Search All Applications in Z-ARCHIVE-Cannabis
Application US20200330602
Published 2020-10-22
Method For Improving The Oral Bioavailability Of A Drug
The invention is in the field of medical sciences. It provides new pharmaceutical methods and preparations. In particular, the invention relates to a method for increasing the oral bioavailability of drugs. The invention also provides new compositions comprising a drug covalently attached to a saccharide as in formula (I) below. More in particular, the invention relates to a method for increasing the oral bioavailability of a drug by covalently attaching a sugar-linked, N-substituted or unsubstituted carbamoylalkylidene moiety to a hydroxyl or thiol group of a drug, wherein the substituents are as defined in the claims.
![embedded image]()
Much More than Average Length Specification
View the Patent Matrix® Diagram to Explore the Claim Relationships
USPTO Full Text Publication >
- 1. A method for increasing the oral bioavailability of a drug HX-DM. wherein HX represents an OH or SH functional group,
comprising the step of linking a sugar-carbamoylalkylidene unit of formula (II) Sugar is selected from the group consisting of alpha- and beta-linked monosaccharides and disaccharides, wherein optionally one or more OH groups are replaced by a group R4;
wherein R4 is selected from the group consisting of C1-C6 alkoxy, chlorine, fluorine, cyano, CF3, NH2, C1-C6 alkyl-NH, C1-C6 dialkyl-N, C1-C6 cycloalkyl-N, C1-C6 alkyl-C(O)NH, C1-C6 alkyl-C(O)(C1-C6 alkyl)—N, HC(O)(C1-C6 alkyl)—N, C1-C6 alkyl-O—C(O)NH, C1-C6 alkyl-O—C(O)(C1-C6 alkyl)—N, and C1-C6 alkyl-O—C(O)—O;
R1 is selected from the group consisting of H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, —R5—O—R7, —R5—S—R7, —R6—C(O)—R7, —R6—C(O)—O—R7, —R5—SO2—R7, —R5—SO2—NR7R8, C3-C7 cycloalkyl, C4-C7 cycloalkenyl, a 4 to 7 membered heterocycle, aryl and (C1-C3alkyl)-aryl;
wherein R5 is C2 or C3 alkyl, R6 is C1-C3 alkyl, R7 and R8 are independently hydrogen or C1-C3-alkyl;
and wherein the C3-C7 cycloalkyl, C4-C7 cycloalkenyl, a 4 to 7 membered heterocycle, aryl and (C1-C3alkyl)-aryl groups can be optionally substituted by R9,
wherein R9 is selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, chlorine, fluorine, cyano, CF3, amine, amide, carbamate and —C(O)O—(C1-C4-alkyl);
R2 and R3 are both H, or one of R2 and R3 is H and the other is C1-C6 alkyl; and wherein ----- represents a leaving group,
- 8. The method according to any one of the preceding claims wherein R2 and R3 are both H.
- 9. The method according to any one of the preceding claims, wherein the drug moiety is selected from the group consisting of quetiapine, montelukast, venlafaxine, mesalazine, desvenlafaxine, metoprolol, paliperidone, buprenorphine, morphine, ganciclovir, tapentadol, rotigotine, abiraterone, acetaminophen, saxagliptin, fulvestrant, afimoxifene, testosterone, simvastatin, tolterodine, tramadol, atenolol, naloxone, nabilone, metaraminol, dihydroartemisinin, orciprenaline, labetalol, kalydeco, azacitidine, niclosamide, tetrahydrocannabinol, raloxifene, propofol, gemcitabine, cannabidiol, carvedilol, edavarone, cytaribine, dasatinib, perrilyl alcohol, butorphanol and bazedoxifene.
- 17. The compound according to any one of the preceding claims wherein R2 and R3 are both H.
