Granted Patent B2

US 9,006,305 · App. 13/601,123 · Granted Apr 14, 2015

Abstract

Claims (43)

1. A monomer of formula (I):

wherein:

W is (CR 1 2 ) n ;

Z is a zwitterionic group selected from the group consisting of (IIA), (IIB), (IIC), (IID) and (IIE), wherein group (IIA) has the formula:

wherein each R 3 and R 3A is independently selected from hydrogen and C 1-4 alkyl and a is an integer from 2 to 4;

group (IIB) has the formula:

wherein each R 4 and R 4A is independently selected from hydrogen and C 1-4 alkyl and b is an integer from 1 to 4;

group (IIC) has the formula:

wherein each R 5 and R 5C is independently selected from hydrogen and C 1-4 alkyl; R 5A is hydrogen or a group —C(O)B 1 R 5B , wherein R 5B is hydrogen or methyl, B 1 is selected from the group consisting of a bond; C 1-10 alkylene, C 2-10 alkenylene, C 2-10 alkynylene, C 3-10 cycloalkylene, C 3-10 cycloalkenylene, C 1-10 heteroalkylene, C 2-10 heteroalkenylene, C 2-10 heteroalkynylene, arylene, heteroarylene, —C(O)R M —, —C(O)OR M —, wherein R M is selected from the group consisting of C 1-10 alkylene, C 2-10 alkenylene and C 2-10 alkynylene, and wherein the alkylene, alkenylene, alkynylene, cycloalkylene, cycloalkenylene, heteroalkylene, heteroalkenylene, heteroalkynylene, arylene and heteroarylene groups may be optionally substituted with one or more R N , wherein each R N is independently selected from the group consisting of —H, —OH, —CN, —NO 2 , —CF 3 , —OCF 3 , —CO 2 H, —NH 2 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, —O(C 1 -C 10 alkyl), —O(C 2 -C 10 alkenyl), —O(C 2 -C 10 alkynyl), halogen, —C(O)H, —C(O)—(C 1 -C 10 alkyl), —C(O)—O(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl), —N(C 1 -C 10 alkyl) 2 , —C(O)—NH(C 1 -C 10 alkyl), —C(O)—N(C 1 -C 10 alkyl) 2 , —NH—C(O)—(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl)-C(O)—(C 1 -C 10 alkyl), —NH—S(O) 2 —(C 1 -C 10 alkyl), —NH—(C 1 -C 10 alkyl)-S(O) 2 —(C 1 -C 10 alkyl), —(C 0 -C 10 )—SH, —S(O)—(C 1 -C 10 alkyl), —S(O) 2 —(C 1 -C 10 alkyl), —S(O) 2 —NH 2 , —S(O) 2 —NH—(C 1 -C 10 alkyl), —S(O) 2 —N(C 1 -C 10 alkyl) 2 and ═O, and c is an integer from 1 to 4, wherein if Z is directly bonded to an O or N atom, z is 0 and otherwise z is 1;

group (IID) has the formula:

wherein each R 6 and R 6C is independently selected from hydrogen and C 1-4 alkyl; R 6A is hydrogen or a group —C(0)B 2 R 6B , wherein R 6B is hydrogen or methyl, B 2 is selected from the group consisting of a bond; C 1-10 alkylene, C 2-10 alkenylene, C 2-10 alkynylene, C 3-10 cycloalkylene, C 3-10 cycloalkenylene, C 1-10 heteroalkylene, C 2-10 heteroalkenylene, C 2-10 heteroalkynylene, arylene, heteroarylene, —C(O)R M —, —C(O)OR M —, wherein R M is selected from the group consisting of C 1-10 alkylene, C 2-10 alkenylene and C 2-10 alkynylene, and wherein the alkylene, alkenylene, alkynylene, cycloalkylene, cycloalkenylene, heteroalkylene, heteroalkenylene, heteroalkynylene, arylene and heteroarylene groups may be optionally substituted with one or more R N , wherein each R N is independently selected from the group consisting of —H, —OH, —CN, —NO 2 , —CF 3 , —OCF 3 , —CO 2 H, —NH 2 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, —O(C 1 -C 10 alkyl), —O(C 2 -C 10 alkenyl), —O(C 2 -C 10 alkynyl), halogen, —C(O)H, —C(O)—(C 1 -C 10 alkyl), —C(O)—O(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl), —N(C 1 -C 10 alkyl) 2 , —C(O)—NH(C 1 -C 10 alkyl), —C(O)—N(C 1 -C 10 alkyl) 2 , —NH—C(O)—(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl)-C(O)—(C 1 -C 10 alkyl), —NH—S(O) 2 —(C 1 -C 10 alkyl), —NH—(C 1 -C 10 alkyl)-S(O) 2 —(C 1 -C 10 alkyl), —(C 0 -C 10 )—SH, —S(O)—(C 1 -C 10 alkyl), —S(O) 2 —(C 1 -C 10 alkyl), —S(O) 2 —NH 2 , —S(O) 2 —NH—(C 1 -C 10 alkyl), —S(O) 2 —N(C 1 -C 10 alkyl) 2 and ═O, and d is an integer from 1 to 4, wherein if Z is directly bonded to an O or N atom, z is 0 and otherwise z is 1;

