ES2184474T3 - Nuevos naftopiranos fotocromicos condensados con nucleo heterociclico de seis elementos. - Google Patents
Nuevos naftopiranos fotocromicos condensados con nucleo heterociclico de seis elementos.Info
- Publication number
- ES2184474T3 ES2184474T3 ES99932363T ES99932363T ES2184474T3 ES 2184474 T3 ES2184474 T3 ES 2184474T3 ES 99932363 T ES99932363 T ES 99932363T ES 99932363 T ES99932363 T ES 99932363T ES 2184474 T3 ES2184474 T3 ES 2184474T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- mono
- phenyl
- alkoxy
- cycloalkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- -1 naphthopyran compound Chemical class 0.000 abstract 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 11
- 125000003118 aryl group Chemical group 0.000 abstract 8
- 125000001624 naphthyl group Chemical group 0.000 abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 6
- 229910052731 fluorine Inorganic materials 0.000 abstract 6
- 239000011737 fluorine Substances 0.000 abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 abstract 5
- 239000001301 oxygen Substances 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 125000001424 substituent group Chemical group 0.000 abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 125000002541 furyl group Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 125000004076 pyridyl group Chemical group 0.000 abstract 4
- 125000001544 thienyl group Chemical group 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 3
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 abstract 3
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 abstract 3
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 3
- 125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 abstract 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 125000001041 indolyl group Chemical group 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 abstract 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 2
- 125000004986 diarylamino group Chemical group 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 150000002829 nitrogen Chemical class 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- JFMSVLANOARLBT-UHFFFAOYSA-N 4-(2-piperidin-1-yl-1-thiomorpholin-4-yl-3,4-dihydroquinolin-2-yl)morpholine Chemical compound N1(CCCCC1)C1(N(C2=CC=CC=C2CC1)N1CCSCC1)N1CCOCC1 JFMSVLANOARLBT-UHFFFAOYSA-N 0.000 abstract 1
- UIYCIISWTDMWTR-UHFFFAOYSA-N C(C=C)(=O)OBrOC(C(=C)C)=O Chemical compound C(C=C)(=O)OBrOC(C(=C)C)=O UIYCIISWTDMWTR-UHFFFAOYSA-N 0.000 abstract 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract 1
- 125000004965 chloroalkyl group Chemical group 0.000 abstract 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004407 fluoroaryl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Chemical group 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Abstract
Un compuesto naftopirano representado por la siguiente fórmula gráfica: donde: (a) R1 y R2 forman juntos un grupo oxo o R1 es hidrógeno y R2 es hidrógeno, alquilo C1-C6, cicloalquilo C3-C7, alilo, fenilo, fenilo mono- o disubstituido, bencilo, bencilo mono- o disubstituido, naftilo, naftilo mono- o disubstituido, bicicloalquilo C4-C12, alquenilo C3-C12 lineal o ramificado, alcoxi(C1- C6)carbonilalquilo(C1-C6), metacriloxialquilo(C1-C6), acriloxialquilo(C1-C6), aciloxi(C1-C6)alquilo(C1-C6), alcoxi(C1-C6)alquilo(C1-C6) o