A.sub.4 B.sub.6 macrotricyclic enantioselective receptors for amino acid derivatives, and other compounds

• US 5,599,926 A
• Filed: 01/27/1994
• Issued: 02/04/1997
• Est. Priority Date: 06/19/1992
• Status: Expired due to Fees

• Current Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Original Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Inventors: Simon, Julian A., Erickson, Shawn D., Yoon, Seung S., Hong, Jong-In, Still, W. Clark
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): SRIPADA, PAVANARAM K
• Application Number:
  US08/188,146
• Time in Patent Office: 1,104 Days
• Field of Search: 540/456, 540/460
• US Class Current: 540/456
• CPC Class Codes: C07B 57/00 Separation of optically-active compounds
• CPC Class Codes: C07B 63/00 Purification; Separation separation of optically-active compounds C07B57/00; Stabilisation; Use of additives
• CPC Class Codes: C07B 63/04 Use of additives anti-oxidant compositions or compositions inhibiting chemical change in general C09K15/00
• CPC Class Codes: C07D 487/18 Bridged systems
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07D 498/18 Bridged systems
• CPC Class Codes: C07D 513/18 Bridged systems
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The subject invention provides chiral receptor molecules having the structure: ##STR1## wherein A has the structure: ##STR2## and R₁ and R₂ are independently the same or different and are H, F, alkyl, aryl, etc.; X is CH₂ or NH; Y is C═O or SO₂ ; and n is 0 to about 3; which are useful for the purification of enantiomers of amino acid derivatives and other compounds. The subject invention also provides methods of preparing said receptor molecules.

Claims

1. A composition of matter having the structure:

##STR52## wherein A has the structure;

##STR53## and R₁ and R₂ are independently the same or different and are H, F, a linear or branched chain alkyl, arylalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, hydroxyalkyl, (cycloalkyl)alkyl, or acylalkyl group, or an aryl group, a linear or branched chain alkylaryl, pyridyl, thiophene, pyrrolyl, indolyl or naphthyl group;

X is CH₂ or NH;

Y is C═

O or SO₂ ; and

n is 0 to about 3.

2. The composition of claim 1 wherein X is NH.

3. The composition of claim 1 wherein X is CH₂, Y is C═

O and n is 1.

4. The composition of claim 3 wherein R₁ and R₂ are H.