JP2017500321A5 - - Google Patents
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- Publication number
- JP2017500321A5 JP2017500321A5 JP2016540623A JP2016540623A JP2017500321A5 JP 2017500321 A5 JP2017500321 A5 JP 2017500321A5 JP 2016540623 A JP2016540623 A JP 2016540623A JP 2016540623 A JP2016540623 A JP 2016540623A JP 2017500321 A5 JP2017500321 A5 JP 2017500321A5
- Authority
- JP
- Japan
- Prior art keywords
- diabetic
- compound
- azetidine
- represents hydrogen
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 50
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 21
- 206010012601 diabetes mellitus Diseases 0.000 claims 20
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 9
- 239000011737 fluorine Substances 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 230000002093 peripheral effect Effects 0.000 claims 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 230000029663 wound healing Effects 0.000 claims 8
- 206010019280 Heart failures Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 6
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 4
- 208000008960 Diabetic foot Diseases 0.000 claims 4
- 206010054044 Diabetic microangiopathy Diseases 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 206010056340 Diabetic ulcer Diseases 0.000 claims 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 201000009101 diabetic angiopathy Diseases 0.000 claims 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 230000001737 promoting effect Effects 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 201000002829 CREST Syndrome Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010022562 Intermittent claudication Diseases 0.000 claims 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 3
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- -1 hydroxy, monofluoromethyl Chemical group 0.000 claims 3
- 208000021156 intermittent vascular claudication Diseases 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000009424 thromboembolic effect Effects 0.000 claims 3
- 206010061666 Autonomic neuropathy Diseases 0.000 claims 2
- 108010078321 Guanylate Cyclase Proteins 0.000 claims 2
- 102000014469 Guanylate cyclase Human genes 0.000 claims 2
- 229940083712 aldosterone antagonist Drugs 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 2
- DJXQYJXQDQXQTG-UHFFFAOYSA-N 4-hydroxythiomorpholine Chemical compound ON1CCSCC1 DJXQYJXQDQXQTG-UHFFFAOYSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229940122434 Calcium sensitizer Drugs 0.000 claims 1
- 208000020446 Cardiac disease Diseases 0.000 claims 1
- 229940122444 Chemokine receptor antagonist Drugs 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000032781 Diabetic cardiomyopathy Diseases 0.000 claims 1
- 208000003790 Foot Ulcer Diseases 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 108020001621 Natriuretic Peptide Proteins 0.000 claims 1
- 102000004571 Natriuretic peptide Human genes 0.000 claims 1
- 102000002512 Orexin Human genes 0.000 claims 1
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 239000002170 aldosterone antagonist Substances 0.000 claims 1
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 claims 1
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 229960004676 antithrombotic agent Drugs 0.000 claims 1
- 230000004596 appetite loss Effects 0.000 claims 1
- 230000002567 autonomic effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 239000002559 chemokine receptor antagonist Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000037149 energy metabolism Effects 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 102000052502 human ELANE Human genes 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000000297 inotrophic effect Effects 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 235000021266 loss of appetite Nutrition 0.000 claims 1
- 208000019017 loss of appetite Diseases 0.000 claims 1
- 239000002394 mineralocorticoid antagonist Substances 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 239000000692 natriuretic peptide Substances 0.000 claims 1
- 239000002658 neuropeptide Y receptor agonist Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 108060005714 orexin Proteins 0.000 claims 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229940001470 psychoactive drug Drugs 0.000 claims 1
- 239000004089 psychotropic agent Substances 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 239000000021 stimulant Substances 0.000 claims 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 claims 1
- 230000002889 sympathetic effect Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 239000002536 vasopressin receptor antagonist Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13198385 | 2013-12-19 | ||
| EP13198385.0 | 2013-12-19 | ||
| EP14192877.0 | 2014-11-12 | ||
| EP14192877 | 2014-11-12 | ||
| PCT/EP2014/077862 WO2015091414A2 (de) | 2013-12-19 | 2014-12-16 | Substituierte piperidinyl-tetrahydrochinoline |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018221834A Division JP2019048875A (ja) | 2013-12-19 | 2018-11-28 | 置換されたピペリジニル−テトラヒドロキノリン類およびそれらのα−２Ｃアドレナリン受容体拮抗薬としての使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017500321A JP2017500321A (ja) | 2017-01-05 |
