JP2009532454A5 - - Google Patents
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- JP2009532454A5 JP2009532454A5 JP2009503673A JP2009503673A JP2009532454A5 JP 2009532454 A5 JP2009532454 A5 JP 2009532454A5 JP 2009503673 A JP2009503673 A JP 2009503673A JP 2009503673 A JP2009503673 A JP 2009503673A JP 2009532454 A5 JP2009532454 A5 JP 2009532454A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- carbonitrile
- pyrrolidine
- glycyl
- racemate
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 claims description 52
- -1 hydroxy, amino Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000005485 noradamantyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229940024606 amino acid Drugs 0.000 claims 4
- 235000001014 amino acid Nutrition 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- YRJCXPFMFZIXRI-UHFFFAOYSA-N nonan-3-amine Chemical compound CCCCCCC(N)CC YRJCXPFMFZIXRI-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- QEOOQFHAQKFLFM-FMVYEHJMSA-N (2S)-1-[2-[(1-ethoxy-3-tricyclo[3.3.1.03,7]nonanyl)amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C1C(OCC)(C2)CC3CC2CC31NCC(=O)N1CCC[C@H]1C#N QEOOQFHAQKFLFM-FMVYEHJMSA-N 0.000 claims 1
- KRVLJXJIGNGWBX-JFQZXIRVSA-N (2S)-1-[2-[(1-fluoro-3-tricyclo[3.3.1.03,7]nonanyl)amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C1C(F)(C2)CC3CC2CC31NCC(=O)N1CCC[C@H]1C#N KRVLJXJIGNGWBX-JFQZXIRVSA-N 0.000 claims 1
- HNCGOBSMBXZKNK-BKAUGGETSA-N (2S)-1-[2-[[1-[(2,4-dioxo-1,3-thiazolidin-3-yl)methyl]-3-tricyclo[3.3.1.03,7]nonanyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC32CN1C(=O)CSC1=O HNCGOBSMBXZKNK-BKAUGGETSA-N 0.000 claims 1
- ICDAXZLJMJBWEU-ZZKWDYDOSA-N (2S)-1-[3-(1,2,4-triazol-1-yl)-2-(3-tricyclo[3.3.1.03,7]nonanylamino)propanoyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)C(NC12C3CC(CC(C2)C3)C1)CN1C=NC=N1 ICDAXZLJMJBWEU-ZZKWDYDOSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- XRILMVFNUGYKBO-ODLGXIMNSA-N (2S,4R)-4-fluoro-1-[2-[[1-(1,2,4-triazol-1-ylmethyl)-3-tricyclo[3.3.1.03,7]nonanyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C1[C@H](F)C[C@@H](C#N)N1C(=O)CNC1(CC(CN2N=CN=C2)(C2)C3)C2CC3C1 XRILMVFNUGYKBO-ODLGXIMNSA-N 0.000 claims 1
- XRILMVFNUGYKBO-JMHWRACVSA-N (2S,4S)-4-fluoro-1-[2-[[1-(1,2,4-triazol-1-ylmethyl)-3-tricyclo[3.3.1.03,7]nonanyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C1[C@@H](F)C[C@@H](C#N)N1C(=O)CNC1(CC(CN2N=CN=C2)(C2)C3)C2CC3C1 XRILMVFNUGYKBO-JMHWRACVSA-N 0.000 claims 1
- AENDDTIGPWLSNR-CJARGZMBSA-N (2s)-1-[n-(2-phenylhexahydro-2,5-methanopentalen-3a(1h)-yl)glycyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC23C1=CC=CC=C1 AENDDTIGPWLSNR-CJARGZMBSA-N 0.000 claims 1
- OJJDGXWIEGTJOZ-JFQZXIRVSA-N (2s)-1-{[(1-hydroxytricyclo[3.3.1.03,7]non-3-yl)amino]acetyl}pyrrolidine-2-carbonitrile Chemical compound C1C(O)(C2)CC3CC2CC31NCC(=O)N1CCC[C@H]1C#N OJJDGXWIEGTJOZ-JFQZXIRVSA-N 0.000 claims 1
