PE20190107A1 - Sintesis de indazoles - Google Patents
Sintesis de indazolesInfo
- Publication number
- PE20190107A1 PE20190107A1 PE2018002251A PE2018002251A PE20190107A1 PE 20190107 A1 PE20190107 A1 PE 20190107A1 PE 2018002251 A PE2018002251 A PE 2018002251A PE 2018002251 A PE2018002251 A PE 2018002251A PE 20190107 A1 PE20190107 A1 PE 20190107A1
- Authority
- PE
- Peru
- Prior art keywords
- formula
- compound
- intermediates
- ethyl
- substituted indazole
- Prior art date
Links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P35/00—Antineoplastic agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Referido a un metodo para preparar un indazol 2-sustituido de formula (I), N-{6- (2-hidroxipropan-2-il)-2-[2-(metilsulfonil)etil]-2H-indazol-5-il}-6-(trifluorometil)piridina-2-carboxamida, que comprende la etapa (A): donde el compuesto de formula (V) se deja reaccionar con un compuesto de vinil sulfona de formula (IX´); en la cual, R representa un grupo alquilo, tal como metilo, etilo o n-propilo, o un grupo arilo, tal como un fenilo; opcionalmente en un solvente de hidrocarburos aromaticos, tal como tolueno; preferentemente a la temperatura de reflujo de dichos solventes, proporcionando de ese modo dicho compuesto de formula (I). Tambien se refiere a compuestos intermedios, a una forma polimorfica B y al uso de estos compuestos intermedios para la preparacion de dicho compuesto de formula (V). Dicho indazol 2-sustituido inhibe a la quinasa 4 asociada con el receptor de interleucina 1 (IRAK4), siendo util para el tratamiento y prevencion de trastornos proliferativos e inflamatorios
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16167652 | 2016-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20190107A1 true PE20190107A1 (es) | 2019-01-15 |
Family
ID=55860769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2018002251A PE20190107A1 (es) | 2016-04-29 | 2017-04-25 | Sintesis de indazoles |
Country Status (43)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3705B1 (ar) | 2014-11-26 | 2021-01-31 | Bayer Pharma AG | إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية |
| JP6947743B2 (ja) | 2016-03-03 | 2021-10-13 | バイエル・ファルマ・アクティエンゲゼルシャフト | 新規な２−置換インダゾール、その製造方法、それを含有する医薬製剤、および薬物を製造するためのその使用 |
| HUE064389T2 (hu) | 2016-04-29 | 2024-03-28 | Bayer Pharma AG | Az N-{6-(2-hidroxipropán-2-il)-2-[2-(metilszulfonil)etil]-2h-indazol-5-il}-6- (trifluormetil)piridin-2-karboxamid polimorf formája |
| US10501437B2 (en) | 2016-04-29 | 2019-12-10 | Bayer Pharma Aktiengesellschaft | Crystalline forms of N-[2-(3-Hydroxy-3-methylbutyl)-6-(2-hydroxypropan-2-yl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide |
| NZ748907A (en) * | 2016-06-01 | 2023-04-28 | Bayer Pharma AG | Use of 2-substituted indazoles for the treatment and prophylaxis of autoimmune diseases |
| UA124237C2 (uk) * | 2016-06-01 | 2021-08-11 | Байєр Енімал Хелс Гмбх | Заміщені індазоли, придатні для лікування і попередження алергійних і/або запальних захворювань у тварин |
| TWI733982B (zh) | 2017-02-16 | 2021-07-21 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒衍生物 |
| US11459337B2 (en) | 2018-06-25 | 2022-10-04 | Chia Tai Tianqing Pharmaceutical Group Co., Inc. | Isothiazolo[5,4-D]pyrimidine compound as IRAK4 inhibitor |
| TWI721483B (zh) | 2018-07-13 | 2021-03-11 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| CN110981903A (zh) * | 2019-11-28 | 2020-04-10 | 南京正济医药研究有限公司 | 一种艾日布林中间体化合物提高光学纯度的精制方法 |
| US10894812B1 (en) | 2020-09-30 | 2021-01-19 | Alpine Roads, Inc. | Recombinant milk proteins |