los grupos heteroaromáticos no substituidos, mono- o disubstituidos piridilo, furanilo, benzofuran-2-ilo, benzofuran-3-ilo, tienilo, benzotien-2-ilo, benzotien-3-ilo, dibenzofuranilo, dibenzotienilo, carbazolilo, benzopiridilo e indolilo, siendo cada uno de dichos substituyentes de los grupos fenilo, bencilo, naftilo y heteroaromáticos alquilo C1- C6, alcoxi C1-C6, morfolino, dialquil(C1-C6)amino, cloro o fluor;(b) R3 es seleccionado entre el grupo consistente en alquilo C1-C6, alcoxi C1-C6, cloro, fluor, fenilo, fenilo mono- y disubstituido, bencilo o bencilo monosubstituido, cicloalquilo C3-C7, ariloxi, dialquil(C1- C6)amino, morfolino, tiomorfolino, piperidino, piridilo, tetrahidroquinolino, isoquinolino, aziridino, diarilamino, N-alquil(C1-C6)piperizino y N- arilpiperizino, donde los grupos arilo son fenilo o naftilo, siendo cada uno de dichos substituyentes de fenilo y bencilo alquilo C1-C6, alcoxi C1-C6, fluor y cloro y n es el número entero 0, 1 ó 2; (c) X es oxígeno o ¿N(R4)-, donde R4 es hidrógeno, alquilo C1-C6, cicloalquilo C3-C7, alilo, vinilo, acilo C1-C5, fenilo, fenilo mono- y disubstituido, bencilo, bencilo monosubstituido, alcoxi(C1-C4)carbonilalqui-lo(C1-C6), metacriloxialquilo(C1-C6), acriloiloxialquilo(C1-C6), fenilalquilo(C1-C6), naftilo, bicicloalquilo C4-C12, aciloxi C3-C4 o los grupos heteroaromáticos no substituidos o substituidos piridilo, furanilo, benzofuran-2-ilo, benzofuran-3-ilo, tienilo, benzotien-2- ilo, benzotien-3-ilo, dibenzofuranilo, dibenzotienilo, carbazolilo, benzopiridilo e indolilo, siendo cada uno de los substituyentes de dichos grupos fenilo, bencilo y heteroaromáticos alquilo C1-C6 o alcoxi C1-C6; (d) Y es oxígeno, -N(R4)- o ¿C(R5)R6-, donde R5 y R6 son cada uno hidrógeno, alquilo C1-C6 o cicloalquilo C3-C7, con la condición de que, cuando Y es ¿(C(R5)R6)-, X sea oxígeno, y (e) B y B¿ son cada uno seleccionados entre el grupo consistente en: (i) los grupos arilo fenilo y naftilo no substituidos, mono-, di- y trisubstituidos; (ii) los grupos heteroaromáticos piridilo, furanilo, benzofuran-2-ilo, benzofuran-3-ilo, tienilo, benzotien-2-ilo, benzotien-3-ilo, dibenzofuranilo, dibenzotienilo, carbazolilo, benzopiridilo, indolilo y fluorenilo no substituidos, mono- y disubstituidos, siendo seleccionado cada uno de dichos substituyentes de arilo y heteroaromáticos de las partes (i) y (ii) entre el grupo consistente en hidroxi, arilo, es decir, fenilo y naftilo, monoalcoxi(C1-C6)arilo, dialcoxi(C1-C6)arilo, monoalquil(C1-C6)arilo, dialquil(C1-C6)arilo, cloroarilo, fluorarilo, cicloalquil(C3-C7)arilo, cicloalquilo C3-C7, cicloalquiloxi C3-C7, cicloalquiloxi(C3-C7)alquilo(C1- C6), cicloalquiloxi(C3-C7)alcoxi(C1-C6), arilalquilo(C1- C6), arilalcoxi(C1-C6), ariloxi, ariloxialquilo(C1-C6), ariloxialcoxi(C1-C6), mono- y dialquil(C1- C6)arilalquilo(C1-C6), mono- y dialcoxi(C1- C6)arilalquilo(C1-C6), mono- y dialquil(C1- C6)arilalcoxi(C1-C6), mono- y dialcoxi(C1- C6)arilalcoxi(C1-C6), amino, monoalquil(C1-C6)amino, dialquil(C1-C6)amino, diarilamino, piperazino, N- alquil(C1-C6)piperazino, N-arilpiperazino, aziridino, indolino, piperidino, morfolino, tiomorfolino, tetrahidroquinolino, tetrahidroisoquinolino, pirrilo, alquilo C1-C6, cloroalquilo C1-C6, fluoralquilo C1- C6,alcoxi C1-C6, monoalcoxi(C1-C6)alquilo(C1-C4), acriloxi, metacriloxi, bromo, cloro