AR054265A1 - PROCESS TO PREPARE OXINDOLS AND THIO-OXINDOLS 3,3-DISUSTITUTED - Google Patents

PROCESS TO PREPARE OXINDOLS AND THIO-OXINDOLS 3,3-DISUSTITUTED

Info

Publication number
AR054265A1
AR054265A1 AR20060101694A ARP060101694A AR054265A1 AR 054265 A1 AR054265 A1 AR 054265A1 AR 20060101694 A AR20060101694 A AR 20060101694A AR P060101694 A ARP060101694 A AR P060101694A AR 054265 A1 AR054265 A1 AR 054265A1
Authority
AR
Argentina
Prior art keywords
substituted
alkyl
methylpropionitrile
compounds
difluorophenyl
Prior art date
Application number
AR20060101694A
Other languages
Spanish (es)
Original Assignee
Wyeth Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wyeth Corp filed Critical Wyeth Corp
Publication of AR054265A1 publication Critical patent/AR054265A1/en

Links

Landscapes

  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Se proporcionan métodos para preparar compuestos de oxindol y tio-oxindol, compuestos que son utiles como precursores de compuestos farmacéuticos utiles. Se proporcionan específicamente métodos para preparar compuestos de 5-pirrol-3,3-oxindol y 5-(7- fluoro-3,3-dimetil-2-oxo-2,3-dihidro-1H-indol-5-il)-1-metil-1H-pirrol-2-carbonitrilo. También se proporcionan métodos para preparar compuestos de iminobenzo[b]tiofeno y benzo[b]tiofenona. Reivindicacion 1: Un método para preparar compuestos de oxindol que comprende los pasos de: (a) sustituir un fluoroareno de formula (1) con un nitrilo secundario: donde: X es halogeno; R1, R2, R3 y R4 son, independientemente, seleccionados del grupo formado por H, halogeno, CN, alquilo C1-6, alquilo C1-6 sustituido, alquenilo C2-6, alquenilo C2-6 sustituido, alquinilo C2-6, alquinilo C2-6 sustituido, cicloalquilo C3-8, cicloalquilo C3-8 sustituido, arilo, arilo sustituido, heteroarilo, heteroarilo sustituido, N2+, OSO2CF3, CF3, NO2, SR5, OR5, N(R5)2, COO(R5)2, CON(R5)2 y SO2N(R5)2; o R1 y R2; R2 y R3, R3 y R4, R1, R2, y R3, o R2, R3, y R4 están fusionados para formar: (i) un anillo de 3 a 15 miembros que contiene C saturado o insaturado; o (ii) un anillo heterocíclico de 3 a 15 miembros que contiene en su esqueleto desde 1 a 3 heteroátomos seleccionados del grupo formado por O, S, y NR11; donde (i) o (ii) están opcionalmente sustituidos con alquilo C1-6, alquilo C1-6 sustituido, halogeno, alcoxi C1-6, alcoxi C1-6 sustituido, o N(R5)2; R5 se selecciona del grupo formado por alquilo C1-6 y alquilo C1-6 sustituido; A, D, E y G son, independientemente, seleccionados del grupo formado por C y N, donde si cualquiera de A, D, E o G son N, el correspondiente R1-R4 está opcionalmente ausente; R11 está ausente, es H, alquilo C1-6, alquilo C1-6 sustituido, arilo o arilo sustituido; o una sal farmacéuticamente aceptable de los mismos (b) convertir el sustituyente nitrilo del producto del paso (a) en una amida; y (c) ciclar el producto del paso (b) a dicho oxindol. Reivindicacion 34: Un compuesto seleccionado del grupo formado por 2-(5-bromo-2-fluorofenil)-2-metilpropionitrilo; 2-(3-cloropiridin-2-il)-2-metilpropionitrilo; 2-(3-cloroquinosalin-2-il)-2- metilpropionitrilo; 2-(2-fluorofenil)-2-metilpropionitrilo, 2-(2,3-difluorofenil)-2-metilpropionitrilo, 2-(2,6-difluorofenil)-2-metilpropionitrilo, 2-(2,3-difluorofenil)isobutiramida, 2-(2,6-difluorofenil)isobutiramina, 