| JP2017500321A5 true JP2017500321A5 (enExample) | 2018-02-01 |
| JP6487922B2 JP6487922B2 (ja) | 2019-03-20 |
Family
ID=52101341
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016540623A Expired - Fee Related JP6487922B2 (ja) | 2013-12-19 | 2014-12-16 | 置換されたピペリジニル−テトラヒドロキノリン類およびそれらのα−２Ｃアドレナリン受容体拮抗薬としての使用 |
| JP2018221834A Pending JP2019048875A (ja) | 2013-12-19 | 2018-11-28 | 置換されたピペリジニル−テトラヒドロキノリン類およびそれらのα−２Ｃアドレナリン受容体拮抗薬としての使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018221834A Pending JP2019048875A (ja) | 2013-12-19 | 2018-11-28 | 置換されたピペリジニル−テトラヒドロキノリン類およびそれらのα−２Ｃアドレナリン受容体拮抗薬としての使用 |
Country Status (38)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CR20160276A (es) | 2013-12-19 | 2016-10-20 | Bayer Pharma AG | "piperidiniltetrahidroquinolinas sustituidas y su uso como antagonistas de los adenoreceptores alpha-2c" |
| KR20180074793A (ko) | 2015-11-13 | 2018-07-03 | 바이엘 파마 악티엔게젤샤프트 | 만성 상처 치료를 위한 4-(4-시아노-2-티오아릴)다이하이드로피리미디논 |
| WO2018197333A1 (en) | 2017-04-27 | 2018-11-01 | Bayer Aktiengesellschaft | Selective adrenoreceptor alpha2c receptor antagonists alone, or in combination with chymase inhibitors for use in the treatment and/or prophylaxis of peripheral artery diseases (pad) |
| CN110917195A (zh) * | 2018-08-20 | 2020-03-27 | 山西惠尔健生物科技有限公司 | 肌松剂阿库氯铵（Alcuronium chloride）可作为抗心律失常药物 |
| AU2019382737A1 (en) * | 2018-11-20 | 2021-05-20 | Bayer Aktiengesellschaft | α2-adrenoceptor subtype C (alpha-2C) antagonists for the treatment of sleep apnea |
| WO2020165031A1 (de) | 2019-02-15 | 2020-08-20 | Bayer Aktiengesellschaft | Substituierte isochinolin-piperidinylmethanon-derivate |
| CN113330009B (zh) * | 2019-03-12 | 2024-02-09 | 四川科伦博泰生物医药股份有限公司 | 氮杂环化合物、其制备方法及用途 |
| US12569481B2 (en) | 2020-06-12 | 2026-03-10 | Vanderbilt University | Methods of treatment for gastrointestinal motility disorders |
| TWI804119B (zh) * | 2020-12-21 | 2023-06-01 | 大陸商上海濟煜醫藥科技有限公司 | 三氮唑類三并環衍生物及其製備方法和應用 |
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| EP0876379A1 (en) | 1996-01-17 | 1998-11-11 | Novo Nordisk A/S | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use |
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| RU2215004C2 (ru) | 1997-07-16 | 2003-10-27 | Ново Нордиск А/С | Конденсированное производное 1,2,4-тиадиазина, фармацевтическая композиция и способ получения лекарственного препарата |
| DE19734557A1 (de) | 1997-08-04 | 1999-02-11 | Oliver Lang | Netzanschlußloses Kleinleistungs-Haushaltsgerät |
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| UA69420C2 (uk) * | 1998-10-06 | 2004-09-15 | Янссен Фармацевтика Н.В. | ТРИЦИКЛІЧНІ <font face="Symbol">D3</font>-ПІПЕРИДИНИ ЯК <font face="Symbol">a<sub></font>2</sub>-АНТАГОНІСТИ |
| KR100439357B1 (ko) | 1999-05-04 | 2004-07-07 | 쉐링 코포레이션 | Ｃｃｒ５ 길항제로서 유용한 피페리딘 유도체 |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
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| US6444681B1 (en) | 2000-06-09 | 2002-09-03 | The Ohio State University Research Foundation | Methods and compositions for treating Raynaud's Phenomenon and scleroderma |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
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| AR036366A1 (es) | 2001-08-29 | 2004-09-01 | Schering Corp | Derivados de piperidina utiles como antagonistas de ccr5, composiciones farmaceuticas, el uso de dichos derivados para la fabricación de un medicamento y un kit |
| US20040110826A1 (en) * | 2001-09-28 | 2004-06-10 | Noriaki Uesaka | Receptor Antagonists |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
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| CN103547580B (zh) | 2011-03-22 | 2016-12-07 | 阿迪维纳斯疗法有限公司 | 取代的稠合三环化合物、其组合物及医药用途 |
| CR20160276A (es) | 2013-12-19 | 2016-10-20 | Bayer Pharma AG | "piperidiniltetrahidroquinolinas sustituidas y su uso como antagonistas de los adenoreceptores alpha-2c" |
| EP3083610A1 (de) * | 2013-12-19 | 2016-10-26 | Bayer Pharma Aktiengesellschaft | Substituierte bipiperidinyl-derivate als adrenrezeptor alpha 2c antagonisten |
| KR20160098424A (ko) * | 2013-12-19 | 2016-08-18 | 바이엘 파마 악티엔게젤샤프트 | 치환된 피페리디닐-테트라히드로퀴놀린 |
-
2014
- 2014-12-16 CR CR20160276A patent/CR20160276A/es unknown
- 2014-12-16 US US15/106,284 patent/US9944621B2/en active Active
- 2014-12-16 HU HUE14812245A patent/HUE039942T2/hu unknown
- 2014-12-16 HR HRP20181536TT patent/HRP20181536T1/hr unknown
- 2014-12-16 ES ES14812245.0T patent/ES2689023T3/es active Active
- 2014-12-16 SG SG11201604978QA patent/SG11201604978QA/en unknown
- 2014-12-16 WO PCT/EP2014/077862 patent/WO2015091414A2/de not_active Ceased
- 2014-12-16 CU CU2016000088A patent/CU24390B1/es unknown
- 2014-12-16 EA EA201600477A patent/EA032250B1/ru not_active IP Right Cessation
- 2014-12-16 EP EP14812245.0A patent/EP3083592B1/de active Active
- 2014-12-16 PL PL14812245T patent/PL3083592T3/pl unknown
- 2014-12-16 CA CA2934108A patent/CA2934108C/en active Active
- 2014-12-16 SI SI201430831T patent/SI3083592T1/sl unknown
- 2014-12-16 EP EP17208289.3A patent/EP3329920A3/de not_active Withdrawn
- 2014-12-16 MX MX2016008113A patent/MX365289B/es active IP Right Grant
- 2014-12-16 NZ NZ758272A patent/NZ758272A/en unknown
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