# US 5,350,854 A · 2-substituted tertiary carbinol derivative of 1,5-iminosugars

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- Number: US 5,350,854 A
- Document ID: US5350854A
- Status: Granted
- Kind: A
- Application number: 08/089,919
- Filed: 1993-07-12
- Granted: 1994-09-27
- Earliest claimed: 1992-04-01
- Assignees: G. D. Searle & Co.
- Inventors: Ish K. Khanna; Richard A. Mueller; Richard M. Weier
- Web page: https://patentgrep.com/patent/US5350854A

## CPC

- C07D 491/04: Ortho-condensed systems
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Novel 2-alkyl carbinol derivatives of deoxynojirimycin (DNJ) and the chemical synthesis of these derivatives and intermediates therefor from DNJ and their method of inhibiting lentiviruses are disclosed.

## Claims

### Claim 1

A compound of the formula ##STR16## wherein R.sub.3 =MEM, SEM, TBDMS or CH.sub.3, and Z is COOCH.sub.2 Ph.

### Claim 2 (depends on 1)

A compound of claim 1 in which R.sub.3 is 2-(trimethylsilyl)ethoxymethyl.

### Claim 3 (depends on 1)

A compound of claim 1 in which R.sub.3 is tert-butyldimethylsilyl.

### Claim 4 (depends on 1)

A compound of claim 1 in which R.sub.3 is 2-methoxyethoxymethyl.

### Claim 5 (depends on 1)

A Compound of claim 1 in which R.sub.3 is CH.sub.3.

### Claim 6

A compound of the formula ##STR17## wherein R.sub.3 =MEM, SEM, TBDMS or CH.sub.3, and Z is COOCH.sub.2 Ph.

### Claim 7 (depends on 6)

A compound of claim 6 in which R.sub.3 is 2-(trimethylsilyl)ethoxymethyl.

### Claim 8 (depends on 6)

A compound of claim 6 in which R.sub.3 is tertbutyldimethylsilyl.

### Claim 9 (depends on 6)

A compound of claim 6 in which R.sub.3 is 2-methoxyethoxymethyl.

### Claim 10 (depends on 6)

A compound of claim 6 in which R.sub.3 is CH.sub.3.

### Claim 11

A compound of the formula ##STR18## wherein R.sub.3 =MEM, SEM, TBDMS or CH.sub.3, and Z is COOCH.sub.2 Ph.

### Claim 12 (depends on 11)

A compound of claim 11 in which R.sub.3 is 2-(trimethylsilyl)ethoxymethyl.

### Claim 13 (depends on 11)

A compound of claim 11 in which R.sub.3 is tertbutyldimethylsilyl.

### Claim 14 (depends on 11)

A compound of claim 11 in which R.sub.3 is 2-methoxyethoxymethyl.

### Claim 15 (depends on 11)

A compound of claim 11 in which R.sub.3 is CH.sub.3.

### Claim 16

A compound of the formula ##STR19## wherein Z is COOCH.sub.2 Ph.

### Claim 17

A compound of the formula ##STR20## wherein Z is COOCH.sub.2 Ph and R.sub.3 is CH.sub.3 or MEM and R.sub.4 is CH.sub.3.

### Claim 18

A compound of the formula ##STR21## wherein Z is COOCH.sub.2 Ph.

### Claim 19

A compound of the formula ##STR22##

### Claim 20

A compound of the formula ##STR23## wherein R.sub.3 =H or SiMe.sub.2 (t-Bu), and Z is COOCH.sub.2 Ph.

### Claim 21 (depends on 20)

A compound of claim 20 in which R.sub.3 is H.

### Claim 22 (depends on 20)

A compound of claim 20 in which R.sub.3 is SiMe.sub.2 (t-Bu).

### Claim 23

A compound of the formula ##STR24## wherein R.sub.3 =H or SiMe.sub.2 (t-Bu), and Z is COOCH.sub.2 Ph.

### Claim 24 (depends on 23)

A compound of claim 23 in which R.sub.3 is H.

### Claim 25 (depends on 23)

A compound of claim 23 in which R.sub.3 is SiMe.sub.2 (t-Bu).

### Claim 26

A compound selected from the group consisting of a 2-epoxide derivative of 1-deoxynojirimycin having the formula ##STR25## wherein Z is COOCH.sub.2 Ph.

### Claim 27

A compound selected from the group consisting of 2-methyl carbinol derivatives having the formula ##STR26## wherein Z is COOCH.sub.2 Ph.