Patent US3432707A successfully refreshed from Google Patents.
Patent US5037825A successfully refreshed from Google Patents.
US5037825A
Expired / Lapsed
US
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Condensed heterocyclic compounds
Assignee: F Hoffmann La Roche AG
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Filing: 1989-07-10
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Granted: 1991-08-06
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Expires: 2009-07-10
Abstract
Abstract The invention relates to compounds of the formula <IMAGE> I wherein R1 is hydrogen, acyl, lower-alkyl or -CHO, -CH2OR10, -COR7 or OR13; R2, R3 and R4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R5 and R6 are, independently, hydrogen or lower-alkyl; R7 is hydroxy, lower-alkoxy or NR8R9; R8 and R9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR14R15, -O-, -S-, >SO, >SO2 or >NR18; R10 and R18 are, independently, hydrogen, lower-alkyl or acyl; M is -C(R11)=C(R12)-, -CONH- or -NH-CO-; R11, R12, R14 and R15 are, independently, hydrogen or lower-alkyl, R13 is hydrogen, lower-alkoxycarbonyl or lower- alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazino; and n is 1, 2, 3 or 4; with the proviso that at least one of X and Y comprises a hetero atom and n is 1, 3 or 4 when X contains a hetero atom, Y is >C(CH3)2 and R1 is lower-alkyl or -CH2OR10 or -COR7, or a salt of a compound of formula I, when R1 is carboxy. The compounds of formula I are useful in the treatment of prophylaxis of neoplasms, dermatoses and ageing of the skin.
Inventors
- 👤 Michael Klaus
- 👤 Peter Mohr
- 👤 Ekkehard Weiss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 10:25
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D223/00; C07D223/14; C07D223/16; A; A61; A61P; A61P17/00; A61P29/00; A61P35/00; A61P43/00; C07D215/00; C07D215/02; C07D215/04; C07D215/06; C07D215/12; C07D215/16; C07D215/48; C07D241/00; C07D241/36; C07D241/50; C07D241/52; C07D243/00; C07D243/06; C07D243/10; C07D243/12; C07D281/00; C07D281/02; C07D281/04; C07D281/08; C07D281/10; C07D311/58; C07D315/00; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/54; C07D317/60; C07D319/00; C07D319/10; C07D319/14; C07D319/16; C07D319/18; C07D321/00; C07D321/02; C07D321/10; C07D327/00; C07D327/02; C07D327/04; C07D327/06; C07D335/00; C07D335/04; C07D335/06; C07D337/00; C07D337/02; C07D337/06; C07D337/08; C07D339/00; C07D339/02; C07D339/06; C07D339/08; C07D417/00; C07D417/02; C07D417/12
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
160 words
A compound of the formula ##STR12## wherein A is --CR 5 R 6 ) n , R 1 is hydrogen, acyl, lower-alkyl or --CHO, --CH 2 OR 10 , --COR 7 or OR 13 ; R 2 , R 3 and R 4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R 5 and R 6 are, independently, hydrogen or lower-alkyl; R 7 is hydroxy, lower-alkoxy or NR 8 R 9 ; R 8 and R 9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, --S--, >SO or SO 2 ; R 10 is hydrogen, lower-alkyl or acyl; M is --C(R 11 )═C(R 12 )--, --CONH-- or --NH--CO--; R 11 and R 12 are, independently, hydrogen or lower-alkyl, R 13 is hydrogen, lower-alkoxycarbonyl or lower-alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazine, and n is 1, 2, 3 or 4, or a salt of a compound of formula I, when R 1 is carboxy.
Claim 2
Dependent Claim
160 words
A compound of the formula ##STR12## wherein A is --CR 5 R 6 ) n , R 1 is hydrogen, acyl, lower-alkyl or --CHO, --CH 2 OR 10 , --COR 7 or OR 13 ; R 2 , R 3 and R 4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R 5 and R 6 are, independently, hydrogen or lower-alkyl; R 7 is hydroxy, lower-alkoxy or NR 8 R 9 ; R 8 and R 9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, --S--, >SO or SO 2 ; R 10 is hydrogen, lower-alkyl or acyl; M is --C(R 11 )═C(R 12 )--, --CONH-- or --NH--CO--; R 11 and R 12 are, independently, hydrogen or lower-alkyl, R 13 is hydrogen, lower-alkoxycarbonyl or lower-alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazine, and n is 1, 2, 3 or 4, or a salt of a compound of formula I, when R 1 is carboxy.
