AR049625A1 - Antagonistas de cgrp, procedimiento para su preparacion asi como su uso como medicamento - Google Patents

Antagonistas de cgrp, procedimiento para su preparacion asi como su uso como medicamento

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Publication number
AR049625A1
AR049625A1 ARP050101139A ARP050101139A AR049625A1 AR 049625 A1 AR049625 A1 AR 049625A1 AR P050101139 A ARP050101139 A AR P050101139A AR P050101139 A ARP050101139 A AR P050101139A AR 049625 A1 AR049625 A1 AR 049625A1
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Argentina
Prior art keywords
alkyl
alkynyl
amino
alkenyl
group
Prior art date
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ARP050101139A
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English (en)
Inventor
Stephan Georg Mueller
Klaus Rudolf
Philipp Lustenberger
Dirk Stenkamp
Alexander Dreyer
Kirsten Arndt
Henri Doods
Marco Santagostino
Fabio Paleari
Gerhard Schaenzle
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Boehringer Ingelheim Int
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Publication date
Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Priority to TW095109753A priority Critical patent/TW200700408A/zh
Priority to ARP060101117A priority patent/AR053344A1/es
Priority to ARP060101118A priority patent/AR053854A1/es
Priority to TW095109968A priority patent/TW200700409A/zh
Priority to US11/277,177 priority patent/US7528129B2/en
Priority to US11/277,175 priority patent/US7491717B2/en
Priority to MYPI20061292A priority patent/MY144635A/en
Priority to PE2006000336A priority patent/PE20061453A1/es
Publication of AR049625A1 publication Critical patent/AR049625A1/es
Priority to US12/186,005 priority patent/US7696196B2/en
Priority to US12/706,853 priority patent/US7985747B2/en

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    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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Abstract

Objeto de la presente son los antagonistas de CGRP de la formula general (1), en la que: A es un átomo de oxígeno o azufre; X es un átomo de oxígeno o azufre; a) D, E, independientemente uno de otro, un grupo metino o el átomo de nitrogeno; y G es un grupo metino sustituido con el grupo Ra; M es un grupo sustituido con el grupo Rb; Q es un grupo metino sustituido con el grupo Rc; en donde uno o dos de los grupos G, M y Q pueden significar en cada caso también un átomo de nitrogeno; o b) D y E, en cada caso, un grupo metino, pudiendo significar uno de los grupos D y E también un átomo de nitrogeno; y G, M y Q en cada caso un átomo de nitrogeno; en donde Ra, Rb y Rc, independientemente uno de otro, significar en cada caso un átomo de hidrogeno o halogeno, un grupo alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, cicloalquenilo C3-7, ciano, hidroxi, hidroxi-alquilo C1-6, hidroxi-alquenilo C3-6, hidroxi-alquinilo C3-6, alcoxi C1-6, alcoxi C1-6-alquilo C1-6, alcoxi C1-6-alquenilo C3-6, alcoxi C1-6-alquinilo C3-6, alquenoxi C3-6-alquilo C1-6, alquenoxi C3-6-alquenilo C3-6, alquenoxi C3-6-alquinilo C3-6, alquinoxi C3-6-alquilo C1-6, alquinoxi C3-6-alquenilo C3-6, alquinoxi C3-6-alquinilo C3-6, tiohidroxi, alquiltio C1-6, alqueniltio C3-6, alquiniltio C3-6, amino, alquil C1-6-amino, alquenil C3-6-amino, alquinil C3-6-amino, di-(alquil