# US 12,109,226 B1 · Polysilane methacrylic compounds and methods of making them

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- Number: US 12,109,226 B1
- Document ID: US12109226B1
- Status: Granted
- Kind: B1
- Application number: 18/634,556
- Filed: 2024-04-12
- Granted: 2024-10-08
- Earliest claimed: 2024-02-05
- Assignees: Zetagen Therapeutics, Inc.
- Applicants: Zetagen Therapeutics, Inc.
- Inventors: Bryan S. Margulies
- Web page: https://patentgrep.com/patent/US12109226B1

## CPC

- A61K 31/80: Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
- A61K 31/485: Morphinan derivatives, e.g. morphine, codeine
- A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08F 230/085: {the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes}
- A61L 2300/204: with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
- A61L 2430/02: for reconstruction of bones; weight-bearing implants
- C08F 2810/30: leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A polysilane methacrylic polymer and processes of preparing the polysilane methacrylic polymer are provided.

## Claims

### Claim 1

A method of treating a bone injury or a bone condition comprising locally administering to a subject in need thereof at a bone injury site or a site affected by a bone condition an effective amount of a composition comprising a compound having a formula (IV):
wherein each of R1, R2, R3, R4, R5, R6, and R7 is selected from the group consisting of H, alkyl, alkenyl, alkoxy, aryl, aralkyl, cycloalkyl, heterocyclyl, heteroaryl groups, hydroxyl, or halo, and n is independently for each occurrence an integer from 1 to 1000000.

### Claim 2 (depends on 1)

The method of claim 1, wherein the composition further comprises N-allyl noroxymorphone hydrochloride.

### Claim 3 (depends on 1)

The method of claim 1, wherein the compound has a formula (IVa):

### Claim 4 (depends on 1)

The method of claim 1, wherein the composition further comprises an OGFR antagonist.

### Claim 5 (depends on 1)

The method of claim 1, wherein n is 1 to 10,000.

### Claim 6 (depends on 1)

The method of claim 1, wherein n is 1 to 100.

### Claim 7 (depends on 1)

The method of claim 1, wherein the compound of formula (I) is prepared by a method comprising reacting methyl methacrylate with tetraethyl orthosilicate and 1,1,3,3-tetramethyldisilane.

### Claim 8 (depends on 7)

The method of claim 7, wherein the tetraethyl orthosilicate and 1,1,3,3-tetramethyldisilane are reacted in a 0.375:0.375 volume ratio.

### Claim 9 (depends on 8)

The method of claim 8, wherein 0.750-mL of the tetraethyl orthosilicate+1,1,3,3-tetramethyldisilane solution are added to 1-gram of polymethyl methacrylate is added.

### Claim 10 (depends on 1)

The method of claim 1, wherein the compound is prepared by a method comprising reacting methyl methacrylate with tetraethyl orthosilicate and 1,1,3,3-tetramethyldisilane to form the SiH3—[SiH2]n—SiH2—[C5H7O2]n wherein n is independently for each occurrence an integer from 1 to 1000000.

### Claim 11 (depends on 10)

The method of claim 10, wherein the methyl methacrylate, tetraethyl orthosilicate, and 1,1,3,3-tetramethyldisilane are reacted for 12 to 18 hours at room temperature.

### Claim 12 (depends on 11)

The method of claim 11, wherein addition of Ca10(PO4)6(OH)2 is performed by annealing with SiH3—[SiH2]n—SiH2—[C5H7O2]n.