PE20140182A1 - Proceso para la preparacion de compuestos heteroarilos inhibidores de pan-cdk e intermediarios de la preparacion - Google Patents
Proceso para la preparacion de compuestos heteroarilos inhibidores de pan-cdk e intermediarios de la preparacionInfo
- Publication number
- PE20140182A1 PE20140182A1 PE2013000617A PE2013000617A PE20140182A1 PE 20140182 A1 PE20140182 A1 PE 20140182A1 PE 2013000617 A PE2013000617 A PE 2013000617A PE 2013000617 A PE2013000617 A PE 2013000617A PE 20140182 A1 PE20140182 A1 PE 20140182A1
- Authority
- PE
- Peru
- Prior art keywords
- formula
- nitrophenyl
- give
- preparation
- sulfoximine
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 abstract 3
- PZHMENGEVRZXBN-UHFFFAOYSA-N imino-nitro-oxo-phenyl-$l^{6}-sulfane Chemical compound [O-][N+](=O)S(=N)(=O)C1=CC=CC=C1 PZHMENGEVRZXBN-UHFFFAOYSA-N 0.000 abstract 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 2
- VQEAOBYESZEWRQ-NXEZZACHSA-N (2r,3r)-3-phenylmethoxybutan-2-ol Chemical compound C[C@@H](O)[C@@H](C)OCC1=CC=CC=C1 VQEAOBYESZEWRQ-NXEZZACHSA-N 0.000 abstract 1
- KELZBYQXUNVXEU-RKDXNWHRSA-N (4r,5r)-4,5-dimethyl-2-phenyl-1,3-dioxolane Chemical compound O1[C@H](C)[C@@H](C)OC1C1=CC=CC=C1 KELZBYQXUNVXEU-RKDXNWHRSA-N 0.000 abstract 1
- MXWVNAOIXKIIJK-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenyl)sulfanylbenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1SC1=CC=CC=C1[N+]([O-])=O MXWVNAOIXKIIJK-UHFFFAOYSA-N 0.000 abstract 1
- -1 4-METHYLPHENYL Chemical class 0.000 abstract 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 238000005984 hydrogenation 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
- 230000001681 protective effect Effects 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- YXFVVABEGXRONW-CNRUNOGKSA-N tritiomethylbenzene Chemical compound [3H]CC1=CC=CC=C1 YXFVVABEGXRONW-CNRUNOGKSA-N 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)
- 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)
- 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)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
REFERIDA A UN PROCESO DE PREPARACION DE UN COMPUESTO DE FORMULA (I), DONDE R4 ES ALQUILO C1-C6 O UN ANILLO CICLOALQUILO C3-C7, QUE COMPRENDE: a) ALQUILACION MEDIANTE X-R4 DE 4-NITROTIOFENOL EN PRESENCIA DE CARBONATO DE POTASIO EN N-METIL-PIRROLIDINONA PARA DAR UN NITROFENIL-SULFURO DE FORMULA (I-1), DONDE X ES Br, Cl, I, O-SO2-CH3 U O-SO2-(4-METILFENILO), b) AMINACION OXIDATIVA DE (I-1) PARA DAR UNA NITROFENIL-SULFILIMINA DE FORMULA (I-10), c) OXIDACION DE (I-10) PARA DAR UNA NITROFENIL-SULFOXIMINA PROTEGIDA CON TRIFLUOROACETATO DE FORMULA (I-3) Y DESPROTECCION PARA DAR UNA NITROFENIL-SULFOXIMINA DE FORMULA (I-11), d) SEPARACION DEL RACEMATO DE (I-11) CON ACIDO (+)-DI-O-P-TOLUIL-D-TARTARICO DONDE EL ENANTIOMERO R DE LA NITROFENIL-SULFOXIMINA SE SEPARA DE LAS SALES Y EL GRUPO PROTECTOR TRIFLUOROACETATO SE INSERTA NUEVAMENTE PARA FORMAR EL ENANTIOMERO R DE LA NITROFENIL-SULFOXIMINA PROTEGIDA CON TRIFLUOROACETATO DE FORMULA (I-3-R), e) HIDROGENACION DE (I-3-R) PARA DAR LAS ANILINO-SULFOXIMINAS PROTEGIDAS CON TRIFLUOROACETATO DE FORMULA (I-4-R) CON UN CATALIZADOR DE PALADIO DOPADO CON HIERRO, f) PREPARACION DE (2R,3R)-3-(BENCILOXI)BUTAN-2-OL (I-5-A) EN UN PROCESO EN DOS ETAPAS POR MEDIO DE (4R,5R)-4,5-DIMETIL-2-FENIL-1,3-DIOXOLANO, DONDE LA PRIMERA ETAPA SE LLEVA A CABO CON P-TOLUENSULFONATO DE PIRIDINIO EN TOLUENO Y LUEGO OCURRE UNA REDUCCION CON HIDRURO DE IISOBUTILALUMINIO EN TOLUENO, ENTRE OTROS PASOS