C1-6)-amino, di-(alquenil C3-6)-amino, di-(alquinil C3-6)-amino, amino-alquilo C1-6, alquil C1-3-amino-alquilo C1-6, di-(alquil C1-3)-amino-alquilo C1-6, amino-alquenilo C3-6, alquil C1-3-amino-alquenilo C3-6, di-(alquil C1-3)-amino-alquenilo C3-6, amino-alquinilo C3-6, alquil C1-3-amino-alquinilo C3-6, di-(alquil C1-3)-amino-alquinilo C3-6, hidroxicarbonilo, fenilcarbonilo, piridilcarbonilo, alquil C1-6-carbonilo, alquenil C2-6-carbonilo, alquinil C2-6-carbonilo, formilo, alcoxi C1-6-carbonilo, alquenoxi C3-6-carbonilo, alquinoxi C3-6-carbonilo, aminocarbonilo, alquil C1-6-aminocarbonilo, alquenil C3-6- aminocarbonilo, alquinil C3-6-aminocarbonilo, di-(alquil C1-6)-aminocarbonilo, di-(alquenil C3-6)-aminocarbonilo, di-(alquinil C3-6)-aminocarbonilo, formilamino, alquil C1-6-carbonilamino, alquenil C2-6-carbonilamino, alquinil C2-6-carbonilamino, formil-alquil C1-6-amino, formil-alquenil C3-6-amino, formil-alquinil C3-6-amino, alquil C1-6-carbonil-alquil C1-6-amino, alquenil C2-6-carbonil-alquil C1-6-amino, alquinil C2-6-carbonil-alquil C1-6-amino, alquil C1-6-carbonil-alquenil C3-6-amino, alquenil C2-6-carbonil-alquenil C3-6-amino, alquinil C2-6-carbonil-alquenil C3-6-amino, alquil C1-6-carbonil-alquinil C3-6-amino, alquenil C2-6-carbonil-alquinil C3-6-amino, alquinil C2-6-carbonil-alquinil C3-6-amino, alquil C1-6-sulfonilo, alquenil C2-6-sulfonilo, alquinil C2-6-sulfonilo, alquil C1-6-sulfinilo, alquenil C2-6-sulfinilo, alquilnil C2-6-sulfinilo, alquil C1-6-sulfonilamino, alquenil C2-6-sulfonilamino, alquinil C2-6-sulfonilamino, alquil C1-6-sulfonil-alquil C1-6-amino, alquil C1- 6-sulfonil-alquenil C3-6-amino, alquil C1-6-sulfonil-alquinil C3-6-amino, alquenil C2-6-sulfonil-alquil C1-6-amino, alquenil C2-6-sulfonil-alquenil C3-6-amino, alquenil C2-6-sulfonil-alquinil C3-6-amino, alquinil C2-6-sulfonil-alquil C1-6-amino, alquinil C2-6-sulfonil-alquenil C3-6-amino, alquinil C2-6-sulfonil-alquinil C3-6-amino, aminosulfonilo, alquil C1-6-aminosulfonilo, di-(alquil C1-6)-aminosulfonilo, alquenil C3-6-aminosulfonilo, di-(alquenil C3-6)-aminosulfonilo, alquinil C3-6- aminosulfonilo o di-(alquinil C3-6)-aminosulfonilo; con las condiciones de que, en la medida en que ninguno de los grupos D, E, G, M y Q represente un átomo de nitrogeno; i) Ra no signifique un átomo de hidrogeno, cuando Rb, así como Rc representan en cada caso un grupo alquilo C1-6; ii) Rc no signifique un átomo de hidrogeno, cuando Ra, así como Rb representan en cada caso un grupo alquilo C1-6; iii) Ra no adopte los significados de un átomo de hidrogeno, fluor, cloro, bromo o yodo o de un grupo difluoro o trifluorometilo, cuando Rc representa un grupo alquilo C1-6, alquenilo C2-6 o alquinilo C2-6 y Rb representa un átomo de cloro o bromo, un grupo amino, metilamino o hidroxi; iv) Rc no adopte los significados de un átomo de hidrogeno, fluor, cloro, bromo o yodo o de un grupo difluoro o trifluorometilo, cuando Ra representa un grupo alquilo C1-6, alquenilo C2-6 o alquinilo C2-6 y Rb representa un átomo de cloro o bromo, un grupo amino, metilamino o hidroxi; R1 es un heterociclo aza, diaza, triaza, oxaza, tiaza, tiadiaza o S,S-dioxido-tiadiaza de 5 a 7 miembros, saturado, insaturado una vez o dos veces; estando los heterociclos precedentemente mencionados enlazados con el anillo de piperidina de formula (1) a través de un átomo de carbono o de nitrogeno; o estando enlazados de forma espirocíclica con el anillo de piperidina en la formula (1) a través de dos átomos de carbono, a través de un átomo de carbono y un átomo de oxígeno o a través de un átomo de carbono y un átomo de azufre; conteniendo uno o dos grupos carbonilo o tiocarbonilo contiguos a un átomo de nitrogeno; pudiendo estar sustituidos en uno de los átomos de nitrogeno con un grupo alquilo C1-6, alquenilo C3-6 o alquinilo C3-6; pudiendo estar sustituidos en uno o en dos átomos de carbono con un grupo alquilo C1-6, alquenilo C2-6 o alquinilo C2-6, con un grupo fenilo, fenilmetilo, naftilo, bifenililo, piridinilo, diazinilo, furilo, tienilo, pirrolilo, 1,3-oxazolilo, 1,3-tiazolilo, isoxazolilo, pirazolilo, 1-(alquil C1-3)-pirazolilo, imidazolilo o 1-(alquil C1-3)-imidazolilo, pudiendo los sustituyentes ser iguales o diferentes, y pudiendo estar condensado un doble enlace olefínico de uno de los heterociclos insaturados precedentemente mencionados con un anillo de fenilo, naftilo, piridina, diazina, 1,3-oxazol, tienilo, furano, tiazol, pirrolo, N-alquil C1-3-pirrolo o quinolina, con un anillo de 1H-quinolin-2-ona sustituido en el átomo de nitrogeno eventualmente con un grupo alquilo C1-6, alquenilo C3-6 o alquinilo C3-6, o pudiendo estar condensado con un anillo de imidazol o N-alquil C1-3-imidazol, pudiendo también estar condensados dos dobles enlaces olefínicos de uno de los heterociclos insaturados precedentemente mencionados en cada caso con un anillo de fenilo o piridina; pudiendo los grupos fenilo, piridinilo, diazinilo, furilo, tienilo, pirrolilo, 1,3-oxazolilo, 1,3-tiazolilo, isoxazolilo, pirazolilo, 1-alquil C1-3-pirazolilo, imidazolilo o 1-alquil C1-3-imidazolilo contenidos en R1, así como los heterociclos condensados con benzo, tieno, pirido y diazino estar mono-, di- o tri-sustituidos en el entramado de carbonos adicionalmente con átomos de halogeno, grupos alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, cicloalquenilo C3-7, ciano, hidroxi, hidroxi-alquilo C1-6, hidroxi-alquenilo C3-6, hidroxi-alquinilo C3-6, alcoxi C1-6, alcoxi C1-6-alquilo C1-6, alcoxi C1-6-alquenilo C3-6, alcoxi C1-6-alquinilo C3- 6, alquenoxi C3-6-alquilo C1-6, alquenoxi C3-6-alquenilo C3-6, alquenoxi C3-6-alquinilo C3-6, alquinoxi C3-6-alquilo C1-6, alquinoxi C3-6-alquenilo C3-6, alquinoxi C3-6-alquinilo C3-6, tiohidroxi, alquiltio C1-6, alqueniltio C3-6, alquiniltio C3-6, amino, alquil C1-6-amino, alquenil C3-6-amino, alquinil C3-6-amino, di-(alquil C1-6)-amino, di-(alquenil C3-6)-amino, di-(alquinil C3-6)-amino, amino-alquilo C1-6, alquil C1-3-amino-alquilo C1-6, di-(alquil C1-3)-amino-alquilo C1-6, amino-alquenilo C3-6, alquil C1-3-amino-alquenilo C3-6, di-(alquil C1-3)-amino-alquenilo C3-6, amino-alquinilo C3-6, alquil C1-3-amino-alquinilo C3-6, di-(alquil C1-3)-amino-alquinilo C3-6, hidroxicarbonilo, fenilcarbonilo, piridilcarbonilo, alquil C1-6-carbonilo, alquenil C2-6-carbonilo, alquinil C2-6-carbonilo, formilo, alcoxi C1-6-carbonilo, alquenoxi C3-6-carbonilo, alquinoxi C3-6-carbonilo, aminocarbonilo, alquil C1-6-aminocarbonilo, alquenil C3-6-aminocarbonilo, alquinil C3-6-aminocarbonilo, di-(alquil C1-6)-aminocarbonilo, di-(alquenil C3-6)-aminocarbonilo, di-(alquinil C3-6)-aminocarbonilo, formilamino, alquil