Claims
- 1. A diphenylheteroalkyl derivative of the formula I ##STR17## where A is --X--CH.sub.2 -- or ##STR18## where X can be linked to the left or right phenyl nucleus and is oxygen, --S(O).sub.n -- or --NR.sup.7 -- (with n being 0, 1 or 2),
- R.sup.1, R.sup.2 and R.sup.3 are, independently of one another, hydrogen or halogen, C.sub.1-6 -alkyl or OR.sup.7, and one of the three radicals can also be nitro,
- R.sup.4 and R.sup.5 are, independently of one another, hydrogen, OR.sup.7, C.sub.1-6 -alkyl or together form a --C(CH.sub.3).sub.2 --B-- C(CH.sub.3).sub.2 -ring (with B being --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --CH.sub.2 CHOH--, --CH.dbd.CH-- or --CH(CH.sub.3)--) or a --O--C(CH.sub.3) (Z )--CH.sub.2 --CH.sub.2 -- ring (with Z=methyl or ethyl, each of which can be substituted by OR.sup.7), with R.sup.4 and R.sup.5 together forming a ring of the said type, or R.sup.4 being a branched C.sub.3-6 -alkyl or -alkoxy when R.sup.1 to R.sup.3 are hydrogen, and R.sup.4 and R.sup.5 together forming a ring of the said type, or R.sup.4 (alone) or R.sup.3 and R.sup.5 (together) each being a branched C.sub.1-3 -alkyl when R.sup.6 is hydrogen, methyl, nitro, OH or SH,
- R.sup.6 is hydrogen, methyl, nitro, cyano, tetrazolyl or --CH.sub.2 OR.sup.7, --OR.sup.8, --NR.sup.9 R.sup.10, --CH.sub.2 NR.sup.9 R.sup.10, --SR.sup.10, --CH(OR.sup.11).sub.2, --S(O).sub.n R.sup.12 (n=1 or 2), --PO(OR.sup.13).sub.2, --NR.sup.13 OR.sup.19, --SO.sub.3 H or --C(O)R.sup.14, where
- R.sup.7 is hydrogen, C.sub.1-6 -alkyl or C.sub.1-6 -alkanoyl,
- R.sup.8 is hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -alkanoyl, or benzoyl which can be substituted, or --CH.sub.2 C(O)R.sup.15 -- with R.sup.15 being hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, hydroxyl or --NR.sup.16 R.sup.17),
- R.sup.9 and R.sup.10 are, independently of one another, hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkanoyl, or benzyl or benzoyl which can be substituted by hydroxyl or C.sub.1-4 -alkoxy,
- R.sup.11 is C.sub.1-6 -alkoxy, it being possible for the two R.sup.11 radicals to form a cyclic acetal with the CH group,
- R.sup.12 is C.sub.1-6 -alkyl, n being 1 or 2
- R.sup.13 and R.sup.19 are, independently of one another, hydrogen or C.sub.1-3 -alkyl,
- R.sup.14 is hydrogen or halogen, hydroxyl, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, or phenoxy or benzyloxy which can be substituted by hydroxyl or C.sub.1-4 -alkoxy, or --NR.sup.16 R.sup.17 with R.sup.16 and R.sup.17 being, independently of one another, hydrogen, C.sub.1-4 -alkyl, or benzyl which can be substituted by hydroxyl or C.sub.1-4 -alkoxy,
- and the physiologically tolerated salts thereof.
- 2. A diphenylheteroalkyl derivative of the formula I as claimed in claim 1, wherein
- X is oxygen, sulfur or NH,
- R.sup.4 and R.sup.5 together form a ring of the type mentioned in claim 1, or
- R.sup.3 and R.sup.5 is each branched C.sub.3-6 -alkyl.
- 3. A diphenylheteroalkyl derivative of the formula I as claimed in claim 1, wherein R.sup.6 is --CH.sub.2 OR.sup.7, --OR.sup.8, --SR.sup.10, --SO.sub.2 R.sup.12, --SO.sub.3 H, --PO(OR.sup.13).sub.2 or --C(O)R.sup.14.
- 4. A diphenylheteroalkyl derivative of the formula I as claimed in claim 1, wherein
- X is oxygen, sulfur or NH,
- R.sup.4 and R.sup.5 together form a ring of the type mentioned in claim 1, or
- R.sup.3 and R.sup.5 are each branched C.sub.3-6 -alkyl with R.sup.4 being hydrogen or --OR.sup.7, and
- R.sup.6 is --CH.sub.2 OR.sup.7, --OR.sup.8, --SR.sup.10, --SO.sub.2 R.sup.12, --SO.sub.3 H, --PO(OR.sup.13).sub.2 or --C(O)R.sup.14.
- 5. A drug for topical use which contains as active substance 0.001 to 1% by weight of a diphenylheteroalkyl derivative of the formula I as claimed in claim 1 in addition to conventional pharmaceutical auxiliaries.
- 6. A drug for systemic use which contains as active substance 0.1 to 250 mg of a diphenylheteroalkyl derivative of the formula I as claimed in claim 1 per single dose, in addition to conventional pharmaceutical auxiliaries.
- 7. A cosmetic preparation which contains 0.001 to 1% by weight of a diphenylheteroalkyl derivative of the formula I as claimed in claim 1 in addition to conventional cosmetic auxiliaries.
- 8. A drug or cosmetic as claimed in claim 5 or 7 for the treatment of acne or psoriasis or other dermatological disorders associated with pathological keratinization as well as of eczema, warts, vitiligo, UV-induced or iatrogenic damage to the skin and of precanceroses and tumors and dry eyes and other corneopathies.
- 9. A drug as claimed in claim 6 for the treatment of rheumatic and arthritic disorders.
Priority Claims (1)
Number |
Date |
Country |
Kind |
39 03 989.7 |
Feb 1989 |
DEX |
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Parent Case Info
This is a division of application Ser. No. 08/297,537, filed on Aug. 31, 1994, U.S. Pat. No. 5,527,945, which is a continuation of application Ser. No. 08/085,101, filed Jul. 2, 1993, abandoned, which is a divisional of application Ser. No. 07/985,934, filed Dec. 4, 1992 now U.S. Pat. No. 5,248,823, which is a divisional of application Ser. No. 07/785,829, filed Oct. 31, 1991 now U.S. Pat. No. 5,225,601, which is a divisional of application Ser. No. 07/469,063, filed Jan. 23, 1990 now U.S. Pat. No. 5,087,743.
US Referenced Citations (6)
Foreign Referenced Citations (4)
Number |
Date |
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0170105 |
Feb 1986 |
EPX |
0276065 |
Jul 1988 |
EPX |
2413382 |
Jul 1979 |
FRX |
3524199 |
Jan 1986 |
DEX |
Non-Patent Literature Citations (1)
Entry |
Journal Of Medicinal Chemistry, vol. 31, No. 11, pp. 2182-2192, Nov. 1988, H. Kagechika, et al., "Retinobenzoic Acids. 1. Structure-Activity Relationships Of Aromatic Amides With Retinoidal Activity". |
Divisions (4)
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297537 |
Aug 1994 |
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985934 |
Dec 1992 |
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785829 |
Oct 1991 |
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469063 |
Jan 1990 |
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Continuations (1)
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85101 |
Jul 1993 |
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