ES2369837T3 - Compuestos triheterocíclicos como antagonistas de receptor cfr. - Google Patents
Compuestos triheterocíclicos como antagonistas de receptor cfr. Download PDFInfo
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- ES2369837T3 ES2369837T3 ES07111569T ES07111569T ES2369837T3 ES 2369837 T3 ES2369837 T3 ES 2369837T3 ES 07111569 T ES07111569 T ES 07111569T ES 07111569 T ES07111569 T ES 07111569T ES 2369837 T3 ES2369837 T3 ES 2369837T3
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- Prior art keywords
- substituted
- mono
- alkyl
- ring
- oxygen
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- 150000001875 compounds Chemical class 0.000 title abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 50
- 229910052760 oxygen Inorganic materials 0.000 abstract 27
- 239000001301 oxygen Substances 0.000 abstract 26
- 229910052717 sulfur Inorganic materials 0.000 abstract 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 25
- 229910052757 nitrogen Inorganic materials 0.000 abstract 25
- 239000011593 sulfur Substances 0.000 abstract 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 17
- 125000005843 halogen group Chemical group 0.000 abstract 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 14
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000002837 carbocyclic group Chemical group 0.000 abstract 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 5
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract 1
- 208000035193 Ring chromosome 10 syndrome Diseases 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- -1 cyano, nitro, amino Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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Abstract
Compuesto de fórmulas (I-i), (I-ii) o (I-x) en las que R2 es (i) hidrógeno, (ii) alquilo C1-8, (iii) alquenilo C2-8, (iv) alquinilo C2-8, (v) átomo de halógeno, (vi) CF3, (vii) ciano, (viii) nitro, (ix) NR9R10 en el que R9 y R10 son cada uno independientemente, (i) hidrógeno, (ii) alquilo C1-4, (iii) anillo mono o bicarbocíclico C3-10, (iv) anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) o (v) alquilo C1-4 sustituido con anillo mono o bicarbocíclico C3-10 o anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s), (x) OR11 en el que R11 es (i) hidrógeno, (ii) alquilo C1-4, (iii) anillo carbocíclico C5-6, (iv) anillo heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre o (v) alquilo C1-4 sustituido con anillo carbocíclico C5-6 o anillo heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre, (xi) SH, (xii) S(O)nR12 en el que n es 0, 1 ó 2, R12 es (i) alquilo C1-4, (ii) anillo carbocíclico C5-6, (iii) anillo heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre o (iv) alquilo C1-4 sustituido con anillo carbocíclico C5-6 o anillo 5 heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre, (xiii) COR11, (xiv) COOR11, (xv) CONR9R10, (xvi) anillo mono o bicarbocíclico C3-10, (xvii) anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) o (xviii) alquilo C1-4 sustituido con 1-2 sustituyentes seleccionados de átomo de halógeno, CF3, OCF3, ciano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, anillo mono o bicarbocíclico C3- 10 y anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s), en los que G es O, S o NH; Rx es alquilo C1-4, alcoxilo C1-4, átomo de halógeno o CF3; m es 0-3, R1 es (i) alquilo C1-8 que no está sustituido o está sustituido con 1-5 R14, (ii) alquenilo C2-8 que no está sustituido o está sustituido con 1-5 R14, (iii) alquinilo C2-8 que no está sustituido o está sustituido con 1-5 R14, (iv) NR4R5 en el que R4 y R5 son cada uno independientemente, (i) hidrógeno, (ii) alquilo C1-15 que no está sustituido o está sustituido con 1-5 R17, (iii) alquenilo C2-15 que no está sustituido o está sustituido con 1-5 R17, (iv) alquinilo C2-15 que no está sustituido o está sustituido con 1-5 R17, (v) anillo mono o bicarbocíclico