AR075248A1 - DERIVATIVES OF 6- (6-O-CICLOALQUIL OR 6-NH-CICLOALQUIL-TRIAZOLOPIRIDAZINA-SULFANIL) BENZOTIAZOLES AND BENCIMIDAZOLS: PREPARATION, APPLICATION AS MEDICATIONS AND USE AS INHIBITORS OF THE MET. - Google Patents

DERIVATIVES OF 6- (6-O-CICLOALQUIL OR 6-NH-CICLOALQUIL-TRIAZOLOPIRIDAZINA-SULFANIL) BENZOTIAZOLES AND BENCIMIDAZOLS: PREPARATION, APPLICATION AS MEDICATIONS AND USE AS INHIBITORS OF THE MET.

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Publication number
AR075248A1
AR075248A1 ARP100100316A ARP100100316A AR075248A1 AR 075248 A1 AR075248 A1 AR 075248A1 AR P100100316 A ARP100100316 A AR P100100316A AR P100100316 A ARP100100316 A AR P100100316A AR 075248 A1 AR075248 A1 AR 075248A1
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Argentina
Prior art keywords
radical
optionally substituted
phenyl
heterocycloalkyl
cycloalkyl
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ARP100100316A
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Spanish (es)
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Sylvie Wentzler
Eric Bacque
Antonio Ugolini
Conception Nemecek
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Sanofi Aventis
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Publication of AR075248A1 publication Critical patent/AR075248A1/en

