CU20150165A7 - Proceso para la preparación de (2r,3r)-3-{[ 2-}[4-(s-ciclopropilsulfonimidoil)fenil]amino{ -5-(trifluorometil)pirimidin-4-il]oxi}butan-2-ol - Google Patents
Proceso para la preparación de (2r,3r)-3-{[ 2-}[4-(s-ciclopropilsulfonimidoil)fenil]amino{ -5-(trifluorometil)pirimidin-4-il]oxi}butan-2-olInfo
- Publication number
- CU20150165A7 CU20150165A7 CUP2015000165A CU20150165A CU20150165A7 CU 20150165 A7 CU20150165 A7 CU 20150165A7 CU P2015000165 A CUP2015000165 A CU P2015000165A CU 20150165 A CU20150165 A CU 20150165A CU 20150165 A7 CU20150165 A7 CU 20150165A7
- Authority
- CU
- Cuba
- Prior art keywords
- preparation
- cyclopropilsulfonimidoil
- trifluorometil
- pirimidin
- oxi
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- -1 AMINO Chemical class 0.000 title 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 title 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrrole Compounds (AREA)
Abstract
La invención provee un nuevo proceso para la preparación deinhibidores de pan-CDK de la fórmula (I) ESPACIO PARA LA FÓRMULA que comprende pasos de alquilación, aminación oxidativa, oxidación, desprotección, separación de racemato, hidrogenación, preparación en dos etapas, acoplamiento, preparación de sales doblemente protegidas y separación de grupos protectores por hidrogenación y también por tratamiento con carbonato de potasio en metanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010046720A DE102010046720A1 (de) | 2010-09-23 | 2010-09-23 | Verfahren zur Herstellung von pan-CDK-Inhibitoren der Formel (l), sowie Intermediate der Herstellung |
| PCT/EP2011/066295 WO2012038411A1 (de) | 2010-09-23 | 2011-09-20 | Verfahren zur herstellung von pan-cdk-inhibitoren der formel (i), sowie intermediate der herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CU20150165A7 true CU20150165A7 (es) | 2016-05-30 |
Family
ID=44677881
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CU2013000044A CU20130044A7 (es) | 2010-09-23 | 2013-03-22 | Proceso para la preparación de inhibidores de pan-cdk de fórmula (i), e intermediarios de la preparación |
| CUP2015000165A CU20150165A7 (es) | 2010-09-23 | 2015-11-30 | Proceso para la preparación de (2r,3r)-3-{[ 2-}[4-(s-ciclopropilsulfonimidoil)fenil]amino{ -5-(trifluorometil)pirimidin-4-il]oxi}butan-2-ol |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CU2013000044A CU20130044A7 (es) | 2010-09-23 | 2013-03-22 | Proceso para la preparación de inhibidores de pan-cdk de fórmula (i), e intermediarios de la preparación |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US9359306B2 (es) |
| EP (1) | EP2619186A1 (es) |
| JP (1) | JP5969993B2 (es) |
| KR (1) | KR20130109145A (es) |
| CN (1) | CN103119026B (es) |
| AP (1) | AP2013006816A0 (es) |
| AR (1) | AR083171A1 (es) |
| AU (1) | AU2011304365B2 (es) |
| BR (1) | BR112013006720A2 (es) |
| CA (1) | CA2811807A1 (es) |
| CL (1) | CL2013000797A1 (es) |
| CO (1) | CO6690779A2 (es) |
| CR (1) | CR20130138A (es) |
| CU (2) | CU20130044A7 (es) |
| DE (1) | DE102010046720A1 (es) |
| DO (1) | DOP2013000063A (es) |
| EC (1) | ECSP13012520A (es) |
| GT (1) | GT201300078A (es) |
| IL (1) | IL225352A0 (es) |
| MX (1) | MX2013003338A (es) |
| MY (1) | MY160625A (es) |
| NZ (1) | NZ608448A (es) |
| PE (1) | PE20140182A1 (es) |
| PH (1) | PH12013500554A1 (es) |
| RU (1) | RU2585621C2 (es) |
| SA (1) | SA111320775B1 (es) |
| SG (1) | SG188967A1 (es) |
| TW (1) | TWI530488B (es) |
| UA (1) | UA110626C2 (es) |
| UY (1) | UY33624A (es) |
| WO (1) | WO2012038411A1 (es) |
| ZA (1) | ZA201301799B (es) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201418243A (zh) * | 2012-11-15 | 2014-05-16 | Bayer Pharma AG | 含有磺醯亞胺基團之ｎ－（吡啶－２－基）嘧啶－４－胺衍生物 |
| WO2014173815A1 (en) * | 2013-04-23 | 2014-10-30 | Bayer Pharma Aktiengesellschaft | Use of (rs)-s-cyclopropyl-s-(4-{[4-{[(1r, 2r)-2-hydroxy-1-methylpropyl]oxy}-5- (trifluoromethyl)pyrimidin-2-yl]amino}phenyl)sulphoximide for the treatment of specific tumours |
| DK3692039T3 (da) | 2017-10-05 | 2023-03-13 | Innovative Molecules Gmbh | Enantiomerer af substituerede thiazoler som antivirale forbindelser |
| KR102764122B1 (ko) | 2018-02-13 | 2025-02-05 | 바이엘 악티엔게젤샤프트 | 미만성 거대 b-세포 림프종을 치료하기 위한 5-플루오로-4-(4-플루오로-2-메톡시페닐)-n-[4-[(s-메틸술폰이미도일)메틸]피리딘-2-일]피리딘-2-아민의 용도 |
| IL322686A (en) | 2023-02-16 | 2025-10-01 | Gasherbrum Bio Inc | Heterocyclic glp-1 agonists |
| CN121712509A (zh) | 2023-05-04 | 2026-03-20 | 锐新医药公司 | 用于ras相关疾病或病症的组合疗法 |