C1-6-carbonilamino, alquenil C2-6-carbonilamino, alquinil C2-6-carbonilamino, formil-alquil C1-6-amino, formil-alquenil C3-6-amino, formil-alquinil C3-6-amino, alquil C1-6-carbonil-alquil C1-6-amino, alquenil C2-6-carbonil-alquil C1-6-amino, alquinil C2-6-carbonil-alquil C1-6-amino, alquil C1-6-carbonil-alquenil C3-6-amino, alquenil C2-6-carbonil-alquenil C3-6-amino, alquinil C2- 6-carbonil-alquenil C3-6-amino, alquil C1-6-carbonil-alquinil C3-6-amino, alquenil C2-6-carbonil-alquinil C3-6-amino, alquinil C2-6-carbonil-alquinil C3-6-amino, alquil C1-6-sulfonilo, alquenil C2-6-sulfonilo, alquinil C2-6-sulfonilo, alquil C1-6- sulfinilo, alquenil C2-6-sulfinilo, alquinil C2-6-sulfinilo, alquil C1-6-sulfonilamino, alquenil C2-6-sulfonilamino, alquinil C2-6-sulfonilamino, alquil C1-6-sulfonil-alquil C1-6-amino, alquil C1-6-sulfonil-alquenil C3-6-amino, alquil C1-6-sulfonil- alquinil C3-6-amino, alquenil C2-6-sulfonil-alquil C1-6-amino, alquenil C2-6-sulfonil-alquenil C3-6-amino, alquenil C2-6-sulfonil-alquinil C3-6-amino, alquinil C2-6-sulfonil-alquil C1-6-amino, alquinil C2-6-sulfonil-alquenil C3-6-amino, alquinil C2- 6-sulfonil-alquinil C3-6-amino, aminosulfonilo, alquil C1-6-aminosulfonilo, di-(alquil C1-6)-aminosulfonilo, alquenil C3-6-aminosulfonilo, di-(alquenil C3-6)-aminosulfonilo, alquinil C3-6-aminosulfonilo, di-(alquinil C3-6)-aminosulfonilo, pudiendo los sustituyentes ser iguales o diferentes; y estando los dobles y triples enlaces de los grupos alquenilo C3-6 o alquinilo C3-6 contenidos en los grupos definidos precedentemente para Ra, Rb, Rc y R1 aislados de heteroátomos eventualmente asimismo contenidos en estos grupos; R2 es el átomo de hidrogeno; un grupo fenilmetilo, o un grupo alquilo C2-7, que en posicion w puede estar sustituido con un grupo cicloalquilo C3-7, cicloalquenilo C3-7, fenilo, piridinilo, diazinilo, hidroxi, amino, alquil C1-6-amino, di-(alquil C1-6)-amino, alquenil C3-6-amino, di-(alquenil C3-6)-amino, alquinil C3-6-
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TW095109753A TW200700408A (en) 2005-03-23 2006-03-22 New cgrp-antagonists, process for preparing them and their use as pharmaceutical compositions
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ARP060101118A AR053854A1 (es) 2005-03-23 2006-03-22 2-oxo-1,2,4,5-tetrahidro-1,3-benzodiazepin-3-il-piperidinas como antagonistas de cgrp
TW095109968A TW200700409A (en) 2005-03-23 2006-03-22 Selected cgrp-antagonists, process for preparing them and their use as pharmaceutical compositions
US11/277,177 US7528129B2 (en) 2005-03-23 2006-03-22 CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions
US11/277,175 US7491717B2 (en) 2005-03-23 2006-03-22 Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions
MYPI20061292A MY144635A (en) 2005-03-23 2006-03-23 2-oxo-1,2,4,5-tetrahydro-1,-3-benzodiazepin-3-yl-piperidines used as cgrp antagonists
PE2006000336A PE20061453A1 (es) 2005-03-23 2006-03-23 Compuestos derivados de 2-oxo-1,2,4,5-tetrahidro-1,3-benzodiazepin-3-il piperidinas como antagonistas de cgpr
US12/186,005 US7696196B2 (en) 2005-03-23 2008-08-05 Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions
US12/706,853 US7985747B2 (en) 2005-03-23 2010-02-17 Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions

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