ES2828704T3 - Procedimiento para la preparación de (4S)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida y su purificación para su uso como principio activo farmacéutico - Google Patents
Procedimiento para la preparación de (4S)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida y su purificación para su uso como principio activo farmacéutico Download PDFInfo
- Publication number
- ES2828704T3 ES2828704T3 ES15742306T ES15742306T ES2828704T3 ES 2828704 T3 ES2828704 T3 ES 2828704T3 ES 15742306 T ES15742306 T ES 15742306T ES 15742306 T ES15742306 T ES 15742306T ES 2828704 T3 ES2828704 T3 ES 2828704T3
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- SWJVFAOGXDGTCX-UHFFFAOYSA-N CC(CC(OCCC#N)=O)=O Chemical compound CC(CC(OCCC#N)=O)=O SWJVFAOGXDGTCX-UHFFFAOYSA-N 0.000 description 3
- YMXQYZABFWVXEK-UHFFFAOYSA-N COc1cc(Br)ccc1C=O Chemical compound COc1cc(Br)ccc1C=O YMXQYZABFWVXEK-UHFFFAOYSA-N 0.000 description 2
- FYAKLZKQJDBBKW-UHFFFAOYSA-N OC(c(ccc(Br)c1)c1O)=O Chemical compound OC(c(ccc(Br)c1)c1O)=O FYAKLZKQJDBBKW-UHFFFAOYSA-N 0.000 description 2
- LWXFCZXRFBUOOR-UHFFFAOYSA-N OC(c(ccc(Cl)c1)c1O)=O Chemical compound OC(c(ccc(Cl)c1)c1O)=O LWXFCZXRFBUOOR-UHFFFAOYSA-N 0.000 description 2
- RFJLQSVKIAMLCX-ZROIWOOFSA-N CC(/C(/C(OCCC#N)=O)=C/c(ccc(C#N)c1)c1OC)=O Chemical compound CC(/C(/C(OCCC#N)=O)=C/c(ccc(C#N)c1)c1OC)=O RFJLQSVKIAMLCX-ZROIWOOFSA-N 0.000 description 1
- RFJLQSVKIAMLCX-NTEUORMPSA-N CC(/C(/C(OCCC#N)=O)=C\c(ccc(C#N)c1)c1OC)=O Chemical compound CC(/C(/C(OCCC#N)=O)=C\c(ccc(C#N)c1)c1OC)=O RFJLQSVKIAMLCX-NTEUORMPSA-N 0.000 description 1
- IXGGTEVAHGIOIC-UHFFFAOYSA-N CC(C1=C2C(c(ccc(N)c3)c3OC)C(C(OCCC#N)=O)=C(C)N1)=CNC2=O Chemical compound CC(C1=C2C(c(ccc(N)c3)c3OC)C(C(OCCC#N)=O)=C(C)N1)=CNC2=O IXGGTEVAHGIOIC-UHFFFAOYSA-N 0.000 description 1
- WFWLLONBVSJAGN-UHFFFAOYSA-N CCOc1c(C(c(ccc(N)c2)c2OC)C(C(OCCN)=O)=C(C)N2)c2c(C)cn1 Chemical compound CCOc1c(C(c(ccc(N)c2)c2OC)C(C(OCCN)=O)=C(C)N2)c2c(C)cn1 WFWLLONBVSJAGN-UHFFFAOYSA-N 0.000 description 1
- ZXENVSJZOHXCKL-UHFFFAOYSA-N COc1c(C=O)ccc(C#N)c1 Chemical compound COc1c(C=O)ccc(C#N)c1 ZXENVSJZOHXCKL-UHFFFAOYSA-N 0.000 description 1
- IVBZHFWJBYTRNG-UHFFFAOYSA-N COc1c(C=O)ccc(Cl)c1 Chemical compound COc1c(C=O)ccc(Cl)c1 IVBZHFWJBYTRNG-UHFFFAOYSA-N 0.000 description 1
- AXXPZAITCCIOIA-UHFFFAOYSA-N COc1c(CO)ccc(Cl)c1 Chemical compound COc1c(CO)ccc(Cl)c1 AXXPZAITCCIOIA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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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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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
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- Public Health (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14179544 | 2014-08-01 | ||
| PCT/EP2015/067340 WO2016016287A1 (de) | 2014-08-01 | 2015-07-29 | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid und dessen aufreinigung für die verwendung als pharmazeutischer wirkstoff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2828704T3 true ES2828704T3 (es) | 2021-05-27 |
Family
ID=51260727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15742306T Active ES2828704T3 (es) | 2014-08-01 | 2015-07-29 | Procedimiento para la preparación de (4S)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida y su purificación para su uso como principio activo farmacéutico |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | USRE49575E1 (enExample) |
