CO5410192A1 - Nuevos naftopiranos fotocromicos - Google Patents
Nuevos naftopiranos fotocromicosInfo
- Publication number
- CO5410192A1 CO5410192A1 CO00070475A CO00070475A CO5410192A1 CO 5410192 A1 CO5410192 A1 CO 5410192A1 CO 00070475 A CO00070475 A CO 00070475A CO 00070475 A CO00070475 A CO 00070475A CO 5410192 A1 CO5410192 A1 CO 5410192A1
- Authority
- CO
- Colombia
- Prior art keywords
- alkyl
- group
- mono
- phenyl
- alkoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pyrane Compounds (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Eyeglasses (AREA)
- Optical Filters (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
La presente invención se relaciona con un compuesto naftopirano de estructura 2H-nafto(1,2-b)pirano, representado por la siguiente fórmula gráfica: <EMI FILE="00070475_1" ID="1" IMF=JPEG >donde,(a) R1 es el grupo T representado por la fórmula:-E[(OC2H4)x (OC3H6)y (OC4H8)z]EAND#39 o-[(OC2H4)x (OC3H6)y (OC4H8)z]EAND#39donde -E es -C(O)- o -CH2- y EAND#39 es C1-C3 alcoxi o un grupo polimerizable. Las letras x, y, z son, cada una, un número entre 0 y 50, y la suma de x, y, z es de entre 2 y 50. La suma de x, y, z es un número entre 2 y 50; R2 es el grupo T, o fenilo mono- T -sustituido, siempre y cuando que si R1 no es el grupo T, o R2 no es del grupo T, o fenilo mono- T -sustituido, entonces:(b) R1 se selecciona del grupo formado por -CH2X, -C(V)2X o -C(O)Y, donde: X es hidrógeno, C1-C6 alquilo, cloro, fluor, bromo, hidroxi, benzoiloxi, C1-C6 alcoxi, C2-C6 aciloxi, amino, mono(C1-C6)alquilamino, di(C1-C6) alquilamino, morfolino, piperidino, 1-indolinilo, pirrolidilo, trimetilsililoxi, o el grupo -OCH(R7)Z; V es C1-C6 alquilo, el insustituido, grupos arilo fenilo o naftilo mono- o di- sustituidos; Y es hidrógeno, hidroxi, C1-C6 alquilo, el insustituido, grupos arilo, fenilo o naftilo mono- o di- sustituidos, el grupo, -OCH(R7)Z, -OR8, o -N(R9)(R10), o un anillo heterocíclico insustituido, mono-sustituido, o di-sustituido seleccionado en el grupo formado por 1-indolinilo, morfolino, piperidino, 1-pirrolidilo, 1-imidazolidilo, 2-imidazolin-1-ilo, pirazolidilo, pirazolinilo y 1-piperazinilo; Z es -CN, -CF3, cloro, fluor o -C(O)R11; R7 es hidrógeno o C1-C6 alquilo; R11 es hidrógeno, C1-C6 alquilo o C1-C6 alcoxi; R8 es hidrógeno, C1-C6 alquilo, alilo, fenil(C1-C3)alquil, fenil(C1-C3)alquil mono (C1-C6) alquilo sustituido, fenil(C1-C3)alquil mono (C1-C6) alcoxi sustituido, (C1-C6) alcoxi (C2-C4)alquil, C1-C6 haloalquil, o los grupos arilo, fenil o naftil insustituido, mono o di-sustituido, siendo dichos sustituyentes halo cloro o fluor; y R9 y R10 se seleccionan del grupo formado por hidrógeno, C1-C6 alquilo, C5-C7 cicloalquilo, fenil, fenil mono y di - sustituido, siendo cada uno de dichos sustituyentes fenil, naftil o anillo heterociclico C1-C6 alquilo o C1-C6 alcoxi; - 2 -(c) R2 se selecciona entre hidrógeno, C1-C6 alquilo, C1-C6 alcoxi, los grupos arilo fenil o naftil