CA2835261C - Partially saturated tricyclic compounds and methods of making and using same - Google Patents
Partially saturated tricyclic compounds and methods of making and using same Download PDFInfo
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- CA2835261C CA2835261C CA2835261A CA2835261A CA2835261C CA 2835261 C CA2835261 C CA 2835261C CA 2835261 A CA2835261 A CA 2835261A CA 2835261 A CA2835261 A CA 2835261A CA 2835261 C CA2835261 C CA 2835261C
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- 6alkyl
- chromene
- carboxylic acid
- substituted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 238
- 238000000034 method Methods 0.000 title claims abstract description 154
- 229920006395 saturated elastomer Polymers 0.000 title claims description 13
- 208000008589 Obesity Diseases 0.000 claims abstract description 24
- 235000020824 obesity Nutrition 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims description 239
- -1 heteroaryl-(NR a)- Chemical group 0.000 claims description 159
- 229910052739 hydrogen Inorganic materials 0.000 claims description 139
- 239000001257 hydrogen Substances 0.000 claims description 130
- 125000001424 substituent group Chemical group 0.000 claims description 105
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 104
- 150000002431 hydrogen Chemical class 0.000 claims description 91
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 89
- 125000000623 heterocyclic group Chemical group 0.000 claims description 89
- 125000001153 fluoro group Chemical group F* 0.000 claims description 87
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 79
- 235000019000 fluorine Nutrition 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 68
- 229910052731 fluorine Inorganic materials 0.000 claims description 68
- 239000011737 fluorine Substances 0.000 claims description 61
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 38
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 34
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000002837 carbocyclic group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 230000004580 weight loss Effects 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 241000282326 Felis catus Species 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QJMGLVARDLSSLY-FNHZYXHNSA-N (1ar,7bs)-5-[[2-[[(3s)-1-ethylpyrrolidin-3-yl]oxymethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1OCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O QJMGLVARDLSSLY-FNHZYXHNSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052705 radium Inorganic materials 0.000 claims description 3
- 238000007920 subcutaneous administration Methods 0.000 claims description 3
- VBPSPUGMCIMMDS-LXKGCQHHSA-N (1ar,7bs)-5-[[2-[(1-ethylpiperidin-3-yl)methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CCCC1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O VBPSPUGMCIMMDS-LXKGCQHHSA-N 0.000 claims description 2
- CPAFKFCQMRZTSG-ZSZQSSIHSA-N (1as,7br)-5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O CPAFKFCQMRZTSG-ZSZQSSIHSA-N 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- WYSQERQGMBCNST-LRYGQEGESA-N 5-[[2-[2-[(3r)-1-ethylpyrrolidin-3-yl]ethylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O WYSQERQGMBCNST-LRYGQEGESA-N 0.000 claims description 2
- CPAFKFCQMRZTSG-ASFAAARLSA-N 5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O CPAFKFCQMRZTSG-ASFAAARLSA-N 0.000 claims description 2
- 230000033115 angiogenesis Effects 0.000 claims description 2
- 230000003579 anti-obesity Effects 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 230000003834 intracellular effect Effects 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims description 2
- 108060008226 thioredoxin Proteins 0.000 claims description 2