| US20250049810A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| IL327306A (en) | 2023-10-12 | 2026-05-01 | Revolution Medicines Inc | Macrocyclic RAS inhibitors |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025217307A1 (en) | 2024-04-09 | 2025-10-16 | Revolution Medicines, Inc. | Methods for predicting response to a ras(on) inhibitor and combination therapies |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025255438A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026015825A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Use of ras inhibitor for treating pancreatic cancer |
| WO2026015790A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015801A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015796A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026050446A1 (en) | 2024-08-29 | 2026-03-05 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026072904A2 (en) | 2024-09-26 | 2026-04-02 | Revolution Medicines, Inc. | Compositions and methods for treating lung cancer |
| WO2026090116A2 (en) | 2024-10-21 | 2026-04-30 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026090245A1 (en) | 2024-10-22 | 2026-04-30 | Revolution Medicines, Inc. | Use of ras inhibitors for treating cancer |
| US20260108528A1 (en) | 2024-10-22 | 2026-04-23 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA964426B (en) * | 1995-06-05 | 1997-03-06 | Rhone Poulenc Agrochimie | Pesticidal sulfur compounds |
| EP1291336A3 (en) | 2001-09-05 | 2003-10-08 | Solvias AG | Preparation of optically active alpha-hydroxyethers |
| DE10349423A1 (de) * | 2003-10-16 | 2005-06-16 | Schering Ag | Sulfoximinsubstituierte Parimidine als CDK- und/oder VEGF-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| DE102005062742A1 (de) * | 2005-12-22 | 2007-06-28 | Bayer Schering Pharma Ag | Sulfoximin substituierte Pyrimidine, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel |
| EP2022785A1 (en) * | 2007-06-20 | 2009-02-11 | Bayer Schering Pharma Aktiengesellschaft | Alkynylpyrimidines as Tie2 kinase inhibitors |
| EP2179991A1 (de) | 2008-10-21 | 2010-04-28 | Bayer Schering Pharma Aktiengesellschaft | Sulfoximinsubstituierte Anilino-Pyrimidinderivate als CDK-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
-
2010
- 2010-09-23 DE DE102010046720A patent/DE102010046720A1/de not_active Withdrawn
-
2011
- 2011-09-20 PH PH1/2013/500554A patent/PH12013500554A1/en unknown
- 2011-09-20 EP EP11761054.3A patent/EP2619186A1/de not_active Withdrawn
- 2011-09-20 NZ NZ608448A patent/NZ608448A/en not_active IP Right Cessation
- 2011-09-20 KR KR1020137010236A patent/KR20130109145A/ko not_active Withdrawn
- 2011-09-20 SG SG2013018361A patent/SG188967A1/en unknown
- 2011-09-20 RU RU2013118432/04A patent/RU2585621C2/ru not_active IP Right Cessation
- 2011-09-20 CN CN201180045115.7A patent/CN103119026B/zh not_active Expired - Fee Related
- 2011-09-20 MY MYPI2013000997A patent/MY160625A/en unknown
- 2011-09-20 US US13/824,160 patent/US9359306B2/en not_active Expired - Fee Related
- 2011-09-20 WO PCT/EP2011/066295 patent/WO2012038411A1/de not_active Ceased
- 2011-09-20 BR BR112013006720A patent/BR112013006720A2/pt not_active IP Right Cessation
- 2011-09-20 UA UAA201305209A patent/UA110626C2/uk unknown
- 2011-09-20 JP JP2013529628A patent/JP5969993B2/ja not_active Expired - Fee Related
- 2011-09-20 PE PE2013000617A patent/PE20140182A1/es not_active Application Discontinuation
- 2011-09-20 AU AU2011304365A patent/AU2011304365B2/en not_active Ceased
- 2011-09-20 MX MX2013003338A patent/MX2013003338A/es not_active Application Discontinuation
- 2011-09-20 CA CA2811807A patent/CA2811807A1/en not_active Abandoned
- 2011-09-20 AP AP2013006816A patent/AP2013006816A0/xx unknown
- 2011-09-21 SA SA111320775A patent/SA111320775B1/ar unknown
- 2011-09-22 UY UY0001033624A patent/UY33624A/es unknown
- 2011-09-23 TW TW100134438A patent/TWI530488B/zh active
- 2011-09-23 AR ARP110103498A patent/AR083171A1/es not_active Application Discontinuation
-
2013
- 2013-03-08 ZA ZA2013/01799A patent/ZA201301799B/en unknown
- 2013-03-20 IL IL225352A patent/IL225352A0/en unknown
- 2013-03-22 CR CR20130138A patent/CR20130138A/es unknown
- 2013-03-22 GT GT201300078A patent/GT201300078A/es unknown
- 2013-03-22 CU CU2013000044A patent/CU20130044A7/es unknown
- 2013-03-22 CL CL2013000797A patent/CL2013000797A1/es unknown
- 2013-03-22 CO CO13057092A patent/CO6690779A2/es unknown
- 2013-03-22 EC ECSP13012520 patent/ECSP13012520A/es unknown
- 2013-03-22 DO DO2013000063A patent/DOP2013000063A/es unknown
-
2015
- 2015-11-30 CU CUP2015000165A patent/CU20150165A7/es unknown
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