insustituidos, mono o di-sustituidos, amino, mono(C1-C6)alquilamino, di(C1-C6)alquiloamino, fenilamino, fenilamino mono - o di- (C1-C6) alquilo sustituido, fenilamino mono - o di-(C1-C6) alcoxi sustituido, difenilamino, difenilamino mono - o di- (C1-C6) alquilo sustituido, difenilamino mono- o di-(C1-C6) alcoxi sustituido, morfolino, piperidino, diciclohexilamino o pirrolidilo, siendo dichos sustituyentes arilo seleccionados del grupo formado por C1-C6 alquilo, C1-C6 alcoxi, C3-C6 cicloalquilo, benzilo, amino, mono(C1-C6)alquiloamino, di(C1-C6)alquilamino, diciclohexiloamino, difenilamino, piperidino, morfolino, pirrolidilo, piridilo, bromo, cloro, fluor, fenilo y naftilo.(d) R3 se selecciona del grupo formado por: (i) o el grupo -OR12 donde R12 es hidrógeno, C1-C6 alquilo, el insustituido, un grupo arilo fenilo o naftilo mono- o di-sustituido, fenilo(C1-C3)alquilo, fenilo(C1-C3)alquilo mono (C1-C6) alquilo sustituido, fenilo(C1-C3)alquilo mono (C1-C6) alcoxi sustituido, C1-C6 alcoxi(C2-C4)alquilo, C3-C7 cicloalquilo, C3-C7 cicloalquilo mono(C1-C4)alquilo sustituido, C1-C6 cloroalquilo, C1-C6 fluoroalquilo, alilo, o R12 es el grupo -CH(R13)Q, donde R13 es hidrógeno o C1-C3 alquilo y Q es -CN, -CF3, o COOR7, siendo cada uno de dichos grupo sustituyentes de arilo, C1-C6 alquilo, o C1-C6 alcoxi (ii) un grupo -N(R14)R15, donde cada R14 y R15 se selecciona en el grupo formado por hidrógeno, C1-C8 alquilo, fenilo, naftilo, los grupos heteroaromáticos furanilo, benzofuran-2-ilo, benzofuran-3-ilo, tienilo, benzotien-2-ilo, benzotien-3-ilo, dibenzofuranilo, dibenzotienilo, benzopiridilo y fluorenilo, C1-C8 alquiloarilo, C3-C20 cicloalquilo, C4-C20 bicicloalquilo, C5-C20 tricicloalquilo y C1-C20 alcoxialquilo, donde dicho grupo arilo es fenilo o naftilo;(iii) un anillo que contenga nitrógeno representado por la siguiente fórmula gráfica:<EMI FILE="00070475_2" ID="2" IMF=JPEG >donde W se selecciona del grupo formado por -CH2-, -CH(R16)-, -C(R16)(R16)-, -CH(arilo)-, -C(arilo)2-, y -C(R16)(arilo)-, y G se selecciona del grupo formado por -W-, -O-, -S-, -S(O)-, -S(O2)-, -NH-, -NR16- y -N-arilo, donde R16 es C1-C6 alquilo, el arilo es fenilo o naftilo, m es el número entero 1, 2 o 3, y p es el número entero 0, 1, 2, o 3, y cuando p sea 0, G es W; y(iv) un grupo representado por las siguientes fórmulas gráficas:<EMI FILE="00070475_3" ID="3" IMF=JPEG >donde cada R18, R19 y R20 es hidrógeno, C1-C5 alquilo, fenilo o naftilo, o los grupos R18 y R19 pueden unirse para formar un anillo que tenga entre 5 y 8 átomos de carbono, y R17 es C1-C6 alquilo, C1-C6 alcoxi, fluor o cloro. (e) R4 es el grupo ( d) (i) según se define más adelante y (f) R3 y R4, juntos, forman las siguientes fórmulas gráfica;<EMI FILE="00070475_4" ID="4" IMF=JPEG >donde cada J y K es oxígeno, o el grupo-NR14-, (g) B y BAND#39, en la fórmula gráfica I, puede, cada uno seleccionarse del grupo formado por(i) fenilo mono- T -sustituido;(ii) el