group (IIE) has the formula:

wherein each R 7 and R 7C is independently selected from hydrogen and C 1-4 alkyl; R 7A is hydrogen or a group —C(O)B 2 R 7B , wherein R 7B is hydrogen or methyl, B 2 is selected from the group consisting of a bond; C 1-10 alkylene, C 2-10 alkenylene, C 2-10 alkynylene, C 3-10 cycloalkylene, C 3-10 cycloalkenylene, C 1-10 heteroalkylene, C 2-10 heteroalkenylene, C 2-10 heteroalkynylene, arylene, heteroarylene, —C(O)R M —, —C(O)OR M —, wherein R M is selected from the group consisting of C 1-10 alkylene, C 2-10 alkenylene and C 2-10 alkynylene, and wherein the alkylene, alkenylene, alkynylene, cycloalkylene, cycloalkenylene, heteroalkylene, heteroalkenylene, heteroalkynylene, arylene and heteroarylene groups may be optionally substituted with one or more R N , wherein each R N is independently selected from the group consisting of —H, —OH, —CN, —NO 2 , —CF 3 , —OCF 3 , —CO 2 H, —NH 2 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, —O(C 1 -C 10 alkyl), —O(C 2 -C 10 alkenyl), —O(C 2 -C 10 alkynyl), halogen, —C(O)H, —C(O)—(C 1 -C 10 alkyl), —C(O)—O(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl), —N(C 1 -C 10 alkyl) 2 , —C(O)—NH(C 1 -C 10 alkyl), —C(O)—N(C 1 -C 10 alkyl) 2 , —NH—C(O)—(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl)-C(O)—(C 1 -C 10 alkyl), —NH—S(O) 2 —(C 1 -C 10 alkyl), —NH—(C 1 -C 10 alkyl)-S(O) 2 —(C 1 -C 10 alkyl), —(C 0 -C 10 )—SH, —S(O)—(C 1 -C 10 alkyl), —S(O) 2 —(C 1 -C 10 alkyl), —S(O) 2 —NH 2 , —S(O) 2 —NH—(C 1 -C 10 alkyl), —S(O) 2 —N(C 1 -C 10 alkyl) 2 and ═O, and e is an integer from 1 to 4, wherein if Z is directly bonded to an O or N atom, z is 0 and otherwise z is 1;

each R 1 is independently selected from H, halogen or C 1-4 alkyl;

m is an integer from 0 to 6; and

X is NR 2 ;

where R 2 , Y and the N atom to which they are bonded taken together form a 5 to 7 membered heterocyclic ring, wherein the heterocyclic ring may be optionally substituted with one or more R N , wherein each R N is independently selected from the group consisting of —H, —OH, —CN, —NO 2 , —CF 3 , —OCF 3 , —CO 2 H, —NH 2 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, —O(C)—(C 1 -C 10 alkyl), —O(C 2 -C 10 alkenyl), —O(C 2 -C 10 alkynyl), halogen, —C(O)H, —C(O)—(C 1 -C 10 alkyl), —C(O)—O(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl), —N(C 1 -C 10 alkyl) 2 , —C(O)—NH(C 1 -C 10 alkyl), —C(O)—N(C 1 -C 10 alkyl) 2 , —NH—C(O)—(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl)-C(O)—(C 1 -C 10 alkyl), —NH—S(O) 2 —(C 1 -C 10 alkyl), —NH—(C 1 -C 10 alkyl)-S(O) 2 —(C 1 -C 10 alkyl), —(C 0 -C 10 )—SH, —S(O)—(C 1 -C 10 alkyl), —S(O) 2 —(C 1 -C 10 alkyl), —S(O) 2 —NH 2 , —S(O) 2 —NH—(C 1 -C 10 alkyl), —S(O) 2 —N(C 1 -C 10 alkyl) 2 and ═O;

