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US 7,888,519 B2Granted
Pyran compound or at least one derivative thereof
AssigneeMerck Patent Gesellschaft
InventorsEike Poetsch, Werner Binder, Volker Meyer, Michael Heckmeier, Georg Luessem
Life of this patent
Estimating the term…
Abstract
The invention relates to pyran derivatives of the formula I and to a process and intermediates for their preparation and derivatisation, and to the use thereof in liquid-crystalline media.
Claims65
A compound of formula I
- wherein
- a, b, c, d and e are each, independently of one another, 0 or 1, and the sum of a+b+c+d+e is ≧1;
- W is —CH2—;
- R11 is an alkyl radical having 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- R12 is halogen, —CN, —NCS, aralkyl, O-aralkyl or an alkyl radical having from 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —O—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- Z11 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH— or —C≡C—;
- Z12 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2— or —CF2CF2—;
- Z13, Z14 and Z15 are each, independently of one another, a single bond, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH—, —C≡C—, —CH2O—, —CF2O—, —C(O)— or —C(O)—O—;
- A11 and A12, independently of one another, are
- A13 and A14, independently of one another, are
- A15 is
- or
- A15-R12 together are
- or
- Z13-[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e-R12 is
- L17, L18 and L19, independently of one another, are H or F;
- q is 0, 1, 2, 3 or 4;
- p is 0, 1, 2 or 3;
- and
- R13 and R14, independently of one another, are an alkanyl radical having from 1 to 7 carbon atoms or together are an alkylene bridge having from 2 to 7 carbon atoms;
- with the provisos that:
- (a) if Z13 is directly linked to R12 to give —Z13—R12, then (i) Z13 is not —CH2O— or —CF2O—, and (ii) if Z13 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (b) if Z14 is directly linked to R12 to give —Z14—R12, then (i) Z14 is not —CH2O— or —CF2O—, and (ii) if Z14 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (c) if Z15 is directly linked to R12 to give —Z15—R12, then (i) Z15 is not —CH2O— or —CF2O—, and (ii) if Z15 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- and
- (d) R11 is not CH3 if a and b are both simultaneously zero, Z12 and Z13 are each a single bond, and -[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e-R12 is unsubstituted phenyl;
- wherein alkanyl is an unsaturated alkyl group which is optionally mono- or polysubstituted, identically or differently, by halogen or —CN.
24 more elements
An allyl compound of the formula IV-Bb
- wherein
- a is zero and b is 1 or a is 1 and b is zero or a and b are both 1;
- X11a is chlorine, bromine, iodine, a sulfonic acid radical, —OH, alkoxy or O-aralkyl, or —X11a is ═O;
- R11 is H, an alkyl radical having from 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —O—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- Z11 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH— or —C≡C—;
- Z12 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2— or —CF2CF2—;
- and
- A11 and A12, independently of one another, are
5 more elements
A compound of formula I
- wherein
- a, b, c, d and e are each, independently of one another, 0 or 1, and the sum of a+b+c+d+e is ≧1;
- W is —CH2— or —C(═O)—;
- R11 is an alkyl radical having 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- R12 is H, halogen, —CN, —NCS, aralkyl, O-aralkyl or an alkyl radical having from 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —O—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- Z11 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH— or —C≡C—;
- Z12 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2— or —CF2CF2—;
- Z13, Z14 and Z15 are each, independently of one another, a single bond, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH—, —C≡C—, —CH2O—, —CF2O—, —C(O)— or —C(O)—O—;
- A11 and A12, independently of one another, are
- A13 and A14, independently of one another, are
- A15 is
- or
- A15-R12 together are
- or
- Z13-[-A13-Z14-]c[-A14-Z15-]d-[-A15-]e-R12 is
- L17, L18 and L19, independently of one another, are H or F;
- q is 0, 1, 2, 3 or 4;
- p is 0, 1, 2 or 3;
- and
- R13 and R14, independently of one another, are an alkanyl radical having from 1 to 7 carbon atoms or together are an alkylene bridge having from 2 to 7 carbon atoms;
- with the provisos that:
- (a) if Z13 is directly linked to R12 to give —Z13—R12, then (i) Z13 is not —CH2O— or —CF2O—, and (ii) if Z13 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (b) if Z14 is directly linked to R12 to give —Z14—R12, then (i) Z14 is not —CH2O— or —CF2O—, and (ii) if Z14 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (c) if Z15 is directly linked to R12 to give —Z15—R12, then (i) Z15 is not —CH2O— or —CF2O—, and (ii) if Z15 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- and
- (d) R11 is not CH3 if a and b are both simultaneously zero, Z12 and Z13 are each a single bond, W is —CH2—, and -[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e—R12 is unsubstituted phenyl;
- wherein alkanyl is an unsaturated alkyl group which is optionally mono- or polysubstituted, identically or differently, by halogen or —CN.
