CA2808590A1 - Sulfonylpiperazine derivatives that interact with glucokinase regulatory protein for the treatment of diabetes - Google Patents
Sulfonylpiperazine derivatives that interact with glucokinase regulatory protein for the treatment of diabetes Download PDFInfo
- Publication number
- CA2808590A1 CA2808590A1 CA2808590A CA2808590A CA2808590A1 CA 2808590 A1 CA2808590 A1 CA 2808590A1 CA 2808590 A CA2808590 A CA 2808590A CA 2808590 A CA2808590 A CA 2808590A CA 2808590 A1 CA2808590 A1 CA 2808590A1
- Authority
- CA
- Canada
- Prior art keywords
- piperazinyl
- phenyl
- trifluoro
- methyl
- propanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 238000011282 treatment Methods 0.000 title claims description 22
- 102100040880 Glucokinase regulatory protein Human genes 0.000 title abstract description 35
- 101710148430 Glucokinase regulatory protein Proteins 0.000 title abstract description 35
- 206010012601 diabetes mellitus Diseases 0.000 title description 10
- ZECNLXUZYQZMAL-UHFFFAOYSA-N 2-sulfonylpiperazine Chemical class O=S(=O)=C1CNCCN1 ZECNLXUZYQZMAL-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- 150000003839 salts Chemical class 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 66
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 439
- -1 -CHF2 Chemical group 0.000 claims description 190
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 107
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 64
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000003107 substituted aryl group Chemical group 0.000 claims description 38
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 10
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 206010022489 Insulin Resistance Diseases 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 208000017169 kidney disease Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- 208000002177 Cataract Diseases 0.000 claims description 3
- 206010036049 Polycystic ovaries Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 230000007823 neuropathy Effects 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 3
- RSICISVEQSVJAZ-GGUNXXMASA-N 1,1,1-trifluoro-2-[4-[2-[[(1r,4r)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@]1(OC[C@@]2([H])C1)[H])N2CC1CN(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 RSICISVEQSVJAZ-GGUNXXMASA-N 0.000 claims description 2
- RSOJSFYJLQADDM-UHFFFAOYSA-N ethanesulfonamide Chemical compound [CH2]CS(N)(=O)=O RSOJSFYJLQADDM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 2
- FTXKDYBMOPKENQ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 FTXKDYBMOPKENQ-UHFFFAOYSA-N 0.000 claims 3
- HHBBWUAHCMXUKM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[4-(2-fluorophenyl)sulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C(=CC=CC=2)F)CC1 HHBBWUAHCMXUKM-UHFFFAOYSA-N 0.000 claims 3
- NBFNBWBAINARSB-UHFFFAOYSA-N 2-[4-[4-(2-chlorophenyl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 NBFNBWBAINARSB-UHFFFAOYSA-N 0.000 claims 3
- XDMGJUIQDYSQIL-UHFFFAOYSA-N 2-[4-[4-(3-chlorophenyl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C=C(Cl)C=CC=2)CC1 XDMGJUIQDYSQIL-UHFFFAOYSA-N 0.000 claims 3
- SSQMPLPIAHOOEP-UHFFFAOYSA-N 2-[4-[4-(benzenesulfonyl)piperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 SSQMPLPIAHOOEP-UHFFFAOYSA-N 0.000 claims 3
- AHKIWAZGLMLGGP-PPUHSXQSSA-N 1,1,1-trifluoro-2-[4-[(2r)-2-[(4-fluorophenyl)sulfanylmethyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CSC=2C=CC(F)=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 AHKIWAZGLMLGGP-PPUHSXQSSA-N 0.000 claims 2
- PYHXHNXXKUYKLO-INIZCTEOSA-N 2-[2-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-(oxan-4-ylmethyl)piperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)N1C[C@H](CC2CCOCC2)N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 PYHXHNXXKUYKLO-INIZCTEOSA-N 0.000 claims 2
- UZUAGXOWENMSAT-UHFFFAOYSA-N 2-[4-[4-[(5-amino-1,3,4-thiadiazol-2-yl)sulfonyl]-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2SC(N)=NN=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 UZUAGXOWENMSAT-UHFFFAOYSA-N 0.000 claims 2
- YCEQAJBFIXGCSK-XARADAHVSA-N (1r,5r,6r)-8-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-[(2r)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenyl]piperazin-2-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-ol Chemical compound C([C@@H]1CN2[C@@]3([H])[C@H](O)C[C@@]2(COC3)[H])N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C([C@@](C)(O)C(F)(F)F)C=C1 YCEQAJBFIXGCSK-XARADAHVSA-N 0.000 claims 1
- YCEQAJBFIXGCSK-GJTYKATRSA-N (1r,5r,6r)-8-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-[(2s)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenyl]piperazin-2-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-ol Chemical compound C([C@@H]1CN2[C@@]3([H])[C@H](O)C[C@@]2(COC3)[H])N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C([C@](C)(O)C(F)(F)F)C=C1 YCEQAJBFIXGCSK-GJTYKATRSA-N 0.000 claims 1
- MUXBPXDFPYQATC-PDOZGGDVSA-N (1r,5r,6r)-8-[[(2s)-4-thiophen-2-ylsulfonyl-1-[5-[(2r)-1,1,1-trifluoro-2-hydroxypropan-2-yl]pyrimidin-2-yl]piperazin-2-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-ol Chemical compound C([C@@H]1CN2[C@@]3([H])[C@H](O)C[C@@]2(COC3)[H])N(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C([C@@](C)(O)C(F)(F)F)C=N1 MUXBPXDFPYQATC-PDOZGGDVSA-N 0.000 claims 1
- MUXBPXDFPYQATC-PLQGUWCTSA-N (1r,5r,6r)-8-[[(2s)-4-thiophen-2-ylsulfonyl-1-[5-[(2s)-1,1,1-trifluoro-2-hydroxypropan-2-yl]pyrimidin-2-yl]piperazin-2-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-ol Chemical compound C([C@@H]1CN2[C@@]3([H])[C@H](O)C[C@@]2(COC3)[H])N(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C([C@](C)(O)C(F)(F)F)C=N1 MUXBPXDFPYQATC-PLQGUWCTSA-N 0.000 claims 1
- YCEQAJBFIXGCSK-DXGJXXFVSA-N (1s,5s,6s)-8-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-[(2r)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenyl]piperazin-2-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-ol Chemical compound C([C@@H]1CN2[C@]3([H])[C@@H](O)C[C@]2(COC3)[H])N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C([C@@](C)(O)C(F)(F)F)C=C1 YCEQAJBFIXGCSK-DXGJXXFVSA-N 0.000 claims 1
- MUXBPXDFPYQATC-VPMQLGLMSA-N (1s,5s,6s)-8-[[(2s)-4-thiophen-2-ylsulfonyl-1-[5-[(2r)-1,1,1-trifluoro-2-hydroxypropan-2-yl]pyrimidin-2-yl]piperazin-2-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-ol Chemical compound C([C@@H]1CN2[C@]3([H])[C@@H](O)C[C@]2(COC3)[H])N(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C([C@@](C)(O)C(F)(F)F)C=N1 MUXBPXDFPYQATC-VPMQLGLMSA-N 0.000 claims 1