- 229940094937 thioredoxin Drugs 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 31
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 28
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 101100521345 Mus musculus Prop1 gene Proteins 0.000 claims 2
- 108700017836 Prophet of Pit-1 Proteins 0.000 claims 2
- AFKYQMDFOQZUFV-FOGAVDIQSA-N (1ar,7bs)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1-difluoro-2,7b-dihydro-1ah-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@H]2C([C@H]2CO2)(F)F)C2=C1C(O)=O AFKYQMDFOQZUFV-FOGAVDIQSA-N 0.000 claims 1
- GCHDTSWCKKSVAG-MIGHCRNESA-N (1ar,7bs)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O GCHDTSWCKKSVAG-MIGHCRNESA-N 0.000 claims 1
- BQCTVQSCCVVOIO-GPAZVNKHSA-N (1ar,7bs)-5-[[2-[(z)-3-(ethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCNC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O BQCTVQSCCVVOIO-GPAZVNKHSA-N 0.000 claims 1
- NUHCYWPBZHFFHV-QRFRQXIXSA-N (1ar,7bs)-5-[[2-[2-[(2r)-1-ethylpyrrolidin-2-yl]ethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN1CCC[C@H]1CCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O NUHCYWPBZHFFHV-QRFRQXIXSA-N 0.000 claims 1
- RHVINQVUJABXKB-LPHOPBHVSA-N (1ar,7bs)-5-[[2-[3-(diethylamino)propyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)CCCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O RHVINQVUJABXKB-LPHOPBHVSA-N 0.000 claims 1
- OZSBDXQWHQBWBN-RDJZCZTQSA-N (1ar,7bs)-5-[[2-[4-(dimethylamino)butylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O OZSBDXQWHQBWBN-RDJZCZTQSA-N 0.000 claims 1
- CPAFKFCQMRZTSG-QOKNQOGYSA-N (1ar,7bs)-5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O CPAFKFCQMRZTSG-QOKNQOGYSA-N 0.000 claims 1
- QJMGLVARDLSSLY-YJLNNSPDSA-N (1ar,7bs)-5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]oxymethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1OCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O QJMGLVARDLSSLY-YJLNNSPDSA-N 0.000 claims 1
- VSJGXPKALXORRY-PDNKVIRKSA-N (1ar,7bs)-5-[[4-fluoro-2-[(z)-3-pyrrolidin-1-ylprop-1-enyl]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C([C@@H]1C[C@@H]1C=1C=C2)OC=1C(C(=O)O)=C2NS(=O)(=O)C1=CC=C(F)C=C1\C=C/CN1CCCC1 VSJGXPKALXORRY-PDNKVIRKSA-N 0.000 claims 1
- AFKYQMDFOQZUFV-CGYSWORWSA-N (1as,7br)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1-difluoro-2,7b-dihydro-1ah-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2C([C@@H]2CO2)(F)F)C2=C1C(O)=O AFKYQMDFOQZUFV-CGYSWORWSA-N 0.000 claims 1
- GCHDTSWCKKSVAG-FOVLHFFESA-N (1as,7br)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O GCHDTSWCKKSVAG-FOVLHFFESA-N 0.000 claims 1
- ICNANHHADNBANV-WZKLPCIESA-N (1as,7br)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O ICNANHHADNBANV-WZKLPCIESA-N 0.000 claims 1
- BQCTVQSCCVVOIO-SWTGODCJSA-N (1as,7br)-5-[[2-[(z)-3-(ethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCNC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O BQCTVQSCCVVOIO-SWTGODCJSA-N 0.000 claims 1
- SCCNKTSIBMOCLE-SYRUPOHGSA-N (1as,7br)-5-[[2-[(z)-4-(diethylamino)but-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)CC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O SCCNKTSIBMOCLE-SYRUPOHGSA-N 0.000 claims 1
- OZSBDXQWHQBWBN-NVXWUHKLSA-N (1as,7br)-5-[[2-[4-(dimethylamino)butylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O OZSBDXQWHQBWBN-NVXWUHKLSA-N 0.000 claims 1
- HHKAHYNPEQELBS-UHFFFAOYSA-N 5-[[2-(1-ethylazetidin-3-yl)-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC1C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HHKAHYNPEQELBS-UHFFFAOYSA-N 0.000 claims 1
- HUMNCXLVRGALON-UHFFFAOYSA-N 5-[[2-[(1-ethylazetidin-3-yl)methylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC1CNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HUMNCXLVRGALON-UHFFFAOYSA-N 0.000 claims 1