2-(2- fluorofenil)isobutiramida, y 2-(3-cloropiridin-2-il)isobutiramida, amida de ácido 1-(2,6-difluorofenil)ciclopropancarboxílico; o una sal farmacéuticamente aceptable de los mismos.Methods for preparing oxindole and thio-oxindole compounds are provided, compounds that are useful as precursors of useful pharmaceutical compounds. Methods for preparing compounds of 5-pyrrole-3,3-oxindole and 5- (7- fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-5-yl) - are specifically provided - 1-methyl-1H-pyrrole-2-carbonitrile. Methods for preparing iminobenzo [b] thiophene and benzo [b] thiophene compounds are also provided. Claim 1: A method for preparing oxindole compounds comprising the steps of: (a) replacing a fluoroarene of formula (1) with a secondary nitrile: where: X is halogen; R1, R2, R3 and R4 are independently selected from the group consisting of H, halogen, CN, C1-6 alkyl, substituted C1-6 alkyl, C2-6 alkenyl, substituted C2-6 alkenyl, C2-6 alkynyl, alkynyl C2-6 substituted, C3-8 cycloalkyl, C3-8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, N2 +, OSO2CF3, CF3, NO2, SR5, OR5, N (R5) 2, COO (R5) 2, CON (R5) 2 and SO2N (R5) 2; or R1 and R2; R2 and R3, R3 and R4, R1, R2, and R3, or R2, R3, and R4 are fused to form: (i) a 3 to 15 member ring containing saturated or unsaturated C; or (ii) a 3 to 15-membered heterocyclic ring containing from its skeleton from 1 to 3 heteroatoms selected from the group consisting of O, S, and NR11; wherein (i) or (ii) are optionally substituted with C1-6 alkyl, substituted C1-6 alkyl, halogen, C1-6 alkoxy, substituted C1-6 alkoxy, or N (R5) 2; R5 is selected from the group consisting of C1-6 alkyl and substituted C1-6 alkyl; A, D, E and G are independently selected from the group consisting of C and N, where if any of A, D, E or G are N, the corresponding R1-R4 is optionally absent; R11 is absent, it is H, C1-6 alkyl, substituted C1-6 alkyl, aryl or substituted aryl; or a pharmaceutically acceptable salt thereof (b) converting the nitrile substituent of the product of step (a) into an amide; and (c) cycling the product of step (b) to said oxindole. Claim 34: A compound selected from the group consisting of 2- (5-bromo-2-fluorophenyl) -2-methylpropionitrile; 2- (3-Chloropyridin-2-yl) -2-methylpropionitrile; 2- (3-Chloroquinosalin-2-yl) -2-methylpropionitrile; 2- (2-fluorophenyl) -2-methylpropionitrile, 2- (2,3-difluorophenyl) -2-methylpropionitrile, 2- (2,6-difluorophenyl) -2-methylpropionitrile, 2- (2,3-difluorophenyl) isobutyramide , 2- (2,6-difluorophenyl) isobutyramine, 2- (2- fluorophenyl) isobutyramide, and 2- (3-chloropyridin-2-yl) isobutyramide, 1- (2,6-difluorophenyl) cyclopropancarboxylic acid amide; or a pharmaceutically acceptable salt thereof.

AR20060101694A 2005-04-29 2006-04-27 PROCESS TO PREPARE OXINDOLS AND THIO-OXINDOLS 3,3-DISUSTITUTED AR054265A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76738105P 2005-04-29 2005-04-29

Publications (1)

Publication Number Publication Date
AR054265A1 true AR054265A1 (en) 2007-06-13

Family

ID=38134465

Family Applications (1)

Application Number Title Priority Date Filing Date
AR20060101694A AR054265A1 (en) 2005-04-29 2006-04-27 PROCESS TO PREPARE OXINDOLS AND THIO-OXINDOLS 3,3-DISUSTITUTED

Country Status (1)

Country Link
AR (1) AR054265A1 (en)