C3-15 que no está sustituido o está sustituido con 1-5 R18, (vi) anillo mono o biheterocíclico de 3-15 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18, (v) OR6 en el que R6 es (i) hidrógeno, (ii) alquilo C1-10, (iii) alquenilo C2-10, (iv) alquinilo C2-10, (v) anillo mono o bicarbocíclico C3-15 que no está sustituido o está sustituido con 1-5 R18, (vi) anillo mono o biheterocíclico de 3-15 miembros que contiene 1-4 nitrógeno(s), 1-2 10 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18, (vii) alquilo C1-4 sustituido con 1-2 sustituyentes seleccionados de átomo de halógeno, CF3, OCF3, ciano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, anillo mono o bicarbocíclico C3-10 que no está sustituido o está sustituido con 1-5 R18, y anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18, (vi) SH, (vii) S(O)nR7 en el que n es tal como se definió anteriormente en el presente documento, R7 es (i) alquilo C1-8, (ii) anillo mono o bicarbocíclico C3-10 que no está sustituido o está sustituido con 1-5 R18, (iii) anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18, (iv) alquilo C1-4 sustituido con anillo mono o bicarbocíclico C3-10, que no está sustituido o está sustituido con 1-5 R18 o anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1- 5 R18, (viii) COR6, (ix) COOR6, (x) CONR4R5, (xi) NR8COR6a en el que R6a es (i) hidrógeno, (ii) alquilo C1-10, (iii) alquenilo C2-10, (iv) alquinilo C2-10 o (v) alquilo C1-4 sustituido con 1-2 sustituyentes seleccionados de átomo de halógeno, CF3, OCF3, ciano, nitro, NR9R10, OR11a, =N-OR11, SH, S(O)nR12, COR11, COOR11 y CONR9R10, (xii) NR8COOR6 en el que R6 es tal como se definió anteriormente en el presente documento, R8 es (i) hidrógeno, (ii) alquilo C1-8, (iii) alquenilo C2-8, (iv) alquinilo C2-8, (v) anillo mono o bicarbocíclico C3-10 que no está sustituido o está sustituido con 1-5 R18, (vi) anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18 o (vii) alquilo C1-4 sustituido con 1-2 sustituyentes seleccionados de átomo de halógeno, CF3, OCF3, ciano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, anillo mono o bicarbocíclico C3-10 que no está sustituido 5 o está sustituido con 1-5 R18 y anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18, (xiii) NR8CONR4R5, (xiv) anillo mono o bicarbocíclico C3-15 que no está sustituido o está sustituido con 1-5 R15 o (xv) anillo mono o biheterocíclico de 3-15 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R15, R11a es (i) hidrógeno, (ii) alquilo C1-4 o (iii) alquilo C1-4 sustituido con anillo carbocíclico C5-6 o anillo heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre, R14 es (a) átomo de halógeno, (b) CF3, (c) OCF3, (d) ciano, (e) nitro, (f) NR4R5, (g) OR6, (h) =N-OR6, (j) SH, (k) S(O)nR7, (l) COR6, (m) COOR6, (n) CONR4R5, (o) NR8COR6, (p) NR8COOR6, (q) NR8CONR4R5, (r) anillo mono o bicarbocíclico C3-15 que no está sustituido o está sustituido con 1-5 R15 o (s) anillo mono o biheterocíclico de 3-15 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R15, R15 es (a) alquilo C1-8, (b) alquenilo C2-8, (c) alquinilo C2-8, (d) alcoxi C1-4-alquilo (C1-4), (e) átomo de halógeno, (f) CF3, (g) OCF3, (h) ciano, (j) nitro, (k) NR4R5, (l) OR6, (m) SH, (n) S(O)nR7, (o) COR6, (p) COOR6, (q) CONR4R5, (r) NR8COR6, (s) NR8COOR6, (t) NR8CONR4R5, (u) anillo mono o bicarbocíclico C3- que no está sustituido o está sustituido con 1-5 R20, (v) anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R20 o (w) alquilo C1-4 sustituido con 1-2 sustituyentes seleccionados de átomo de halógeno, CF3, OCF3, ciano, nitro, NR4R5, OR6, =N-OR6, SH, S(O)nR7, COR6, COOR6, CONR4R5, NR8COR6, NR8COOR6, NR8CONR4R5, anillo mono o bicarbocíclico C3-10 que no está sustituido o está sustituido con 1-5 R20, y anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R20, R17 es (a) átomo de