- SBPYXYZNFNHMNS-UHFFFAOYSA-N 5-[[2-[(1-ethylpiperidin-4-yl)methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1CN(CC)CCC1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O SBPYXYZNFNHMNS-UHFFFAOYSA-N 0.000 claims 1
- RFYAVNPEHZYDNY-UHFFFAOYSA-N 5-[[2-[(4-ethyl-2-oxopiperazin-1-yl)methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound O=C1CN(CC)CCN1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O RFYAVNPEHZYDNY-UHFFFAOYSA-N 0.000 claims 1
- UUNFSQNJJFGUEO-VOTSOKGWSA-N 5-[[2-[(e)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-7b-methyl-1a,2-dihydro-1h-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C\C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C2C3(C)CC3COC2=C1C(O)=O UUNFSQNJJFGUEO-VOTSOKGWSA-N 0.000 claims 1
- YUIRRDWVLSMXIU-GDNBJRDFSA-N 5-[[2-[(z)-3-(diethylamino)-2-methylprop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C(C)=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O YUIRRDWVLSMXIU-GDNBJRDFSA-N 0.000 claims 1
- AFKYQMDFOQZUFV-WAYWQWQTSA-N 5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1-difluoro-2,7b-dihydro-1ah-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2CO2)(F)F)C2=C1C(O)=O AFKYQMDFOQZUFV-WAYWQWQTSA-N 0.000 claims 1
- GCHDTSWCKKSVAG-WAYWQWQTSA-N 5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O GCHDTSWCKKSVAG-WAYWQWQTSA-N 0.000 claims 1
- UUNFSQNJJFGUEO-SREVYHEPSA-N 5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-7b-methyl-1a,2-dihydro-1h-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C2C3(C)CC3COC2=C1C(O)=O UUNFSQNJJFGUEO-SREVYHEPSA-N 0.000 claims 1
- BQCTVQSCCVVOIO-ARJAWSKDSA-N 5-[[2-[(z)-3-(ethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCNC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O BQCTVQSCCVVOIO-ARJAWSKDSA-N 0.000 claims 1
- IDKNGDBGNTZLGL-UHFFFAOYSA-N 5-[[2-[2-(4-ethylpiperazin-1-yl)ethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1CN(CC)CCN1CCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O IDKNGDBGNTZLGL-UHFFFAOYSA-N 0.000 claims 1
- WYSQERQGMBCNST-MUYFXNHWSA-N 5-[[2-[2-[(3s)-1-ethylpyrrolidin-3-yl]ethylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1CCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O WYSQERQGMBCNST-MUYFXNHWSA-N 0.000 claims 1
- PXZAIHKPFBAMQC-KGXSXCIVSA-N 5-[[2-[2-[[(3r)-1-ethylpyrrolidin-3-yl]amino]ethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1NCCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O PXZAIHKPFBAMQC-KGXSXCIVSA-N 0.000 claims 1
- HCFNHHNSUKJEIN-IPCDKGFNSA-N 5-[[2-[2-[[(3s)-1-ethylpyrrolidin-3-yl]-methylamino]-2-oxoethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1N(C)C(=O)CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HCFNHHNSUKJEIN-IPCDKGFNSA-N 0.000 claims 1
- XEQUAXOMVWGQKR-RMXPPQQLSA-N 5-[[2-[2-[[(3s)-1-ethylpyrrolidin-3-yl]amino]-2-oxoethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1NC(=O)CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O XEQUAXOMVWGQKR-RMXPPQQLSA-N 0.000 claims 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| PCT/US2012/036789 WO2012154676A1 (en) | 2011-05-06 | 2012-05-07 | Partially saturated tricyclic compounds and methods of making and using same |
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| US20120004162A1 (en) | 2008-12-04 | 2012-01-05 | Vath James E | Methods of Treating an Overweight or Obese Subject |
| KR20120083905A (ko) | 2009-10-09 | 2012-07-26 | 자프겐 코포레이션 | 비만의 치료에 사용하기 위한 설폰 화합물 |
| CA2786603C (en) | 2010-01-08 | 2018-02-20 | James E. Vath | Fumagillol type compounds and methods of making and using same |
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| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| KR20130043207A (ko) | 2010-07-22 | 2013-04-29 | 자프겐 인크. | 트리시클릭 화합물 및 이의 제조 및 사용 방법 |
| JP5913333B2 (ja) | 2010-10-12 | 2016-04-27 | ザフゲン，インコーポレイテッド | スルホンアミド化合物、およびそれを製造し使用する方法 |