n is an integer from 0 to 6; or

X is NR 2 , where R 2 is H or C 1-4 alkyl;

Y is —C(O)O— or —C(O)N(R M )—, where R M is H or C 1-4 alkyl; and

n is 0; or

X is O;

Y is —C(=V)A-; where V is S or O; and A is selected from NR M , O and S, where

R M is hydrogen or C 1-4 alkyl; and

n is 0.

2. The monomer of claim 1 , wherein X is NR 2 , and where R 2 , Y and the N atom to which they are bonded taken together form a 5 to 7 membered heterocyclic ring, wherein the heterocyclic ring may be optionally substituted with one or more R N , wherein each R N is independently selected from the group consisting of —H, —OH, —CN, —NO 2 , —CF 3 , —OCF 3 , —CO 2 H, —NH 2 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, —O(C 1 -C 10 alkyl), —O(C 2 -C 10 alkenyl), —O(C 2 -C 10 alkynyl), halogen, —C(O)H, —C(O)—(C 1 -C 10 alkyl), —C(O)—O(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl), —N(C 1 -C 10 alkyl) 2 , —C(O)—NH(C 1 -C 10 alkyl), —C(O)—N(C 1 -C 10 alkyl) 2 , —NH—C(O)—(C 1 -C 10 alkyl), —NH(C 1 -C 10 alkyl)-C(O)—(C 1 -C 10 alkyl), —NH—S(O) 2 —(C 1 -C 10 alkyl), —NH—(C 1 -C 10 alkyl)-S(O) 2 —(C 1 -C 10 alkyl), —(C 0 -C 10 )—SH, —S(O)—(C 1 -C 10 alkyl), —S(O) 2 —(C 1 -C 10 alkyl), —S(O) 2 —NH 2 , —S(O) 2 —NH—(C 1 -C 10 alkyl), —S(O) 2 —N(C 1 -C 10 alkyl) 2 and ═O.

3. The monomer of claim 2 , wherein R 2 , Y and the N atom to which they are bonded taken together form a 5-membered heterocyclic ring.

4. The monomer of claim 3 , wherein the 5-membered heterocyclic ring is substituted with ═O.

5. The monomer of claim 4 , which has the formula (IA):

wherein W, R 1 , and Z as defined for formula (I).

6. The monomer of claim 5 , wherein n is 0.

7. The monomer of claim 1 , wherein X is NR 2 where R 2 is H or C 1-4 alkyl; Y is —C(O)O—; n is 0; and m is 1 to 4.

8. The monomer of claim 7 , wherein m is 2.

9. The monomer of claim 1 , wherein m is 0.

10. The monomer of claim 1 , wherein Z is a group (IIB).

11. The monomer of claim 10 , wherein R 4 is methyl and b is 2.

12. The monomer of claim 1 , wherein n is 0.

13. The monomer of claim 4 , wherein n is 0; m is 2; and Z is a group of formula (IIB), wherein each R 4 is methyl and b is 2.

14. The monomer of claim 1 of formula (ID):

wherein W is as defined in connection with formula (I), each R 4 and R 4A is independently selected from hydrogen and C 1-4 alkyl and b is an integer from 1 to 4.

15. The monomer of claim 1 , which has formula (IE):

wherein W is as defined in connection with formula (I), each R 4 and R 4A is independently selected from hydrogen and C 1-4 alkyl and b is an integer from 1 to 4.

16. The monomer of claim 1 wherein X is O; Y is —C(=V)A-; where V is S or O; and A is selected from NR M , O and S, where R M is hydrogen or C 1-4 alkyl; and n is 0.

Assignments (19)