# US 4,396,553 A · Tetrahydronaphthalene and indane compounds useful as anti-tumor agents

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- Number: US 4,396,553 A
- Document ID: US4396553A
- Status: Granted
- Kind: A
- Application number: 06/345,518
- Filed: 1982-02-04
- Granted: 1983-08-02
- Earliest claimed: 1981-02-13
- Assignees: Hoffmann-La Roche Inc.
- Inventors: Michael Klaus
- Web page: https://patentgrep.com/patent/US4396553A

## CPC

- C07C 321/00: Thiols, sulfides, hydropolysulfides or polysulfides
- C07C 17/2635: {involving a phosphorus compound, e.g. Wittig synthesis}
- C07C 309/00: Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C 317/00: Sulfones; Sulfoxides
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

This invention is directed to tetrahydronaphthalene and indane compounds and processes thereto. These compounds are useful as tumor inhibiting agents, in the treatment of neoplasms and dermatological conditions.

## Claims

### Claim 1

Compounds of the formula ##STR8## wherein n represents 1 or 2; Z represents mercapto or --S(O).sub.m R, wherein m represents 0, 1 or 2; R represents lower-alkyl, lower-alkenyl, lower-alkoxy-lower-alkyl, lower-alkanoyl-lower-alkyl, hydroxy-lower-alkyl, halo-lower-alkyl, lower-carbalkoxy-lower-alkyl or, when m is 1 or 2, R represents also lower-alkoxy, hydroxy, mono-lower-alkyl amino or di-lower-alkylamino,
and pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

Compounds according to claim 1 wherein n is 2, m is 0 and R is selected from the group consisting of methyl and ethyl.

### Claim 3 (depends on 2)

A compound according to claim 2 which is methyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phide.

### Claim 4 (depends on 2)

A compound according to claim 2 which is ethyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phide.

### Claim 5 (depends on 1)

Compounds according to claim 1 wherein n is 2, m is 1 and R is selected from the group consisting of methyl and ethyl.

### Claim 6 (depends on 5)

A compound according to claim 5 which is methyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phoxide.

### Claim 7 (depends on 5)

A compound according to claim 5 which is ethyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsup hhoxide.

### Claim 8 (depends on 1)

A compound according to claim 1 wherein n is 2, m is 2 and R is selected from the group consisting of methyl, ethyl, propyl, isopropyl, methylpropyl, chloroethyl, allyl, vinyl, trifluoroethyl, ethoxy, acetyl, hydroxyethyl, hydroxy and ethylamino.

### Claim 9 (depends on 8)

A compound according to claim 8 which is N-ethyl-p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]b enzenesulphonamide.

### Claim 10 (depends on 8)

A compound according to claim 8 which is ethyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzenesu lphinate.

### Claim 11 (depends on 8)

A compound according to claim 8 which is ethyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 12 (depends on 8)

A compound according to claim 8 which is methyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 13 (depends on 8)

A compound according to claim 8 which is allyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-phenylsu lphone.

### Claim 14 (depends on 8)

A compound according to claim 8 which is 2,2,2-trifluoroethyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 15 (depends on 8)

A compound according to claim 8 which is propyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 16 (depends on 8)

A compound according to claim 8 which is isopropyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 17 (depends on 8)

A compound according to claim 8 which is 1-methylpropyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 18 (depends on 8)

A compound according to claim 8 which is 2-[[p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]pheny l]sulphonyl]-ethanol.

### Claim 19 (depends on 8)

A compound according to claim 8 which is vinyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 20 (depends on 8)

A compound according to claim 8 which is 2-chloroethyl p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]phenylsul phone.

### Claim 21 (depends on 8)

A compound according to claim 8 which is ethyl[[p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]ph enyl]sulphonyl]acetate.

### Claim 22 (depends on 8)

A compound according to claim 8 which is p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzenesu lphonic acid.

### Claim 23 (depends on 1)

Compounds according to claim 1 which are salts of sulphonic acids or sulphinic acids.

### Claim 24 (depends on 23)

A compound according to claim 23 which is sodium p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzenesu lphinate.

### Claim 25 (depends on 23)

A compound according to claim 23 which is sodium p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzenesu lphonate.