFFFAOYSA-N 0.000 claims 1
- TYQFYVYCKZCRQG-UHFFFAOYSA-N 2-methyl-1-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)C)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 TYQFYVYCKZCRQG-UHFFFAOYSA-N 0.000 claims 1
- LMLZGWZOVMFXRY-UHFFFAOYSA-N 3-[1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperidin-4-yl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1CCN(CC=2C=C3C=CC(OC=4N=CC(=CC=4)C=4NN=CC=4)=CC3=NC=2)CC1 LMLZGWZOVMFXRY-UHFFFAOYSA-N 0.000 claims 1
- JSIXHLXAGSLVFU-UHFFFAOYSA-N 3-methyl-1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]azetidin-3-ol Chemical compound C1C(C)(O)CN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 JSIXHLXAGSLVFU-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- UJCLDEJIIDCLMM-UHFFFAOYSA-N OCC(=O)N1CCN(Cc2cnc3cc(Oc4ccc(cn4)-c4ccn[nH]4)ccc3c2)CC1 Chemical compound OCC(=O)N1CCN(Cc2cnc3cc(Oc4ccc(cn4)-c4ccn[nH]4)ccc3c2)CC1 UJCLDEJIIDCLMM-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- DIRGZKJGPPSACG-UHFFFAOYSA-N cyclopropyl-[4-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperazin-1-yl]methanone Chemical compound C1CN(CC=2C=C3C=CC(OC=4N=CC(=CC=4)C=4NN=CC=4)=CC3=NC=2)CCN1C(=O)C1CC1 DIRGZKJGPPSACG-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- OXLCEIIBHVACRX-UHFFFAOYSA-N n,n-dimethyl-1-[[7-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-3-yl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CN=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=C1 OXLCEIIBHVACRX-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361846137P | 2013-07-15 | 2013-07-15 | |
| US61/846,137 | 2013-07-15 | ||
| PCT/US2014/046489 WO2015009609A1 (en) | 2013-07-15 | 2014-07-14 | Inhibitors of leukotriene production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016525113A JP2016525113A (ja) | 2016-08-22 |
| JP2016525113A5 true JP2016525113A5 (https=) | 2017-08-31 |
| JP6353899B2 JP6353899B2 (ja) | 2018-07-04 |
Family
ID=51261274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016527007A Active JP6353899B2 (ja) | 2013-07-15 | 2014-07-14 | ロイコトリエン生成の阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US9303018B2 (https=) |
| EP (1) | EP3022193B1 (https=) |
| JP (1) | JP6353899B2 (https=) |
| WO (1) | WO2015009609A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ719169A (en) | 2013-12-20 | 2018-08-31 | Novartis Ag | Heteroaryl butanoic acid derivatives as lta4h inhibitors |
| JP7545570B2 (ja) | 2020-08-14 | 2024-09-04 | ノバルティス アーゲー | ヘテロアリール置換スピロピペリジニル誘導体及びその薬学的使用 |
| US11932630B2 (en) | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| AU2022376563A1 (en) | 2021-11-01 | 2023-12-07 | Alkahest, Inc. | Benzodioxane modulators of leukotriene a4 hydrolase (lta4h) for prevention and treatment of aging-associated diseases |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918092A (en) | 1983-12-21 | 1990-04-17 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
| US5120758A (en) | 1991-02-08 | 1992-06-09 | Ciba-Geigy Corporation | Certain benzodioxole, benzodioxane and benzodioxepin derivatives useful as 5-lipoxygenase inhibitors |
