US4462923A
Expired / Lapsed
US
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Disubstituted pyrimidines
Assignee: F Hoffmann La Roche AG
•
Filing: 1981-10-07
•
Granted: 1984-07-31
•
Expires: 2001-10-07
Abstract
Abstract Pyrimidines of the formula: ##STR1## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14 are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.
Inventors
- 👤 Arthur Boller
- 👤 Martin Schadt
- 👤 Alois Villiger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 10:16
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C255/00; C07C45/00; C07C45/004; C07C45/45; C07C45/46; C07C45/56; C07C45/562; C07C45/61; C07C45/62; C07C49/00; C07C49/29; C07C49/313; C07C49/323; C07C49/587; C07C49/613; C07C49/617; C07C49/623; C07C49/637; C07C49/76; C07C49/782; C07C49/792; C07C61/00; C07C61/12; C07C61/125; C07C61/13; C07C63/00; C07C63/33; C07C63/49; C07D239/28; C07D239/30; C07D295/00; C07D295/02; C07D295/027; C07D295/033; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3402; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469; C07C2531/00; C07C2531/16; C07C2531/22; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/26; C07C2602/28; C09K2019/3422; C09K2019/3425
Claims Analysis
Total Claims: 91
Claim 1
Independent Claim
119 words
A compound of the formula: ##STR30## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 2
Dependent Claim
119 words
A compound of the formula: ##STR30## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 3
Dependent Claim
13 words
The compound of claim 1 wherein Y is nitrogen and Z is ═CH--.
Claim 4
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is cyano.
Claim 5
Dependent Claim
14 words
The compound of claim 3 wherein R 1 is said straight chain alkyl group.
Claim 6
Dependent Claim
20 words
The compound of claim 4 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 7
Dependent Claim
6 words
The compound of claim 3, trans-2-(4-propylcyclohexyl)-5-pyrimidinecarbonitrile.
Claim 8
Dependent Claim
6 words
The compound of claim 3, trans-2-(4-methylcyclohexyl)-5-pyrimidinecarbonitrile.
Claim 9
Dependent Claim
6 words
The compound of claim 3, trans-2-(4-ethylcyclohexyl)-5-pyrimidinecarbonitrile.
Claim 10
Dependent Claim
6 words
The compound of claim 3, trans-2-(4-butylcyclohexyl)-5-pyrimidinecarbonitrile.
Claim 11
Dependent Claim
6 words
The compound of claim 3, trans-2-(4-pentylcyclohexyl)-5-pyrimidinecarbonitrile.
Claim 12
Dependent Claim
14 words
The compound of claim 2 wherein R 2 is said straight chain alkyl group.
Claim 13
Dependent Claim
20 words
The compound of claim 11 wherein said straight chain alkyl group for R 2 has 2 to 7 carbon atoms.
Claim 14
Dependent Claim
14 words
The compound of claim 12 wherein R 1 is said straight chain alkyl group.
Claim 15
Dependent Claim
20 words
The compound of claim 13 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 16
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-pentylcyclohexyl)-5-heptylpyrimidine.
Claim 17
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-propylcyclohexyl)-5-propylpyrimidine.
Claim 18
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-propylcyclohexyl)-5-butylpyrimidine.
Claim 19
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-pentylcyclohexyl)-5-propylpyrimidine.
Claim 20
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-pentylcyclohexyl)-5-butylpyrimidine.
Claim 21
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-pentylcyclohexyl)-5-pentylpyrimidine.
Claim 22
Dependent Claim
6 words
The compound of claim 14, trans-2-(4-heptylcyclohexyl)-5-heptylpyrimidine.
Claim 23
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is p-alkylphenyl.
Claim 24
Dependent Claim
17 words
The compound of claim 22 wherein the alkyl in said p-alkylphenyl is said straight chain alkyl group.
Claim 25
Dependent Claim
19 words
The compound of claim 23 wherein said straight chain alkyl group in p-alkylphenyl has 2 to 7 carbon atoms.
Claim 26
Dependent Claim
14 words
The compound of claim 22 wherein R 1 is said straight chain alkyl group.
Claim 27
Dependent Claim
20 words
The compound of claim 25 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 28
Dependent Claim
6 words
The compound of claim 26, trans-2-(4-pentylcyclohexyl)-5-(p-butylphenyl)pyrimidine.
Claim 29
Dependent Claim
6 words
The compound of claim 26, trans-2-(4-propylcyclohexyl)-5-(p-butylphenyl)pyrimidine.
Claim 30
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is trans-4-alkylcyclohexyl.
Claim 31
Dependent Claim
17 words
The compound of claim 29 wherein the alkyl in said trans-4-alkylcyclohexyl is said straight chain alkyl group.