24 more elements
A compound of formula I
- wherein
- a, b, c, d and e are each, independently of one another, 0 or 1, and the sum of a+b+c+d+e is ≧1;
- W is —CH2— or —C(═O)—;
- R11 is an alkyl radical having 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- R12 is halogen, —CN, —NCS, aralkyl, O-aralkyl or an alkyl radical having from 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —O—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- Z11 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH— or —C≡C—;
- Z12 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2— or —CF2CF2—;
- Z13, Z14 and Z15 are each, independently of one another, a single bond, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH—, —C≡C—, —CH2O—, —CF2O—, —C(O)— or —C(O)—O—;
- A11 and A12, independently of one another, are
- A13 and A14, independently of one another, are
- A15 is
- or
- A15-R12 together are
- or
- Z13-[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e-R12 is
- L17, L18 and L19, independently of one another, are H or F;
- q is 0, 1, 2, 3 or 4;
- p is 0, 1, 2 or 3;
- and
- R13 and R14, independently of one another, are an alkanyl radical having from 1 to 7 carbon atoms or together are an alkylene bridge having from 2 to 7 carbon atoms;
- with the provisos that:
- (a) if Z13 is directly linked to R12 to give —Z13—R12, then (i) Z13 is not —CH2O— or —CF2O—, and (ii) if Z13 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (b) if Z14 is directly linked to R12 to give —Z14—R12, then (i) Z24 is not —CH2O— or —CF2O—, and (ii) if Z14 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (c) if Z15 is directly linked to R12 to give —Z15—R12, then (i) Z15 is not —CH2O— or —CF2O—, and (ii) if Z15 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- and
- (d) R11 is not CH3 if a and b are both simultaneously zero, Z12 and Z13 are each a single bond, W is —CH2—, and -[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e-R12 is unsubstituted phenyl;
- wherein alkanyl is an unsaturated alkyl group which is optionally mono- or polysubstituted, identically or differently, by halogen or —CN.
24 more elements
A compound of formula I
- wherein
- a is 1 and b is 0, or a is 0, and b is 1;
- c, d and e are each, independently of one another, 0 or 1;
- W is —CH2— or —C(═O)—;
- R11 is an alkyl radical having 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- R12 is halogen, —CN, —NCS, aralkyl, O-aralkyl or an alkyl radical having from 1 to 15 carbon atoms optionally mono- or polysubstituted, identically or differently, by halogen or —CN, wherein optionally, one or more CH2 groups in this radical may be replaced by —C≡C—, —CH═CH—, —O—, —S—, —C(O)—O— and/or —O—C(O)— in such a way that hetero atoms O and S are not linked directly to one another;
- Z11 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH— or —C≡C—;
- Z12 is a single bond, —CH2—, —CH2CH2—, —CF2CH2—, —CH2CF2— or —CF2CF2—;
- Z13, Z14 and Z15 are each, independently of one another, a single bond, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CH—, —C≡C—, —CH2O—, —CF2O—, —C(O)— or —C(O)—O—;
- A11 and A12, independently of one another, are
- A13 and A14, independently of one another, are
- A15 is
- A15-R12 together are
- or
- Z13-[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e-R12 is
- L17, L18 and L19, independently of one another, are H or F;
- q is 0, 1, 2, 3 or 4;
- p is 0, 1, 2 or 3;
- and
- R13 and R14, independently of one another, are an alkanyl radical having from 1 to 7 carbon atoms or together are an alkylene bridge having from 2 to 7 carbon atoms;
- with the provisos that:
- (a) if Z13 is directly linked to R12 to give —Z13—R12, then (i) Z13 is not —CH2O— or —CF2O—, and (ii) if Z13 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (b) if Z14 is directly linked to R12 to give —Z14—R12, then (i) Z14 is not —CH2O— or —CF2O—, and (ii) if Z14 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- (c) if Z15 is directly linked to R12 to give —Z15—R12, then (i) Z15 is not —CH2O— or —CF2O—, and (ii) if Z15 is —C(═O)—O— or —C(═O)—, then R12 is H, aralkyl, alkanyl or alkenyl;
- and
- (d) R11 is not CH3 if a and b are both simultaneously zero, Z12 and Z13 are each a single bond, W is —CH2—, and -[-A13-Z14-]c-[-A14-Z15-]d-[-A15-]e—R12 is unsubstituted phenyl;
- wherein alkanyl is an unsaturated alkyl group which is optionally mono- or polysubstituted, identically or differently, by halogen or —CN.
24 more elements
Dependencies are inferred from the claim text.