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US4894181A
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Carbocyclic compounds
Assignee: Merck Patent GmbH
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Filing: 1988-05-16
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Granted: 1990-01-16
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Expires: 2008-05-16
Abstract
Abstract Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH 2 --(CH 2 ) p -- where it is also possible for one or two non-adjacent CH 2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH═CH--, p is 0, 1 or 2, A 1 and A 2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH 3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH 2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group, Z is --CO--O--, --O--CO--, --O--, --CH 2 --, --CH 2 O--, --OCH 2 --, --CH 2 CH 2 --, --CHCN--CH 2 --, --CH 2 --CHCN--, --CH═CH--, --CH═N--, --N═CH--, --NO═N--, --N═NO-- or a single bond, n is 0, 1 or 2 and R is alkyl having 1 to 20 C atoms wherein it would also be possible for one or more non-adjacent CH 2 groups to be replaced by --O--, --CO--, --O--CO--, --CO--O-- or --CH═CH--, H, F, Cl, Br, I, OH, NH 2 , COOH or CN, m being 6 in the event that Q=benzene or cyclohexane and being 8 in the event that Q=naphthalene, subject to the proviso that, in the event that X=--OCH 2 -- and --(A 1 --Z) n --A 2 --R=p-alkoxyphenyl, Q is a cyclohexane ring, are suitable for use as components of discotic, liquid-crystal phases.
Inventors
- 👤 Klaus Praefcke
- 👤 Bernd Kohne
- 👤 Eike Poetsch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:43
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07C; C07C13/00; C07C13/28; C07C15/00; C07C15/20; C07C15/24; C07C255/00; C07C321/00; C07C323/00; C07C43/00; C07C43/02; C07C43/20; C07C43/205; C07C43/21; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/42
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
228 words
A carbocyclic compound of the formula 1a, 1b or 1c ##STR6## wherein the substituents [X-(A 1 -Z) n -A 2 -R] opposite each other are situated equatorially and in the trans-position, ##STR7## wherein X is --CH 2 --(CH 2 ) p -- or --CH 2 --(CH 2 ) p -- wherein one or two non-adjacent CH 2 groups are replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH═CH, p is 0, 1 or 2, A 1 and A 2 independently are each 1,4-phenylene or 1,4-phenylene substituted by halogen, CH 3 or CN; 1,4-phenylene or 1,4-phenylene substituted by halogen, CH 3 or CN wherein one or more CH groups are replaced by N atoms; 1,4-cyclohexylene, 1,4-cyclohexylene substituted in the 1-position or 4-position by CN or 1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups are replaced by --O-- or --S--; piperidine-1,4-diyl; or 1,4-bicyclo[2.2.2]octylene, Z is --CO--O--, --O--CO--, --O--, --CH 2 --, --CH 2 O--, --OCH 2 --, --CH 2 CH 2 , --CHCN--CH 2 --, --CH 2 --CHCN--, --CH═CH--, --CH═N, --N═CH--, --NO═N--, --N═NO-- or a single bond, n is 0, 1 or 2 and R is alkyl of 1 to 20 C atoms or alkyl having 1 to 20 C atoms wherein one or more non-adjacent CH 2 groups are replaced by --O--, --CO--, --O--CO--, --CO--O-- or --CH═CH--, F, Cl, Br, I, OH, NH 2 , COOH or CN.
Claim 2
Dependent Claim
228 words
A carbocyclic compound of the formula 1a, 1b or 1c ##STR6## wherein the substituents [X-(A 1 -Z) n -A 2 -R] opposite each other are situated equatorially and in the trans-position, ##STR7## wherein X is --CH 2 --(CH 2 ) p -- or --CH 2 --(CH 2 ) p -- wherein one or two non-adjacent CH 2 groups are replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH═CH, p is 0, 1 or 2, A 1 and A 2 independently are each 1,4-phenylene or 1,4-phenylene substituted by halogen, CH 3 or CN; 1,4-phenylene or 1,4-phenylene substituted by halogen, CH 3 or CN wherein one or more CH groups are replaced by N atoms; 1,4-cyclohexylene, 1,4-cyclohexylene substituted in the 1-position or 4-position by CN or 1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups are replaced by --O-- or --S--; piperidine-1,4-diyl; or 1,4-bicyclo[2.2.2]octylene, Z is --CO--O--, --O--CO--, --O--, --CH 2 --, --CH 2 O--, --OCH 2 --, --CH 2 CH 2 , --CHCN--CH 2 --, --CH 2 --CHCN--, --CH═CH--, --CH═N, --N═CH--, --NO═N--, --N═NO-- or a single bond, n is 0, 1 or 2 and R is alkyl of 1 to 20 C atoms or alkyl having 1 to 20 C atoms wherein one or more non-adjacent CH 2 groups are replaced by --O--, --CO--, --O--CO--, --CO--O-- or --CH═CH--, F, Cl, Br, I, OH, NH 2 , COOH or CN.
Claim 3
Dependent Claim
9 words
A compound of claim 1, of the formula ##STR8##
Claim 4
Dependent Claim
9 words
A compound of claim 1, of the formula ##STR9##
Claim 5
Dependent Claim
9 words
A compound of claim 1, of the formula ##STR10##
Claim 6
Dependent Claim
96 words
A compound of claim 1, of the formula Ch[--O--CO--(A 1 --Z) n --A 2 --R] 6 Ch[--CO--O--(A 1 --Z) n --A 2 --R] 6 Ch[--O--CH 2 --(A 1 --Z) n --A 2 R] 6 Ch[--CH 2 --O--(A 1 --Z) n --A 2 --R] 6 Ch[--CH 2 CH 2 --(A 1 --Z) n --A 2 --R] 6 Ch[--OCH 2 CH 2 --(A 1 --Z) n --A 2 --R] 6 Ch[--CH 2 CH 2 CH 2 --(A 1 --Z) n --A 2 --R] 6 Ch[--SCH 2 --(A 1 --Z) n --A 2 --R] 6 wherein Ch is 1,2,3,4,5,6-cyclohexylene.