insustituido, un grupo arilo fenilo o naftilo mono-, di-, y tri-sustituido;(iii) 9-julolidinilo y el insustituido, un grupo heterocíclico aromático mono- o di-sustituido, piridilo, furanilo, benzofuran-2-ilo, benzofuran-3-ilo, tienilo, benzotien-2-ilo, benzotien-3-ilo, dibenzofuranilo, dibenzotienilo, carbazoilo, benzopiridilo, indolinilo y fluorenilo, siendo cada uno de los sustituyentes arilos y heterocíclicos aromáticos indicados en estos puntos (g), (ii) y (iii) seleccionados de entre el grupo formado por hidroxi, arilo, mono(C1-C6)alcoxiarilo, di(C1-C6)alcoxiarilo, mono(C1-C6)alquiloarilo, di(C1-C6)alquiloarilo, cloroarilo, fluoroarilo, C3-C7 cicloalquiloarilo, C3-C7 cicloalquilo, C3-C7 cicloalquiloxi, C3-C7 cicloalquiloxi(C1-C6)alquilo, C3-C7 cicloalquiloxi(C1-C6)alcoxi, arilo(C1-C6)alquilo, arilo(C1-C6)alcoxi, ariloxi, ariloxi(C1-C6)alquilo, ariloxi(C1-C6)alcoxi, mono- y di-(C1-C6)alquiloarilo(C1-C6)alquilo, mono- y - 3 -di-(C1-C6)alcoxiarilo(C1-C6)alquilo, mono- y di-(C1-C6)alquiloarilo(C1-C6)alcoxi, mono- y al-(C1-C6)alcoxiarilo(C1-C6)alcoxi, amino, mono(C1-C6)alquiloamino, di(C1-C6)alquiloamino, diariloamino, piperazino, N-(C1-C6)alquilopiperazino, N-arilopiperazino, aziridino, indolino, piperidino, morfolino, tiomorfolino, tetrahidroquinolino, tetrahidroisoquinolino, pirrolidilo, C1-C6 alquilo, C1-C6 cloroalquilo, C1-C6 fluoroalquilo, C1-C6 alcoxi, mono(C1-C6)alcoxi(C1-C4)alquilo, acriloxi, metacriloxi, bromo, cloro y fluor, siendo cada sustituyente de dicho grupo arilo o heteroaromático, fenilo o naftilo;(iv) el grupo insustituido o monosustituido, pirazolilo, imidazolilo, piridilo, pirazolinilo, imidazolinilo, pirrolinilo, fenotiazinilo, fenoxazinilo, fenazinilo, acrinidilo o carbazxonilo, siendo dicho grupo arilo fenil o naftil, siendo dichos sustituyentes seleccionados en el grupo formado por C1-C6 alquilo, C1-C6 alcoxi, fenilo, fluor, cloro y bromo;(v) fenilo monosustituido, que tenga un sustituyente en la posición para, que sea un grupo de enlace-(CH2)t- o -O-(CH2)t-, donde t es el número entero 1, 2, 3, 4, 5 o 6, asociado a un grupo arilo, e.j. fenilo o naftilo, que sea un miembro de otro naftopirano fotocrómico, como nafto[2,1-b]pirano o nafto[1,2-b]pirano;(vi) los grupos representados por las siguientes fórmulas gráficas:<EMI FILE="00070475_5" ID="5" IMF=JPEG >donde A es metileno, u oxígeno, y D es oxígeno, o nitrógeno sustituido, dado que cuando D sea nitrógeno sustituido, A es metileno, y dichos sustituyentes del nitrógeno se seleccionen del grupo formado por hidrógeno, C1-C6 alquilo, y C2-C6 acilo; cada R23 sea C1-C6 alquilo, C1-C6 alcoxi, hidroxi, cloro o fluor; cada R21 y R22 sea hidrógeno o C1-C6 alquilo; y q sea el número entero 0, 1, o 2;(vii) C1-C6 alquilo, C1-C6 cloroalquilo, C1-C6 fluoroalquilo, C1-C6 alcoxi(C1-C4)alquilo, C3-C6 cicloalquilo, mono(C1-C6)alcoxi(C3-C6)cicloalquilo, mono(C1-C6)alquilo(C3-C6)cicloalquilo, cloro(C3-C6)cicloalquilo, fluoro(C3-C6)cicloalquilo