- OGIXCFLTWALFFH-XWTIBIIYSA-N (2s)-1-{[(1-methoxytricyclo[3.3.1.03,7]non-3-yl)amino]acetyl}pyrrolidine-2-carbonitrile Chemical compound C1C(OC)(C2)CC3CC2CC31NCC(=O)N1CCC[C@H]1C#N OGIXCFLTWALFFH-XWTIBIIYSA-N 0.000 claims 1
- JSZZPAUDNNQCHU-WILFJHKZSA-N (2s)-1-{n-[2-(2-oxopyrrolidin-1-yl) hexahydro-2,5-methanopentalen-3a (1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC23N1CCCC1=O JSZZPAUDNNQCHU-WILFJHKZSA-N 0.000 claims 1
- YCIVZIZGYIKFTP-RZCQSOCGSA-N (2s)-1-{n-[2-(4-nitrophenyl) hexahydro-2,5-methanopentalen-3a(1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C2)CC3(NCC(=O)N4[C@@H](CCC4)C#N)CC2CC3C1 YCIVZIZGYIKFTP-RZCQSOCGSA-N 0.000 claims 1
- RJSCBDBTMNIANO-HPHPMKLRSA-N (2s)-1-{n-[2-(thiomorpholin-4-ylmethyl)hexahydro-2,5-methanopentalen-3a(1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC32CN1CCSCC1 RJSCBDBTMNIANO-HPHPMKLRSA-N 0.000 claims 1
- BTDWFBQWYGHVEL-HMHLJQIMSA-N (2s)-1-{n-[2-[(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound C1C(CC(CN2C(C3=CC=CC=C3C2=O)=O)(C2)C3)CC3C12NCC(=O)N1CCC[C@H]1C#N BTDWFBQWYGHVEL-HMHLJQIMSA-N 0.000 claims 1
- YQCPTICMGCERIB-XLDCJCGGSA-N (2s)-1-{n-[2-[(4-methylpiperazin-1-yl) methyl]hexahydro-2,5-methanopentalen-3a (1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound C1CN(C)CCN1CC1(C2)CC3(NCC(=O)N4[C@@H](CCC4)C#N)CC2CC3C1 YQCPTICMGCERIB-XLDCJCGGSA-N 0.000 claims 1
- BNGOLXKXYCLTJV-CKAFBJMISA-N (2s)-1-{n-[2-[4-(1h-pyrrol-1-yl)phenyl]hexahydro-2,5-methano pentalen-3a (1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC23C(C=C1)=CC=C1N1C=CC=C1 BNGOLXKXYCLTJV-CKAFBJMISA-N 0.000 claims 1
- CYDZZJJSDVFEIA-CXKWIIFHSA-N (2s)-1-{n-[2-[4-(2-oxoimidazolidin-1-yl)phenyl]hexahydro-2,5-methanopentalen-3a(1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC23C(C=C1)=CC=C1N1CCNC1=O CYDZZJJSDVFEIA-CXKWIIFHSA-N 0.000 claims 1
- VRTKKVMEAIMWFU-QCARMVEWSA-N (2s)-1-{n-[2-[4-(2-oxopyrrolidin-1-yl)phenyl]hexahydro-2,5-methano pentalen-3a(1h)-yl]glycyl}pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC23C(C=C1)=CC=C1N1CCCC1=O VRTKKVMEAIMWFU-QCARMVEWSA-N 0.000 claims 1
- LJILFHYCOZCSLK-SYQKBPBVSA-N (4R)-3-[2-[[1-(1,2,4-triazol-1-ylmethyl)-3-tricyclo[3.3.1.03,7]nonanyl]amino]acetyl]-1,3-thiazolidine-4-carbonitrile Chemical compound N1([C@@H](CSC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC32CN1C=NC=N1 LJILFHYCOZCSLK-SYQKBPBVSA-N 0.000 claims 1
- ARZRSILGRFLJIZ-DALUGEBXSA-N (4R)-3-[2-[[1-[4-(2-oxopyrrolidin-1-yl)phenyl]-3-tricyclo[3.3.1.03,7]nonanyl]amino]acetyl]-1,3-thiazolidine-4-carbonitrile Chemical compound N1([C@@H](CSC1)C#N)C(=O)CNC1(C2)CC(C3)CC1CC23C(C=C1)=CC=C1N1CCCC1=O ARZRSILGRFLJIZ-DALUGEBXSA-N 0.000 claims 1
- AKLOVIGZTFADFG-UHFFFAOYSA-N 1-(1h-1,2,4-triazol-1-ylmethyl) tricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C2(N)CC(C3)CC2CC31CN1C=NC=N1 AKLOVIGZTFADFG-UHFFFAOYSA-N 0.000 claims 1
- NDXLENSPELOJMJ-UHFFFAOYSA-N 1-(1h-tetrazol-1-ylmethyl)tricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C2(N)CC(C3)CC2CC31CN1C=NN=N1 NDXLENSPELOJMJ-UHFFFAOYSA-N 0.000 claims 1
