JP2011526616A5 - - Google Patents
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- Publication number
- JP2011526616A5 JP2011526616A5 JP2011515631A JP2011515631A JP2011526616A5 JP 2011526616 A5 JP2011526616 A5 JP 2011526616A5 JP 2011515631 A JP2011515631 A JP 2011515631A JP 2011515631 A JP2011515631 A JP 2011515631A JP 2011526616 A5 JP2011526616 A5 JP 2011526616A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazolidine
- dione
- methylidene
- phenyl
- methyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- -1 nitro, cyano, hydroxy, amino, mercapto, formyl Chemical group 0.000 description 207
- 125000000217 alkyl group Chemical group 0.000 description 29
- 229910052736 halogen Inorganic materials 0.000 description 21
- 150000002367 halogens Chemical class 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- 125000004452 carbocyclyl group Chemical group 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 8
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 5
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HVMFXMXOKHYZGH-QPEQYQDCSA-N (5z)-5-[[2-(3-amino-4-methylpiperidin-1-yl)-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N)C(C)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 HVMFXMXOKHYZGH-QPEQYQDCSA-N 0.000 description 1
- JXSNYJNREMWSDJ-DKBJHAQFSA-N (5z)-5-[[2-[(3r)-3-(aminomethyl)pyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](CN)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 JXSNYJNREMWSDJ-DKBJHAQFSA-N 0.000 description 1
- MDFJCKNNJJLLKS-HDOAHBKWSA-N (5z)-5-[[2-[(3r)-3-[[4-(aminomethyl)phenyl]methylamino]piperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(CN)=CC=C1CN[C@H]1CN(C=2C(=CC=CC=2Cl)\C=C/2C(NC(=O)S\2)=O)CCC1 MDFJCKNNJJLLKS-HDOAHBKWSA-N 0.000 description 1
- DXTSXAULWQSFNT-NUBYWOLOSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(2,2,2-trifluoroethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(OCC(F)(F)F)C=CC=C1\C=C/1C(=O)NC(=O)S\1 DXTSXAULWQSFNT-NUBYWOLOSA-N 0.000 description 1
- NQPRGWXCFHMQPV-NWFCWYBLSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(2-methoxyethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OCCOC)=CC=CC=1\C=C1/SC(=O)NC1=O NQPRGWXCFHMQPV-NWFCWYBLSA-N 0.000 description 1
- FBEUTZRQCSCWQM-SLVCOGOPSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(2-methylpropoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OCC(C)C)=CC=CC=1\C=C1/SC(=O)NC1=O FBEUTZRQCSCWQM-SLVCOGOPSA-N 0.000 description 1
- PYWZTKODXYPZLR-VPMLRQHESA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-bromophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(Br)C=CC=C1\C=C/1C(=O)NC(=O)S\1 PYWZTKODXYPZLR-VPMLRQHESA-N 0.000 description 1
- ZLDXTUTZYPVCKG-VPMLRQHESA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 ZLDXTUTZYPVCKG-VPMLRQHESA-N 0.000 description 1
- ILDFZJPHSLRCEK-YDRQLGOLSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-cyclobutyloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OC1CCC1 ILDFZJPHSLRCEK-YDRQLGOLSA-N 0.000 description 1
- YCYIBOYEPOLGSN-PWDRBQJJSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-cyclohexyloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OC1CCCCC1 YCYIBOYEPOLGSN-PWDRBQJJSA-N 0.000 description 1
- BVHIMRZDAQRPHV-RQNDZEIBSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-cyclopentyloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OC1CCCC1 BVHIMRZDAQRPHV-RQNDZEIBSA-N 0.000 description 1
- YPGUAMCIYVJFOJ-OJLMPMFISA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-ethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OCC)=CC=CC=1\C=C1/SC(=O)NC1=O YPGUAMCIYVJFOJ-OJLMPMFISA-N 0.000 description 1
- GJSKIXCETHIGQQ-JYVXZMADSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OC)=CC=CC=1\C=C1/SC(=O)NC1=O GJSKIXCETHIGQQ-JYVXZMADSA-N 0.000 description 1
- MCUJKPPARUPFJM-UWCCDQBKSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-phenylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)C=2C=CC=CC=2)=C1\C=C/1C(=O)NC(=O)S\1 MCUJKPPARUPFJM-UWCCDQBKSA-N 0.000 description 1
- ULMRMVZQMKZWKJ-MLJKTZRHSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-propan-2-yloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OC(C)C)=CC=CC=1\C=C1/SC(=O)NC1=O ULMRMVZQMKZWKJ-MLJKTZRHSA-N 0.000 description 1
- WLJWSUVXFQUAHY-JYVXZMADSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 WLJWSUVXFQUAHY-JYVXZMADSA-N 0.000 description 1
- NJYIOPRYGAGQCB-NJQKBMNKSA-N (5z)-5-[[2-[(3r)-3-aminopyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 NJYIOPRYGAGQCB-NJQKBMNKSA-N 0.000 description 1
- DGGXDXTZQQQTKL-OYHMZJHOSA-N (5z)-5-[[2-[(3r,4r)-3-amino-4-hydroxypiperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C[C@@H](O)[C@H](N)CN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 DGGXDXTZQQQTKL-OYHMZJHOSA-N 0.000 description 1
- JXSNYJNREMWSDJ-TXEUWIOXSA-N (5z)-5-[[2-[(3s)-3-(aminomethyl)pyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](CN)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 JXSNYJNREMWSDJ-TXEUWIOXSA-N 0.000 description 1
