Claims
- 1. A compound of formula I ##STR18## wherein R.sub.1 denotes C.sub.1 -C.sub.6 -alkyl, substituted C.sub.1 -C.sub.6 -alkyl, C(O)O--C.sub.1 -C.sub.4 -alkyl, C(O)OH, or a residue selected from ##STR19## wherein R.sub.5 is one, two, three, or four of the residues which are independent of each other and selected from the group consisting of H, C.sub.1 -C.sub.6 -alkyl, substituted C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy, carboxy, cyano, NHC(O)C.sub.1 -C.sub.3 -alkyl, --OC.sub.1 -C.sub.3 -alkyl-phenyl, C.sub.1 -C.sub.4 -alkyl-O--C.sub.1 -C.sub.4 -alkyl, --O--C(O)--C.sub.1 -C.sub.4 -alkyl, --C(O)--O--C.sub.1 -C.sub.4 -alkyl, halogen, amino, nitro, --NH--C.sub.1 -C.sub.4 -alkyl, --N--(C.sub.1 -C.sub.4 -alkyl).sub.2, and --C.sub.1 -C.sub.4 -alkyl-R.sub.6 wherein R.sub.6 is a residue selected from ##STR20## X is O, S, N--H, N--C.sub.1 -C.sub.6 -alkyl; R.sub.2 is H, C.sub.1 -C.sub.6 -alkyl, --C(O)--C.sub.1 -C.sub.6 -alkyl;
- R.sub.3 is one, two, or three of the residues which are independent of each other and selected from the group consisting of H, C.sub.1 -C.sub.6 -alkyl, --C(O)--C.sub.1 -C.sub.6 -alkyl, --C(O)--O--C.sub.1 -C.sub.6 -alkyl, OH, O--C.sub.1 -C.sub.6 -alkyl, --O--C(O)--C.sub.1 -C.sub.6 -alkyl, halogen;
- R.sub.4 is H, --OH, --O--C.sub.1 -C.sub.6 -alkyl, --O--C(O)--C.sub.1 -C.sub.6 -alkyl, --C(O)--OH, --C(O)--O--C.sub.1 -C.sub.6 -alkyl, O--C(O)--(C.sub.1 -C.sub.4 -alkyl)-NH.sub.2, O--C(O)--(C.sub.1 -C.sub.4 -alkyl-NH--(C.sub.1 -C.sub.4 -alkyl), O--C(O)--(C.sub.1 -C.sub.4 -alkyl)-N--(C.sub.1 -C.sub.4 -alkyl).sub.2,
- n=0, 1 or 2 and
- a represents an optional additional single bond,
- or a physiologically tolerable salt thereof.
- 2. A compound of formula I as claimed in claim 1, wherein said compound has the formula ##STR21## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and a are as previously defined, or a physiologically tolerable salt thereof.
- 3. A compound of formula I as claimed in claim 1, in which R.sub.1 is ##STR22## R.sub.5 denoting H, C.sub.1 -C.sub.6 -alkyl, substituted C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.3 -alkoxy, halogen, C.sub.1 -C.sub.4 -alkyl-R.sub.6 wherein R.sub.6 stands for ##STR23## R.sub.4 denotes H, OH or --O--C(O)--(C.sub.1 -C.sub.4 -alkyl)-NH.sub.2 ; X stands for O, NH, S, N--C.sub.1 -C.sub.6 -alkyl; and
- a stands for an optional additional bond,
- or a physiologically tolerable salt thereof.
- 4. A process for the production of a compound of formula I as claimed in claim 1 wherein a compound of formula V ##STR24## A) is converted into a compound of formula VI, R.sub.4 denoting OH ##STR25## by treatment with a borane-solvent-complex followed by oxidation or B) to get a compound of formula VI, a compound of formula V is treated with a peracid and the epoxide thus produced is treated with a hydride reagent or
- C) the compound of formula VI is produced by condensation of a suitable arene with cyclohexene oxide in the presence of an acid catalyst and
- D) a compound of formula VI is treated with acetic anhydride and a mineral acid to give a compound of formula VII, ##STR26## wherein R.sub.2 is methyl and R.sub.4 is O--C(O)--Me and E) a compound of formula VII as described under D) is demethylated by treatment with a Lewis acid or a demethylating agent to give a compound of formula VII wherein R.sub.2 denotes H and R.sub.4 denotes OC(O)Me and
- F) a compound of formula VII wherein R.sub.2 denotes H and R.sub.4 denotes OH is produced by treatment of a compound produced under E) with dilute alkali, and
- G) the compound of formula VII is converted into a compound of formula I (a=additional bond) by treatment with an appropriate aldehyde in the presence of a base and a compound of formula I (a=no additional bond) is produced by hydrogenation of the compound of formula I (a=additional bond), R.sub.1, R.sub.2 and R.sub.3, where not explained explicitly, having the meaning as defined in claim 1.
- 5. A pharmaceutical composition containing an effective amount for the treatment of inflammatory conditions of at least one compound of the formula I or physiologically tolerated salt thereof as claimed in claim 1 together with a pharmaceutically acceptable carrier.
- 6. A method for the treatment of inflammatory conditions, which comprises administering an effective amount of at least one compound of the formula I or physiologically tolerated salt thereof as claimed in claim 1 to a host in need of such treatment.
- 7. A method as claimed in claim 6 for the treatment of chronic inflammatory conditions.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 92 100 664 |
Jan 1992 |
EPX |
|
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of application Ser. No. 08/692,129 filed Aug. 5, 1996 now U.S. Pat. No. 5,776,977, issued Jul. 7, 1998, which is a division of application Ser. No. 08/444,518 filed May 19, 1995, now U.S. Pat. No. 5,589,514 issued Dec. 31, 1996, which was a continuation of application Ser. No. 08/002,863 filed Jan. 14, 1993, abandoned, all of which are incorporated herein by reference.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
|
5776977 |
Naik et al. |
Jul 1998 |
|
Divisions (1)
|
Number |
Date |
Country |
| Parent |
444518 |
May 1995 |
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Continuations (1)
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Number |
Date |
Country |
| Parent |
002863 |
Jan 1993 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
| Parent |
692129 |
Aug 1996 |
|
Patent Grant
6159988