- YNHWSZNKSJNGFO-UHFFFAOYSA-N 1-(3-aminotricyclo[3.3.1.03,7]non-1-yl) pyrrolidin-2-one Chemical compound C1C2(N)CC(C3)CC2CC13N1CCCC1=O YNHWSZNKSJNGFO-UHFFFAOYSA-N 0.000 claims 1
- IJZVIEBWKZNZPM-UHFFFAOYSA-N 1-(4-aminophenyl)tricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1=CC(N)=CC=C1C1(C2)CC3(N)CC2CC3C1 IJZVIEBWKZNZPM-UHFFFAOYSA-N 0.000 claims 1
- LUIQIWIEHBNEBJ-UHFFFAOYSA-N 1-(4-nitrophenyl)tricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C2(N)CC(C3)CC2CC13C1=CC=C([N+]([O-])=O)C=C1 LUIQIWIEHBNEBJ-UHFFFAOYSA-N 0.000 claims 1
- SQQYQNYXONNZNE-UHFFFAOYSA-N 1-[(4-methylpiperazin-1-yl)methyl]tricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1CN(C)CCN1CC1(C2)CC3(N)CC2CC3C1 SQQYQNYXONNZNE-UHFFFAOYSA-N 0.000 claims 1
- WZDCYCHLLRXMSU-UHFFFAOYSA-N 1-[4-(3-amino tricyclo[3.3.1.03,7]non-1-yl)phenyl]imidazolidin-2-one Chemical compound C1C2(N)CC(C3)CC2CC13C(C=C1)=CC=C1N1CCNC1=O WZDCYCHLLRXMSU-UHFFFAOYSA-N 0.000 claims 1
- AMZNGHJDIOMSDA-UHFFFAOYSA-N 1-[4-(3-aminotricyclo[3.3.1.03,7]non-1-yl)phenyl]pyrrolidin-2-one Chemical compound C1C2(N)CC(C3)CC2CC13C(C=C1)=CC=C1N1CCCC1=O AMZNGHJDIOMSDA-UHFFFAOYSA-N 0.000 claims 1
- FEQPMKIVZSVOJW-UHFFFAOYSA-N 1-ethoxytricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C(C2)C3(N)CC2CC1(OCC)C3 FEQPMKIVZSVOJW-UHFFFAOYSA-N 0.000 claims 1
- SMJVGTJYMDVAKV-UHFFFAOYSA-N 1-fluorotricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C(C2)C3(N)CC2(F)CC1C3 SMJVGTJYMDVAKV-UHFFFAOYSA-N 0.000 claims 1
- ABAVZBZYALFACX-UHFFFAOYSA-N 1-methoxytricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C(C2)C3(N)CC2CC1(OC)C3 ABAVZBZYALFACX-UHFFFAOYSA-N 0.000 claims 1
- MGEVPZRSDMICIV-UHFFFAOYSA-N 1-phenyltricyclo[3.3.1.03,7]nonan-3-amine Chemical compound C1C2(N)CC(C3)CC2CC13C1=CC=CC=C1 MGEVPZRSDMICIV-UHFFFAOYSA-N 0.000 claims 1
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 claims 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- CIISBNCSMVCNIP-UHFFFAOYSA-N cyclopentane-1,2-dione Chemical compound O=C1CCCC1=O CIISBNCSMVCNIP-UHFFFAOYSA-N 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
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| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US8338450B2 (en) | 2007-09-21 | 2012-12-25 | Lupin Limited | Compounds as dipeptidyl peptidase IV (DPP IV) inhibitors |
| NZ593361A (en) | 2009-01-09 | 2012-12-21 | Orchid Res Lab Ltd | Dipeptidyl peptidase iv inhibitors |
| WO2010146597A1 (en) | 2009-06-18 | 2010-12-23 | Lupin Limited | 2-amino-2- [8-(dimethyl carbamoyl)- 8-aza- bicyclo [3.2.1] oct-3-yl]-exo- ethanoyl derivatives as potent dpp-iv inhibitors |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| RU2485952C2 (ru) * | 2011-08-18 | 2013-06-27 | Открытое акционерное общество "Химико-фармацевтический комбинат "АКРИХИН" (ОАО "АКРИХИН") | Ингибирующее дипептидилпептидазу iv средство и фармацевтическая композиция на его основе |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US20150297573A1 (en) | 2012-10-24 | 2015-10-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | TPL2 KINASE INHIBITORS FOR PREVENTING OR TREATING DIABETES AND FOR PROMOTING Beta-CELL SURVIVAL |