- SESNUYWFMSZFPR-XHDPSFHLSA-N (2r)-1,1,1-trifluoro-2-[2-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]pyrimidin-5-yl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C([C@@](C)(O)C(F)(F)F)C=N1 SESNUYWFMSZFPR-XHDPSFHLSA-N 0.000 claims 1
- PJNADDDYXCZBMQ-MRXNPFEDSA-N (2r)-1,1,1-trifluoro-2-[4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 PJNADDDYXCZBMQ-MRXNPFEDSA-N 0.000 claims 1
- XYVKOMVNXJFBFF-IFMALSPDSA-N (2r)-1,1,1-trifluoro-2-[4-[(2r)-2-(oxan-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@H](CC2CCOCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 XYVKOMVNXJFBFF-IFMALSPDSA-N 0.000 claims 1
- KCZXTYNCTVVXFR-IFMALSPDSA-N (2r)-1,1,1-trifluoro-2-[4-[(2r)-2-[(1-methylimidazol-4-yl)methoxymethyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound CN1C=NC(COC[C@@H]2N(CCN(C2)S(=O)(=O)C=2SC=CC=2)C=2C=CC(=CC=2)[C@@](C)(O)C(F)(F)F)=C1 KCZXTYNCTVVXFR-IFMALSPDSA-N 0.000 claims 1
- XYVKOMVNXJFBFF-RBBKRZOGSA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-(oxan-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC2CCOCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 XYVKOMVNXJFBFF-RBBKRZOGSA-N 0.000 claims 1
- HASNVFMCDATTPN-OHSXHVKISA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3r)-3-(4-fluorophenyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@@H](COCC2)C=2C=CC(F)=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 HASNVFMCDATTPN-OHSXHVKISA-N 0.000 claims 1
- DSCDGCNNIKOKFI-TUNNFDKTSA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3r)-3-(hydroxymethyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@@H](COCC2)CO)CN(S(=O)(=O)C=2SC=CC=2)CC1 DSCDGCNNIKOKFI-TUNNFDKTSA-N 0.000 claims 1
- HASNVFMCDATTPN-ZWEKWIFMSA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3s)-3-(4-fluorophenyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@H](COCC2)C=2C=CC(F)=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 HASNVFMCDATTPN-ZWEKWIFMSA-N 0.000 claims 1
- DSCDGCNNIKOKFI-JAXLGGSGSA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3s)-3-(hydroxymethyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@H](COCC2)CO)CN(S(=O)(=O)C=2SC=CC=2)CC1 DSCDGCNNIKOKFI-JAXLGGSGSA-N 0.000 claims 1
- DTIRPEOHQAFODS-BLLLJJGKSA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-methyl-4-(1,3-thiazol-2-ylsulfonyl)piperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CN=2)CCN1C1=CC=C([C@@](C)(O)C(F)(F)F)C=C1 DTIRPEOHQAFODS-BLLLJJGKSA-N 0.000 claims 1
- WAVKEANTCLSSBK-SUMWQHHRSA-N (2r)-1,1,1-trifluoro-2-[4-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C([C@@](C)(O)C(F)(F)F)C=C1 WAVKEANTCLSSBK-SUMWQHHRSA-N 0.000 claims 1
- QREDMPDNKVIQDV-KBXCAEBGSA-N (2r)-2-[2-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]pyrimidin-5-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1C#CC)N(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=NC=C([C@@](C)(O)C(F)(F)F)C=N1 QREDMPDNKVIQDV-KBXCAEBGSA-N 0.000 claims 1
- ZIPIZEYPTSKTAT-NFBKMPQASA-N (2r)-2-[4-[(2r)-2-(benzenesulfonylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CS(=O)(=O)C=2C=CC=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 ZIPIZEYPTSKTAT-NFBKMPQASA-N 0.000 claims 1
- UVNIGCUQKUJRSU-NZQKXSOJSA-N (2r)-2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-(oxan-4-ylmethyl)piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC2CCOCC2)CN(S(=O)(=O)C=2C=NC(N)=CC=2)CC1 UVNIGCUQKUJRSU-NZQKXSOJSA-N 0.000 claims 1
- VQLCDVDEIIOMDL-DHJUGAMNSA-N (2r)-2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-[[(3r)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C[C@@H]1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)[C@@](C)(O)C(F)(F)F)CCN(S(=O)(=O)C=2C=NC(N)=CC=2)C1 VQLCDVDEIIOMDL-DHJUGAMNSA-N 0.000 claims 1
- FOKWKBQHMYNDFN-FXAWDEMLSA-N (2r)-2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1C#CC)N(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=CC=C([C@@](C)(O)C(F)(F)F)C=C1 FOKWKBQHMYNDFN-FXAWDEMLSA-N 0.000 claims 1
- OXOOSCVZZWWWHE-GOSISDBHSA-N (2r)-2-[4-[4-(benzenesulfonyl)piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC([C@](O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 OXOOSCVZZWWWHE-GOSISDBHSA-N 0.000 claims 1
- MKGCHOIRCRCXSL-INIZCTEOSA-N (2r)-3,3,3-trifluoro-2-[4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propane-1,2-diol Chemical compound C1=CC([C@@](O)(CO)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 MKGCHOIRCRCXSL-INIZCTEOSA-N 0.000 claims 1
- GYVCOQSHKOEINP-XJABCFGWSA-N (2r)-3,3,3-trifluoro-2-[4-[(2s)-2-[[(3s)-3-methylmorpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propane-1,2-diol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)[C@@](O)(CO)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 GYVCOQSHKOEINP-XJABCFGWSA-N 0.000 claims 1
- SESNUYWFMSZFPR-NHYWBVRUSA-N (2s)-1,1,1-trifluoro-2-[2-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]pyrimidin-5-yl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C([C@](C)(O)C(F)(F)F)C=N1 SESNUYWFMSZFPR-NHYWBVRUSA-N 0.000 claims 1
- PJNADDDYXCZBMQ-INIZCTEOSA-N (2s)-1,1,1-trifluoro-2-[4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 PJNADDDYXCZBMQ-INIZCTEOSA-N 0.000 claims 1
- XYVKOMVNXJFBFF-IRLDBZIGSA-N (2s)-1,1,1-trifluoro-2-[4-[(2r)-2-(oxan-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@H](CC2CCOCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 XYVKOMVNXJFBFF-IRLDBZIGSA-N 0.000 claims 1
- KCZXTYNCTVVXFR-IRLDBZIGSA-N (2s)-1,1,1-trifluoro-2-[4-[(2r)-2-[(1-methylimidazol-4-yl)methoxymethyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound CN1C=NC(COC[C@@H]2N(CCN(C2)S(=O)(=O)C=2SC=CC=2)C=2C=CC(=CC=2)[C@](C)(O)C(F)(F)F)=C1 KCZXTYNCTVVXFR-IRLDBZIGSA-N 0.000 claims 1
- XYVKOMVNXJFBFF-UNMCSNQZSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-(oxan-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC2CCOCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 XYVKOMVNXJFBFF-UNMCSNQZSA-N 0.000 claims 1
- HASNVFMCDATTPN-KLJDGLGGSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3r)-3-(4-fluorophenyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@@H](COCC2)C=2C=CC(F)=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 HASNVFMCDATTPN-KLJDGLGGSA-N 0.000 claims 1
- DSCDGCNNIKOKFI-VWPQPMDRSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3r)-3-(hydroxymethyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@@H](COCC2)CO)CN(S(=O)(=O)C=2SC=CC=2)CC1 DSCDGCNNIKOKFI-VWPQPMDRSA-N 0.000 claims 1