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20140182A1 true PE20140182A1 (es) | 2014-02-14 |
Family
ID=44677881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2013000617A PE20140182A1 (es) | 2010-09-23 | 2011-09-20 | Proceso para la preparacion de compuestos heteroarilos inhibidores de pan-cdk e intermediarios de la preparacion |
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 (11)
| 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 |
| AR113344A1 (es) | 2017-10-05 | 2020-04-22 | Innovative Molecules Gmbh | Enantiómeros de una serie de compuestos antivirales |
| US11701347B2 (en) | 2018-02-13 | 2023-07-18 | Bayer Aktiengesellschaft | Use of 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{4-[(S-methylsulfonimidoyl)methyl]pyridin-2-yl}pyridin-2-amine for treating diffuse large B-cell lymphoma |
| IL322686A (en) | 2023-02-16 | 2025-10-01 | Gasherbrum Bio Inc | Heterocyclic glp-1 agonists |
| TW202508595A (zh) | 2023-05-04 | 2025-03-01 | 美商銳新醫藥公司 | 用於ｒａｓ相關疾病或病症之組合療法 |
| WO2025034702A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Rmc-6291 for use in the treatment of ras protein-related disease or disorder |
| WO2025080946A2 (en) | 2023-10-12 | 2025-04-17 | Revolution Medicines, Inc. | 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 |
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 CA CA2811807A patent/CA2811807A1/en not_active Abandoned
- 2011-09-20 AP AP2013006816A patent/AP2013006816A0/xx unknown
- 2011-09-20 MX MX2013003338A patent/MX2013003338A/es not_active Application Discontinuation
- 2011-09-20 CN CN201180045115.7A patent/CN103119026B/zh not_active Expired - Fee Related
- 2011-09-20 EP EP11761054.3A patent/EP2619186A1/de not_active Withdrawn
- 2011-09-20 RU RU2013118432/04A patent/RU2585621C2/ru not_active IP Right Cessation
- 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 JP JP2013529628A patent/JP5969993B2/ja not_active Expired - Fee Related
- 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 PH PH1/2013/500554A patent/PH12013500554A1/en unknown
- 2011-09-20 KR KR1020137010236A patent/KR20130109145A/ko not_active Withdrawn
- 2011-09-20 AU AU2011304365A patent/AU2011304365B2/en not_active Ceased
- 2011-09-20 MY MYPI2013000997A patent/MY160625A/en unknown
- 2011-09-20 SG SG2013018361A patent/SG188967A1/en unknown
- 2011-09-20 NZ NZ608448A patent/NZ608448A/en not_active IP Right Cessation
- 2011-09-20 PE PE2013000617A patent/PE20140182A1/es not_active Application Discontinuation
- 2011-09-21 SA SA111320775A patent/SA111320775B1/ar unknown
- 2011-09-22 UY UY0001033624A patent/UY33624A/es unknown
- 2011-09-23 AR ARP110103498A patent/AR083171A1/es not_active Application Discontinuation
- 2011-09-23 TW TW100134438A patent/TWI530488B/zh active
-
2013
- 2013-03-08 ZA ZA2013/01799A patent/ZA201301799B/en unknown
- 2013-03-20 IL IL225352A patent/IL225352A0/en unknown
- 2013-03-22 CL CL2013000797A patent/CL2013000797A1/es unknown
- 2013-03-22 CR CR20130138A patent/CR20130138A/es unknown
- 2013-03-22 CO CO13057092A patent/CO6690779A2/es unknown
- 2013-03-22 DO DO2013000063A patent/DOP2013000063A/es unknown
- 2013-03-22 GT GT201300078A patent/GT201300078A/es unknown
- 2013-03-22 CU CU2013000044A patent/CU20130044A7/es unknown
- 2013-03-22 EC ECSP13012520 patent/ECSP13012520A/es unknown
-
2015
- 2015-11-30 CU CUP2015000165A patent/CU20150165A7/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD | Application declared void or lapsed |