| US10426818B2 (en) | 2015-03-24 | 2019-10-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Method and pharmaceutical composition for use in the treatment of diabetes |
| CA3011538A1 (en) | 2016-01-18 | 2017-07-27 | Arisan Therapeutics | Adamantane derivatives for the treatment of filovirus infection |
| WO2019018185A1 (en) | 2017-07-15 | 2019-01-24 | Arisan Therapeutics Inc. | ENANTIOMERICALLY PURE ADAMATANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTIONS |
| RU2712097C1 (ru) * | 2018-09-28 | 2020-01-24 | Общество с ограниченной ответственностью "Необиотек" | Ингибитор дипептидилпептидазы-4 для лечения сахарного диабета 2-го типа, соединения (варианты) |
| JP2024535246A (ja) * | 2021-09-17 | 2024-09-30 | サムスン ディスプレイ カンパニー リミテッド | 新規なキャッピング層用化合物およびそれを含む有機発光素子 |
| CN115819309B (zh) * | 2021-12-01 | 2026-01-30 | 衍科(上海)生化科技有限公司 | 一种纯度高的氨基酸衍生物及其制备方法 |
| WO2023135528A1 (en) | 2022-01-11 | 2023-07-20 | Suven Life Sciences Limited | Heteroalicyclic derivatives and their use in the treatment of cns disorders |
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|---|---|---|---|---|
| US5948777A (en) * | 1997-03-18 | 1999-09-07 | Smithkline Beecham Corporation | Cannabinoid receptor agonists |
| CO5150173A1 (es) * | 1998-12-10 | 2002-04-29 | Novartis Ag | Compuestos n-(glicilo sustituido)-2-cianopirrolidinas inhibidores de peptidasa de dipeptidilo-iv (dpp-iv) los cuales son efectivos en el tratamiento de condiciones mediadas por la inhibicion de dpp-iv |
| TWI243162B (en) * | 2000-11-10 | 2005-11-11 | Taisho Pharmaceutical Co Ltd | Cyanopyrrolidine derivatives |
| CA2768674A1 (en) * | 2002-09-19 | 2004-04-01 | Abbott Laboratories | Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-iv (dpp-iv) |
| AU2003261487A1 (en) * | 2002-11-27 | 2004-06-10 | Astellas Pharma Inc. | DPP-IV inhibitor |
| US20050239853A1 (en) * | 2004-02-04 | 2005-10-27 | Tjeerd Barf | New compounds |
| EP1719757B1 (en) * | 2004-02-27 | 2013-10-09 | Kyorin Pharmaceutical Co., Ltd. | Bicyclo derivative |
| WO2005095339A1 (en) * | 2004-03-31 | 2005-10-13 | Pfizer Products Inc. | Dicyanopyrrolidines as dipeptidyl peptidase iv inhibitors |
| US7842707B2 (en) * | 2004-07-23 | 2010-11-30 | Nuada, Llc | Peptidase inhibitors |
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2007
- 2007-03-30 AU AU2007232311A patent/AU2007232311B2/en not_active Ceased
- 2007-03-30 JP JP2009503673A patent/JP2009532454A/ja active Pending
- 2007-03-30 EP EP07734152A patent/EP2004601B1/en not_active Not-in-force
- 2007-03-30 WO PCT/IB2007/000830 patent/WO2007113634A1/en not_active Ceased
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