- HASNVFMCDATTPN-WEWMWRJBSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3s)-3-(4-fluorophenyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@H](COCC2)C=2C=CC(F)=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 HASNVFMCDATTPN-WEWMWRJBSA-N 0.000 claims 1
- DSCDGCNNIKOKFI-ONTIZHBOSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-[[(3s)-3-(hydroxymethyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2[C@H](COCC2)CO)CN(S(=O)(=O)C=2SC=CC=2)CC1 DSCDGCNNIKOKFI-ONTIZHBOSA-N 0.000 claims 1
- DTIRPEOHQAFODS-LRDDRELGSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-methyl-4-(1,3-thiazol-2-ylsulfonyl)piperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CN=2)CCN1C1=CC=C([C@](C)(O)C(F)(F)F)C=C1 DTIRPEOHQAFODS-LRDDRELGSA-N 0.000 claims 1
- WAVKEANTCLSSBK-GUYCJALGSA-N (2s)-1,1,1-trifluoro-2-[4-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C([C@](C)(O)C(F)(F)F)C=C1 WAVKEANTCLSSBK-GUYCJALGSA-N 0.000 claims 1
- FOKWKBQHMYNDFN-XLIONFOSSA-N (2s)-2-[4-[(2r)-4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@H]1C#CC)N(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=CC=C([C@](C)(O)C(F)(F)F)C=C1 FOKWKBQHMYNDFN-XLIONFOSSA-N 0.000 claims 1
- ZIJJRPQKSWPOPH-GMAHTHKFSA-N (2s)-2-[4-[(2s)-2-benzyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC=2C=CC=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 ZIJJRPQKSWPOPH-GMAHTHKFSA-N 0.000 claims 1
- OXOOSCVZZWWWHE-SFHVURJKSA-N (2s)-2-[4-[4-(benzenesulfonyl)piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC([C@@](O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 OXOOSCVZZWWWHE-SFHVURJKSA-N 0.000 claims 1
- VPIJJJYCTFZBKX-OBXNSHGQSA-N (3r)-1-[[4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]pyrrolidin-3-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CN2C[C@H](O)CC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 VPIJJJYCTFZBKX-OBXNSHGQSA-N 0.000 claims 1
- ZSILXOFHESRCTQ-MAUKXSAKSA-N (3r)-4-[[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-1-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyrimidin-2-yl]piperazin-2-yl]methyl]-3-propan-2-ylpiperazin-2-one Chemical compound C1CNC(=O)[C@@H](C(C)C)N1C[C@@H]1N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC(N)=CC=2)C1 ZSILXOFHESRCTQ-MAUKXSAKSA-N 0.000 claims 1
- GQJDSPZSUQEHDL-ZDOMSUIMSA-N (3s)-1-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]piperidin-3-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C[C@@H](O)CCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 GQJDSPZSUQEHDL-ZDOMSUIMSA-N 0.000 claims 1
- ZSILXOFHESRCTQ-YJBOKZPZSA-N (3s)-4-[[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-1-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyrimidin-2-yl]piperazin-2-yl]methyl]-3-propan-2-ylpiperazin-2-one Chemical compound C1CNC(=O)[C@H](C(C)C)N1C[C@@H]1N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC(N)=CC=2)C1 ZSILXOFHESRCTQ-YJBOKZPZSA-N 0.000 claims 1
- PLXUQWMUTYPEBK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-(2-prop-1-ynyl-4-thiophen-2-ylsulfonylpiperazin-1-yl)pyrimidin-5-yl]propan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 PLXUQWMUTYPEBK-UHFFFAOYSA-N 0.000 claims 1
- YPPJNCYUFVQKBH-INIZCTEOSA-N 1,1,1,3,3,3-hexafluoro-2-[2-[(2s)-2-(oxan-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]pyrimidin-5-yl]propan-2-ol Chemical compound N1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CN=C1N1[C@@H](CC2CCOCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 YPPJNCYUFVQKBH-INIZCTEOSA-N 0.000 claims 1
- MICUUXOVOGVSIV-HOCLYGCPSA-N 1,1,1,3,3,3-hexafluoro-2-[2-[(2s)-2-[[(3s)-3-methylmorpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]pyrimidin-5-yl]propan-2-ol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 MICUUXOVOGVSIV-HOCLYGCPSA-N 0.000 claims 1
- DUZIMLLGKSZSHX-VIFPVBQESA-N 1,1,1,3,3,3-hexafluoro-2-[2-[(2s)-2-methyl-4-(1,3-thiazol-2-ylsulfonyl)piperazin-1-yl]pyrimidin-5-yl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CN=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 DUZIMLLGKSZSHX-VIFPVBQESA-N 0.000 claims 1
- KBPIFHFANHCJIY-JTQLQIEISA-N 1,1,1,3,3,3-hexafluoro-2-[2-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]pyrimidin-5-yl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 KBPIFHFANHCJIY-JTQLQIEISA-N 0.000 claims 1
- GJUJQEHTTVWMEN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-(3-hydroxyprop-1-ynyl)-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound OCC#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 GJUJQEHTTVWMEN-UHFFFAOYSA-N 0.000 claims 1
- IQCDUSZPCXLVMY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-(3-methoxy-4-methylpent-1-ynyl)-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound COC(C(C)C)C#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 IQCDUSZPCXLVMY-UHFFFAOYSA-N 0.000 claims 1
- WJLLQOWJLASUKQ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-(3-methoxypent-1-ynyl)-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound CCC(OC)C#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 WJLLQOWJLASUKQ-UHFFFAOYSA-N 0.000 claims 1
- BPAMFUPKSOLRMA-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-(3-methoxyphenyl)-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound COC1=CC=CC(C=2C(=CC=C(C=2)C(O)(C(F)(F)F)C(F)(F)F)N2CCN(CC2)S(=O)(=O)C=2SC=CC=2)=C1 BPAMFUPKSOLRMA-UHFFFAOYSA-N 0.000 claims 1
- XISUXEJKOJBXHL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-(3-methoxyprop-1-ynyl)-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound COCC#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 XISUXEJKOJBXHL-UHFFFAOYSA-N 0.000 claims 1
- USPVFQOWDVLOCU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-phenyl-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C=1C=CC=CC=1C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N(CC1)CCN1S(=O)(=O)C1=CC=CS1 USPVFQOWDVLOCU-UHFFFAOYSA-N 0.000 claims 1
- MZGFWTNSMNTWLE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-prop-1-ynyl-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound CC#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 MZGFWTNSMNTWLE-UHFFFAOYSA-N 0.000 claims 1
- YCBSEFNYSVMFAQ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-pyridin-3-yl-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C=1C=CN=CC=1C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N(CC1)CCN1S(=O)(=O)C1=CC=CS1 YCBSEFNYSVMFAQ-UHFFFAOYSA-N 0.000 claims 1
- BUIPPALMYVSWLS-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[3-thiophen-3-yl-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C1=CSC=C1C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N(CC1)CCN1S(=O)(=O)C1=CC=CS1 BUIPPALMYVSWLS-UHFFFAOYSA-N 0.000 claims 1