| CA2819251A1 (en) | 2010-11-29 | 2012-06-07 | Zafgen Corporation | Treatment of obesity using non-daily administration of 6 - 0 - (4 - dimethylaminoethoxy) cinnamoyl fumagillol |
| CA2825408A1 (en) | 2011-01-26 | 2012-08-02 | Zafgen, Inc. | Tetrazole compounds and methods of making and using same |
| JP5876513B2 (ja) | 2011-03-08 | 2016-03-02 | ザフゲン，インコーポレイテッド | オキサスピロ［２．５］オクタン誘導体および類似体 |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| KR101979039B1 (ko) | 2011-05-06 | 2019-05-15 | 자프겐 인크. | 부분 포화된 삼환식 화합물 및 그리고 그의 제조방법 및 그를 이용하는 방법 |
| BR112013028665A2 (pt) | 2011-05-06 | 2016-09-06 | Zafgen Inc | compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| EP2763671A2 (en) | 2011-10-03 | 2014-08-13 | Zafgen, Inc. | Methods of treating age related disorders |
| EP2804856B1 (en) * | 2012-01-18 | 2017-03-15 | Zafgen, Inc. | Tricyclic sulfone compounds and methods of making and using same |
| BR112014017673A8 (pt) | 2012-01-18 | 2017-07-11 | Zafgen Inc | Compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| BR112014028041A2 (pt) | 2012-05-08 | 2017-06-27 | Zafgen Inc | tratamento de obesidade hipotalâmica com inibidores de metap2 |
| CA2873574A1 (en) | 2012-05-09 | 2013-11-14 | Zafgen, Inc. | Fumagillol type compounds and methods of making and using same |
| US9868717B2 (en) | 2012-11-05 | 2018-01-16 | Zafgen, Inc. | Tricyclic sulphonamide compounds and methods of making and using same |
| CN104918615B (zh) * | 2012-11-05 | 2018-10-12 | 扎夫根股份有限公司 | 治疗肝病的方法 |
| BR112015010225A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos e seus métodos de produção e utilização |
| AU2014236528A1 (en) | 2013-03-14 | 2015-09-24 | Zafgen, Inc. | Methods of treating renal disease and other disorders |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
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| US5164410A (en) | 1988-01-09 | 1992-11-17 | Takeda Chemical Industries, Ltd. | Fumagillol derivatives and pharmaceutical compositions thereof |
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| US5166172A (en) | 1988-09-01 | 1992-11-24 | Takeda Chemical Industries, Ltd. | Fumagillol derivatives and pharmaceutical compositions thereof |
| US5288722A (en) | 1989-03-06 | 1994-02-22 | Takeda Chemical Industries, Ltd. | 6-amino-6-desoxyfumagillols, production and use thereof |
| EP0387650B1 (en) | 1989-03-06 | 1993-03-31 | Takeda Chemical Industries, Ltd. | 6-epifumagillols, production and use thereof |
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-
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- 2012-05-07 CN CN201280033359.8A patent/CN103764641B/zh not_active Expired - Fee Related
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| AU2012253757B2 (en) | 2017-04-13 |
| IL229246A0 (en) | 2014-01-30 |
| WO2012154676A1 (en) | 2012-11-15 |
| CN103764641A (zh) | 2014-04-30 |
| NZ617388A (en) | 2015-11-27 |
| US20140088078A1 (en) | 2014-03-27 |
| AU2012253757A8 (en) | 2015-10-22 |
| CN103764641B (zh) | 2016-10-26 |
| PH12013502261A1 (en) | 2022-10-26 |
| KR20140047611A (ko) | 2014-04-22 |
| US20180002307A1 (en) | 2018-01-04 |
| US9617237B2 (en) | 2017-04-11 |
| MX2013012921A (es) | 2014-02-27 |
| SG194812A1 (en) | 2013-12-30 |
| US20170001973A1 (en) | 2017-01-05 |
| BR112013028534A2 (pt) | 2016-09-06 |
| IL229246A (en) | 2017-05-29 |
| JP6062423B2 (ja) | 2017-01-18 |
| EP2705030B1 (en) | 2016-07-27 |
| WO2012154676A9 (en) | 2014-03-27 |
| JP2014514349A (ja) | 2014-06-19 |
| KR101979039B1 (ko) | 2019-05-15 |
| US9290472B2 (en) | 2016-03-22 |
| AU2012253757A1 (en) | 2013-11-21 |
| CA2835261A1 (en) | 2012-11-15 |
| EA201391644A1 (ru) | 2014-11-28 |
| MX345535B (es) | 2017-02-03 |
| EP2705030A1 (en) | 2014-03-12 |
| EA025526B1 (ru) | 2017-01-30 |
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