y C4-C12 bicicloalquilo; y(viii) el grupo representado por la siguiente fórmula gráfica: <EMI FILE="00070475_6" ID="6" IMF=JPEG >donde L, es hidrógeno o C1-C4 alquilo y M, en la fórmula gráfica IIH, se selecciona entre los miembros insustituidos, mono-, y di-sustituidos del grupo formado por naftilo, fenilo, furanilo, y tienilo, siendo cada uno de dichos grupos los sustituyentes, C1-C4 alquilo, C1-C4 alcoxi, fluor, o cloro; o(h) B y BAND#39, juntos forman a fluoren-9-iloideno, fluoren-9-iloideno monosustituido o un miembro seleccionado del grupo formado por anillos de hidrocarburos C3-C12 espiro-monocíclicos saturados,anillos de hidrocarburos C7-C12 espiro-bicíclicos saturados y anillos de hidrocarburos C7-C12 espiro-tricíclicos saturados, siendo cada uno de dichos sustituyentes de fluoren-9-iloideno seleccionado del grupo formado por C1-C4alquilo, C1-C4 alcoxi, fluor y cloro; dado que dicho naftopirano demostró una calificación de al menos 80 en el ?OD relativo del Test de Saturación. Igualmente, se refiere a un artículo fotocrómico.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15442999P | 1999-09-17 | 1999-09-17 | |
US16465299P | 1999-11-10 | 1999-11-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CO5410192A1 true CO5410192A1 (es) | 2004-06-30 |
Family
ID=40973053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CO00070475A CO5410192A1 (es) | 1999-09-17 | 2000-09-18 | Nuevos naftopiranos fotocromicos |
Country Status (12)
Country | Link |
---|---|
US (1) | US6348604B1 (es) |
EP (1) | EP1214310B1 (es) |
JP (1) | JP4969005B2 (es) |
AU (1) | AU774601B2 (es) |
BR (1) | BR0014574A (es) |
CA (1) | CA2385728C (es) |
CO (1) | CO5410192A1 (es) |
DE (1) | DE60019770T2 (es) |
ES (1) | ES2240164T3 (es) |
MX (1) | MXPA02002915A (es) |
WO (1) | WO2001019812A1 (es) |
ZA (1) | ZA200202038B (es) |
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- 2000-09-15 AU AU74936/00A patent/AU774601B2/en not_active Ceased
- 2000-09-15 WO PCT/US2000/025414 patent/WO2001019812A1/en active IP Right Grant
- 2000-09-15 EP EP00963533A patent/EP1214310B1/en not_active Expired - Lifetime
- 2000-09-15 ES ES00963533T patent/ES2240164T3/es not_active Expired - Lifetime
- 2000-09-15 BR BR0014574-2A patent/BR0014574A/pt not_active Application Discontinuation
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- 2000-09-15 JP JP2001523390A patent/JP4969005B2/ja not_active Expired - Fee Related
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WO2001019812A1 (en) | 2001-03-22 |
DE60019770T2 (de) | 2006-01-19 |
AU774601B2 (en) | 2004-07-01 |
BR0014574A (pt) | 2003-02-25 |
JP2003509418A (ja) | 2003-03-11 |
ZA200202038B (en) | 2003-06-12 |
DE60019770D1 (de) | 2005-06-02 |
EP1214310A1 (en) | 2002-06-19 |
MXPA02002915A (es) | 2003-10-14 |
JP4969005B2 (ja) | 2012-07-04 |
CA2385728A1 (en) | 2001-03-22 |
EP1214310B1 (en) | 2005-04-27 |
AU7493600A (en) | 2001-04-17 |
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