Back to results
US 2016/0354338 A1Published application
Tricyclic compounds and methods of making and using same
AssigneeZafgen, Inc.
InventorsDavid Clark, Susan M. Cramp, Hazel J. Dyke, Thomas D. Pallin, Robert Zahler
Life of this patent
Estimating the term…
Abstract
The invention provides tricyclic compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.
Claims23
A method of treating and/or controlling obesity, comprising administering to a patient in need thereof an effective amount of a tricyclic compound represented by:
- wherein
- B is a 5-membered heteroaryl having one or two heteroatoms independently selected from the group consisting of S, O or N, optionally substituted on a carbon with one or two substituents each independently selected from RB1, and, optionally substituted, on nitrogen, if present, with one or two substituents each independently selected from RB2;
- D is a 6- or 7-membered heterocyclic, carbocyclic, heteroaryl or aryl ring;
- wherein B is fused to D such that the two atoms shared by D and B are both carbon;
- E is selected from the group consisting of:
- —W—C(RC3RC4)—;
- —W—C(═O)—;
- —C(═O)—V—;
- —C(RC1RC2)—C(RC3RC4)—;
- —C(RC1RC2)—V—;
- —N═C(RD2)—;
- —C(RD1)═N—;
- —C(RD1)═C(RD2)—;
- —N═N—;
- —W—C(RC3RC4)—C(RC5RC6)—;
- —C(RC1RC2)—V—C(═O)—;
- —W—C(═O)—C(RC5RC6)—;
- —C(RC1RC2)—C(═O)—U—;
- —C(═O)—V—C(RC5RC6)—;
- —C(RC1RC2)—C(RC3RC4)—U—;
- —C(RC1RC2)—C(RC3RC4)—C(RC5RC6)—;
- and —C(RC1RC2)—V—C(RC5RC6)—;
- wherein the left hand substituent of E is attached to the phenyl ring of Formula I and the right hand substituent of E is attached to B;
- W is selected from the group consisting of O, S, and N(RN1);
- V is selected from the group consisting of O, S, and N(RN2);
- U is selected from the group consisting of O, S, and N(RN3);
- Y is:
- —C(RY1RY2)— or —N(RY3)—;
- X is selected from the group consisting of —S—, —S(═O)—, —SO2— with the proviso that, if Y is —N(RY3)—, then X is —SO2—;
- A is a ring selected from the group consisting of phenyl, a 5-6 membered heteroaryl having 1, 2 or 3 heteroatoms each selected from S, N or O, and a 4-7 membered heterocycle having 1, 2 or 3 heteroatoms each selected from N or O;
- RA1 is selected, independently for each occurrence, from the group consisting of hydrogen, hydroxyl, cyano, halogen, C1-4alkyl or C1-3alkoxy, wherein C1-4alkyl, or C1-3alkoxy may be optionally substituted by one or more halogens;
- n is 1 or 2;
- RA2 is selected from the group consisting of hydrogen, RiRjN—, heterocyclyl, heterocyclyloxy, heterocyclyl-(NRa)—;
- wherein said heterocyclyl is a 4-7 membered ring optionally substituted by one or more substituents selected from Rg and wherein if said heterocyclyl contains a —NH moiety that nitrogen may be optionally substituted by one or more groups Rh;
- or
- RA2 is selected from the group consisting of C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C3-6alkenyloxy, C3-6alkynyloxy, C3-6cycloalkoxy, C1-6alkyl-S(O)w— (wherein w is 0, 1 or 2), C1-6alkyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl, C1-6alkyl-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)—SO2—, C1-6alkyl-SO2—N(Ra)—, C1-6alkoxy-carbonyl-N(Ra)—, C1-6alkyl-carbonyl-N(Ra)—C1-6alkyl, C1-6alkyl-N(Ra)-carbonyl-C1-6alkyl, C1-6alkoxyC1-6alkyl;
- wherein C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C3-6alkenyloxy, C3-6alkynyloxy, C3-6cycloalkoxy, C1-6alkyl-S(O)w—, C1-6alkyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl-, C1-6alkyl-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)—SO2—, C1-6alkyl-S O2—N(Ra)—, C1-6alkoxycarbonyl-N(Ra)—, C1-6alkyl-carbonyl-N(Ra)C1-6alkyl-, C1-6alkyl-N(Ra)-carbonyl-C1-6alkyl-, C1-6alkoxyC1-6alkyl may be optionally substituted by RP2, phenyl, phenoxy, heteroaryl, heteroaryloxy, heteroaryl-(NRa)—, heterocyclyl, heterocyclyloxy or heterocyclyl-N(Ra)—;
- wherein said heteroaryl is a 5-6 membered monocyclic ring having one, two or three heteroatoms selected from O, S, or N, and wherein said heteroaryl or phenyl is optionally substituted with one or more substituents selected from Rf;