| EP (2) | EP3660015A1 (enExample) |
| JP (1) | JP6818674B2 (enExample) |
| KR (3) | KR102527893B1 (enExample) |
| CN (3) | CN116655627A (enExample) |
| AR (1) | AR101403A1 (enExample) |
| AU (1) | AU2015295376C1 (enExample) |
| BR (1) | BR112017001678B1 (enExample) |
| CA (2) | CA2956529A1 (enExample) |
| CL (1) | CL2017000263A1 (enExample) |
| CO (1) | CO2017000886A2 (enExample) |
| DK (1) | DK3174875T3 (enExample) |
| ES (1) | ES2828704T3 (enExample) |
| HR (1) | HRP20201800T1 (enExample) |
| HU (1) | HUE051350T2 (enExample) |
| IL (1) | IL250239B (enExample) |
| JO (1) | JO3648B1 (enExample) |
| LT (1) | LT3174875T (enExample) |
| MX (1) | MX369467B (enExample) |
| MY (1) | MY198066A (enExample) |
| PE (1) | PE20170141A1 (enExample) |
| PL (1) | PL3174875T3 (enExample) |
| PT (1) | PT3174875T (enExample) |
| RS (1) | RS60921B1 (enExample) |
| RU (1) | RU2729998C9 (enExample) |
| SG (1) | SG11201700785UA (enExample) |
| SI (1) | SI3174875T1 (enExample) |
| TW (1) | TWI684593B (enExample) |
| UA (1) | UA122773C2 (enExample) |
| UY (1) | UY36251A (enExample) |
| WO (1) | WO2016016287A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116655627A (zh) * | 2014-08-01 | 2023-08-29 | 拜耳医药股份有限公司 | 一种化合物的制备方法及其纯化以用作活性药物成分 |
| LT3337800T (lt) | 2015-08-21 | 2019-08-12 | Bayer Pharma Aktiengesellschaft | (4s)-4-(4-ciano-2-metoksifenil)-5-etoksi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-karboksamido, skirto naudoti kaip veikliojo farmacinio ingrediento, gamybos būdas ir gryninimas |
| EP3560922A1 (de) | 2018-04-24 | 2019-10-30 | Bayer Aktiengesellschaft | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester |
| JOP20210243A1 (ar) | 2019-03-05 | 2023-01-30 | Bayer Ag | طريقة لتحضير 4-أمينو-5-مثيل بيريدون |
| BR112021014815A2 (pt) | 2019-03-05 | 2021-09-28 | Bayer Aktiengesellschaft | Método para preparação de 4-amino-5-metilpiridona |
| CN114555599B (zh) * | 2019-10-17 | 2024-06-07 | 拜耳公司 | 制备(4s)-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-羧酸的酰氧基甲基酯的方法 |
| CA3158167A1 (en) * | 2019-10-17 | 2021-04-22 | Bayer Aktiengesellschaft | Photochemical process for producing (4r,4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxamide |
| IL292192A (en) * | 2019-10-17 | 2022-06-01 | Bayer Ag | Process for the preparation of (2-cyanoethyl(4s)-4-(4-cyano-2-methoxy-phenyl)-5-hydroxy-8,2-dimethyl-4,1-dihydro-6,1-naphthyridine-3-carboxylate By separating the racemate using tartaric acid esters and diastereomers |
| MX2022004467A (es) * | 2019-10-17 | 2022-05-03 | Bayer Ag | Procedimiento para preparar (4s)-4-(4-ciano-2-metoxi-fenil)-5-etox i-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxilato de 2-cianoetilo mediante separacion de racematos utilizando esteres diastereomericos de acido tartarico. |
| EP3900722A1 (en) | 2020-04-22 | 2021-10-27 | Bayer AG | Combination of finerenone and pecavaptan for the treatment and/or prevention of cardiovascular and/or renal diseases |
| WO2021214023A1 (en) | 2020-04-22 | 2021-10-28 | Bayer Aktiengesellschaft | Combination of finerenone and a sglt2 inhibitor for the treatment and/or prevention of cardiovascular and/or renal diseases |
