# US 5,344,925 A · Imidazolidyl macrolides having immunosuppressive activity

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,344,925 A
- Document ID: US5344925A
- Status: Granted
- Kind: A
- Application number: 08/124,137
- Filed: 1993-09-20
- Granted: 1994-09-06
- Earliest claimed: 1991-09-09
- Assignees: Merck & Co., Inc.
- Inventors: Mark Goulet; Peter J. Sinclair; Frederick Wong; Matthew J. Wyvratt
- Web page: https://patentgrep.com/patent/US5344925A

## CPC

- C07H 19/01: sharing oxygen
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Imidazolidyl macrolides of the general structural Formula I: ##STR1## have been prepared from suitable precursors by alkylation and/or arylation at C-3" and/or C-4" of the cyclohexyl ring. These macrolide immunosuppressants are useful in a mammalian host for the treatment of autoimmune diseases, infectious diseases the prevention of rejection of foreign organ transplants and/or related afflictions, diseases and illnesses.

## Claims

### Claim 1

A compound which is selected from the group consisting of:
17-ethyl-1,14-dihydroxy-12-[2'-(4"-(4"'-(meta-phenoxy-tert-butyl acetate)-2"'-imidazolylmethyloxy)-3"-methoxycyclohexyl)-1'-methyl-vinyl]-2 3,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0.s up.4,9 ]octacos-18-ene-2,3,10,16-tetraone;
17-ethyl-1,14-dihydroxy-12-[2'-(4"-(4"'-(meta-phenoxyacetic acid)-2"'-imidazolylmethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25 -dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4azatricyclo[22.3.1.0.sup.4, 9 ]octacos-18-ene-2,3,10,16-tetraone;
17-ethyl-1-hydroxy-14-(N,N-dimethylaminoacetoxy)-12-[2'-(4"-(4"'-(3"",5""-d imethoxyphenyl)-2"'-imidazolylmethyloxy)-3"-methoxycyclohexyl)-1'-methylvin yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3. 1.0.sup.4,9 ]octacos-18-ene-2,3,10,16-tetraone;
17-ethyl-1-hydroxy-14-(3""'-(N,N-diethylamino)-propanoyloxy)-12-[2'-(4"-(4" '-(3"",5""-dimethoxyphenyl)-2"'-imidazolylmethyloxy)-3"-methoxycyclohexyl)- 1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetra-methyl-11,28-dioxa-4-azat ricyclo[22.3.1.0.sup.4,9 ]octacos-18-ene-2,3,10,16-tetraone;
17-ethyl-1-hydroxy-14-(3""'-aminopropanoyloxy)-12-[2'-(4"-(4"'-(3"",5""-dim ethoxyphenyl) -2"'-imidazolylmethyloxy) -3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,2 1,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0.sup.4,9 ]octacos-18-ene-2,3,10,16-tetraone;
17-ethyl-1-hydroxy-14-(2""',6""'-diaminohexanoyloxy)-12-[2'-(4"-(4"'-(3"",5 ""-dimethoxyphenyl)-2"'-imidazolylmethyloxy)-3"-methoxycyclohexyl)-1'-methy lvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[2 2.3.1.0.sup.4,9 ]octacos-18-ene-2,3,10,16-tetraone;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1 which is: ##STR56##

### Claim 3 (depends on 1)

The compound of claim 1 which is: ##STR57##

### Claim 4 (depends on 1)

The compound of claim 1 which is: ##STR58##

### Claim 5 (depends on 1)

The compound of claim 1 which is: ##STR59##

### Claim 6 (depends on 1)

The compound of claim 1 which is: ##STR60##

### Claim 7 (depends on 1)

The compound of claim 1 which is: ##STR61##