Claim 32
Dependent Claim
14 words
The compound of claim 29 wherein R 1 is said straight chain alkyl group.
Claim 33
Dependent Claim
13 words
The compound of claim 1 wherein Z is nitrogen and Y is ═CH--.
Claim 34
Dependent Claim
10 words
The compound of claim 32 wherein R 2 is cyano.
Claim 35
Dependent Claim
14 words
The compound of claim 33 wherein R 1 is said straight chain alkyl group.
Claim 36
Dependent Claim
20 words
The compound of claim 34 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 37
Dependent Claim
6 words
The compound of claim 35, trans-5-(4-pentylcyclohexyl)-2-pyrimidinecarbonitrile.
Claim 38
Dependent Claim
6 words
The compound of claim 35, trans-5-(4-heptylcyclohexyl)-2-pyrimidinecarbonitrile.
Claim 39
Dependent Claim
14 words
The compound of claim 33 wherein R 1 is said branched chain alkyl group.
Claim 40
Dependent Claim
6 words
The compound of claim 38, (+)-trans-5-[4-(2-methylbutyl)cyclohexyl]-2-pyrimidinecarbonitrile.
Claim 41
Dependent Claim
14 words
The compound of claim 32 wherein R 2 is said straight chain alkyl group.
Claim 42
Dependent Claim
20 words
The compound of claim 40 wherein said straight chain alkyl group for R 2 has 2 to 7 carbon atoms.
Claim 43
Dependent Claim
14 words
The compound of claim 40 wherein R 1 is said straight chain alkyl group.
Claim 44
Dependent Claim
20 words
The compound of claim 42 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 45
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-propylcyclohexyl)-2-pentylpyrimidine.
Claim 46
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-ethylcyclohexyl)-2-pentylpyrimidine.
Claim 47
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-propylcyclohexyl)-2-propylpyrimidine.
Claim 48
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-propylcyclohexyl)-2-butylpyrimidine.
Claim 49
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-pentylcyclohexyl)-2-propylpyrimidine.
Claim 50
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-pentylcyclohexyl)-2-butylpyrimidine.
Claim 51
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-pentylcyclohexyl)-2-pentylpyrimidine.
Claim 52
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-heptylcyclohexyl)-2-propylpyrimidine.
Claim 53
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-heptylcyclohexyl)-2-butylpyrimidine.
Claim 54
Dependent Claim
6 words
The compound of claim 43, trans-5-(4-heptylcyclohexyl)-2-pentylpyrimidine.
Claim 55
Dependent Claim
10 words
The compound of claim 32 wherein R 2 is p-alkylphenyl.
Claim 56
Dependent Claim
17 words
The compound of claim 54 wherein the alkyl in said p-alkylphenyl is said straight chain alkyl group.
Claim 57
Dependent Claim
20 words
The compound of claim 55 wherein said straight chain alkyl group in said p-alkylphenyl has 2 to 7 carbon atoms.
Claim 58
Dependent Claim
14 words
The compound of claim 55 wherein R 1 is said straight chain alkyl group.
Claim 59
Dependent Claim
20 words
The compound of claim 57 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 60
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-propylcyclohexyl)-2-(p-pentylphenyl)pyrimidine.
Claim 61
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-ethylcyclohexyl)-2-(p-propylphenyl)pyrimidine.
Claim 62
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-ethylcyclohexyl)-2-(p-butylphenyl)pyrimidine.
Claim 63
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-ethylcyclohexyl)-2-(p-pentylphenyl)pyrimidine.
Claim 64
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-ethylcyclohexyl)-2-(p-heptylphenyl)pyrimidine.
Claim 65
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-propylcyclohexyl)-2(p-propylphenyl)pyrimidine.
Claim 66
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-pentylcyclohexyl)-2-(p-propylphenyl)pyrimidine.
Claim 67
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-pentylcyclohexyl)-2-(p-butylphenyl)pyrimidine.
Claim 68
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-heptylcyclohexyl)-2-(p-ethylphenyl)pyrimidine.
Claim 69
Dependent Claim
6 words
The compound of claim 58, trans-5-(4-heptylcyclohexyl)-2-(p-pentylphenyl)pyrimidine.
Claim 70
Dependent Claim
10 words
The compound of claim 32 wherein R 2 is trans-4-alkylcyclohexyl.
Claim 71
Dependent Claim
18 words
The compound of claim 69 wherein the alkyl group in said trans-4-alkylcyclohexyl is said straight chain alkyl group.
Claim 72
Dependent Claim
20 words
The compound of claim 70 wherein said straight chain alkyl group in said trans-4-alkylcyclohexyl has 2 to 7 carbon atoms.