- IADZKNKMUNIFPU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-(4-pyridin-2-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2N=CC=CC=2)CC1 IADZKNKMUNIFPU-UHFFFAOYSA-N 0.000 claims 1
- VUUDHBOJIINKBG-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-(4-thiophen-3-ylsulfonylpiperazin-1-yl)phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C2=CSC=C2)CC1 VUUDHBOJIINKBG-UHFFFAOYSA-N 0.000 claims 1
- LJKUKPPCBQEXTR-LPHOPBHVSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[(2s)-2-[[(3s)-3-methylmorpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 LJKUKPPCBQEXTR-LPHOPBHVSA-N 0.000 claims 1
- CSYRYFNDVIDBEO-NSHDSACASA-N 1,1,1,3,3,3-hexafluoro-2-[4-[(2s)-2-methyl-4-(1,3-thiazol-2-ylsulfonyl)piperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CN=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 CSYRYFNDVIDBEO-NSHDSACASA-N 0.000 claims 1
- YDLPLFFRQFVSRQ-LBPRGKRZSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 YDLPLFFRQFVSRQ-LBPRGKRZSA-N 0.000 claims 1
- PGKMOZLFWLFGIV-GFCCVEGCSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[(3r)-3-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@H]1C)N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN1S(=O)(=O)C1=CC=CS1 PGKMOZLFWLFGIV-GFCCVEGCSA-N 0.000 claims 1
- PGKMOZLFWLFGIV-LBPRGKRZSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[(3s)-3-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C([C@@H]1C)N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN1S(=O)(=O)C1=CC=CS1 PGKMOZLFWLFGIV-LBPRGKRZSA-N 0.000 claims 1
- ZIIICKIMOSZOAK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-(oxan-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1C(CC2CCOCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 ZIIICKIMOSZOAK-UHFFFAOYSA-N 0.000 claims 1
- YBCJQAJGJLGUHB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(2-methoxyphenyl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound COC1=CC=CC=C1CC1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 YBCJQAJGJLGUHB-UHFFFAOYSA-N 0.000 claims 1
- BIJZMWCYSSNDOL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(2-methoxypyridin-3-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound COC1=NC=CC=C1CC1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 BIJZMWCYSSNDOL-UHFFFAOYSA-N 0.000 claims 1
- GWBPVWSDNOVERA-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(3-methoxyphenyl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound COC1=CC=CC(CC2N(CCN(C2)S(=O)(=O)C=2SC=CC=2)C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)=C1 GWBPVWSDNOVERA-UHFFFAOYSA-N 0.000 claims 1
- UCYRDIDDQQLXJK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(3-methylphenyl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound CC1=CC=CC(CC2N(CCN(C2)S(=O)(=O)C=2SC=CC=2)C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)=C1 UCYRDIDDQQLXJK-UHFFFAOYSA-N 0.000 claims 1
- RHUIPLOWSWQJPW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(4-methoxyphenyl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1CC1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 RHUIPLOWSWQJPW-UHFFFAOYSA-N 0.000 claims 1
- LSLMNJRTAAXMPC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(4-methylphenyl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(C)=CC=C1CC1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 LSLMNJRTAAXMPC-UHFFFAOYSA-N 0.000 claims 1
- ANKRKOLVPYRIQK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[2-[(6-methoxypyridin-2-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound COC1=CC=CC(CC2N(CCN(C2)S(=O)(=O)C=2SC=CC=2)C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)=N1 ANKRKOLVPYRIQK-UHFFFAOYSA-N 0.000 claims 1
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- DSCDGCNNIKOKFI-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[2-[[3-(hydroxymethyl)morpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CN2C(COCC2)CO)CN(S(=O)(=O)C=2SC=CC=2)CC1 DSCDGCNNIKOKFI-UHFFFAOYSA-N 0.000 claims 1
- KCJVRSYUKZUOBY-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[4-(1,3-thiazol-2-ylsulfonyl)piperazin-1-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CN=2)CC1 KCJVRSYUKZUOBY-UHFFFAOYSA-N 0.000 claims 1
- DPQVIGCGZYABTB-UHFFFAOYSA-N 1-[2-[4-(benzenesulfonyl)piperidin-1-yl]-5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]pent-1-yn-3-ol Chemical compound CCC(O)C#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCC(S(=O)(=O)C=2C=CC=CC=2)CC1 DPQVIGCGZYABTB-UHFFFAOYSA-N 0.000 claims 1
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- VAIILBJBXNOPQB-UHFFFAOYSA-N 1-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]pent-1-yn-3-ol Chemical compound CCC(O)C#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 VAIILBJBXNOPQB-UHFFFAOYSA-N 0.000 claims 1
- UFOQKBHBJTWGRZ-YDNXMHBPSA-N 1-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]piperidin-4-one Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2CCC(=O)CC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 UFOQKBHBJTWGRZ-YDNXMHBPSA-N 0.000 claims 1
- KABIBFZEJCKTGA-UHFFFAOYSA-N 1-[[4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]azetidin-3-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CN2CC(O)C2)CN(S(=O)(=O)C=2SC=CC=2)CC1 KABIBFZEJCKTGA-UHFFFAOYSA-N 0.000 claims 1
- UKDIEAMXFIACNE-NSHDSACASA-N 2-[2-[(2s)-4-(2-aminophenyl)sulfonyl-2-methylpiperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2C(=CC=CC=2)N)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 UKDIEAMXFIACNE-NSHDSACASA-N 0.000 claims 1
- LTLRGHHANGQGNV-HNNXBMFYSA-N 2-[2-[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-2-(oxan-4-ylmethyl)piperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound S1C(N)=CC=C1S(=O)(=O)N1C[C@H](CC2CCOCC2)N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 LTLRGHHANGQGNV-HNNXBMFYSA-N 0.000 claims 1
- AGFGWEOPXCGKGX-DJZRFWRSSA-N 2-[2-[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-2-(oxan-4-ylmethyl)piperazin-1-yl]pyrimidin-5-yl]-1,1,1-trifluoropropan-2-ol Chemical compound N1=CC(C(O)(C)C(F)(F)F)=CN=C1N1[C@@H](CC2CCOCC2)CN(S(=O)(=O)C=2SC(N)=CC=2)CC1 AGFGWEOPXCGKGX-DJZRFWRSSA-N 0.000 claims 1
- DUXFOACMJKARDZ-MYHCZTBNSA-N 2-[2-[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-2-methylpiperazin-1-yl]pyrimidin-5-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC(N)=CC=2)CCN1C1=NC=C(C(C)(O)C(F)(F)F)C=N1 DUXFOACMJKARDZ-MYHCZTBNSA-N 0.000 claims 1