| DE4127849A1 (de) | 1991-08-22 | 1993-02-25 | Merck Patent Gmbh | Benzodioxanderivate |
| US5585492A (en) | 1994-10-11 | 1996-12-17 | G. D. Searle & Co. | LTA4 Hydrolase inhibitors |
| US6506876B1 (en) | 1994-10-11 | 2003-01-14 | G.D. Searle & Co. | LTA4 hydrolase inhibitor pharmaceutical compositions and methods of use |
| DE19705450A1 (de) | 1997-02-13 | 1998-08-20 | Merck Patent Gmbh | Bicyclische aromatische Aminosäuren |
| US5925654A (en) * | 1997-03-12 | 1999-07-20 | G.D. Searle & Co. | LTA4 , hydrolase inhibitors |
| DE19821003A1 (de) | 1998-05-11 | 1999-11-18 | Dresden Arzneimittel | Neue 1,2,5-trisubstituierte 1,2-dihydro-indazol-3-one mit antiasthmatischer, antiallergischer, entzündungshemmender, immunmodulierender und neuroprotektiver Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| IL154946A0 (en) | 2000-10-26 | 2003-10-31 | Pfizer Prod Inc | Pyrimidine-2,4,6-trione metalloproteinase inhibitors |
| US20060019269A1 (en) | 2002-10-17 | 2006-01-26 | Decode Genetics, Inc. | Susceptibility gene for myocardial infarction, stroke, and PAOD, methods of treatment |
| KR100897642B1 (ko) | 2002-12-20 | 2009-05-14 | 글락소 그룹 리미티드 | 신경 장애 치료용 벤즈아제핀 유도체 |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| KR100896380B1 (ko) | 2005-01-07 | 2009-05-08 | 화이자 프로덕츠 인코포레이티드 | 헤테로방향족 퀴놀린 화합물 및 ｐｄｅ10 저해제로서의그의 용도 |
| CA2603122A1 (en) | 2005-03-31 | 2006-10-05 | Janssen Pharmaceutica N.V. | Phenyl and pyridyl lta4h modulators |
| JP5133889B2 (ja) | 2005-09-21 | 2013-01-30 | デコード ジェネティクス イーエイチエフ | 炎症治療のためのビアリール基置換複素環ｌｔａ４ｈ阻害剤 |
| CA2634699A1 (en) | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of lta4h for treating inflammation |
| CA2636929A1 (en) | 2005-12-21 | 2007-07-12 | Decode Genetics, Ehf | Biaryl nitrogen heterocycle inhibitors of lta4h for treating inflammation |
| WO2008052086A1 (en) | 2006-10-24 | 2008-05-02 | Wyeth | Benzodioxane derivatives and uses thereof |
| US9481675B2 (en) * | 2009-09-11 | 2016-11-01 | Merck Sharp & Dohme Corp. | Gyrase inhibitors |
| CN102946877B (zh) | 2010-03-18 | 2019-07-05 | 香港科技大学 | 乳突果及其分离的化合物在制备用于治疗神经疾病的药物中的用途 |
| CN103415513B (zh) * | 2011-03-14 | 2016-01-20 | 勃林格殷格翰国际有限公司 | 白三烯产物的苯并二氧杂环己烷抑制剂 |
| WO2013012844A1 (en) | 2011-07-19 | 2013-01-24 | Boehringer Ingelheim International Gmbh | Arylpyrazole ethers as inhibitors of leukotriene a4 hydrolase |
| JP6080227B2 (ja) | 2012-03-06 | 2017-02-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成を阻害するためのベンゾジオキサン |
| US9662339B2 (en) | 2012-03-06 | 2017-05-30 | Boehringer Ingelheim International Gmbh | Benzodioxane inhibitors of leukotriene production for combination therapy |
| AR091786A1 (es) * | 2012-07-17 | 2015-02-25 | Boehringer Ingelheim Int | Inhibidores de la produccion de leucotrienos |
-
2014
- 2014-07-14 WO PCT/US2014/046489 patent/WO2015009609A1/en not_active Ceased
- 2014-07-14 EP EP14745322.9A patent/EP3022193B1/en active Active
- 2014-07-14 US US14/330,297 patent/US9303018B2/en active Active
- 2014-07-14 JP JP2016527007A patent/JP6353899B2/ja active Active
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