ES2397947T3 - 4-amino-3,5-diciano-2-tiopiridinas sustituidas y su uso - Google Patents
4-amino-3,5-diciano-2-tiopiridinas sustituidas y su uso Download PDFInfo
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- ES2397947T3 ES2397947T3 ES07846652T ES07846652T ES2397947T3 ES 2397947 T3 ES2397947 T3 ES 2397947T3 ES 07846652 T ES07846652 T ES 07846652T ES 07846652 T ES07846652 T ES 07846652T ES 2397947 T3 ES2397947 T3 ES 2397947T3
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- Prior art keywords
- alkyl
- amino
- formula
- alkoxy
- substituted
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- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- -1 amino, carboxyl Chemical group 0.000 claims abstract description 70
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 41
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 36
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
- 239000011737 fluorine Substances 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000000464 thioxo group Chemical group S=* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 238000011321 prophylaxis Methods 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 230000036772 blood pressure Effects 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000003146 anticoagulant agent Substances 0.000 claims description 7
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 230000037356 lipid metabolism Effects 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 5
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 230000003178 anti-diabetic effect Effects 0.000 claims description 5
- 230000002785 anti-thrombosis Effects 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 208000029078 coronary artery disease Diseases 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims 1
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 1
- DOVOVWITCHWXJD-UHFFFAOYSA-N 8-methoxy-2-oxo-n-(4-sulfamoylphenyl)chromene-3-carboxamide Chemical compound O=C1OC=2C(OC)=CC=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 DOVOVWITCHWXJD-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 3
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
- 239000003480 eluent Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
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- 238000012360 testing method Methods 0.000 description 20
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 14
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Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| PCT/EP2007/009963 WO2008064789A1 (de) | 2006-12-01 | 2007-11-17 | Substituierte 4-amino-3,5-dicyano-2-thiopyridine und ihre verwendung |
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| DE102006042143A1 (de) | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate und ihre Verwendung |
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| DE102008013587A1 (de) * | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
| US8791146B2 (en) * | 2008-05-29 | 2014-07-29 | Bayer Intellectual Property Gmbh | 2-alkoxy-substituted dicyanopyridines and their use |
| DE102008062567A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Dipeptoid-Prodrugs und ihre Verwendung |
| DE102009006602A1 (de) * | 2009-01-29 | 2010-08-05 | Bayer Schering Pharma Aktiengesellschaft | Alkylamino-substituierte Dicyanopyridine und deren Aminosäureester-Prodrugs |
| US20110294767A1 (en) | 2010-05-26 | 2011-12-01 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| DE102010030688A1 (de) | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
| US20120058983A1 (en) | 2010-09-02 | 2012-03-08 | Bayer Pharma Aktiengesellschaft | Adenosine A1 agonists for the treatment of glaucoma and ocular hypertension |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| ES2633766T3 (es) | 2011-10-28 | 2017-09-25 | Lumena Pharmaceuticals Llc | Inhibidores de reciclaje de ácido biliar para el tratamiento de enfermedades de hígado colestático pediátrico |
| AU2012328453B2 (en) | 2011-10-28 | 2017-05-04 | Shire Human Genetic Therapies, Inc. | Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease |
| KR20230152818A (ko) | 2013-03-15 | 2023-11-03 | 샤이어 휴먼 지네틱 테라피즈 인크. | 원발성 담관염 및 염증성 장 질환 치료용 담즙산 재순환 억제제 |
| JP2016514678A (ja) | 2013-03-15 | 2016-05-23 | ルメナ ファーマシューティカルズ エルエルシー | バレット食道と胃食道逆流性疾患を処置するための胆汁酸再利用阻害剤 |
| WO2018153899A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit stimulatoren und/oder aktivatoren der löslichen guanylatcyclase (sgc) |
| WO2018153897A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit hcn-kanal-hemmern |
| WO2018153898A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit mineralocorticoid-rezeptor-antagonisten |
| WO2018153895A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit einem inhibitor der neutralen endopeptidase und/oder einem angiotensin ii rezeptor-antagonisten |
| WO2018153900A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit sglt-2-hemmern |
| WO2019072143A1 (zh) * | 2017-10-11 | 2019-04-18 | 上海迪诺医药科技有限公司 | 4-氨基吡啶衍生物、其药物组合物、制备方法及应用 |
| CN109957584A (zh) * | 2017-12-25 | 2019-07-02 | 尚科生物医药（上海）有限公司 | 一种用于制备（r）-(4-氯苯基)-2-吡啶甲醇的生物催化方法 |
| US11839614B2 (en) | 2018-01-31 | 2023-12-12 | Intra-Cellular Therapies, Inc. | Methods for treating or mitigating cardiotoxicity characterized by inhibition of adenosine A2 signaling and/or adenosine A2 receptor expression |
| ES2982943T3 (es) | 2019-02-12 | 2024-10-21 | Mirum Pharmaceuticals Inc | Métodos para aumentar el crecimiento en sujetos pediátricos con hepatopatía colestásica |
| CA3196009A1 (en) * | 2020-10-20 | 2022-04-28 | Mikhail SHAFEEV | Agonists of free fatty acid receptor 1 and their use in diseases associated with said receptor |
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| WO2007073855A1 (en) | 2005-12-23 | 2007-07-05 | Bayer Healthcare Ag | Use of adenosine a1 receptor agonists for the protection of renal cells against toxic effects caused by aminoglycosides during treatment of infectious diseases |
| DE102006009813A1 (de) * | 2006-03-01 | 2007-09-06 | Bayer Healthcare Ag | Verwendung von A2b/A1 Rezeptor Agonisten zur Modulation der Lipidspiegel |
| JP2009535307A (ja) * | 2006-04-28 | 2009-10-01 | アベキサ・リミテッド | インテグラーゼ阻害剤３ |
| DE102006042143A1 (de) | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate und ihre Verwendung |
| DE102006056740A1 (de) | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Cyclisch substituierte 3,5-Dicyano-2-thiopyridine und ihre Verwendung |
| DE102007035367A1 (de) | 2007-07-27 | 2009-01-29 | Bayer Healthcare Ag | Substituierte Aryloxazole und ihre Verwendung |
| DE102007036076A1 (de) | 2007-08-01 | 2009-02-05 | Bayer Healthcare Aktiengesellschaft | Dipeptoid-Produgs und ihre Verwendung |
| DE102008013587A1 (de) | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
| US8791146B2 (en) | 2008-05-29 | 2014-07-29 | Bayer Intellectual Property Gmbh | 2-alkoxy-substituted dicyanopyridines and their use |
| DE102008062567A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Dipeptoid-Prodrugs und ihre Verwendung |
| DE102009006602A1 (de) | 2009-01-29 | 2010-08-05 | Bayer Schering Pharma Aktiengesellschaft | Alkylamino-substituierte Dicyanopyridine und deren Aminosäureester-Prodrugs |
-
2006
- 2006-12-01 DE DE102006056739A patent/DE102006056739A1/de not_active Withdrawn
-
2007
- 2007-11-17 CA CA002671127A patent/CA2671127A1/en not_active Abandoned
- 2007-11-17 WO PCT/EP2007/009963 patent/WO2008064789A1/de not_active Ceased
- 2007-11-17 ES ES07846652T patent/ES2397947T3/es active Active
- 2007-11-17 US US12/516,939 patent/US8703934B2/en not_active Expired - Fee Related
- 2007-11-17 EP EP07846652A patent/EP2099781B1/de not_active Not-in-force
- 2007-11-17 JP JP2009538617A patent/JP5317980B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2099781A1 (de) | 2009-09-16 |
| DE102006056739A1 (de) | 2008-06-05 |
| WO2008064789A1 (de) | 2008-06-05 |
| CA2671127A1 (en) | 2008-06-05 |
| JP2010510999A (ja) | 2010-04-08 |
| US20100069363A1 (en) | 2010-03-18 |
| JP5317980B2 (ja) | 2013-10-16 |
| US8703934B2 (en) | 2014-04-22 |
| EP2099781B1 (de) | 2012-10-24 |
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