.beta.-aminoalkyl and .beta.-N-peptidylaminoalkyl boronic acids

• US 5,442,100 A
• Filed: 08/14/1992
• Issued: 08/15/1995
• Est. Priority Date: 08/14/1992
• Status: Expired due to Fees

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Panandiker, Rajan K., Bjorkquist, David W.
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): BURN, BRIAN M
• Application Number:
  US07/931,809
• Time in Patent Office: 1,096 Days
• Field of Search: 564/8, 549/213, 562/7, 560/29
• US Class Current: 562/7
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: C07K 5/06191 containing heteroatoms different from O, S, or N
• CPC Class Codes: C11D 3/38663 Stabilised liquid enzyme compositions
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

A compound having the formula: ##STR1## where R₁, R₂, and R₃ are independently hydrogen or C_1-C4 alkyl; n is 2-4; X is aryl, substituted aryl or C_1-C6 alkyl; Y is selected from the group consisting of hydrogen, amino acid, dipeptide or tripeptide linked through the C-terminal carboxylic acid, and amine protecting group is presented.

Claims

1. A compound having the formula:

##STR32## where R₁, R₂, and R₃ are independently hydrogen or C₁ -C₄ alkyl;

n is 2-4;

X is phenyl or C₁ -C₆ alkyl; and

Y is selected from the group consisting of

a) hydrogen;

b) an amine protecting group selected from the group consisting of

i) t-butoxycarbonyl,

ii) methoxycarbonyl,

iii) benzyloxycarbonyl, and

iv) ##STR33## wherein R₅ is phenyl or C₁ -C₄ alkyl; and

c) ##STR34## wherein A is independently selected from naturally occurring amino acids;

m is 1 to 3; and

P is selected from the amine protecting groups of Component b).

2. A compound according to claim 1 having the following structure:

##STR35## where R₁ and R₂ are independently hydrogen or methyl;

X is phenyl or C₁ -C₄ alkyl; and

Y is an amine protecting group selected from the group consisting of t-butoxycarbonyl, methoxycarbonyl, benzyloxycarbonyl, and ##STR36## where R₅ is phenyl, C₁ -C₄ alkyl.

3. A compound according to claim 1 having the following structure:

##STR37## where R₁ and R₂ are each hydrogen or methyl;

X is phenyl or C₁ -C₄ alkyl; and

Y is ##STR38## where A is independently selected from naturally occurring amino acids, m=1-3, and P is hydrogen or an amine protecting group selected from the group consisting of t-butoxycarbonyl, methoxycarbonyl, benzyloxycarbonyl, and ##STR39## where R₅ is phenyl or C₁ -C₄ alkyl.

4. A compound having the following structure:

##STR40## where R₅ is phenyl or C₁ -C₄ alkyl;

m=1-3;

A is independently selected from the group consisting of alanine, valine, leucine, phenylalanine, glycine, isoleucine and threonine; and

P is selected from the group consisting of t-butoxycarbonyl, methoxycarbonyl, benzyloxycarbonyl, and ##STR41##

5. A compound according to claim 4 having the following structure:

##STR42## where n=2-4;

A i s independently selected from the group consisting of alanine, glycine, leucine, valine and phenylalanine; and

P is selected from the group consisting of t-butoxycarbonyl, methoxycarbonyl, benzyl oxycarbonyl and ##STR43##