- HDMGZEHZHAVLRK-OFLPRAFFSA-N 2-[2-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-(3-oxa-8-azabicyclo[3.2.1]octan-8-ylmethyl)piperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)N1C[C@H](CN2C3CCC2COC3)N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 HDMGZEHZHAVLRK-OFLPRAFFSA-N 0.000 claims 1
- CPTKDVKNTFQSOG-HOCLYGCPSA-N 2-[2-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-[[(3s)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2C=NC(N)=CC=2)C1 CPTKDVKNTFQSOG-HOCLYGCPSA-N 0.000 claims 1
- OEGKCSXBCSBCPY-PHIGLHEMSA-N 2-[2-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-[[(3s)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]pyrimidin-5-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2N=CC(=CN=2)C(C)(O)C(F)(F)F)CCN(S(=O)(=O)C=2C=NC(N)=CC=2)C1 OEGKCSXBCSBCPY-PHIGLHEMSA-N 0.000 claims 1
- FABWXIYXWHGVNM-JTQLQIEISA-N 2-[2-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-methylpiperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 FABWXIYXWHGVNM-JTQLQIEISA-N 0.000 claims 1
- VCNVAWWFSYBKAF-UHFFFAOYSA-N 2-[2-[4-(6-aminopyridin-3-yl)sulfonyl-2-(2-hydroxypropyl)piperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC(O)CC1CN(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 VCNVAWWFSYBKAF-UHFFFAOYSA-N 0.000 claims 1
- CWDXIMHMPWZRFK-FIBGUPNXSA-N 2-[2-[4-(6-aminopyridin-3-yl)sulfonyl-2-(3,3,3-trideuterioprop-1-ynyl)piperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound [2H]C([2H])([2H])C#CC1CN(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 CWDXIMHMPWZRFK-FIBGUPNXSA-N 0.000 claims 1
- ARSWJEMMKYIFOM-UHFFFAOYSA-N 2-[2-[4-(6-aminopyridin-3-yl)sulfonyl-2-methylphenyl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC1=CC(S(=O)(=O)C=2C=NC(N)=CC=2)=CC=C1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 ARSWJEMMKYIFOM-UHFFFAOYSA-N 0.000 claims 1
- CWDXIMHMPWZRFK-UHFFFAOYSA-N 2-[2-[4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=NC=C(C(O)(C(F)(F)F)C(F)(F)F)C=N1 CWDXIMHMPWZRFK-UHFFFAOYSA-N 0.000 claims 1
- QREDMPDNKVIQDV-UHFFFAOYSA-N 2-[2-[4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]pyrimidin-5-yl]-1,1,1-trifluoropropan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=NC=C(C(C)(O)C(F)(F)F)C=N1 QREDMPDNKVIQDV-UHFFFAOYSA-N 0.000 claims 1
- IBDJORYQEKQDSY-UHFFFAOYSA-N 2-[2-[4-(6-aminopyridin-3-yl)sulfonylphenyl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)C1=CC=C(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)C=C1 IBDJORYQEKQDSY-UHFFFAOYSA-N 0.000 claims 1
- RFVUCTPSBWQFOS-UHFFFAOYSA-N 2-[2-[4-(benzenesulfonyl)phenyl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound N1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CN=C1C1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1 RFVUCTPSBWQFOS-UHFFFAOYSA-N 0.000 claims 1
- OPXPSZIRQVJDNN-UHFFFAOYSA-N 2-[2-[6-(6-aminopyridin-3-yl)sulfonylpyridin-3-yl]pyrimidin-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)C1=CC=C(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)C=N1 OPXPSZIRQVJDNN-UHFFFAOYSA-N 0.000 claims 1
- GDSHLPYLHQTDPM-UHFFFAOYSA-N 2-[3-(3-aminoprop-1-ynyl)-4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NCC#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 GDSHLPYLHQTDPM-UHFFFAOYSA-N 0.000 claims 1
- ZIPIZEYPTSKTAT-PPUHSXQSSA-N 2-[4-[(2r)-2-(benzenesulfonylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CS(=O)(=O)C=2C=CC=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 ZIPIZEYPTSKTAT-PPUHSXQSSA-N 0.000 claims 1
- ATBJQIPEPYSVAA-BBQAJUCSSA-N 2-[4-[(2s)-2-(anilinomethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CNC=2C=CC=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 ATBJQIPEPYSVAA-BBQAJUCSSA-N 0.000 claims 1
- IAEOBDLQHSKOCI-ZQRQZVKFSA-N 2-[4-[(2s)-2-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2CCS(=O)(=O)CC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 IAEOBDLQHSKOCI-ZQRQZVKFSA-N 0.000 claims 1
- HXAHKUOGGBRSKY-YNEXMFEJSA-N 2-[4-[(2s)-2-[(3-cyclopropyl-1,1-dioxo-1,4-thiazinan-4-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C(CS(=O)(=O)CC2)C2CC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 HXAHKUOGGBRSKY-YNEXMFEJSA-N 0.000 claims 1
- WTIZOCLETXHLIP-SWCONJRYSA-N 2-[4-[(2s)-2-[(3-ethylmorpholin-4-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CCC1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)C(C)(O)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 WTIZOCLETXHLIP-SWCONJRYSA-N 0.000 claims 1
- XMMIXCWSCVWBES-LROBGIAVSA-N 2-[4-[(2s)-2-[(cyclopropylamino)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CNC2CC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 XMMIXCWSCVWBES-LROBGIAVSA-N 0.000 claims 1
- USTILTNZVDMGIK-YIMBBBAVSA-N 2-[4-[(2s)-2-[[(3ar,6as)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]pyrrol-5-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C[C@H]3COC[C@H]3C2)CN(S(=O)(=O)C=2SC=CC=2)CC1 USTILTNZVDMGIK-YIMBBBAVSA-N 0.000 claims 1
- UZDYZEIMVZIANF-BTEHJBJGSA-N 2-[4-[(2s)-2-[[(3as,6as)-2,3,3a,4,6,6a-hexahydrofuro[2,3-c]pyrrol-5-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C[C@H]3OCC[C@H]3C2)CN(S(=O)(=O)C=2SC=CC=2)CC1 UZDYZEIMVZIANF-BTEHJBJGSA-N 0.000 claims 1
- YLUQEUDVDYSBDB-HWYAHNCWSA-N 2-[4-[(2s)-2-[[bis(oxetan-3-yl)amino]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN(C2COC2)C2COC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 YLUQEUDVDYSBDB-HWYAHNCWSA-N 0.000 claims 1
- TWQZXYRBBAFYSN-FKHAVUOCSA-N 2-[4-[(2s)-2-[[di(propan-2-yl)amino]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1CN(C(C)C)C(C)C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 TWQZXYRBBAFYSN-FKHAVUOCSA-N 0.000 claims 1
- ZIJJRPQKSWPOPH-BBQAJUCSSA-N 2-[4-[(2s)-2-benzyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC=2C=CC=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 ZIJJRPQKSWPOPH-BBQAJUCSSA-N 0.000 claims 1
- TZHJYXCTEVSDBU-BBQAJUCSSA-N 2-[4-[(2s)-2-benzyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-3,3,3-trifluoropropane-1,2-diol Chemical compound C1=CC(C(O)(CO)C(F)(F)F)=CC=C1N1[C@@H](CC=2C=CC=CC=2)CN(S(=O)(=O)C=2SC=CC=2)CC1 TZHJYXCTEVSDBU-BBQAJUCSSA-N 0.000 claims 1
- YMLIKWUGHQAVNU-ZDUSSCGKSA-N 2-[4-[(2s)-4-(2-aminophenyl)sulfonyl-2-methylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2C(=CC=CC=2)N)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 YMLIKWUGHQAVNU-ZDUSSCGKSA-N 0.000 claims 1
- BHWVEUCTEUUAJE-AJZOCDQUSA-N 2-[4-[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-2-benzylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC=2C=CC=CC=2)CN(S(=O)(=O)C=2SC(N)=CC=2)CC1 BHWVEUCTEUUAJE-AJZOCDQUSA-N 0.000 claims 1