Claim 3
Dependent Claim
26 words
A compound in accordance with claim 1, wherein R 13 is hydrogen or unsubstituted lower-alkyl or lower-alkyl substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazino.
Claim 4
Dependent Claim
15 words
A compound in accordance with claim 2, wherein M is --C(R 11 )═C(R 12 )--.
Claim 5
Dependent Claim
11 words
A compound in accordance with claim 2, wherein M is --CONH--.
Claim 6
Dependent Claim
13 words
A compound in accordance with claim 4, wherein X and Y are --S--.
Claim 7
Dependent Claim
19 words
A compound in accordance with claim 1, selected from the group consisting of p-[(E)-2-(3,4-Dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoic acid and its lower-alkyl esters.
Claim 8
Dependent Claim
9 words
A compound in accordance with claim 1, Ethyl p-[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoate.
Claim 9
Dependent Claim
168 words
A pharmaceutical composition comprising a compound of the formula ##STR13## wherein A is --CR 5 R 6 ) n , R 1 is hydrogen, acyl, lower-alkyl or --CHO, --CH 2 OR 10 , --COR 7 or OR 13 ; R 2 , R 3 and R 4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R 5 and R 6 are, independently, hydrogen or lower-alkyl; R 7 is hydroxy, lower-alkoxy or NR 8 R 9 ; R 8 and R 9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, --S--, >SO or SO 2 ; R 10 is hydrogen, lower-alkyl or acyl; M is --C(R 11 )═C(R 12 )--, --CONH-- or --NH--CO--; R 11 and R 12 are, independently, hydrogen or lower-alkyl, R 13 is hydrogen, lower-alkoxycarbonyl or lower-alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazine, and n is 1, 2, 3 or 4, or a salt of a compound of formula I, when R 1 is carboxy, and an inert carrier.
Claim 10
Dependent Claim
168 words
A pharmaceutical composition comprising a compound of the formula ##STR13## wherein A is --CR 5 R 6 ) n , R 1 is hydrogen, acyl, lower-alkyl or --CHO, --CH 2 OR 10 , --COR 7 or OR 13 ; R 2 , R 3 and R 4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R 5 and R 6 are, independently, hydrogen or lower-alkyl; R 7 is hydroxy, lower-alkoxy or NR 8 R 9 ; R 8 and R 9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, --S--, >SO or SO 2 ; R 10 is hydrogen, lower-alkyl or acyl; M is --C(R 11 )═C(R 12 )--, --CONH-- or --NH--CO--; R 11 and R 12 are, independently, hydrogen or lower-alkyl, R 13 is hydrogen, lower-alkoxycarbonyl or lower-alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazine, and n is 1, 2, 3 or 4, or a salt of a compound of formula I, when R 1 is carboxy, and an inert carrier.
Claim 11
Dependent Claim
27 words
A pharmaceutical composition in accordance with claim 8, wherein R 13 is hydrogen or unsubstituted lower-alkyl or lower-alkyl substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazino.
Claim 12
Dependent Claim
16 words
A pharmaceutical composition in accordance with claim 9, wherein M is --C(R 11 )═C(R 12 ).
Claim 13
Dependent Claim
12 words
A pharmaceutical composition in accordance with claim 9, wherein M is --CONH--.
Claim 14
Dependent Claim
14 words
A pharmaceutical composition in accordance with claim 11, wherein X and Y are --S--.
Claim 15
Dependent Claim
24 words
A pharmaceutical composition in accordance with claim 8, wherein compound I is selected from the group consisting of p-[(E)-2-(3,4-Dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoic acid and its lower-alkyl esters.
Claim 16
Dependent Claim
10 words
A pharmaceutical composition in accordance with claim 8, Ethyl p-[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoate.
Claim 17
Dependent Claim
182 words
Method of treating inflammatory, allergic rheumatic or immunological disorders which comprises administering to a host requiring such treatment an effective amount of a compound of the formula ##STR14## wherein A is --CR 5 R 6 ) n , R 1 is hydrogen, acyl, lower-alkyl or --CHO, --CH 2 OR 10 , --COR 7 or OR 13 ; R 2 , R 3 and R 4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R 5 and R 6 are, independently, hydrogen or lower-alkyl; R 7 is hydroxy, lower-alkoxy or NR 8 R 9 ; R 8 and R 9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, --S--, >SO or SO 2 ; R 10 is hydrogen, lower-alkyl or acyl; M is --C(R 11 )═C(R 12 )--, --CONH-- or --NH--CO--; R 11 and R 12 are, independently, hydrogen or lower-alkyl, R 13 is hydrogen, lower-alkoxycarbonyl or lower-alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazine, and n is 1, 2, 3 or 4, or a salt of a compound of formula I, when R 1 is carboxy.