Similar Documents

Publication Publication Date Title
PE20090276A1 (en) COMPOUNDS DERIVED FROM IMIDAZOQUINOLINE AS MODULATORS OF TLR7
AR054560A1 (en) SPIROPIPERIDINE AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
PE20130229A1 (en) PIPERIDINONE DERIVATIVES AS MDM2 INHIBITORS FOR THE TREATMENT OF CANCER
PE20121500A1 (en) 2-AMINO-5,5-DIFLUOR-5,6-DIHYDRO-4H-OXAZINES AS INHIBITORS OF BACE 1 AND / OR BACE 2
PE20120172A1 (en) FUSED HETEROCYCLIC COMPOUNDS CONTAINING NITROGEN AS INHIBITORS OF BETA-AMYLOID PRODUCTION
AR062125A1 (en) COMPOUNDS THAT MODULATE THE CB2 RECEIVER AND ITS USE AS MEDICATIONS
PE20150352A1 (en) HETEROARYL KETONE FUSED AZADECALINE GLUCOCORTICOID RECEPTOR MODULATORS
AR085960A1 (en) 1,3-OXAZINES AS INHIBITORS OF THE BACE1 AND / OR THE BACE2
AR079495A1 (en) HETEROAROMATIC PHENYLIMIDAZOL DERIVATIVES AS ENZYME PDE10A INHIBITORS
PE20091492A1 (en) COMPOUNDS AND COMPOSITIONS AS INHIBITORS OF C-KIT AND PDGFR KINASE
AR072166A1 (en) PIPERIDINE DERIVATIVE AND ITS USE AS A SUPERIOR RENINA INHIBITOR
PE20050951A1 (en) GLUCOCORTICOID MIMETIC COMPOUNDS, METHODS OF PREPARATION AND PHARMACEUTICAL COMPOSITIONS
CL2012001171A1 (en) Process for the preparation of the ester n - [[2 - [[[4 - [[[(hexyloxycarbonyl)] 4-amino] iminomethyl] phenyl] amino] methyl] 1-alkyl-1h-benzimidazol-5-yl] carbonyl] n-2-pyridinyl-ethyl beta-alanine; and one of the intermediate compounds considered.
ES2600636T3 (en) Spiro- [1,3] -oxazines and spiro- [1,4] -oxazepines as inhibitors of BACE1 and / or BACE2
PE20110924A1 (en) DERIVATIVES OF 2,4-DIAMINE-PYRIMIDINE N2, N4-DISUSTITUTED AS JAK3 INHIBITORS
PE20090477A1 (en) OXAZOLE DERIVATIVES AS INHIBITORS OF SODIUM CHANNELS
PE20121440A1 (en) OXAZINE DERIVATIVES AND THEIR USE AS BACE INHIBITORS FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
RU2011116160A (en) Pyridine derivatives substituted with a heterocyclic ring and y-glutamylamino group and containing antifungal agents
PE20091436A1 (en) SULFONAMID DERIVATIVES SUBSTITUTED AS B1R MODULATORS
AR079496A1 (en) DERIVATIVES OF ARIL TRIAZOL HETEROAROMATICOS AS INHIBITORS OF ENZYME PDE10A
AR079498A1 (en) HETEROAROMATIC 2-ARYLIMIDAZOL DERIVATIVES AS ENZYME PDE10A INHIBITORS
AR060604A1 (en) NEW ARILAMINO N- HETEROARILOS AS MEK INHIBITORS
AR046222A1 (en) PHARMACEUTICAL COMPOSITIONS OF SUSTAINED LIBERATION INCLUDING APLINDORE AND ITS DERIVATIVES
AR083926A1 (en) IMIDAZOL DERIVATIVES AS INHIBITORS OF THE ENZYME PDE10A
CL2012000516A1 (en) Compounds derived from 3- [4- (4- (phenyl / pyridin / pyrimidin) -piperazin -1-yl) -butyl] -2,3-dihydro-4h-chroman-4-one, modulators of the dopamine d3 receptor; Preparation process; pharmaceutical composition; and its use for the treatment of a neurological or psychiatric disorder, erectile dysfunction or drug dependence, among others.

Legal Events

Date Code Title Description
FA Abandonment or withdrawal