- GENCFSKQBYXKHZ-NSHDSACASA-N 2-[4-[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-2-methylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC(N)=CC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 GENCFSKQBYXKHZ-NSHDSACASA-N 0.000 claims 1
- QSIMCOJLVSWPFO-WHUIICBVSA-N 2-[4-[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-2-methylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC(N)=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 QSIMCOJLVSWPFO-WHUIICBVSA-N 0.000 claims 1
- QNPMHAQUESSJEW-IBGZPJMESA-N 2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-(oxan-4-ylmethyl)piperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)N1C[C@H](CC2CCOCC2)N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 QNPMHAQUESSJEW-IBGZPJMESA-N 0.000 claims 1
- UVNIGCUQKUJRSU-AJZOCDQUSA-N 2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-(oxan-4-ylmethyl)piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CC2CCOCC2)CN(S(=O)(=O)C=2C=NC(N)=CC=2)CC1 UVNIGCUQKUJRSU-AJZOCDQUSA-N 0.000 claims 1
- KGOFRGFKZZOJIC-LPHOPBHVSA-N 2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-[[(3s)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2C=NC(N)=CC=2)C1 KGOFRGFKZZOJIC-LPHOPBHVSA-N 0.000 claims 1
- VQLCDVDEIIOMDL-BAOGEJLYSA-N 2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-[[(3s)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)C(C)(O)C(F)(F)F)CCN(S(=O)(=O)C=2C=NC(N)=CC=2)C1 VQLCDVDEIIOMDL-BAOGEJLYSA-N 0.000 claims 1
- CPMFVNJWJZCROC-LBPRGKRZSA-N 2-[4-[(2s)-4-(6-aminopyridin-3-yl)sulfonyl-2-methylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 CPMFVNJWJZCROC-LBPRGKRZSA-N 0.000 claims 1
- QIBBOISFFZBQAX-AWEZNQCLSA-N 2-[4-[(2s)-4-(benzenesulfonyl)-2-methylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2C=CC=CC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 QIBBOISFFZBQAX-AWEZNQCLSA-N 0.000 claims 1
- PVZTUKLIPRHHTC-FUKCDUGKSA-N 2-[4-[(2s)-4-(benzenesulfonyl)-2-methylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2C=CC=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 PVZTUKLIPRHHTC-FUKCDUGKSA-N 0.000 claims 1
- FJMJECGENSZQHL-SFHVURJKSA-N 2-[4-[(2s)-4-(benzenesulfonyl)-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C([C@@H]1C#CC)N(S(=O)(=O)C=2C=CC=CC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 FJMJECGENSZQHL-SFHVURJKSA-N 0.000 claims 1
- CJJQQFPOEBLREP-MYHCZTBNSA-N 2-[4-[(2s)-4-[(5-amino-1,3,4-thiadiazol-2-yl)sulfonyl]-2-methylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC(N)=NN=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 CJJQQFPOEBLREP-MYHCZTBNSA-N 0.000 claims 1
- LUEXOGWKGCLACL-INIZCTEOSA-N 2-[4-[(3r)-3-cyclopropyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1C[C@@H](C2CC2)N(S(=O)(=O)C=2SC=CC=2)CC1 LUEXOGWKGCLACL-INIZCTEOSA-N 0.000 claims 1
- UWRXVXWZYGQAJA-UHFFFAOYSA-N 2-[4-[2-(2,5-dichlorophenyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(C=2C(=CC=C(Cl)C=2)Cl)CN(S(=O)(=O)C=2SC=CC=2)CC1 UWRXVXWZYGQAJA-UHFFFAOYSA-N 0.000 claims 1
- UONULAATMSHHAQ-UHFFFAOYSA-N 2-[4-[2-(cyclohexylmethyl)-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CC2CCCCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 UONULAATMSHHAQ-UHFFFAOYSA-N 0.000 claims 1
- HCRJKCNSQFVXAL-UHFFFAOYSA-N 2-[4-[2-[(2,2-dimethylmorpholin-4-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CN2CC(C)(C)OCC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 HCRJKCNSQFVXAL-UHFFFAOYSA-N 0.000 claims 1
- DHWILEOQAVRHSB-UHFFFAOYSA-N 2-[4-[2-[(4,4-difluoropiperidin-1-yl)methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CN2CCC(F)(F)CC2)CN(S(=O)(=O)C=2SC=CC=2)CC1 DHWILEOQAVRHSB-UHFFFAOYSA-N 0.000 claims 1
- QKFBFWQSHYUXAZ-UHFFFAOYSA-N 2-[4-[2-[[benzyl(methyl)amino]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC=CC=1CN(C)CC1CN(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 QKFBFWQSHYUXAZ-UHFFFAOYSA-N 0.000 claims 1
- FEVBRZDMUNBMGV-UHFFFAOYSA-N 2-[4-[4-(2,4-diaminophenyl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC1=CC(N)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 FEVBRZDMUNBMGV-UHFFFAOYSA-N 0.000 claims 1
- NMGJCJOAFBEMKP-UHFFFAOYSA-N 2-[4-[4-(2,6-diaminopyridin-3-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC1=NC(N)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 NMGJCJOAFBEMKP-UHFFFAOYSA-N 0.000 claims 1
- VEHSZTVWBQTWGH-UHFFFAOYSA-N 2-[4-[4-(2-aminophenyl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC1=CC=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 VEHSZTVWBQTWGH-UHFFFAOYSA-N 0.000 claims 1
- MCPRVPLMGZYXJU-UHFFFAOYSA-N 2-[4-[4-(2-aminopyrimidin-5-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=NC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 MCPRVPLMGZYXJU-UHFFFAOYSA-N 0.000 claims 1
- AQDUFBHQDOLTKE-UHFFFAOYSA-N 2-[4-[4-(4-amino-3-fluorophenyl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=C(F)C(N)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 AQDUFBHQDOLTKE-UHFFFAOYSA-N 0.000 claims 1
- OXAMCUVKMNJUGK-UHFFFAOYSA-N 2-[4-[4-(4-aminophenyl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(N)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 OXAMCUVKMNJUGK-UHFFFAOYSA-N 0.000 claims 1
- WAQMSCDSEDIXRO-UHFFFAOYSA-N 2-[4-[4-(4-aminopyridin-3-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC1=CC=NC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 WAQMSCDSEDIXRO-UHFFFAOYSA-N 0.000 claims 1
- UMSBASLVZLSLGY-UHFFFAOYSA-N 2-[4-[4-(4-aminothiophen-2-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC1=CSC(S(=O)(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)=C1 UMSBASLVZLSLGY-UHFFFAOYSA-N 0.000 claims 1
- FICNNVHSHKPWIU-UHFFFAOYSA-N 2-[4-[4-(4-bromothiophen-3-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C(=CSC=2)Br)CC1 FICNNVHSHKPWIU-UHFFFAOYSA-N 0.000 claims 1
- DKKUEURZSZFKOQ-UHFFFAOYSA-N 2-[4-[4-(5-aminothiophen-2-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC(N)=CC=2)CC1 DKKUEURZSZFKOQ-UHFFFAOYSA-N 0.000 claims 1
- FBZDNMFUNNKTJX-UHFFFAOYSA-N 2-[4-[4-(6-amino-5-fluoropyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2C=C(F)C(N)=NC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 FBZDNMFUNNKTJX-UHFFFAOYSA-N 0.000 claims 1
- MCCJYISEXCQPCR-UHFFFAOYSA-N 2-[4-[4-(6-amino-5-fluoropyridin-3-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=C(F)C(N)=NC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 MCCJYISEXCQPCR-UHFFFAOYSA-N 0.000 claims 1
