Back to results
US 5,580,981 AGranted
Azahydroxybenzotriazoles and derivatives thereof for peptide coupling reactions
AssigneeResearch Corporation Technologies, Inc.
InventorLouis A. Carpino
Life of this patent
Estimating the term…
Abstract
This invention relates to a process for forming an amide or an ester from a reaction between an amine or an alcohol, respectively and an acylating derivative of a carboxylic acid, in the presence of an effective amount of a compound having the formula: ##STR1## and N-oxides thereof and salts thereof.
Claims93
A compound of the formula:
- ##STR56## or N-oxides thereof or salts thereof wherein D is CR.sub.16 or N;
- E is CR.sub.17 or N;
- A is CR.sub.15 or N;
- G is CR.sub.18 or N;
- provided that one and only one of A, E. D or G is N;
- R.sub.15, R.sub.16, R.sub.17 and R.sub.18 are independently hydrogen, lower alkyl or an electron donating group;
- X is CR.sub.7 or N;
- Y is N or CR.sub.5 ;
- R.sub.7 and R.sub.5 are independently hydrogen or lower alkyl;
- R.sub.3 is SO.sub.2 R.sub.14 lower alkyl carbonyl, aryl carbonyl, aryl lower alkyl carbonyl, a positively charged electron withdrawing group or AA.sub.1 -BLK.sub.1 ;
- R.sub.14 is lower alkyl, aryl or aryl lower alkyl;
- BLK.sub.1 is an amino acid protecting group;
- and AA.sub.1 is an amino acid or peptide less a hydrogen on the N-terminus and an OH on the C-terminus.
10 more elements
A compound of the formula:
- ##STR65## or N-oxides thereof or salts thereof wherein D is CR.sub.16 or N;
- E is CR.sub.17 or N;
- A is CR.sub.15 or N;
- G is CR.sub.18 or N;
- and at least two of A, E, D and G are N;
- R.sub.15, R.sub.17 and R.sub.18 are independently hydrogen, lower alkyl or an electron donating group;
- R.sub.3 is hydrogen, lower alkyl carbonyl, aryl carbonyl, aryl lower alkyl carbonyl, SO.sub.2 R.sub.14, a positively charged electron withdrawing group or AA.sub.1 -BLK.sub.1 ;
- R.sub.14 is lower alkyl, aryl, or aryl lower alkyl;
- BLK.sub.1 is an amino acid protecting group, and
- AA.sub.1 is an amino acid or peptide less a hydrogen on the N-terminus and an OH on the C-terminus.
7 more elements
A compound of the formula:
- ##STR69## or N-oxides thereof or salts thereof;
- wherein
- X is CR.sub.7 or N;
- Y is CR.sub.5 or N;
- with the proviso that X and Y cannot both represent N simultaneously;
- R.sub.5 and R.sub.7 are independently hydrogen or lower alkyl;
- D is CR.sub.16 or N;
- E is CR.sub.17 or N;
- A is CR.sub.15 or N;
- G is CR.sub.18 or N;
- with the further proviso that one and only one of A, E, D and G is N;
- R.sub.15, R.sub.16, R.sub.17 and R.sub.18 are independently hydrogen, lower alkyl or an electron donating group;
- R.sub.3 is hydrogen, SO.sub.2 R.sub.14 lower alkyl carbonyl, aryl carbonyl, aryl lower alkyl carbonyl, a positively charged electron withdrawing group or AA.sub.1 -BLK.sub.1 ;
- R.sub.14 is lower alkyl, aryl or aryl lower alkyl;
- BLK.sub.1 is an amino acid protecting group and
- AA.sub.1 is an amino acid or peptide less an hydrogen on the N-terminus and an OH on the C-terminus.
13 more elements
A compound of the formula:
- ##STR71## wherein D is CR.sub.16 or N;
- E is CR.sub.17 or N;
- A is CR.sub.15 ;
- G is CR.sub.18 ;
- provided that one and only one of D and E is N;
- R.sub.15, R.sub.16, R.sub.17 and R.sub.18 are independently hydrogen, lower alkyl or an electron donating group,
- R.sub.3 is hydrogen, SO.sub.2 R.sub.14 lower alkyl carbonyl, aryl carbonyl, aryl lower alkyl carbonyl, a positively charged electron withdrawing group or AA.sub.1 -BLK.sub.1 ;
- R.sub.14 is lower alkyl, aryl or aryl lower alkyl;
- BLK.sub.1 is an amino acid or peptide less an hydrogen on the N-terminus and an OH on the C-terminus.
6 more elements
A compound of the formula:
- ##STR72## or N-oxides thereof or salts thereof wherein D is CR.sub.16 or N;
- E is CR.sub.17 or N;
- A is CR.sub.15 or N;
- G is CR.sub.18 or N;
- provided that one and only one of D, E, A, and G is N;
- at least one of R.sub.15, R.sub.16, R.sub.17 and R.sub.18 is an electron donating group, and the remainder is independently hydrogen, lower alkyl or an electron donating group;
- X is CR.sub.7 or N;
- Y is N or CR.sub.5 ;
- R.sub.7 and R.sub.5 are independently hydrogen or lower alkyl;
- R.sub.3 is hydrogen, SO.sub.2 R.sub.14 lower alkyl carbonyl, aryl carbonyl, aryl lower alkyl carbonyl, a positively charged electron withdrawing group or AA.sub.1 -BLK.sub.1 ;
- R.sub.14 is lower alkyl, aryl or aryl lower alkyl;
- BLK.sub.1 is an amino acid protecting group and
- AA.sub.1 is an amino acid or peptide less a hydrogen on the N-terminus and an OH on the C-terminus.
10 more elements
An N-oxide of a compound of the formula:
- ##STR77## or a salt thereof, wherein
- D is CR.sub.16 or N;
- E is CR.sub.17 or N;
- A is CR.sub.15 or N;
- G is CR.sub.18 or N;
- provided that one and only one of A, E,D or G is N;
- R.sub.15, R.sub.16, R.sub.17 and R.sub.18 are independently hydrogen, lower alkyl and an electron donating group,
- X is CR.sub.7 or N;
- Y is CR.sub.5 or N;
- R.sub.7 and R.sub.5 are independently hydrogen or lower alkyl;
- R.sub.3 is hydrogen, SO.sub.2 R.sub.14 , lower alkyl carbonyl, aryl carbonyl, lower alkyl carbonyl, a positively charged electron withdrawing group or BLK.sub.1 -AA.sub.1 ;
- R.sub.14 is lower alkyl, aryl or aryl lower alkyl;
- BLK.sub.1 is an amino acid protecting group and
- AA.sub.1 is an amino acid or peptide less a hydrogen on the N-terminus and an OH on the C-terminus.
11 more elements
Dependencies are inferred from the claim text.