y fluor; (iii) los grupos representados por las siguientes fórmulas gráficas: IIA IIB donde A puede ser carbono u oxígeno y D puede ser oxígeno o nitrógeno substituido, siempre que, cuando D es nitrógeno substituido, A sea carbono, siendo seleccionados dichos substituyentes del nitrógeno entre el grupo consistente en hidrógeno, alquilo C1-C6 y acilo C2-C6; cada R7 es alquilo C1-C6, alcoxi C1-C6, hidroxi, cloro o fluor; R8 y R9 son cada uno hidrógeno o alquilo C1-C6, y p es un número entero 0, 1 ó 2; (iv) alquilo C1-C6, cloroalquilo C1-C6, fluoralquilo C1-C6, alcoxi (C1-C6)alquilo(C1-C4), cicloalquilo C3-C6, monoalcoxi(C1-C6)cicloalquilo(C3-C6), monoalquil(C1-C6)cicloalquilo(C3-C6), clorocicloalquilo C3-C6, fluorcicloalquilo C3-C6 y bicicloalquiloC4-C12, y (v) el grupo representado por la siguiente fórmula gráfica: donde W puede ser hidrógeno o alquilo C1-C4 y Z puede ser seleccionado entre los miembros no substituidos, mono- y disubstituidos del grupo consistente en naftilo, fenilo, furanilo y tienilo, siendo cada uno de los substituyentes de dichos grupos en esta parte (v) alquilo C1-C4, alcoxi C1-C4, fluor o cloro; o (vi) B y B¿, tomados juntos, forman fluoren-9- ilideno o fluoren-9-ilideno mono- o disubstituido, o forman un miembro seleccionado entre el grupo consistente en anillos hidrocarbonados espiromonocíclicos C3-C12 saturados, anillos hidrocarbonados espirobicíclicos C7- C12 saturados y anillos hidrocarbonados espirotricíclicos C7-C12 saturados, siendo seleccionado cada uno de dichos substituyentes de fluoren-9-ilideno entre el grupo consistente en alquilo C1-C4, alcoxi C1-C4, fluor y cloro.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11410298A | 1998-07-10 | 1998-07-10 | |
| US09/273,086 US6022497A (en) | 1998-07-10 | 1999-03-19 | Photochromic six-membered heterocyclic-fused naphthopyrans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2184474T3 true ES2184474T3 (es) | 2003-04-01 |
Family
ID=26811831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99932363T Expired - Lifetime ES2184474T3 (es) | 1998-07-10 | 1999-07-09 | Nuevos naftopiranos fotocromicos condensados con nucleo heterociclico de seis elementos. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6153126A (es) |
| EP (1) | EP1097155B1 (es) |
| AU (1) | AU741671B2 (es) |
| DE (1) | DE69903042T2 (es) |
| ES (1) | ES2184474T3 (es) |
| WO (1) | WO2000002883A2 (es) |
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-
1999
- 1999-07-09 ES ES99932363T patent/ES2184474T3/es not_active Expired - Lifetime
- 1999-07-09 EP EP99932363A patent/EP1097155B1/en not_active Expired - Lifetime
- 1999-07-09 AU AU48680/99A patent/AU741671B2/en not_active Expired
- 1999-07-09 DE DE69903042T patent/DE69903042T2/de not_active Expired - Lifetime
- 1999-07-09 WO PCT/US1999/015524 patent/WO2000002883A2/en not_active Ceased
-
2000
- 2000-02-07 US US09/498,810 patent/US6153126A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000002883A2 (en) | 2000-01-20 |
| WO2000002883A3 (en) | 2000-02-24 |
| EP1097155B1 (en) | 2002-09-18 |
| EP1097155A2 (en) | 2001-05-09 |
| AU741671B2 (en) | 2001-12-06 |
| DE69903042T2 (de) | 2003-08-07 |
| DE69903042D1 (de) | 2002-10-24 |
| US6153126A (en) | 2000-11-28 |
| AU4868099A (en) | 2000-02-01 |
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