- wherein said heterocyclyl is a 4-7 membered ring optionally substituted by one or more substituents selected from Rg and wherein if said heterocyclyl contains a —NH moiety that nitrogen may be optionally substituted by one or more groups Rh;
- RB1 is selected, independently for each occurrence, from the group consisting of hydrogen, cyano, halogen, C1-2alkyl or C1-2alkoxy, wherein C1-2alkyl or C1-2alkoxy, may be optionally substituted with one or more halogens;
- RB2 is selected, independently for each occurrence, from the group consisting of hydrogen or C1-2alkyl, wherein C1-2alkyl may be optionally substituted with one or more halogens;
- RY1 and RY2 are independently selected from the group consisting of hydrogen, C1-4alkyl;
- RY3 is selected from the group consisting of hydrogen, C1-4alkyl;
- RC1 and RC2 are each selected independently from the group consisting of hydrogen, halogen, hydroxyl, C1-2alkyl, C1-2alkoxy, wherein C1-2alkyl or C1-2alkoxy may be optionally substituted by one or more substituents selected from halogen, cyano or hydroxyl;
- RN1 is selected from the group consisting of hydrogen and C1-2alkyl, wherein C1-2alkyl may be optionally substituted by one or more substituents selected from halogen, cyano or hydroxyl;
- RD1 is selected from the group consisting of hydrogen, halogen, C1-2alkyl, C1-2alkoxy;
- and wherein C1-2alkyl, and C1-2alkoxy may be optionally substituted by halogen, cyano or hydroxyl;
- RC3 and RC4 are selected independently from the group consisting of hydrogen, hydroxyl, cyano, halogen, C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy and wherein C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy may be optionally substituted by one or more substituents selected from RP1;
- RN2 is selected for each occurrence from the group consisting of hydrogen, C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl or C3-4alkynyl, and wherein C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl, or C3-4alkynyl may be optionally substituted by one or more substituents selected from RP1;
- RD2 is selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, C1-4alkyl, C1-3alkoxy, C2-4alkynyl, C2-4alkenyl, C1-3alkyl-carbonyl-N(Ra)— and wherein C1-4alkyl, C1-3alkoxy, C2-4alkynyl, C2-4alkenyl and C1-3alkyl-carbonyl-N(Ra)— may be optionally substituted by one or more substituents selected from RP1;
- RC5 and RC6 are selected independently from the group consisting of hydrogen, hydroxyl, cyano, halogen, C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy and wherein C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy may be optionally substituted by one or more substituents selected from RP1;
- RN3 is selected for each occurrence from the group consisting of hydrogen, C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl or C3-4alkynyl, and wherein C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl, or C3-4alkynyl may be optionally substituted by one or more substituents selected from RP1;
- Ra and Rb are independently selected, for each occurrence, from the group consisting of hydrogen and C1-4alkyl, or Ra and Rb, together with the nitrogen to which they are attached, may form a 4-6 membered heterocyclic ring which may have an additional heteroatom selected from O, S, or N, and wherein C1-4alkyl may be optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, oxo and hydroxyl, and wherein the 4-6 membered heterocyclic ring may be optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, oxo or hydroxyl;
- Rf is independently selected, for each occurrence, from the group consisting of RP2, hydrogen, halogen, cyano, hydroxyl, C1-6alkyl, C3-6cycloalkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C1-6alkyl-S(O)w— (wherein w is 0, 1 or 2), C1-6alkylcarbonyl-N(Ra)—;
- C1-6alkoxycarbonyl-N(Ra)—;
- and wherein C1-6alkyl, C3-6cycloalkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C1-6alkyl-S(O)w—, C1-6alkylcarbonyl-N(Ra)—, C1-6alkoxycarbonyl-N(Ra)— may be optionally substituted by one or more substituents selected from RP2;
- Rg is independently selected for each occurrence from the group consisting of RP2, hydrogen, halogen, cyano, hydroxyl, oxo, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C1-6alkyl-S(O)w— (wherein w is 0, 1 or 2), C1-6alkylcarbonyl-N(Ra)—;