Claim 73
Dependent Claim
20 words
The compound of claim 70 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 74
Dependent Claim
20 words
The compound of claim 72 wherein said straight chain alkyl group for R 1 has 2 to 7 carbon atoms.
Claim 75
Dependent Claim
6 words
The compound of claim 73, 5-(trans-4-propylcyclohexyl)-2-(trans-4-pentylcyclohexyl)pyrimidine.
Claim 76
Dependent Claim
6 words
The compound of claim 73, 5-(trans-4-heptylcyclohexyl)-2-(trans-4-pentylcyclohexyl)pyrimidine.
Claim 77
Dependent Claim
62 words
The compound of claim 1 wherein Y is nitrogen; Z is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl, where each alkyl denotes a straight chain alkyl group of 2 to 7 carbon atoms; with the proviso that the sum of the carbon atoms in all the alkyl groups within the compound is at most 14.
Claim 78
Dependent Claim
30 words
The compound of claim 1 wherein Y is nitrogen; Z is ═CH--, R 1 and R 2 each are a straight chain alkyl group of 2 to 7 carbon atoms.
Claim 79
Dependent Claim
63 words
The compound of claim 1 wherein Z is nitrogen; Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl, where each alkyl denotes a straight chain alkyl group of 2 to 7 carbon atoms; with the proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 80
Dependent Claim
61 words
The compound of claim 1 wherein Z is nitrogen; Y is ═CH--; R 1 is alkyl; and R 2 is p-alkylphenyl or cyano; where each alkyl denotes a straight chain alkyl group of 2 to 7 carbon atoms with the proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 81
Dependent Claim
130 words
An electro-optical cell containing a liquid crystalline mixture comprising at least one compound of the formula: ##STR31## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 82
Dependent Claim
130 words
An electro-optical cell containing a liquid crystalline mixture comprising at least one compound of the formula: ##STR31## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 83
Dependent Claim
125 words
A liquid crystalline mixture comprising at least one compound of the formula: ##STR32## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 84
Dependent Claim
125 words
A liquid crystalline mixture comprising at least one compound of the formula: ##STR32## wherein Y is nitrogen and Z is ═CH--, or Z is nitrogen and Y is ═CH--; R 1 is alkyl and R 2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched alkyl group of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n , n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14.
Claim 85
Dependent Claim
32 words
The liquid crystalline mixture of claim 81 further comprising a compound of the formula: ##STR33## wherein R 3 is a straight chain alkyl or alkoxy group of 2 to 7 carbon atoms.
Claim 86
Dependent Claim
32 words
The liquid crystalline mixture of claim 81 further comprising at least one compound of the formula: ##STR34## wherein R 4 is a straight chain alkyl group of 3 to 7 carbon atoms.
Claim 87
Dependent Claim
32 words
The liquid crystalline mixture of claim 81 further comprising at least one compound of the formula: ##STR35## wherein R 4 is a straight chain alkyl group of 3 to 7 carbon atoms.
Claim 88
Dependent Claim
32 words
The liquid crystalline mixture of claim 81 further comprising at least one compound of the formula: ##STR36## wherein R 4 is a straight chain alkyl group of 2 to 7 carbon atoms.
Claim 89
Dependent Claim
31 words
The liquid crystalline mixture of claim 81 further comprising at least one compound of the formula: ##STR37## wherein R 5 is straight chain alkyl group of 2 to 7 carbon atoms.
Claim 90
Dependent Claim
49 words
The liquid crystalline mixture of claim 81 further comprising at least one compound of the formula: ##STR38## wherein R 4 is a straight chain alkyl group of 2 to 7 carbon atoms and R 6 is cyano or a straight chain alkoxy group of 1 to 3 carbon atoms.
Claim 91
Dependent Claim
32 words
The liquid crystalline mixture of claim 81 further comprising at least one compound of the formula: ##STR39## wherein R 5 is a straight chain alkyl group of 2 to 7 carbon atoms.
References Cited (Backward Citations)
DE2257588A1
Cited
US3997536A
Cited
US4062798A
Cited
US4130502A
Cited
DE2846409A1
Cited
GB2014130A
Cited
US4309539A
Cited
GB2025449A
Cited
US4348298A
Cited
DE2835492A1
Cited
US4358589A
Cited
US4273929A
Cited
DD145913A1
Cited
DE3014912A1
Cited
DD144409A1
Cited
US4364838A
Cited
US4344856A
Cited
EP0036711A2
Cited
US4335011A
Cited
EP0056501A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-07-31 | 1988-01-30 | 1988-07-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-31 | 1992-01-30 | 1992-07-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-31 | 1996-01-30 | 1996-07-31 | $7700.00 | Window Closed / Lapsed |