Claim 18
Dependent Claim
182 words
Method of treating inflammatory, allergic rheumatic or immunological disorders which comprises administering to a host requiring such treatment an effective amount of a compound of the formula ##STR14## wherein A is --CR 5 R 6 ) n , R 1 is hydrogen, acyl, lower-alkyl or --CHO, --CH 2 OR 10 , --COR 7 or OR 13 ; R 2 , R 3 and R 4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R 5 and R 6 are, independently, hydrogen or lower-alkyl; R 7 is hydroxy, lower-alkoxy or NR 8 R 9 ; R 8 and R 9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, --S--, >SO or SO 2 ; R 10 is hydrogen, lower-alkyl or acyl; M is --C(R 11 )═C(R 12 )--, --CONH-- or --NH--CO--; R 11 and R 12 are, independently, hydrogen or lower-alkyl, R 13 is hydrogen, lower-alkoxycarbonyl or lower-alkyl, which can be substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazine, and n is 1, 2, 3 or 4, or a salt of a compound of formula I, when R 1 is carboxy.
Claim 19
Dependent Claim
26 words
A method in accordance with claim 15, wherein R 13 is hydrogen or unsubstituted lower-alkyl or lower-alkyl substituted by amino, mono-alkylamino, di-alkylamino, morpholino, thiomorpholino or piperazino.
Claim 20
Dependent Claim
15 words
A method in accordance with claim 16, wherein M is --C(R 11 )═C(R 12 )--.
Claim 21
Dependent Claim
11 words
A method in accordance with claim 16, wherein M is --CONH--.
Claim 22
Dependent Claim
13 words
A method in accordance with claim 18, wherein X and Y are --S--.
Claim 23
Dependent Claim
23 words
A method in accordance with claim 15, wherein compound I is selected from the group consisting of p-[(E)-2-(3,4-Dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoic acid and its lower-alkyl esters.
Claim 24
Dependent Claim
13 words
A method in accordance with claim 15, wherein compound I is Ethyl p-[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoate.
Claim 25
Dependent Claim
9 words
A compound in accordance with claim 6, p-[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7'-yl)propenyl)benzoic acid.
Claim 26
Dependent Claim
41 words
A compound in accordance with claim 1, selected from the group consisting of: ethyl p-[(E)-2-(1,4-benzodithian-6-yl)propenyl]benzoate, p-[(E)-2-(1,4-benzodithian-6-yl)propenyl]benzoic acid, ethyl p-[(E)-2-(3,4-dihydro-3-methyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoate, ethyl p-[(E)-2-(3,4-dihydro-2H-1,5-benzodithiepin-7-yl)propenyl]benzoate, ethyl p-[(E)-2-(3',4'-dihydro-3',3'-dimethyl-2'H-1,5-benzodithiepin-7'-yl)propenyl]benzoate 1',1',5',5'-tetroxide, p-[(E)-2-(3,4-dihydro-3-methyl-2-H-1,5-benzodithiepin-7-yl)propenyl]benzoic acid, methyl -p[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]benzoate, 4-[2-[p-[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]phenoxy]ethyl]morpholine, N,N-dimethyl-2-[p-[(E)-2-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl)propenyl]phenoxy]ethylamine, p-[(E)-2-(3,4-dihydro-2H-1,5-benzodithiepin-7-yl)propenyl]benzoic acid, methyl p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]benzoate, 4-[2-[p-(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine, 2,2-dimethyl-5-[(E)-α-methylstyryl]-1,3-benzodithiol, p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenyl carbonate, p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenol, p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]benzoic acid,
Claim 27
Dependent Claim
4 words
4-dihydro-3,3-dimethyl-7-[(E)-α-methylstyryl]-2H-1,5-benzodithiepine, and p-[(E)-2-(2-methyl-1,3-benzodithiol-5-yl)propenyl]benzoic acid.
Claim 28
Dependent Claim
4 words
4-dihydro-3,3-dimethyl-7-[(E)-α-methylstyryl]-2H-1,5-benzodithiepine, and p-[(E)-2-(2-methyl-1,3-benzodithiol-5-yl)propenyl]benzoic acid.
Claim 29
Dependent Claim
18 words
A compound in accordance with claim 1, selected from the group consisting of ethyl p-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepine-7-carboxamido)benzoate, and p-(3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepine-7-carboxyamido)benzoic acid.
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