- C1-6alkoxycarbonyl-N(Ra)—, and wherein C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C1-6alkyl-S(O)w—, C1-6alkylcarbonyl-N(Ra)—;
- C1-6alkoxycarbonyl-N(Ra)— may be optionally substituted by one or more substituents selected from RP2;
- Rh is independently selected for each occurrence from the group consisting of RP3, hydrogen, C1-6alkyl, C3-6alkenyl, C3-6alkynyl, C3-6cycloalkyl, C1-6alkyl-S(O)2—;
- C1-6alkoxycarbonyl-;
- and wherein C1-6alkyl, C3-6alkenyl, C3-6alkynyl, C3-6cycloalkyl, C1-6alkyl-S(O)2—, C1-6alkylcarbonyl- may be optionally substituted by one or more substituents selected from RP2;
- Ri and Rj, are selected independently for each occurrence from group consisting of hydrogen, C1-4alkyl and C3-6cycloalkyl optionally substituted by one or more substituents selected from R1;
- or Ri and Rj taken together with the nitrogen to which they are attached form a 4-7 membered heterocyclyl ring which may have an additional heteroatom selected from O, S, or N, optionally substituted on carbon by one or more substituents selected from the group consisting of halogen, hydroxyl, oxo, cyano, C1-6alkyl, C1-6alkoxy, RaRbN—, RaRbN—SO2—, RaRbN-carbonyl-, and wherein C1-6alkyl or C1-6alkoxy may be optionally substituted by RP4;
- or optionally substituted on nitrogen by one or more substituents selected from the group consisting of C1-6alkyl, RaRbN-carbonyl-, and wherein C1-6alkyl may be optionally substituted by RP4;
- RP1 is independently selected, for each occurrence, from the group consisting of halogen, hydroxyl, cyano, RaRbN—, RaRbN-carbonyl-, C1-3alkoxy;
- RP2 is independently selected, for each occurrence, from the group consisting of halogen, hydroxyl, cyano, C1-6alkoxy, RiRjN—, RiRjN-carbonyl-, RiRjN—SO2—, RiRjN-carbonyl-N(Ra)—;
- RP3 is independently selected, for each occurrence, from the group consisting of RiRjN-carbonyl- and RiRjN—SO2—;
- RP4 is independently selected, for each occurrence, from the group consisting of, halogen, hydroxyl, cyano;
- and
- pharmaceutically acceptable salts, stereoisomers, esters and prodrugs thereof.
68 more elements
A method of treating and/or controlling obesity, comprising administering to a patient in need thereof an effective amount of a tricyclic compound represented by:
- wherein:
- E is selected from the group consisting of:
- —O—C(RC3RC4)—;
- —O—C(═O)—;
- —N(RN1)—C(═O)—;
- —N(RN1)—C(═O)—C(RC5RC6)—;
- C(RC1RC2)—O—;
- —N═C(RD2)—;
- —C(RD1)═N—;
- —C(RD1)═C(RD2)—;
- —N═N—;
- —O—C(RC3RC4)—C(RC5RC6)—;
- —C(RC1RC2)—O—C(═O)—;
- —O—C(═O)—C(RC5RC6)—;
- —C(RC1RC2)—C(═O)—N(RN3)—;
- —C(RC1RC2)—C(RC3RC4)—O—;
- —C(RC1RC2)—N(RN2)—C(═O)—;
- and —C(RCRC2)—C(RC3RC4)—C(RC5RC6)—;
- Y is:
- —C(RY1RY2)— or —N(RY3)—;
- RA1 is selected from the group consisting of hydrogen, hydroxyl, cyano, halogen, C1-4alkyl or C1-3alkoxy, wherein C1-4alkyl, or C1-3alkoxy may be optionally substituted by one or more halogens;
- RA2 is selected from the group consisting of hydrogen, RiRjN—, heterocyclyl, heterocyclyloxy, heterocyclyl-(NRa)—;
- wherein said heterocyclyl is a 4-7 membered ring optionally substituted by one or more substituents selected from Rg and wherein if said heterocyclyl contains a —NH moiety that nitrogen may be optionally substituted by one or more groups Rh;
- or
- RA2 is selected from the group consisting of C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C3-6alkenyloxy, C3-6alkynyloxy, C3-6cycloalkoxy, C1-6alkyl-S(O)w— (wherein w is 0, 1 or 2), C1-6alkyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl, C1-6alkyl-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)—SO2—, C1-6alkyl-SO2—N(Ra)—, C1-6alkoxy-carbonyl-N(Ra)—, C1-6alkyl-carbonyl-N(Ra)C1-6alkyl, C1-6alkyl-N(Ra)-carbonyl-C1-6alkyl, C1-6alkoxyC1-6alkyl;
- wherein C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C3-6alkenyloxy, C3-6alkynyloxy, C3-6cycloalkoxy, C1-6alkyl-S(O)2—, C1-6alkyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl, C1-6alkyl-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)-carbonyl-N(Ra)—, C1-6alkyl-N(Ra)—SO2—, C1-6alkyl-SO2—N(Ra)—, C1-6alkoxycarbonyl-N(Ra)—, C1-6alkyl-carbonyl-N(Ra)C1-6alkyl, C1-6alkyl-N(Ra)-carbonyl-C1-6alkyl-, C1-6alkoxyC1-6alkyl may be optionally substituted by RP2, heterocyclyl, heterocyclyloxy or heterocyclyl-N(Ra)—;