- RYGHOAWCZCMATR-UHFFFAOYSA-N 2-[4-[4-(6-aminopyridazin-3-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound N1=NC(N)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 RYGHOAWCZCMATR-UHFFFAOYSA-N 0.000 claims 1
- SIFKNECWLVONIH-UHFFFAOYSA-N 2-[4-[4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 SIFKNECWLVONIH-UHFFFAOYSA-N 0.000 claims 1
- FOKWKBQHMYNDFN-UHFFFAOYSA-N 2-[4-[4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CC#CC1CN(S(=O)(=O)C=2C=NC(N)=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 FOKWKBQHMYNDFN-UHFFFAOYSA-N 0.000 claims 1
- KSFOBWMWXKUTRU-UHFFFAOYSA-N 2-[4-[4-(6-aminopyridin-3-yl)sulfonylpiperazin-1-yl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CC1 KSFOBWMWXKUTRU-UHFFFAOYSA-N 0.000 claims 1
- BBJFQVWXESGMJT-UHFFFAOYSA-N 2-[4-[4-(benzenesulfonyl)-2-(oxan-4-ylmethyl)piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CC2CCOCC2)CN(S(=O)(=O)C=2C=CC=CC=2)CC1 BBJFQVWXESGMJT-UHFFFAOYSA-N 0.000 claims 1
- UAZQWMWJTVBFHG-UHFFFAOYSA-N 2-[4-[4-(benzenesulfonyl)-3-chlorophenyl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1C1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C(Cl)=C1 UAZQWMWJTVBFHG-UHFFFAOYSA-N 0.000 claims 1
- XHTKMODTMNAZSQ-UHFFFAOYSA-N 2-[4-[4-(benzenesulfonyl)phenyl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1 XHTKMODTMNAZSQ-UHFFFAOYSA-N 0.000 claims 1
- OXOOSCVZZWWWHE-UHFFFAOYSA-N 2-[4-[4-(benzenesulfonyl)piperazin-1-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 OXOOSCVZZWWWHE-UHFFFAOYSA-N 0.000 claims 1
- CVBZYTFHVLZITL-UHFFFAOYSA-N 2-[4-[4-(benzenesulfonyl)piperidin-1-yl]-3-(3-methoxypent-1-ynyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CCC(OC)C#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCC(S(=O)(=O)C=2C=CC=CC=2)CC1 CVBZYTFHVLZITL-UHFFFAOYSA-N 0.000 claims 1
- PLCAUDYBTOHBSH-KQVJYAISSA-N 2-[4-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]morpholin-3-yl]acetic acid Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C(COCC2)CC(O)=O)CN(S(=O)(=O)C=2SC=CC=2)CC1 PLCAUDYBTOHBSH-KQVJYAISSA-N 0.000 claims 1
- ZVQAEGVABLFEAW-UHFFFAOYSA-N 2-[4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]acetonitrile Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1C(CC#N)CN(S(=O)(=O)C=2SC=CC=2)CC1 ZVQAEGVABLFEAW-UHFFFAOYSA-N 0.000 claims 1
- OWHJVXHDOFJZEK-UHFFFAOYSA-N 2-[6-[4-(6-aminopyridin-3-yl)sulfonylphenyl]pyridin-3-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=CC=C1S(=O)(=O)C1=CC=C(C=2N=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)C=C1 OWHJVXHDOFJZEK-UHFFFAOYSA-N 0.000 claims 1
- FZBLIUNKFLHHSW-UHFFFAOYSA-N 2-[6-[4-(benzenesulfonyl)-3-chlorophenyl]pyridin-3-yl]-1,1,1-trifluoropropan-2-ol Chemical compound N1=CC(C(O)(C)C(F)(F)F)=CC=C1C1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C(Cl)=C1 FZBLIUNKFLHHSW-UHFFFAOYSA-N 0.000 claims 1
- SNFFAHBGFULGLF-UHFFFAOYSA-N 2-[6-[4-(benzenesulfonyl)phenyl]pyridin-3-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound N1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1 SNFFAHBGFULGLF-UHFFFAOYSA-N 0.000 claims 1
- FBSQHUBLAJYWFU-UHFFFAOYSA-N 2-[6-[4-(benzenesulfonyl)piperazin-1-yl]pyridin-3-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound N1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 FBSQHUBLAJYWFU-UHFFFAOYSA-N 0.000 claims 1
- MNJILEVDEUZNTI-UHFFFAOYSA-N 2-[[1-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-4-thiophen-2-ylsulfonylpiperazin-2-yl]methyl]phenol Chemical compound OC1=CC=CC=C1CC1N(C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 MNJILEVDEUZNTI-UHFFFAOYSA-N 0.000 claims 1
- SIPUEVFMFKRWAS-UHFFFAOYSA-N 2-methyl-2-[[4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methylamino]propan-1-ol Chemical compound OCC(C)(C)NCC1CN(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C(C(C)(O)C(F)(F)F)C=C1 SIPUEVFMFKRWAS-UHFFFAOYSA-N 0.000 claims 1
- MKGCHOIRCRCXSL-UHFFFAOYSA-N 3,3,3-trifluoro-2-[4-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]propane-1,2-diol Chemical compound C1=CC(C(O)(CO)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 MKGCHOIRCRCXSL-UHFFFAOYSA-N 0.000 claims 1
- GYVCOQSHKOEINP-BJQRHOHNSA-N 3,3,3-trifluoro-2-[4-[(2s)-2-[[(3s)-3-methylmorpholin-4-yl]methyl]-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propane-1,2-diol Chemical compound C[C@H]1COCCN1C[C@@H]1N(C=2C=CC(=CC=2)C(O)(CO)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 GYVCOQSHKOEINP-BJQRHOHNSA-N 0.000 claims 1
- KXJGJMJNNFPQRM-CWQZNGJJSA-N 3,3,3-trifluoro-2-[4-[(2s)-2-methyl-4-thiophen-2-ylsulfonylpiperazin-1-yl]phenyl]propane-1,2-diol Chemical compound C([C@@H]1C)N(S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=C(C(O)(CO)C(F)(F)F)C=C1 KXJGJMJNNFPQRM-CWQZNGJJSA-N 0.000 claims 1
- HHOZFCIJIJWDNX-HSTJUUNISA-N 3,3-dimethyl-4-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]piperazin-2-one Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C(C(=O)NCC2)(C)C)CN(S(=O)(=O)C=2SC=CC=2)CC1 HHOZFCIJIJWDNX-HSTJUUNISA-N 0.000 claims 1
- PWAYCLXYBRGFFK-UHFFFAOYSA-N 3-[4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]piperazin-1-yl]sulfonylphenol Chemical compound OC1=CC=CC(S(=O)(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)=C1 PWAYCLXYBRGFFK-UHFFFAOYSA-N 0.000 claims 1
- OBFLBZWBONPHJO-UHFFFAOYSA-N 3-[[1-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-4-thiophen-2-ylsulfonylpiperazin-2-yl]methyl]phenol Chemical compound OC1=CC=CC(CC2N(CCN(C2)S(=O)(=O)C=2SC=CC=2)C=2C=CC(=CC=2)C(O)(C(F)(F)F)C(F)(F)F)=C1 OBFLBZWBONPHJO-UHFFFAOYSA-N 0.000 claims 1
- BJTMNMWSZOJTPR-URXUWMLESA-N 3-fluoro-9-[[(2s)-1-[4-(1,1,1,2-tetrafluoropropan-2-yl)phenyl]-4-thiophen-2-ylsulfonylpiperazin-2-yl]methyl]-9-azabicyclo[3.3.1]nonane Chemical compound C1=CC(C(F)(C)C(F)(F)F)=CC=C1N1[C@@H](CN2C3CCCC2CC(F)C3)CN(S(=O)(=O)C=2SC=CC=2)CC1 BJTMNMWSZOJTPR-URXUWMLESA-N 0.000 claims 1
- MEEATLRMXGMVAW-INVBSJAUSA-N 3-propan-2-yl-4-[[(2s)-4-thiophen-2-ylsulfonyl-1-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]piperazin-2-yl]methyl]piperazin-2-one Chemical compound C1CNC(=O)C(C(C)C)N1C[C@@H]1N(C=2C=CC(=CC=2)C(C)(O)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 MEEATLRMXGMVAW-INVBSJAUSA-N 0.000 claims 1
- YUISBRDPCBPQCB-UHFFFAOYSA-N 4-[2-(benzenesulfonyl)-5-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]phenyl]-2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#CC1=CC(C=2C=CC(=CC=2)C(C)(O)C(F)(F)F)=CC=C1S(=O)(=O)C1=CC=CC=C1 YUISBRDPCBPQCB-UHFFFAOYSA-N 0.000 claims 1
