Oligomers, their uses and formulations

Claim 2

A water-soluble, rigid backbone oligomer having a molecular weight less than 10,000 comprising recurring units coupled by carbonyl linking moieties, said oligomer having anionic groups and predominantly linear geometry such that regular spacing between anionic groups exists in an aqueous medium.

Claim 3

An oligomer of Claim 1 wherein the oligomer is a polyurea, polycarbonate, polyester or polyamide.

Claim 4

An oligomer of Claim 1 or 2 wherein the recurring unit has two or more anionic groups.

Claim 5

An oligomer as claimed in any one of Claims 1, 2 or 3, wherein the oligomer is in the form of its salt.

Claim 6

An oligomer of Claim 4, wherein the salt is pharmaceutically-acceptable.

Claim 7

An oligomer of Claim 2 wherein the number average molecular weight is from 500 to 10,000.

Claim 8

An oligomer of Claim 6 wherein the number average molecular weight is from 1,000 to 6,000.

Claim 9

An oligomer of Claim 2 which is represented by any one of the following formulae: A) a polyurea of the formula: wherein: R represents a hydrogen atom, a C 1 -C 4 alkyl group, a phenyl group, or a phenyl group substituted with from 1 to 2 R 1 moieties and up to 3 substituents independently selected from a chloro or bromo atom or C 1 -C 4 alkyl group; R 1 represents a -S0 3 R 2 , -C0 2 R 2 , -P03(R2)2, or -OP0 3 R 2 ; R 2 represents a hydrogen atom or a pharmaceutically-acceptable cation; m is an integer 0 or 1, with the proviso that when m is 0, R is a hydrogen atom; X represents Y represents -C0 2 -, -C≡C-, -N = N-, R 3 represents -R or -X-NH 2 , where R and X are defined as before; B) a polycarbonate of the formula: wherein: X and n are defined as in Formula I in Claim 8(A); X 1 represents a HO-X- group, where X is defined as in Formula I in Claim 8(A), or a C 1 -C 4 alkyl group, a phenyl group, or a phenyl group substituted with from 1 to 2 R 1 moieties and up to 3 substituents independently selected from a chloro or bromo atom or C 1 -C 4 alkyl group; and X 2 represents a hydrogen atom, or -CO 2 X 1 , where X 1 is defined as above; C) a polyester of the formula wherein: X and n are defined as in Formula I in Claim 8(A); R 4 represents -R 2 , as defined in Formula I in Claim 8(A), or -X 1 , as defined in Formula II in Claim 8(B); R 5 represents where R 4 is defined as in Formula III in Claim 8(C) or - R 2 , where R 2 is defined as in Formula I in Claim 8(A); X 3 represents or wherein R 1 and Y are defined as in Formula I in Claim 8(A); or D) a polyamide of the formula: wherein: X and n are defined as in Formula I in Claim 8(A); X 3 is defined as in Formula III in Claim 8(C); R 6 represents H 2 N-X-NH-, R 2 0-, RNH- or R-C(O)-NH-X-NH-, where R, R 2 and X are defined as in Formula I in Claim 8(A); R 7 represents a hydrogen atom, where R and R 2 are defined as in Formula I in Claim 8(A); and X 3 is defined as in Formula III in Claim 8(C).

Claim 10

An oligomer of Claim 8 wherein n is from 3 to 50.

Claim 11

An oligomer of Claim 9 wherein n is from 3 to 15.

Claim 12

An oligomer of Claim 8 which is a polyurea of Formula I wherein R and R 3 are a 4-methylphenyl group; m is 1; n is 3 to 15; X represents or and R 2 is defined as in Claim 8.

Claim 13

An oligomer of Claim 11 which is StDS/P/T and named as poly[imino(3-sulfo-1,4-phenylene)-1,2- ethenediyl-(2-sulfo-1,4-phenylene)iminocarbonyl], alpha-{[(4-methylphenyl)aminocarbonyl}-omega-[(4-methylphenyl)amino-and is represented by Formula I in Claim 8 when R and R 3 is 4-methylphenyl, R 2 is hydrogen, X is where n is defined as for Formula I in Claim 8.

Claim 14

The oligomer of Claim 12 wherein n is 6.

Claim 15

The oligomer of Claim 12 wherein n is 9.

Claim 16

An oligomer of Claim 11 which is PDS/P/T and named as poly[imino(2,5-disulfo-1,4-phenylene)-iminocarbonyl], alpha-{[(4-methylphenyl)amino]carbonyl}-omega[(4-methylphenyl)amino]- and is represented by Formula I in Claim 8 when R and R 3 is 4-methylphenyl, R 2 is hydrogen, X is and n is defined as for Formula I in Claim 8.

Claim 17

The oligomer of Claim 15 wherein n is 9.

Claim 18

The oligomer of Claim 15 wherein n is 15.

Claim 19

An oligomer of Claim 11 wherein X is

Claim 20

An oligomer of Claim 18 which is BPDS/P/T, and named as poly{imino[2,2'-disulfo(1,1'-biphenyl)-4,4'-diyl]iminocarbonyl}, alpha-{[(4-methylphenyl)amino]carbonyl}-omega-[(4-methylphenyl)amino]- and is represented by Formula I in Claim 8 when R is 4-methylphenyl, R 2 is hydrogen, X is wherein n is defined as for Formula I in Claim 8.

Claim 21

The oligomer of Claim 19 wherein n is 6.

Claim 22

The oligomer of Claim 19 wherein n is 9.

Claim 23

An oligomer of Claim 8 which is a polycarbonate of Formula II wherein X 1 is a 4-methylphenyl group; X 2 is -C0 2 -(4-methylphenyl) group; n is 3 to 15; and X is as defined in Claim 11.