- and wherein if said heterocyclyl contains a —NH moiety that nitrogen may be optionally substituted by one or more groups Rh;
- RY1 and RY2 are independently selected from the group consisting of hydrogen and C1-4alkyl;
- RY3 is selected from the group consisting of hydrogen and C1-4alkyl;
- RC1 and RC2 are each selected independently from the group consisting of hydrogen, halogen, hydroxyl, C1-2alkyl, C1-2alkoxy, wherein C1-2alkyl or C1-2alkoxy may be optionally substituted by one or more substituents selected from halogen, cyano or hydroxyl;
- RN1 is selected from the group consisting of hydrogen and C1-2alkyl, wherein C1-2alkyl may be optionally substituted by one or more substituents selected from halogen, cyano or hydroxyl;
- RD1 is selected from the group consisting of hydrogen, halogen, C1-2alkyl, C1-2alkoxy;
- and wherein C1-2alkyl, and C1-2alkoxy may be optionally substituted by halogen, cyano or hydroxyl;
- RC3 and RC4 are selected independently from the group consisting of:
- hydrogen, hydroxyl, cyano, halogen, C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy and wherein C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy may be optionally substituted by one or more substituents selected from RP1;
- RN2 is selected for each occurrence from the group consisting of hydrogen, C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl or C3-4alkynyl, and wherein C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl, or C3-4alkynyl may be optionally substituted by one or more substituents selected from RP1;
- RD2 is selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, C1-4alkyl, C1-3alkoxy, C2-4alkynyl, C2-4alkenyl, C1-3alkyl-carbonyl-N(Ra)— and wherein C1-4alkyl, C1-3alkoxy, C2-4alkynyl, C2-4alkenyl and C1-3alkyl-carbonyl-N(Ra)— may be optionally substituted by one or more substituents selected from RP1;
- RC5 and RC6 are selected independently from the group consisting of hydrogen, hydroxyl, cyano, halogen, C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy and wherein C1-4alkyl, C2-4alkenyl, C2-4alkynyl or C1-3alkoxy may be optionally substituted by one or more substituents selected from RP1;
- RN3 is selected for each occurrence from the group consisting of hydrogen, C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl or C3-4alkynyl, and wherein C1-4alkyl, C1-3alkylcarbonyl, C3-4alkenyl, or C3-4alkynyl may be optionally substituted by one or more substituents selected from RP1;
- Ra and Rb are independently selected, for each occurrence, from the group consisting of hydrogen and C1-4alkyl, or Ra and Rb together with the nitrogen to which they are attached may form a 4-6 membered heterocyclic ring which may have an additional heteroatom selected from O, S, or N, and wherein C1-4alkyl may be optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, oxo and hydroxyl, and wherein the 4-6 membered heterocyclic ring may be optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, oxo or hydroxyl;
- Rg is independently selected for each occurrence from the group consisting of RP2, hydrogen, halogen, cyano, hydroxyl, oxo, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C1-6alkyl-S(O)w— (wherein w is 0, 1 or 2), C1-6alkylcarbonyl-N(Ra)—;
- C1-6alkoxycarbonyl-N(Ra)—, and wherein C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C1-6alkoxy, C1-6alkyl-S(O)w—, C1-6alkylcarbonyl-N(Ra)—;
- C1-6alkoxycarbonyl-N(Ra)— may be optionally substituted by one or more substituents selected from RP2;
- Rh is independently selected for each occurrence from the group consisting of RP3, hydrogen, C1-6alkyl, C3-6alkenyl, C3-6alkynyl, C3-6cycloalkyl, C1-6alkyl-S(O)2—, C1-6alkoxycarbonyl-;
- and wherein C1-6alkyl, C3-6alkenyl, C3-6alkynyl, C3-6cycloalkyl, C1-6alkyl-S(O)2—, C1-6alkylcarbonyl- may be optionally substituted by one or more substituents selected from RP2;
- Ri and Rj, are selected independently for each occurrence from group consisting of hydrogen, C1-4alkyl and C3-6cycloalkyl optionally substituted by one or more substituents selected from R1;
