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US 9,051,248 B2Granted
Methods, compounds, and compositions for delivering 1,3-propanedisulfonic acid
AssigneeBHI Limited Partnership
InventorsXianqi Kong, Nigel Levens, Abderrahim Bouzide, Stephane Ciblat, Richard Frenette, Johanne Renaud
Life of this patent
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Abstract
The invention relates to methods, compounds, and compositions for delivering 1,3-propanedisulfonic acid (1,3PDS) in a subject, preferably a human subject. The invention encompasses compounds that will yield or generate 1,3PDS, either in vitro or in vivo. The invention also relates to sulfonate ester prodrugs of 1,3PDS as well as Gemini dimmers and oligomers of 1,3PDS for the prevention or treatment of associated diseases and conditions.
Claims21
A compound of Formula II:
- wherein,
- R3 is selected from hydrogen and a substituted or unsubstituted group selected from C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C3-C15cycloalkyl, C3-C15heterocycloalkyl, C6-C15aryl, and C5-C15heteroaryl;
- R4 is a substituted or unsubstituted group selected from C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C3-C15 cycloalkyl, C3-C15heterocycloalkyl, C6-C15 aryl, and C5-C15heteroaryl;
- wherein at least one of R3 and R4 is a group selected from Formula B, E and F:
- wherein,
- R6, R7 and R8 are each independently a substituted or unsubstituted group selected from C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6heterocycloalkyl, C6-C10aryl, C5-C10heteroaryl, NH2, and NHC(O)OC1-C6alkyl;
- or R7 and R8 are taken together with their adjacent carbon atom to form a group selected from C3-C8cycloalkyl and C3-C8heterocycloalkyl;
- or R6, R7 and R8 are taken together with their adjacent carbon atom to form a C4-C10cycloalkyl fused ring, a C4-C10heterocycloalkyl fused ring, or a C5-C10heteroaryl;
- R22 is a hydrogen atom or a group selected from C1-C6alkyl, C(O)OH, or C(O)OC1-C6alkyl;
- W—Y—Z is selected from C(O)OCH2, OC(O)CH2, CH2C(O)O, and CH2OC(O);
- Rw, Rx, and Ry are each independently selected from a hydrogen atom or a substituted or unsubstituted C1-C3alkyl group, or Rw and Rx are taken together with their adjacent carbon atoms to form a double bond;
- Rz is a substituted or unsubstituted group selected from C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C3-C15 cyclo alkyl, C3-C15heterocycloalkyl, C6-C15aryl, C5-C15heteroaryl, OC1-C12alkyl, OC2-C12alkenyl, OC2-C12 alkynyl, OC3-C15 cycloalkyl, OC3—OC15heterocycloalkyl, OC6-C15aryl, and OC5-C15heteroaryl;
- and
- k is an integer selected from 0, 1 and 2;
- or a pharmaceutically acceptable salt or solvate thereof.
12 more elements
A compound selected from:
- or a pharmaceutically acceptable salt or solvate thereof.
Dependencies are inferred from the claim text.