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US 2003/0125499 A1Published application
Compounds containing quaternary carbons, medical devices, and methods
AssigneeMedtronic, Inc.
InventorsMichael Eric Benz, Edward DiDomenico, Christopher M. Hobot, Randall V. Sparer, Kenneth B. Wagener, John E. Schwendeman
Life of this patent
Estimating the term…
Abstract
Compounds that include diorgano groups having quaternary carbons and optionally urethane groups, urea groups, or combinations thereof (i.e., polyurethanes, polyureas, or polyurethane-ureas), as well as materials and methods for making such compounds.
Claims131
A medical device comprising a polymer comprising a group of the formula:
- —(R1)n—(—Z—(R2)m—)p—
- wherein:
- n=0 or 1;
- m=0 or 1;
- p=1-100,000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, with the proviso that R2 includes at least two carbon atoms;
- and
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring.
5 more elements
A medical device comprising a polymer prepared from a compound of the formula:
- Y—(R1)n—(—Z—(R2)m—)p—Y
- wherein:
- each Y is independently OH or NR4H;
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- and
- each R4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
- with the proviso that at least one of the repeat units —Z—(R2)m— is not a —C(CH3)2CH2— group when both Y groups are OH.
8 more elements
A medical device comprising a polymer comprising a urethane group, a urea group, or combinations thereof, wherein the polymer is prepared from an isocyanate-containing compound and a compound of the formula:
- Y—R5—(—R6—Z—R7—)q—R8—Y
- wherein:
- each Y is independently OH or NH2;
- q=1-2000;
- Z is —C(R9)2—;
- R5, R6, R7, and R8 are each independently a straight chain alkylene group having 1-20 carbon atoms;
- and
- each R9 isindependently a straight chain alkyl group having 1-20 carbon atoms.
5 more elements
A copolymer comprising a group of the formula:
- —(R1)n—(—Z—(R2)m—)p—
- wherein:
- n=0 or 1;
- m=0 or 1;
- p=1-100,000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, with the proviso that R2 includes at least two carbon atoms;
- and
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring.
5 more elements
A polymer comprising a urethane group, a urea group, or combinations thereof, and a group of the formula:
- —(R1)n—(—Z—(R2)m—)p—
- wherein:
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, with the proviso that R2 includes at least two carbon atoms;
- and
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring.
5 more elements
A copolymer prepared from a compound of the formula:
- Y—(R1)n—(—Z—(R2)m—)p—Y
- wherein:
- each Y is independently OH or NR4H;
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- and
- each R4 independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
- with the proviso that at least one of the repeat units —Z—(R2)m— is not a —C(CH3)2CH2— group when both Y groups are OH.
8 more elements
A polymer comprising a urethane group, a urea group, or combinations thereof, wherein the polymer is prepared from a compound of the formula:
- Y—(R1)n—(—Z—(R2)m—)p—Y
- wherein:
- each Y is independently OH or NR4H;
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- and
- each R4 is independently H or a saturated or unsaturated aliphatic groups an aromatic group, or combinations thereof;
- with the proviso that at least one of the repeat units —Z—(R2)m— is not a —C(CH3)2CH2— group when both Y groups are OH.
8 more elements
A polymer comprising a urethane group, a urea group, or combinations thereof, wherein the polymer is prepared from an isocyanate-containing compound and a compound of the formula:
- Y—R5—(—R6—Z—R7—)q—R8—Y
- wherein:
- each Y is independently OH or NH2;
- q=1-2000;
- Z is —C(R9)2—;
- R5, R6, R7, and R8 are each independently a straight chain alkylene group having 1-20 carbon atoms;
- and
- each R9 is independently a straight chain alkyl group having 1-20 carbon atoms.
5 more elements
A copolymer prepared from a compound of the formula:
- Y—R5—(—R6—Z—R7—)q—R8—Y
- wherein:
- each Y is independently OH or NH2;
- q=1-2000;
- Z is —C(R9)2—;
- R5, R6, R7, and R8 are each independently a straight chain alkylene group having 1-20 carbon atoms;
- and
- each R9 is independently a straight chain alkyl group having 1-20 carbon atoms.
5 more elements
A compound of the formula:
- Y—(R1)n—(—Z—(R2)m—)p—Y
- wherein:
- each Y is independently OH, NR4H, or protected forms thereof;
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- and
- each R4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
- with the proviso that at least one of the repeat units —Z—(R2)m— is not a —C(CH3)2CH2— group when both Y groups are OH.
8 more elements
A compound of the formula:
- Y—R5—(—R6—Z—R7—)q—R8—Y
- wherein:
- each Y is independently OH, NH2, or protected forms thereof;
- q=1-2000;
- Z is —C(R9)2—;
- R5, R6, R7, and R8 are each independently a straight chain alkylene group having 1-20 carbon atoms;
- and
- each R9 is independently a straight chain alkyl group having 1-20 carbon atoms.