| WO2021254896A1 (en) | 2020-06-16 | 2021-12-23 | Bayer Aktiengesellschaft | Process for preparing (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide enabled by a catalytic asymmetric hantzsch ester reduction |
| CN112237573B (zh) * | 2020-10-29 | 2023-12-22 | 瑞阳制药股份有限公司 | 含finerenone的片剂及其制备方法 |
| WO2022214206A1 (en) | 2021-04-08 | 2022-10-13 | Bayer Aktiengesellschaft | Combination of finerenone and pecavaptan for the treatment and/or prevention of cardiovascular and/or renal diseases |
| CN114149427A (zh) * | 2021-12-18 | 2022-03-08 | 上海鼎雅药物化学科技有限公司 | 非奈利酮及其中间体的合成方法 |
| CN115340539B (zh) | 2022-01-19 | 2024-02-27 | 奥锐特药业股份有限公司 | 制备非奈利酮及其中间体的方法 |
| CN115340540A (zh) * | 2022-01-20 | 2022-11-15 | 奥锐特药业股份有限公司 | 制备非奈利酮及其中间体的方法 |
| CN114524812A (zh) * | 2022-03-18 | 2022-05-24 | 湖南凯铂生物药业有限公司 | 1,4-二氢-1,6-萘啶化合物的晶型制备以及合成方法 |
| US20250270184A1 (en) | 2022-04-18 | 2025-08-28 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of finerenone |
| EP4286368A1 (de) | 2022-05-31 | 2023-12-06 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 4-formyl-3-methoxybenzonitril |
| WO2024075139A1 (en) * | 2022-10-06 | 2024-04-11 | Maithri Drugs Private Limited | A process for preparation of finerenone and intermediates thereof |
| KR20250099382A (ko) | 2022-11-04 | 2025-07-01 | 난징 브이케어 파마테크 씨오., 엘티디. | 부분입체 이성질체 타르타르산 에스테르를 이용하여 라세미체를 분리하여 피네레논을 제조하는 방법 |
| JP2025536789A (ja) * | 2022-11-23 | 2025-11-07 | バイエル アクチェンゲゼルシャフト | １型糖尿病における慢性腎臓病の治療 |
| EP4634179A1 (en) | 2022-12-16 | 2025-10-22 | Bayer Aktiengesellschaft | Sequential one-pot synthesis for preparing 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| WO2024147053A1 (en) * | 2023-01-03 | 2024-07-11 | Optimus Drugs Pvt Ltd | Improved process for the preparation of finerenone |
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| US20250313559A1 (en) | 2024-01-05 | 2025-10-09 | Bayer Aktiengesellschaft | Method of preventing or treating heart failure in a patient using (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| WO2025247801A1 (en) * | 2024-05-30 | 2025-12-04 | Bayer Aktiengesellschaft | Determination of a dosage of a nonsteroidal mineralocorticoid receptor antagonist |
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| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
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| AU2006201739A1 (en) * | 2005-05-05 | 2006-11-23 | The University Of North Carolina At Chapel Hill | Synthesis and antiprotozoal activity of dicationic 3,5-diphenylisoxazoles |
| EP1902022A1 (en) | 2005-07-12 | 2008-03-26 | Glaxo Group Limited | Piperazine heteroaryl derivates as gpr38 agonists |
| DE102006026583A1 (de) | 2006-06-07 | 2007-12-13 | Bayer Healthcare Aktiengesellschaft | Aryl-substituierte hetero-bicyclische Verbindungen und ihre Verwendung |
| DE102006044696A1 (de) | 2006-09-22 | 2008-03-27 | Bayer Healthcare Ag | 3-Cyano-5-thiazaheteroaryl-dihydropyridine und ihre Verwendung |
| DE102007009494A1 (de) | 2007-02-27 | 2008-08-28 | Bayer Healthcare Ag | Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung |
| CN102020587A (zh) | 2010-11-25 | 2011-04-20 | 大连凯飞精细化工有限公司 | 2-甲氧基-4-氰基苯甲醛的合成方法 |
| CN116655627A (zh) * | 2014-08-01 | 2023-08-29 | 拜耳医药股份有限公司 | 一种化合物的制备方法及其纯化以用作活性药物成分 |
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