Claim 24

An oligomer of Claim 22 which is HBDS/P/C and named as poly[oxy(2,5-disulfo-1,4-phenylene)-oxycarbonyl], alpha-[(4-methylphenoxy)carbonyl]-omega-(4-methylphenoxy)- and is represented by Formula II in Claim 8 when X 1 is 4-methylphenyl, R 2 is hydrogen, X is is and n is defined as for Formula I in Claim 8.

Claim 25

The oligomer of Claim 23 wherein n is 6.

Claim 26

An oligomer of Claim 22 which is HBPDS/P/C and named as poly{oxy[2,2'-disulfo(1,1'-biphenyl)-4,4'-diyl]oxycarbonyl}, alpha-[(4-methylphenoxy)carbonyl]-omega-(4-methylphenoxy)- and is represented by Formula II in Claim 8 when X 1 is 4-methylphenyl, R 2 is hydrogen, X is is and n is defined as for Formula I in Claim 8.

Claim 27

The oligomer of Claim 25 wherein n is 6.

Claim 28

An oligomer of Claim 8 which is a polyester of Formula III wherein R 4 and R 5 are hydrogen; n is 3 to 15; and X 3 represents or and X represents or

Claim 29

An oligomer of Claim 27 which is HBPDS/TPC and named as poly{oxy[2,2'-disulfo(1,1'-biphenyl)-4,4'-diyl]oxycarbonyl-1,4-phenylenecarbonyl}- and is represented by Formula III in Claim 8 when R 4 and R 5 are hydrogen, X 3 is p-phenylene, X is where n is defined as for Formula I in Claim 8.

Claim 30

The oligomer of Claim 28 wherein n is 4.

Claim 31

An oligomer of Claim 27 which is HBDS/TPC and named as poly[oxy(2,5-disulfo-1,4-phenylene)-oxycarbonyl-1,4-phenylenecarbonyl]- and is represented by Formula III in Claim 8 when R 4 and R 5 are hydrogen, X 3 is p-phenylene, X is where n is defined as for Formula I in Claim 8.

Claim 32

The oligomer of Claim 30 wherein n is 3.

Claim 33

An oligomer of Claim 8 which is a polyamide of Formula IV wherein R 6 is phenyl; R 7 is methyl benzoyl; n is 3 to 15; and X 3 represents or and X represents or

Claim 34

An oligomer of Claim 32 which is BPDS/TPC/MBC and named as poly{imino[2,2'-disulfo(1,1'-biphenyl)-4,4'-diyl]iminocarbonyl-1,4-phenylenecarbonyl}, alpha-(((4-methylphenyl)amino]carbonyl)-omega-[(4-methylphenyl)amino]- and is represented by Formula IV in Claim 8 when R 6 is R-C(O)-NH-X-NH-, R is 4-methylphenyl, R 2 is hydrogen, R 7 is 4-methylbenzoyl, X 3 is p-phenylene, X is where n is defined as in Formula I in Claim 8.

Claim 35

The oligomer of Claim 33 wherein n is 6.

Claim 36

The oligomer of Claim 33 wherein n is 3.

Claim 37

The oligomer of Claim 33 wherein n is 9.

Claim 38

A pharmaceutical formulation comprising an oligomer as claimed in any one of the preceeding Claims with a pharmaceutically-acceptable carrier.

Claim 39

A pharmaceutical formulation comprising a mixture of the oligomers as claimed in Claim 8 with a pharmaceutically-acceptable carrier.

Claim 40

A pharmaceutical formulation comprising an oligomer as claimed in any one of Claims 1 through 36 with a detergent.

Claim 41

A pharmaceutical formulation comprising an oligomer as claimed in any one of Claims 1 through 36 as a liquid, powder, douche, jelly or lotion.

Claim 43

A method of Claim 41 wherein the disease state is AIDS and/or ARC.

Claim 44

An oligomer as claimed in any one of Claims 1 through 36 for use as a pharmaceutically active substance.

Claim 45

A formulation as claimed in any one of Claims 37 through 40 for use as a pharmaceutically active substance.

Claim 46

A use of an effective amount of the formulation as claimed in Claim 40 as a prophylaxis.

Claim 48

A process for preparing a polyamide as claimed in Claim 8D Formula IV which comprises reacting a diamine with a difunctional electrophile, at a molar ratio of diamine to diacid halide of from 0.9 to 1.2, with stirring in the presence of an acid acceptor, in either a polar aprotic solvent or combination solvent of water and an organic solvent, and at a temperature from 0 to 50 C.

Claim 49

A process for preparing a polyurea as claimed in Claim 8A Formula I which comprises reacting an aromatic diamine with a difunctional electrophile, in the presence of an acid acceptor, in water as the solvent or water with up to about 1 mole of water immiscible cosolvent, at a temperature of from 0 to 100° C and at a pH between 7 to 9.

Claim 50

A process of Claim 48 wherein a mono-functional end capping agent is used.

Claim 51

A process for preparing a polycarbonate or polyester oligomer as defined in Claim 8B and 8C, respectively, Formulae II and III, respectively, which comprises reacting a diphenol with a difunctional electrophile, at a pH of 7 to 8, at a temperature between 0 to 40 C in a water immiscible solvent.

Claim 52

A process of Claim 50 wherein the difunctional electrophile is a diacid chloride and waiting for 15 to 120 minutes after the addition of the diacid chloride, at a pH of 7 to 8, to ensure conversion.

Claim 53

A process of Claim 50 which comprises pretreating the diphenol with one or two moles of base to form the mono- or diphenoxides.