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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
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    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A—HUMAN NECESSITIES
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Estando estos productos en todas las formas isomeras y las sales, como medicamentos principalmente como inhibidores de la MET Reivindicacion 1: Productos de formula (1) en la que ---- representa un enlace sencillo o doble; Ra representa un radical -O-cicloalquilo o un radical -NH-cicloalquilo, ambos opcionalmente sustituidos; X representa S, SO o SO2; A representa NH o S; W representa un átomo de hidrogeno; un radical alquilo opcionalmente sustituido con alcoxi, heterocicloalquilo o NR3R4; o el radical COR en el que R representa un radical cicloalquilo o un radical alquilo opcionalmente sustituido con un átomo de halogeno o un radical cicloalquilo, NR3R4, alcoxi, hidroxi, fenilo, heteroarilo o heterocicloalquilo, ellos mismos opcionalmente sustituidos; un radical alcoxi opcionalmente sustituido con NR3R4, alcoxi, hidroxi o con heterocicloalquilo; un radical O-fenilo o un radical O-(CH2)n-fenilo, con el fenilo opcionalmente sustituido y n representa un numero entero de 1 a 4; o el radical NR1R2 en el que R1 y R2 son tales que uno de R1 y R2 representa un átomo de hidrogeno, un radical cicloalquilo o un radical alquilo y el otro de R1 y R2 representa un átomo de hidrogeno, un radical cicloalquilo, un radical heterocicloalquilo o un radical alquilo opcionalmente sustituido con uno o varios radicales idénticos o diferentes elegidos entre los radicales hidroxilo, alcoxi, heteroarilo, heterocicloalquilo, NR3R4, fenilo opcionalmente sustituido o bien R1 y R2 forman con el átomo de nitrogeno al que están unidos un radical cíclico que comprende de 3 a 10 eslabones y opcionalmente otro u otros heteroátomos elegido(s) entre O, S, N y NH, pudiendo estar el S opcional eventualmente en forma de SO o de SO2; estando este radical, incluido el NH opcional que contiene, opcionalmente sustituido; representando R3 y R4, idénticos o diferentes, un átomo de hidrogeno, un radical alquilo, un radical cicloalquilo, un radical heterocicloalquilo, un radical heteroarilo o un radical fenilo, todos ellos opcionalmente sustituidos con uno o varios radicales idénticos o diferentes elegidos entre los radicales hidroxilo, alcoxi, heteroarilo, heterocicloalquilo, NH2, NHAIq, N(Alq)2 o fenilo opcionalmente sustituido; o bien R3 y R4 forman con el átomo de nitrogeno al que están unidos un radical cíclico que comprende de 3 a 10 eslabones y opcionalmente otro u otros heteroátomos elegido(s) entre O, S, N y NH, pudiendo estar el S opcional eventualmente en forma de SO o de SO2; estando este radical, incluido el NH opcional que contiene, opcionalmente sustituido; estando todos los radicales definidos anteriormente, alquilo, cicloalquilo, heterocicloalquilo, heteroarilo y fenilo así como los radicales cíclicos que pueden formar R1 y R2 o R3 y R4 con el átomo de nitrogeno al que están unidos, opcionalmente sustituidos con uno o varios radicales elegidos entre los átomos de halogeno, los radicales hidroxilo, oxo, alcoxi, -O-CO-R5, -COOH, -COOR5, -CONH2, -CONHR5, NH2, NHR5, NR5R5', -NH-CO-R5, y los radicales alquilo, cicloalquilo, heterocicloalquilo, CH2-heterocicloalquilo, fenilo, CH2-fenilo, CO-fenilo, heteroarilo y S-heteroarilo, tales que en estos ultimos radicales los radicales alquilo, cicloalquilo, heterocicloalquilo, fenilo y heteroarilo están ellos mismos opcionalmente sustituidos con uno o varios radicales elegidos entre los átomos de halogeno y los radicales hidroxilo, oxo, alquilo y alcoxi que comprenden de 1 a 4 átomos de carbono, NH2, NHAIq y N(alq)2; estando además todos los radicales definidos anteriormente, cicloalquilo, heterocicloalquilo, heteroarilo y fenilo, opcionalmente sustituidos con un radical Si(Alq)3; pudiendo estar todos los radicales cicloalquilo y heterocicloalquilo definidos anteriormente opcionalmente sustituidos en uno de los carbonos del ciclo con un radical espirocicloalquilo o espiroheterocicloalquilo u opcionalmente en dos de los átomos de carbono del ciclo con un radical cicloalquilo o heterocicloalquilo condensado; R5 y R5', idénticos o diferentes, representan un radical alquilo o cicloalquilo que comprende como máxime 6 átomos de carbono; Alq representa un radical alquilo que comprende como máximo 4 átomos de carbono; entendiéndose que W no representa H cuando H representa S, X representa S, Ra representa el radical O-ciclohexilo o el radical NH-ciclohexilo no sustituidos y ---- representa un doble enlace; estando dichos productos de formula (1) en todas las formas isomeras posibles, racémicas, enantiomeras y diastereoisomeras, así como las sales de adicion con los ácidos minerales y orgánicos o con las bases minerales y orgánicas de dichos productos de formula (1). Reivindicacion 31: Como productos industriales nuevos, los intermedios de síntesis de formulas E', M1, M2, M3 y N en las que R6 representa un radical alquilo opcionalmente sustituido con un grupo NR3R4 (un radical -(CH2)n-NR3R4), alcoxi, hidroxi, heterocicloalquilo, fenilo, -(CH2)n-fenilo, con el fenilo opcionalmente sustituido y n representa un numero entero de 1 a 4, tal que OR6 representa los valores correspondientes de R tal como se han definido anteriormente; R7 representa un radical cicloalquilo o un radical alquilo opcionalmente sustituido con un radical NR3R4, alcoxi, hidroxi, o un radical fenilo, heteroarilo o heterocicloalquilo, ellos mismos opcionalmente sustituidos como se ha indicado en la reivindicacion 1; y Ra, R1, R2, R3 y R4 tienen los significados indicados en la reivindicacion 1.These products being in all isomeric forms and salts, as medicaments mainly as MET inhibitors Claim 1: Products of formula (1) in which ---- represents a single or double bond; Ra represents an -O-cycloalkyl radical or a -NH-cycloalkyl radical, both optionally substituted; X represents S, SO or SO2; A represents NH or S; W represents a hydrogen atom; an alkyl radical optionally substituted with alkoxy, heterocycloalkyl or NR3R4; or the COR radical in which R represents a cycloalkyl radical or an alkyl radical optionally substituted with a halogen atom or a cycloalkyl radical, NR3R4, alkoxy, hydroxy, phenyl, heteroaryl or heterocycloalkyl, themselves optionally substituted; an alkoxy radical optionally substituted with NR3R4, alkoxy, hydroxy or with heterocycloalkyl; an O-phenyl radical or an O- (CH2) n-phenyl radical, with the optionally substituted phenyl and n represents an integer from 1 to 4; or the radical NR1R2 in which R1 and R2 are such that one of R1 and R2 represents a hydrogen atom, a cycloalkyl radical or an alkyl radical and the other of R1 and R2 represents a hydrogen atom, a cycloalkyl radical, a radical heterocycloalkyl or an alkyl radical optionally substituted with one or several identical or different radicals chosen from the hydroxyl, alkoxy, heteroaryl, heterocycloalkyl radicals, NR3R4, optionally substituted phenyl or R1 and R2 form with the nitrogen atom to which a cyclic radical is attached comprising from 3 to 10 links and optionally another or other heteroatoms chosen from O, S, N and NH, the optional S may possibly be in the form of SO or SO2; this radical being, including the optional NH it contains, optionally substituted; R3 and R4, identical or different, represent a hydrogen atom, an alkyl radical, a cycloalkyl radical, a heterocycloalkyl radical, a heteroaryl radical or a phenyl radical, all optionally substituted with one or more identical or different radicals chosen from among the radicals hydroxyl, alkoxy, heteroaryl, heterocycloalkyl, NH2, NHAIq, N (Alq) 2 or optionally substituted phenyl; or R3 and R4 form with the nitrogen atom to which they are attached a cyclic radical comprising from 3 to 10 links and optionally another or other heteroatoms chosen from O, S, N and NH, where the optional S may be optionally in the form of SO or SO2; this radical being, including the optional NH it contains, optionally substituted; all the radicals defined above being alkyl, cycloalkyl, heterocycloalkyl, heteroaryl and phenyl as well as the cyclic radicals that can form R1 and R2 or R3 and R4 with the nitrogen atom to which they are attached, optionally substituted with one or more radicals chosen from halogen atoms, hydroxyl radicals, oxo, alkoxy, -O-CO-R5, -COOH, -COOR5, -CONH2, -CONHR5, NH2, NHR5, NR5R5 ', -NH-CO-R5, and alkyl radicals , cycloalkyl, heterocycloalkyl, CH2-heterocycloalkyl, phenyl, CH2-phenyl, CO-phenyl, heteroaryl and S-heteroaryl, such that in these latter radicals the alkyl, cycloalkyl, heterocycloalkyl, phenyl and heteroaryl radicals are themselves optionally substituted with one or several radicals chosen from the halogen atoms and the hydroxyl, oxo, alkyl and alkoxy radicals comprising from 1 to 4 carbon atoms, NH2, NHAIq and N (alq) 2; in addition all the radicals defined above, cycloalkyl, heterocycloalkyl, heteroaryl and phenyl, optionally substituted with a radical Si (Alq) 3; all cycloalkyl and heterocycloalkyl radicals defined above may be optionally substituted on one of the carbons of the cycle with a spirocycloalkyl or spiroheterocycloalkyl radical or optionally on two of the carbon atoms of the cycle with a fused cycloalkyl or heterocycloalkyl radical; R5 and R5 ', identical or different, represent an alkyl or cycloalkyl radical comprising at most 6 carbon atoms; Alq represents an alkyl radical comprising a maximum of 4 carbon atoms; it being understood that W does not represent H when H represents S, X represents S, Ra represents the unsubstituted O-cyclohexyl radical or NH-cyclohexyl radical and ---- represents a double bond; said products of formula (1) being in all possible isomeric, racemic, enantiomeric and diastereomeric forms, as well as the addition salts with the mineral and organic acids or with the mineral and organic bases of said products of formula (1). Claim 31: As new industrial products, the synthesis intermediates of formulas E ', M1, M2, M3 and N in which R6 represents an alkyl radical optionally substituted with a group NR3R4 (a radical - (CH2) n-NR3R4), alkoxy, hydroxy, heterocycloalkyl, phenyl, - (CH2) n-phenyl, with the optionally substituted phenyl and n represents an integer from 1 to 4, such that OR6 represents the corresponding values of R as defined above; R7 represents a cycloalkyl radical or an alkyl radical optionally substituted with an NR3R4 radical, alkoxy, hydroxy, or a phenyl, heteroaryl or heterocycloalkyl radical, themselves optionally substituted as indicated in claim 1; and Ra, R1, R2, R3 and R4 have the meanings indicated in claim 1.