halógeno, (b) CF3, (c) OCF3, (d) ciano, (e) nitro, (f) NR9R10, (g) OR11a, (h) =N-OR11, (j) SH, (k) S(O)nR12, (l) COR11, (m) COOR11, (n) CONR9R10, (o) NR8COR11, (p) NR8COOR11, (q) NR8CONR9R10, (r) anillo mono o bicarbocíclico C3-15 que no está sustituido o está sustituido con 1-5 R18a o (s) anillo mono o biheterocíclico de 3-15 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) que no está sustituido o está sustituido con 1-5 R18a, R18 es (a) alquilo C1-4, (b) alquenilo C2-4, (c) alquinilo C2-4, (d) átomo de halógeno, (e) CF3, (f) OCF3, (g) ciano, (h) nitro, (j) SH, (k) S(O)nR12, (l) NR9R10, (m) OR11, (n) COR11, (o) COOR11, (p) CONR9R10, (q) anillo carbocíclico C5-6, (r) anillo heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre o (s) alquilo C1-4 sustituido con anillo carbocíclico C5-6 o anillo heterocíclico de 5 ó 6 miembros que contiene 1-2 nitrógeno(s), 1 oxígeno y/o 1 azufre, R18a es (a) alquilo C1-4, (b) alquenilo C2-4, (c) alquinilo C2-4, (d) átomo de halógeno, (e) CF3, (f) OCF3, (g) ciano, (h) nitro, (j) SH, (k) S(O)nR12, (l) NR9R10, (m) OR11a, (n) COR11, (o) COOR11 o (p) CONR9R10, R20 es alquilo C1-4, alcoxilo C1-4, átomo de halógeno, CF3, OCF3, ciano, nitro, amino, NH(alquilo C1-4) o N(alquilo C1-4)2, R3 es (i) anillo mono o bicarbocíclico C5-10 sustituido con 1-5 R16 o (ii) anillo mono o biheterocíclico C5-10 que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) sustituido con 1-5 R16, R16 es (a) alquilo C1-8, (b) alquenilo C2-8, (c) alquinilo C2-8, (d) átomo de halógeno, (e) CF3, (f) OCF3, (g) ciano, (h) nitro, (j) NR9R10, (k) OR11, (l) SH, (m) S(O)nR12, con la excepción de feniltio, (n) COR11, (o) COOR11, (p) CONR9R10, (q) NR8COR11, (r) NR8COOR11, (s) NR8CONR9R10, (t) anillo mono o bicarbocíclico C3-10, (u) anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s) (v) alquilo C1-4 sustituido con 1-2 sustituyentes seleccionados de átomo de halógeno, CF3, OCF3, ciano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, NR8COR11, NR8COOR11, NR8CONR9R10, anillo mono o bicarbocíclico C3-10, y anillo mono o biheterocíclico de 3-10 miembros que contiene 1-4 nitrógeno(s), 1-2 oxígeno(s) y/o 1-2 azufre(s), con la condición de que cuando R1 en la fórmula (I-i) es OR6, entonces R3 no es fenilo sustituido con 1 átomo de halógeno, fenilo sustituido con 1 trifluorometilo y fenilo sustituido con trifluorometilo y nitro, una sal farmacéuticamente aceptable del mismo o un hidrato del mismo, con la condición de que el compuesto 8-
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- 2001-12-27 RU RU2003119138/04A patent/RU2291869C2/ru not_active IP Right Cessation
- 2001-12-27 CA CA2432148A patent/CA2432148C/en not_active Expired - Fee Related
- 2001-12-27 PL PL01363381A patent/PL363381A1/xx unknown
- 2001-12-27 MX MXPA03005913A patent/MXPA03005913A/es active IP Right Grant
- 2001-12-27 AT AT01995808T patent/ATE375345T1/de active
- 2001-12-27 IL IL15660901A patent/IL156609A0/xx unknown
- 2001-12-27 AU AU2002226674A patent/AU2002226674B2/en not_active Ceased
- 2001-12-27 ES ES07111569T patent/ES2369837T3/es not_active Expired - Lifetime
- 2001-12-27 AT AT07111569T patent/ATE526330T1/de not_active IP Right Cessation
- 2001-12-27 DE DE60130924T patent/DE60130924T2/de not_active Expired - Lifetime
- 2001-12-27 JP JP2002555088A patent/JP3528968B2/ja not_active Expired - Fee Related
- 2001-12-27 BR BR0116609-3A patent/BR0116609A/pt not_active Application Discontinuation
- 2001-12-28 TW TW090132698A patent/TWI293630B/zh not_active IP Right Cessation
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2003
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- 2003-06-26 NO NO20032956A patent/NO326522B1/no not_active IP Right Cessation
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2005
- 2005-09-07 US US11/219,736 patent/US7459459B2/en not_active Expired - Fee Related
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2008
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