5 more elements
A method of making a polymer comprising a urethane group, a urea group, or combinations thereof, and a group of the formula —(R1)n—(—Z—(R2)m—)p—, the method comprising combining an isocyanate-containing compound and a compound of the formula:
- Y—(R1)n—(—Z—(R2)m—)p—Y
- wherein:
- each Y is independently OH or NR4H;
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- Z is —C(R3)2— wherein each R3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- and
- each R4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
- with the proviso that at least one of the repeat units —Z—(R2)m— is not a —C(CH3)2CH2— group when both Y groups are OH.
8 more elements
A method of making a polymer comprising a urethane group, a urea group, or combinations thereof, and a group of the formula —C(R9)2—, the method comprising combining an isocyanate-containing compound and a compound of the formula:
- Y—R5—(—R6—Z—R7—)q—R8—Y
- wherein:
- each Y is independently OH or NH2;
- q=1-2000;
- Z is —C(R9)2—;
- R5, R6, R7, and R8 are each independently a straight chain alkylene group having 1-20 carbon atoms;
- and
- each R9 is independently a straight chain alkyl group having 1-20 carbon atoms.
5 more elements
A method of making a compound of the formula:
- Y—(R1)n—(—Z—(R2)m—)p—Y
- wherein:
- each Y is independently OH or NR4H;
- n=0 or 1;
- m=0 or 1;
- p=1-2000;
- R1 and R2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- Z is —C(R3)2— wherein each R3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- and
- each R4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
- with the proviso that at least one of the repeat units —Z—(R2)m— is not a —C(CH3)2CH2— group when both Y groups are OH;
- the method comprising:
- polymerizing a diene compound having a quaternary carbon in the presence of a metathesis catalyst to form an intermediate polymer;
- depolymerizing the intermediate polymer in the presence of a chain transfer agent to form an unsaturated telechelic polymer;
- wherein the chain transfer agent comprises protecting groups;
- and
- converting the unsaturated telechelic polymer to a compound of the formula Y—(R1)n—(—Z—(R2)m—)p—Y.
14 more elements
A method of making an alcohol and/or an amine comprising a quaternary carbon, the method comprising:
- polymerizing a compound having a quaternary carbon in the presence of a metathesis catalyst to form an intermediate polymer, wherein the compound having a quaternary carbon has the formula:
- R10HC═CH—(R11)r—Z—(R12)s—CH═CHR13
- wherein:
- r=0 or 1;
- s=0 or 1;
- Z is —C(R3)2—, wherein each R3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- R10 and R13 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms;
- and
- R11 and R12 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- depolymerizing the intermediate polymer in the presence of a chain transfer agent to form an unsaturated telechelic polymer;
- wherein the chain transfer agent comprises protecting groups and has the formula:
- Y—R17—HC═CH—R18—Y
- wherein:
- each Y is independently a protected form of OH or NR4H;
- and
- R17 and R18 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof;
- and
- converting the unsaturated telechelic polymer to an alcohol and/or an amine.
15 more elements
A method of making an alcohol and/or an amine comprising a quaternary carbon, the method comprising:
- polymerizing a compound having a quaternary carbon in the presence of a chain transfer agent and a metathesis catalyst to form an unsaturated telechelic polymer;
- wherein the compound having a quaternary carbon has the formula:
- R10HC═CH—(R11)r—Z—(R12)s—CH═CHR13
- wherein:
- r=0 or 1;
- s=0 or 1;
- Z is —C(R3)2—, wherein each R3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- R10 and R13 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms;
- and
- R11 and R12 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms:
- wherein the chain transfer agent comprises protecting groups and has the formula:
- Y—R17—HC═CH—R18—Y
- wherein:
- each Y is independently a protected form of OH or NR4H;
- and
- R17 and R18 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof;
- and
- converting the unsaturated telechelic polymer to an alcohol and/or an amine.
15 more elements
A method of making an alcohol and/or an amine comprising a quaternary carbon, the method comprising:
- polymerizing a compound having a quaternary carbon in the presence of a metathesis catalyst to form an intermediate polymer, wherein the compound having a quaternary carbon has the formula:
- R10HC═CH—(R11)r—Z—(R12)s—CH═CHR13
- wherein:
- r=0 or 1;
- s=0 or 1;
- Z is —C(R3)2—, wherein each R3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R3 groups within —C(R3)2— can be optionally joined to form a ring;
- R10 and R13 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms;
- and
- R11 and R12 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
- depolymerizing the intermediate polymer by reaction with a compound of the following formula to form an unsaturated telechelic polymer:
- CH2═CH—R21—Y
- wherein:
- each Y is independently a protected form of OH or NR4H;
- and
- R21 is a saturated aliphatic group, an aromatic group, or combinations thereof;
- and
- converting the unsaturated telechelic polymer to an alcohol and/or an amine.
14 more elements
Dependencies are inferred from the claim text.