ARP100100316A 2009-02-06 2010-02-05 DERIVATIVES OF 6- (6-O-CICLOALQUIL OR 6-NH-CICLOALQUIL-TRIAZOLOPIRIDAZINA-SULFANIL) BENZOTIAZOLES AND BENCIMIDAZOLS: PREPARATION, APPLICATION AS MEDICATIONS AND USE AS INHIBITORS OF THE MET. AR075248A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0900510A FR2941949B1 (en) 2009-02-06 2009-02-06 DERIVATIVES OF 6- (6-O-CYCLOALKYL OR 6-NH-CYCLOALKYL-TRIAZOLOPYRIDAZINE-SULFANYL) BENZOTHIAZOLES AND BENZIMIDAZOLES PREPARATION, APPLICATION AS MEDICAMENTS AND USE AS INHIBITORS OF MET.

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AR075248A1 true AR075248A1 (en) 2011-03-16

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EP (1) EP2393790A1 (en)
JP (1) JP2012517407A (en)
KR (1) KR20110126660A (en)
CN (1) CN102388029A (en)
AR (1) AR075248A1 (en)
AU (1) AU2010212231A1 (en)
BR (1) BRPI1011354A2 (en)
CA (1) CA2751525A1 (en)
CO (1) CO6400222A2 (en)
EA (1) EA201171010A1 (en)
FR (1) FR2941949B1 (en)
IL (1) IL214407A0 (en)
MA (1) MA33102B1 (en)
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SG (1) SG173558A1 (en)
TW (1) TW201040187A (en)
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EP2755976B1 (en) 2011-09-15 2018-07-18 Novartis AG 6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridines as c-met tyrosine kinase inhibitors

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AU2006320580B2 (en) * 2005-11-30 2011-06-23 Vertex Pharmaceuticals Incorporated Inhibitors of c-Met and uses thereof
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KR20110126660A (en) 2011-11-23
JP2012517407A (en) 2012-08-02
CA2751525A1 (en) 2010-08-12
WO2010089506A1 (en) 2010-08-12
BRPI1011354A2 (en) 2019-09-24
EA201171010A1 (en) 2012-03-30
TW201040187A (en) 2010-11-16
CN102388029A (en) 2012-03-21
CO6400222A2 (en) 2012-03-15
UY32419A (en) 2010-09-30
FR2941949B1 (en) 2011-04-01
MX2011008312A (en) 2011-11-02
EP2393790A1 (en) 2011-12-14
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