- GSCZVAZFVSJNDT-OGGBREFQSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-(2,2,2-trifluoroethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(OCC(F)(F)F)C=CC=C1\C=C/1C(=O)NC(=O)S\1 GSCZVAZFVSJNDT-OGGBREFQSA-N 0.000 description 1
- LPJHRWXRKNBEMC-CJAAZZPWSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-(2-methoxyethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OCCOC)=CC=CC=1\C=C1/SC(=O)NC1=O LPJHRWXRKNBEMC-CJAAZZPWSA-N 0.000 description 1
- LRGBUXCKVLHMRX-ISAHRAOESA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-bromophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(Br)C=CC=C1\C=C/1C(=O)NC(=O)S\1 LRGBUXCKVLHMRX-ISAHRAOESA-N 0.000 description 1
- FCICTBXGGPCMIE-SYUPGTOSSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 FCICTBXGGPCMIE-SYUPGTOSSA-N 0.000 description 1
- JZCLSXXFXYSNOS-LFTLCWSBSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-ethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OCC)=CC=CC=1\C=C1/SC(=O)NC1=O JZCLSXXFXYSNOS-LFTLCWSBSA-N 0.000 description 1
- YALFZHPIDBMBTI-QENILXLESA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-propan-2-yloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OC(C)C)=CC=CC=1\C=C1/SC(=O)NC1=O YALFZHPIDBMBTI-QENILXLESA-N 0.000 description 1
- OINUTZGUCFIHAF-BZPKPHBRSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 OINUTZGUCFIHAF-BZPKPHBRSA-N 0.000 description 1
- QFGNATOKKPXYOF-DKKOHOGUSA-N (5z)-5-[[2-[(3s,4s)-3-amino-4-hydroxypyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](N)CN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 QFGNATOKKPXYOF-DKKOHOGUSA-N 0.000 description 1
- NJJGZBDOINCOFY-SSZFMOIBSA-N (5z)-5-[[3-(3-piperidin-1-ylpropoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)\C1=C\C1=CC=CC(OCCCN2CCCCC2)=C1 NJJGZBDOINCOFY-SSZFMOIBSA-N 0.000 description 1
- SUPIJQUDABPQAC-UVTDQMKNSA-N (5z)-5-[[3-[(4-methylpiperazin-1-yl)methyl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1CC1=CC=CC(\C=C/2C(NC(=O)S\2)=O)=C1 SUPIJQUDABPQAC-UVTDQMKNSA-N 0.000 description 1
- SZQWWFBBLCIGLS-SSZFMOIBSA-N (5z)-5-[[3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(\C=C/2C(NC(=O)S\2)=O)=C1 SZQWWFBBLCIGLS-SSZFMOIBSA-N 0.000 description 1
- DMKSNYHOCJFURT-XFXZXTDPSA-N (5z)-5-[[3-chloro-2-(1,4-diazepan-1-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CCNCCN1C=1C(Cl)=CC=CC=1\C=C1/SC(=O)NC1=O DMKSNYHOCJFURT-XFXZXTDPSA-N 0.000 description 1
- YKWMZRDTFDCLPC-OJLMPMFISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(2-hydroxyethylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](NCCO)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 YKWMZRDTFDCLPC-OJLMPMFISA-N 0.000 description 1
- OBZOMRZVUQXCFA-OJLMPMFISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(3,3,3-trifluoropropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](NCCC(F)(F)F)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 OBZOMRZVUQXCFA-OJLMPMFISA-N 0.000 description 1
- NNPXGWVESYSMDR-NWFCWYBLSA-N (5z)-5-[[3-chloro-2-[(3r)-3-(3-hydroxypropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](NCCCO)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 NNPXGWVESYSMDR-NWFCWYBLSA-N 0.000 description 1
- STVUNYMVAGCJLS-OKSBFYSISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(dipropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N(CCC)CCC)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 STVUNYMVAGCJLS-OKSBFYSISA-N 0.000 description 1
- ZEZRLGPUJDQXJR-NWFCWYBLSA-N (5z)-5-[[3-chloro-2-[(3r)-3-[2-(methylamino)ethylamino]piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](NCCNC)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 ZEZRLGPUJDQXJR-NWFCWYBLSA-N 0.000 description 1
- OBDFOJUJSKEDRO-ZSOIEALJSA-N (5z)-5-[[3-chloro-2-[4-methyl-3-(methylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(C)C(NC)CN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 OBDFOJUJSKEDRO-ZSOIEALJSA-N 0.000 description 1
- MAXWYVPUCAYEHZ-ZSOIEALJSA-N (5z)-5-[[5-amino-2-[3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C)CCN1C1=CC=C(N)C=C1\C=C/1C(=O)NC(=O)S\1 MAXWYVPUCAYEHZ-ZSOIEALJSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XNMZHEQSIZCWTO-NUBYWOLOSA-N 4-[(3r)-3-aminopiperidin-1-yl]-3-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid Chemical compound C1[C@H](N)CCCN1C1=CC=C(C(O)=O)C=C1\C=C/1C(=O)NC(=O)S\1 XNMZHEQSIZCWTO-NUBYWOLOSA-N 0.000 description 1
- MVKANCZREUZKOU-OGGBREFQSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-3-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid Chemical compound C1[C@@H](N)CCN1C1=CC=C(C(O)=O)C=C1\C=C/1C(=O)NC(=O)S\1 MVKANCZREUZKOU-OGGBREFQSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
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- 2011-01-05 NI NI201100007A patent/NI201100007A/es unknown
- 2011-01-10 CR CR20110016A patent/CR20110016A/es unknown
- 2011-02-01 ZA ZA2011/00844A patent/ZA201100844B/en unknown
- 2011-02-01 CO CO11011427A patent/CO6341555A2/es active IP Right Grant
-
2013
- 2013-02-20 JP JP2013031176A patent/JP2013139459A/ja not_active Ceased
-
2014
- 2014-07-24 US US14/339,981 patent/US20150051185A1/en not_active Abandoned
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