- or Ri and Rj taken together with the nitrogen to which they are attached form a 4-7 membered heterocyclyl ring which may have an additional heteroatom selected from O, S, or N, optionally substituted on carbon by one or more substituents selected from the group consisting of halogen, hydroxyl, oxo, cyano, C1-6alkyl, C1-6alkoxy, RaRbN—, RaRbN—SO2—, RaRbN-carbonyl-, and wherein C1-6alkyl or C1-6alkoxy may be optionally substituted by RP4;
- or optionally substituted on nitrogen by one or more substituents selected from the group consisting of C1-6alkyl, RaRbN-carbonyl-, and wherein C1-6alkyl may be optionally substituted by RP4;
- RP1 is independently selected, for each occurrence, from the group consisting of halogen, hydroxyl, cyano, RaRbN—, RaRbN-carbonyl-, C1-3alkoxy;
- RP2 is independently selected, for each occurrence, from the group consisting of halogen, hydroxyl, cyano, C1-6alkoxy, RiRjN—, RiRjN-carbonyl-, RiRjN—SO2—, RiRjN-carbonyl-N(Ra)—;
- RP3 is independently selected, for each occurrence, from the group consisting of, RiRjN-carbonyl-, RiRjN—SO2—;
- RP4 is independently selected, for each occurrence, from the group consisting of, halogen, hydroxyl, cyano;
- and pharmaceutically acceptable salts, stereoisomers, esters and prodrugs thereof.
50 more elements
A method of treating and/or controlling obesity, comprising administering to a patient in need thereof an effective amount of a compound selected from the group consisting of:
- 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzene-sulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-(benzenesulfonylmethyl)-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 8-(benzenesulfonylmethyl)-4,5-dihydro-3,6-dioxabenzo-[e]azulene-7-carboxylic acid;
- 7-(benzenesulfonylmethyl)-furo[2,3-c]quinoline-6-carboxylic acid;
- 7-(benzenesulfonylmethyl)-4-oxo-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-(benzene-sulfonylmethyl)-4-methyl-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 8-[2-((Z)-3-diethylamino-prop-1-enyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo [e]azulene-7-carboxylic acid;
- 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylic acid;
- 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 8-[2-(3-diethyl-aminopropyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylic acid;
- 7-{4-fluoro-2-[(Z)-3-(morpholin-4-yl)prop-1-enyl]benzenesulfonyl-amino}-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-{4-fluoro-2-[(Z)-3-(pyrrolidin-1-yl)prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-(3-diethyl-aminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4-oxo-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-(3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-4-methyl-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-(3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-(R)-4-methyl-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-(3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-(S)-4-methyl-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylic acid;
- 7-[2-((Z)-3-diethylaminoprop1-enyl)-4-fluorobenzene-sulfonylamino]-4H-chromeno[3,4-d]isothiazole-6-carboxylic acid;
- 7-[2-((Z)-3-diethylamino-prop-1-enyl)-benzenesulfonylamino-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-{4-fluoro-2-[(Z)-3-((R)-3-hydroxypyrrolidin-1-yl)-prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]-chromene-6-carboxylic acid;
- 7-{4-fluoro-2-[(Z)-3-((S)-3-hydroxypyrrolidin-1-yl)-prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-3-diethylamino-prop-1-enyl)-4-fluorobenzenesulfonylamino]-4-oxo-4,5-dihydrofuro[2,3-c]-quinoline-6-carboxylic acid;
- 7-{2-[(Z)-3-(azetidin-1-yl)prop-1-enyl]-4-fluorobenzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-{4-fluoro-2-[(Z)-3-(3-hydroxyazetidin-1-yl)-prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((Z)-3-diethyl-aminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1-fluoro-4H-furo[2,3-c]chromene-6-carboxylic acid;
- 7-[2-((E)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid and pharmaceutically acceptable salts, stereoisomers, esters and prodrugs thereof.
24 more elements
-20. (canceled)
-30. (canceled)
Dependencies are inferred from the claim text.