| US10947552B1 (en) | 2020-09-30 | 2021-03-16 | Alpine Roads, Inc. | Recombinant fusion proteins for producing milk proteins in plants |
| IL301396A (en) | 2020-09-30 | 2023-05-01 | Nobell Foods Inc | Recombinant milk proteins and food compositions comprising the same |
| CN114469979B (zh) * | 2021-12-15 | 2024-04-09 | 安徽贝克生物制药有限公司 | 一种核糖核苷类似物的药物组合物、吸入剂及其应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7163937B2 (en) | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| MX2008010193A (es) | 2006-02-10 | 2008-11-27 | Summit Corp Plc | Tratamiento de distrofia muscular de duchenne. |
| WO2008001883A1 (en) | 2006-06-29 | 2008-01-03 | Nissan Chemical Industries, Ltd. | α-AMINO ACID DERIVATIVE AND PHARMACEUTICAL COMPRISING THE SAME AS ACTIVE INGREDIENT |
| RU2459821C2 (ru) | 2006-09-07 | 2012-08-27 | Байоджен Айдек Ма Инк. | Модуляторы киназы, ассоциированной с рецептором интерлейкина-1 |
| EP2486925A4 (en) | 2009-10-09 | 2014-03-19 | Mitsubishi Tanabe Pharma Corp | Therapeutic agent for cerebral infarction |
| WO2011153588A1 (en) | 2010-06-10 | 2011-12-15 | Biota Scientific Management Pty Ltd | Viral polymerase inhibitors |
| WO2012084704A1 (en) | 2010-12-20 | 2012-06-28 | Merck Serono S.A. | Indazolyl triazole derivatives as irak inhibitors |
| WO2013106254A1 (en) | 2012-01-11 | 2013-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| EP3066090A1 (en) * | 2013-11-08 | 2016-09-14 | iTeos Therapeutics | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
| US9126984B2 (en) | 2013-11-08 | 2015-09-08 | Iteos Therapeutics | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
| TWI667233B (zh) * | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| BR112016015983A2 (pt) | 2014-01-10 | 2017-08-08 | Aurigene Discovery Tech Ltd | Compostos de indazol como inibidores de irak4, seus usos, e composição farmacêutica |
| JO3705B1 (ar) * | 2014-11-26 | 2021-01-31 | Bayer Pharma AG | إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية |
| TW201701879A (zh) | 2015-04-30 | 2017-01-16 | 拜耳製藥公司 | Ｉｒａｋ４抑制劑組合 |
| AU2016293441A1 (en) | 2015-07-15 | 2018-02-01 | Aurigene Discovery Technologies Limited | Indazole and azaindazole compounds as IRAK-4 inhibitors |
| JP6947743B2 (ja) | 2016-03-03 | 2021-10-13 | バイエル・ファルマ・アクティエンゲゼルシャフト | 新規な２−置換インダゾール、その製造方法、それを含有する医薬製剤、および薬物を製造するためのその使用 |
| EP3219329A1 (en) * | 2016-03-17 | 2017-09-20 | Bayer Pharma Aktiengesellschaft | Combinations of copanlisib |
| US10501437B2 (en) | 2016-04-29 | 2019-12-10 | Bayer Pharma Aktiengesellschaft | Crystalline forms of N-[2-(3-Hydroxy-3-methylbutyl)-6-(2-hydroxypropan-2-yl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide |
| HUE064389T2 (hu) | 2016-04-29 | 2024-03-28 | Bayer Pharma AG | Az N-{6-(2-hidroxipropán-2-il)-2-[2-(metilszulfonil)etil]-2h-indazol-5-il}-6- (trifluormetil)piridin-2-karboxamid polimorf formája |
| UA124237C2 (uk) | 2016-06-01 | 2021-08-11 | Байєр Енімал Хелс Гмбх | Заміщені індазоли, придатні для лікування і попередження алергійних і/або запальних захворювань у тварин |
| NZ748907A (en) | 2016-06-01 | 2023-04-28 | Bayer Pharma AG | Use of 2-substituted indazoles for the treatment and prophylaxis of autoimmune diseases |
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2017
- 2017-04-25 HU HUE17718560A patent/HUE064389T2/hu unknown
- 2017-04-25 DK DK17718558.4T patent/DK3448846T3/da active
- 2017-04-25 LT LTEPPCT/EP2017/059767T patent/LT3448848T/lt unknown
- 2017-04-25 ES ES17718560T patent/ES2966772T3/es active Active
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