US5380716A — Sulfated polysaccharides as inhibitors of smooth …

Claim 1

Independent Claim 197 words

A compound that inhibits the proliferation of smooth muscle cells to a greater extent than commercial heparin, and has a decreased ability to act as an anticoagulant as compared to commercial heparin, the compound having the following structural formula: ##STR14## wherein each of A, B, C, and D is independently H or SO 3 R and each R is independently H or a cation, with the proviso that at least two of A, B, C or D is --SO 3 R; noting that hydroxyl groups on the sugars have been omitted in Formulas I and I(a) for greater clarity and the * adjacent the carbon substituted with COOH indicates any possible stereochemistry in either I or I(a); R 1 and R 2 are each independently hydrogen or a unit having the following structure: ##STR15## wherein when a unit of Formula I(a) is connected at one end, the hydrogen at that end is not present; and each of E and F is independently hydrogen or SO 3 R and noting that the hydroxyl group on the 3-position on each sugar is present but has been omitted for greater clarity and further noting that the 3-position is not sulfated.

Claim 2

Dependent Claim 197 words

A compound that inhibits the proliferation of smooth muscle cells to a greater extent than commercial heparin, and has a decreased ability to act as an anticoagulant as compared to commercial heparin, the compound having the following structural formula: ##STR14## wherein each of A, B, C, and D is independently H or SO 3 R and each R is independently H or a cation, with the proviso that at least two of A, B, C or D is --SO 3 R; noting that hydroxyl groups on the sugars have been omitted in Formulas I and I(a) for greater clarity and the * adjacent the carbon substituted with COOH indicates any possible stereochemistry in either I or I(a); R 1 and R 2 are each independently hydrogen or a unit having the following structure: ##STR15## wherein when a unit of Formula I(a) is connected at one end, the hydrogen at that end is not present; and each of E and F is independently hydrogen or SO 3 R and noting that the hydroxyl group on the 3-position on each sugar is present but has been omitted for greater clarity and further noting that the 3-position is not sulfated.

Claim 3

Dependent Claim 19 words

The compound of claim 1, wherein at least three of A, B, C or D are --SO 3 R.

Claim 4

Dependent Claim 17 words

The compound of claim 2, wherein all of A, B, C and D are --SO 3 R.

Claim 5

Dependent Claim 31 words

The compound of claim 1, wherein R 1 and R 2 are H, and each R is H, ----Na + , K + , Ca 2+ or NH 4 + ----.

Claim 6

Dependent Claim 138 words

A hexasaccharide and octasaccharide compound that inhibits the proliferation of smooth muscle cells to a greater extent than commercial heparin, and has a decreased ability to act as an anticoagulant as compared to commercial heparin, the compound having the following structural formula: ##STR16## wherein n is 1 or 2 and each of A, B, C and D is independently H or SO 3 R, wherein each R is independently H or a cation, with the proviso that at least two of said A, B, C and D are SO 3 R; and wherein a hydroxyl group present on the 3 position of each sugar is present but has been omitted from the depiction; and noting that the 3-position is not sulfated; and wherein the asterisk on the carbons substituted with carboxyl indicates that the stereochemistry is not determined.

Claim 7

Dependent Claim 138 words

A hexasaccharide and octasaccharide compound that inhibits the proliferation of smooth muscle cells to a greater extent than commercial heparin, and has a decreased ability to act as an anticoagulant as compared to commercial heparin, the compound having the following structural formula: ##STR16## wherein n is 1 or 2 and each of A, B, C and D is independently H or SO 3 R, wherein each R is independently H or a cation, with the proviso that at least two of said A, B, C and D are SO 3 R; and wherein a hydroxyl group present on the 3 position of each sugar is present but has been omitted from the depiction; and noting that the 3-position is not sulfated; and wherein the asterisk on the carbons substituted with carboxyl indicates that the stereochemistry is not determined.

Claim 8

Dependent Claim 19 words

A compound of claim 5, wherein at least three of A, B, C or D are --SO 3 R.

Claim 9

Dependent Claim 19 words

A compound of claim 5, wherein at least four of A, B, C or D are --SO 3 R.

Claim 10

Dependent Claim 19 words

A compound of claim 5, wherein at least five of A, B, C or D are --SO 3 R.

Claim 11

Dependent Claim 17 words

A compound of claim 5, wherein all of A, B, C and D are --SO 3 R.

Claim 12

Dependent Claim 22 words

A compound of claim 5, wherein each R is H,----Na + , K + , Ca 2+ or NH 4 + ----.

Claim 13

Dependent Claim 138 words

A hexasaccharide and octasaccharide compound that inhibits the proliferation of smooth muscle cells to a greater extent than commercial heparin, and has a decreased ability to act as an anticoagulant as compared with commercial heparin the compound having the following structural formula: ##STR17## wherein n is 1 or 2 and each of A, B, C and D is independently H or SO 3 R, wherein each R is independently H or a cation, with the proviso that at least two of said A, B, C and D are SO 3 R; and wherein a hydroxyl group present on the 3 position of each sugar is present but has been omitted from the depiction and noting that the 3-position is not sulfated; and wherein the asterisk on the carbons substituted with carboxyl indicates that the stereochemistry is not determined.

Claim 14

Dependent Claim 138 words

A hexasaccharide and octasaccharide compound that inhibits the proliferation of smooth muscle cells to a greater extent than commercial heparin, and has a decreased ability to act as an anticoagulant as compared with commercial heparin the compound having the following structural formula: ##STR17## wherein n is 1 or 2 and each of A, B, C and D is independently H or SO 3 R, wherein each R is independently H or a cation, with the proviso that at least two of said A, B, C and D are SO 3 R; and wherein a hydroxyl group present on the 3 position of each sugar is present but has been omitted from the depiction and noting that the 3-position is not sulfated; and wherein the asterisk on the carbons substituted with carboxyl indicates that the stereochemistry is not determined.

Claim 15

Dependent Claim 19 words

A compound of claim 11, wherein at least three of A, B, C or D are --SO 3 R.

Claim 16

Dependent Claim 19 words

A compound of claim 11, wherein at least four of A, B, C or D are --SO 3 R.

Claim 17

Dependent Claim 19 words

A compound of claim 11, wherein at least five of A, B, C or D are --SO 3 R.

Claim 18

Dependent Claim 17 words

A compound of claim 11, wherein all of A, B, C and D are --SO 3 R.

Claim 19

Dependent Claim 23 words

A compound of claim 11, wherein each R is H, ----Na + , K + , Ca 2+ or NH 4 + ----.

Claim 20

Dependent Claim 76 words

A pharmaceutical composition that inhibits unwanted smooth muscle cell proliferation, comprising: a pharmaceutically effective amount of a heparin digest derivative in the form of oligosaccharide fragments selected from the group consisting of a hexasaccharide or octasaccharide compound of claim 5 or pharmaceutically acceptable salts thereof which fragments have an increased ability to inhibit smooth muscle cell proliferation and a decreased ability to act as an anticoagulant as compared with commercial heparin; and a pharmaceutically acceptable carrier.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1998-01-09	1998-07-11	1999-01-10	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2002-01-09	2002-07-11	2003-01-10	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2006-01-09	2006-07-11	2007-01-10	$7700.00	Window Closed / Lapsed

Sulfated polysaccharides as inhibitors of smooth muscle cell proliferation

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