Claim 7
Dependent Claim
59 words
A compound of claim 5, of the formula Ch[--O--CO--(A 1 --Z) n --A 2 --R] 6 Ch[--CO--O--(A 1 --Z) n --A 2 --R] 6 Ch[--O--CH 2 --(A 1 --Z) n --A 2 R] 6 Ch[--CH 2 CH 2 --(A 1 --Z) n --A 2 --R] 6 Ch[--OCH 2 CH 2 --(A 1 --Z) n --A 2 --R] 6 .
Claim 8
Dependent Claim
48 words
A compound of claim 1, wherein A 1 and A 2 are independently 1,4-cyclohexylene (Cy), 1,4-phenylene (Phe), 1,3-dioxane (Dio), 1,3-dithiane-2,5-diyl (Dit), bicyclo-[2.2.2]octylene, piperidine-1,4-diyl (Dip), pyridyl (Pyn), pyrimidine (Pyr), 1,4-phenylene 2-substituted by F, Cl, CN or CH 3 or 1,4-phenylene 3-substituted by F, Cl, CN or CH 3 .
Claim 9
Dependent Claim
17 words
A compound of claim 7, wherein A 1 and A 2 are independently Cy, Phe or Pyn.
Claim 10
Dependent Claim
32 words
A compound according to claim 1, wherein A 1 and A 2 are independently trans-1,4-cyclohexylene, trans-1,4-cyclohexylene 1-substituted in an axial position by CN or trans-1,4-cyclohexylene 4-substituted in an axial position by CN.
Claim 11
Dependent Claim
12 words
A compound according to claim 9, wherein n is 0 or 1.
Claim 12
Dependent Claim
26 words
A compound according to claim 10, wherein Z is --CO--O--, --O--CO--, --CH 2 O--, --OCH 2 --, --CH 2 CH 2 -- or a single bond.
Claim 13
Dependent Claim
16 words
A compound according to claim 1, wherein --(A 1 --Z) n --A 2 -- is ##STR11##
Claim 14
Dependent Claim
47 words
A compound according to claim 7, wherein R is --O-- alkyl, --CO--O--alkyl, --O--CO--alkyl, --CO--alkyl, --CH 2 --CH═CH-- alkyl(trans), --CH 2 CH 2 --CH═CH--alkyl(trans), F, OH, COOH, CN or alkyl in which a non-terminal CH 2 group or two non-adjacent CH 2 groups are replaced by O atoms.
Claim 15
Dependent Claim
90 words
A compound according to claim 7, wherein R is propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, 2-oxapropyl, 2-oxabutyl, 3-oxabutyl, 2-oxapentyl, 3-oxapentyl, 4-oxapentyl, 2-oxahexyl, 3-oxahexyl, 4-oxahexyl, 5-oxahexyl, 2-oxaheptyl, 3-oxaheptyl, 4-oxaheptyl, 5-oxaheptyl, 6-oxaheptyl, ethyl, tetradecyl, pentadecyl, 2-oxaoctyl, 3-oxaoctyl, 4-oxaoctyl, 5-oxaoctyl, 6-oxaoctyl, 7-oxaoctyl, 2-oxanonyl, 3-oxanonyl, 4-oxanonyl, 5-oxanonyl, 6-oxanonyl, 7-oxanonyl, 8-oxanonyl, 2-oxadecyl, 3-oxadecyl, 4-oxadecyl, 5-oxadecyl, 6-oxadecyl, 7-oxadecyl, 8-oxadecyl, 9-oxadecyl, 2-oxaundecyl, 3-oxaundecyl, 4-oxaundecyl, 5-oxaundecyl, 6-oxaundecyl, 7-oxaundecyl, 8-oxaundecyl, 9-oxaundecyl, 10-oxaundecyl, 2-oxatridecyl, 3-oxatridecyl, 4-oxatridecyl, 5-oxatridecyl, 6-oxatridecyl, 7-oxatridecyl, 8-oxatridecyl, 9-oxatridecyl, 10-oxatridecyl, 11-oxatridecyl, 12-oxatridecyl, 2,4-dioxapentyl, 2,4-dioxahexyl, 2,5-dioxahexyl, 3,5-dioxahexyl, 2,4-dioxaheptyl, 2,5-dioxaheptyl, 2,6-dioxaheptyl, 3,5-dioxaheptyl, 3,6-dioxaheptyl or 4,6-dioxaheptyl.
Claim 16
Dependent Claim
21 words
A compound according to claim 7, wherein R is isopropyl, 2-butyl, isobutyl, 2-methylbutyl, isopentyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-oxa-3-methylbutyl or 3-oxa-4-methylpentyl.
Claim 17
Dependent Claim
40 words
A compound of claim 1, wherein X is --O--CO--, --O--CH 2 --, --O--CH 2 CH 2 --, --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --, --CO--O-- or --CH 2 --O--, and p is 0 or 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-01-15 | 1993-07-17 | 1994-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-01-15 | 1997-07-17 | 1998-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-01-15 | 2001-07-17 | 2002-01-16 | $7700.00 | Window Closed / Lapsed |