- YDOWBXSVAMOFDE-UHFFFAOYSA-N 4-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]but-3-yn-1-ol Chemical compound OCCC#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 YDOWBXSVAMOFDE-UHFFFAOYSA-N 0.000 claims 1
- MNUVJJBTTRJOME-UHFFFAOYSA-N 4-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]but-3-yn-2-ol Chemical compound CC(O)C#CC1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 MNUVJJBTTRJOME-UHFFFAOYSA-N 0.000 claims 1
- CCKDZPLNSUQCSQ-UHFFFAOYSA-N 4-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(4-thiophen-2-ylsulfonylpiperazin-1-yl)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 CCKDZPLNSUQCSQ-UHFFFAOYSA-N 0.000 claims 1
- MVDIOCOEBZSLPG-ATNAJCNCSA-N 4-[[(2s)-1-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyrimidin-2-yl]-4-thiophen-2-ylsulfonylpiperazin-2-yl]methyl]-3-propan-2-ylpiperazin-2-one Chemical compound C1CNC(=O)C(C(C)C)N1C[C@@H]1N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC=CC=2)C1 MVDIOCOEBZSLPG-ATNAJCNCSA-N 0.000 claims 1
- ZSILXOFHESRCTQ-BUSXIPJBSA-N 4-[[(2s)-4-(5-aminothiophen-2-yl)sulfonyl-1-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyrimidin-2-yl]piperazin-2-yl]methyl]-3-propan-2-ylpiperazin-2-one Chemical compound C1CNC(=O)C(C(C)C)N1C[C@@H]1N(C=2N=CC(=CN=2)C(O)(C(F)(F)F)C(F)(F)F)CCN(S(=O)(=O)C=2SC(N)=CC=2)C1 ZSILXOFHESRCTQ-BUSXIPJBSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed 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
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Ophthalmology & Optometry (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
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- Neurosurgery (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US37614110P | 2010-08-23 | 2010-08-23 | |
| US61/376,141 | 2010-08-23 | ||
| US201161492634P | 2011-06-02 | 2011-06-02 | |
| US61/492,634 | 2011-06-02 | ||
| PCT/US2011/048596 WO2012027261A1 (en) | 2010-08-23 | 2011-08-22 | Sulfonylpiperazine derivatives that interact with glucokinase regulatory protein for the treatment of diabetes |
Publications (1)
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| CA2808590A1 true CA2808590A1 (en) | 2012-03-01 |
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| CA2808590A Abandoned CA2808590A1 (en) | 2010-08-23 | 2011-08-22 | Sulfonylpiperazine derivatives that interact with glucokinase regulatory protein for the treatment of diabetes |
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| US (1) | US8431563B2 (enExample) |
| EP (1) | EP2609081A1 (enExample) |
| JP (1) | JP2013536233A (enExample) |
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| WO2021072369A1 (en) * | 2019-10-11 | 2021-04-15 | Duke University | Lpxh targeting compounds, compositions thereof, and methods of making and using the same |
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| WO2013123444A1 (en) * | 2012-02-17 | 2013-08-22 | Amgen Inc. | Sulfonyl compounds that interact with glucokinase regulatory protein |
| WO2013173382A1 (en) * | 2012-05-15 | 2013-11-21 | Amgen Inc. | Benzothiophene sulfonamides and other compounds that interact with glucokinase regulatory protein |
| WO2014035872A1 (en) * | 2012-08-27 | 2014-03-06 | Amgen Inc. | Tricyclic alkynes that interact with glucokinase regulatory protein |
| JP6102637B2 (ja) * | 2013-08-22 | 2017-03-29 | Jsr株式会社 | 芳香族ジハライド化合物、重合体、重合体組成物及び成形体 |
| CN108912020B (zh) * | 2018-06-05 | 2021-05-28 | 上海博志研新药物技术有限公司 | 奥当卡替及其中间体的制备方法 |
| CN114349711B (zh) * | 2022-02-28 | 2023-08-15 | 四川依维欣医药科技有限公司 | 一种(R)-1-Boc-3-羟甲基哌嗪的合成方法 |
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| GB9821199D0 (en) | 1998-09-30 | 1998-11-25 | Glaxo Group Ltd | Chemical compounds |
| US7459540B1 (en) | 1999-09-07 | 2008-12-02 | Amgen Inc. | Fibroblast growth factor-like polypeptides |
| PL377091A1 (pl) | 2002-09-06 | 2006-01-23 | Amgen, Inc. | Ludzkie monoklonalne przeciwciało przeciw-IL-1R1, o właściwościach terapeutycznych |
| EP1663193B1 (en) * | 2003-09-12 | 2012-04-04 | Merck Serono SA | Sulfonamide derivatives for the treatment of diabetes |
| FR2874011B1 (fr) | 2004-08-03 | 2007-06-15 | Sanofi Synthelabo | Derives de sulfonamides, leur preparation et leur application en therapeutique |
| GB0505084D0 (en) | 2005-03-11 | 2005-04-20 | Glaxo Group Ltd | Compounds |
| JP2009506988A (ja) | 2005-08-19 | 2009-02-19 | エラン ファーマシューティカルズ,インコーポレイテッド | ガンマセクレターゼの架橋n−環状スルホンアミド阻害剤 |
| CA2632027A1 (en) * | 2005-12-14 | 2007-06-21 | Amgen Inc. | Diaza heterocyclic sulfonamide derivatives and their uses |
| AU2007231594A1 (en) * | 2006-03-23 | 2007-10-04 | Amgen Inc. | 1-phenylsulfonyl-diaza heterocyclic amide compounds and their uses as modulators of hydroxsteroid dehydrogenases |
| US8173645B2 (en) * | 2007-03-21 | 2012-05-08 | Takeda San Diego, Inc. | Glucokinase activators |
| BRPI0816881A2 (pt) | 2007-09-21 | 2015-03-17 | Array Biopharma Inc | Composto, composição farmacêutica, uso de um composto, e, métodos para tratar doenças ou distúrbios e para preparar um composto. |
| JPWO2009096198A1 (ja) * | 2008-02-01 | 2011-05-26 | 一般社団法人ファルマIp | 新規ビアリール誘導体 |
| JOP20190083A1 (ar) | 2008-06-04 | 2017-06-16 | Amgen Inc | بولي ببتيدات اندماجية طافرة لـfgf21 واستخداماتها |
| FR2935380B1 (fr) | 2008-08-29 | 2010-09-10 | Galderma Res & Dev | Nouveaux composes hexafluoro-2-biphenyl-isopropanol, modulateurs des recepteurs de type lxrs, leur procede de preparation et leur application comme medicaments en medecine humaine ou veterinaire ainsi qu'en cosmetique. |
| MX2011002705A (es) | 2008-09-11 | 2011-09-09 | Amgen Inc | Compuestos con anillos espiro-triciclicos como moduladores de beta-secretasas y metodos de uso. |
| EP2358749B1 (en) | 2008-10-10 | 2018-07-18 | Amgen, Inc | Fgf21 mutants and uses thereof |
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2011
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2021072369A1 (en) * | 2019-10-11 | 2021-04-15 | Duke University | Lpxh targeting compounds, compositions thereof, and methods of making and using the same |
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| AR082534A1 (es) | 2012-12-12 |
| UY33568A (es) | 2012-03-30 |
| TW201238941A (en) | 2012-10-01 |
| US8431563B2 (en) | 2013-04-30 |
| EP2609081A1 (en) | 2013-07-03 |
| AU2011293584A1 (en) | 2013-03-07 |
| MX2013002208A (es) | 2013-05-30 |
| AU2011293584B2 (en) | 2014-07-31 |
| US20120225854A1 (en) | 2012-09-06 |
| WO2012027261A1 (en) | 2012-03-01 |
| JP2013536233A (ja) | 2013-09-19 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20160824 |