JP2008524331A - ジペプチジルペプチダーゼ阻害剤 - Google Patents
ジペプチジルペプチダーゼ阻害剤 Download PDFInfo
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- JP2008524331A JP2008524331A JP2007548348A JP2007548348A JP2008524331A JP 2008524331 A JP2008524331 A JP 2008524331A JP 2007548348 A JP2007548348 A JP 2007548348A JP 2007548348 A JP2007548348 A JP 2007548348A JP 2008524331 A JP2008524331 A JP 2008524331A
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- Prior art keywords
- alkyl
- group
- phenyl
- aryl
- substituted
- Prior art date
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- 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 title description 5
- 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 title description 5
- 229940122344 Peptidase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 319
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims abstract description 157
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims abstract description 143
- 238000000034 method Methods 0.000 claims abstract description 64
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 645
- -1 cyano, thio Chemical group 0.000 claims description 588
- 125000001072 heteroaryl group Chemical group 0.000 claims description 322
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 300
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 298
- 125000005842 heteroatom Chemical group 0.000 claims description 239
- 125000003118 aryl group Chemical group 0.000 claims description 233
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 225
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 200
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 198
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 179
- 229910052739 hydrogen Inorganic materials 0.000 claims description 151
- 239000001257 hydrogen Substances 0.000 claims description 151
- 125000003342 alkenyl group Chemical group 0.000 claims description 128
- 125000004104 aryloxy group Chemical group 0.000 claims description 128
- 125000000304 alkynyl group Chemical group 0.000 claims description 127
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 127
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 126
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 118
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 113
- 125000005843 halogen group Chemical group 0.000 claims description 113
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 112
- 125000003545 alkoxy group Chemical group 0.000 claims description 106
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 92
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 89
- 125000004429 atom Chemical group 0.000 claims description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 55
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 48
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 48
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 48
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 48
- 201000010099 disease Diseases 0.000 claims description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000000879 imine group Chemical group 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 29
- 238000001727 in vivo Methods 0.000 claims description 28
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000001475 halogen functional group Chemical group 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 230000000694 effects Effects 0.000 claims description 22
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
- 206010012601 diabetes mellitus Diseases 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 230000007170 pathology Effects 0.000 claims description 12
- 108090000623 proteins and genes Proteins 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 12
- 229910052721 tungsten Inorganic materials 0.000 claims description 12
- 229910052720 vanadium Inorganic materials 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000003335 secondary amines Chemical class 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000005022 packaging material Substances 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 6
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 6
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 208000031886 HIV Infections Diseases 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 210000004698 lymphocyte Anatomy 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 238000007920 subcutaneous administration Methods 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000037357 HIV infectious disease Diseases 0.000 claims description 4
- 206010061598 Immunodeficiency Diseases 0.000 claims description 4
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
- 230000020411 cell activation Effects 0.000 claims description 4
- 238000002512 chemotherapy Methods 0.000 claims description 4
- 230000007812 deficiency Effects 0.000 claims description 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000007813 immunodeficiency Effects 0.000 claims description 4
- 238000001361 intraarterial administration Methods 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 238000007912 intraperitoneal administration Methods 0.000 claims description 4
- 238000007913 intrathecal administration Methods 0.000 claims description 4
- 238000001990 intravenous administration Methods 0.000 claims description 4
- 239000002502 liposome Substances 0.000 claims description 4
- 239000012669 liquid formulation Substances 0.000 claims description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 2
- LBJZHQWXOIQDRG-UHFFFAOYSA-N 1-[5-[[2-(aminomethyl)phenyl]methyl]-4h-pyrazolo[1,5-a]pyrazin-6-yl]piperidin-3-amine Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2N=CC=C2C1 LBJZHQWXOIQDRG-UHFFFAOYSA-N 0.000 claims description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims description 2
- GBIURNYOVIIFDM-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CC2CCCN2C1=O GBIURNYOVIIFDM-UHFFFAOYSA-N 0.000 claims description 2
- VNYBRUFSKVMMHO-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-5,6,7,8-tetrahydro-4ah-pyrido[1,2-c]pyrimidin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CC2CCCCN2C1=O VNYBRUFSKVMMHO-UHFFFAOYSA-N 0.000 claims description 2
- TULXIPMGBSCKHC-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2CCCC2C1=O TULXIPMGBSCKHC-UHFFFAOYSA-N 0.000 claims description 2
- HBSUGJVKOYUPNX-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-6,7,8,9-tetrahydropyridazino[1,2-a][1,2,4]triazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2CCCCN2C1=O HBSUGJVKOYUPNX-UHFFFAOYSA-N 0.000 claims description 2
- ITXFMSWYVPRXNA-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-7,8,9,9a-tetrahydro-6h-pyrazino[1,2-a]pyrazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2CCNCC2C1=O ITXFMSWYVPRXNA-UHFFFAOYSA-N 0.000 claims description 2
- JLLTWIATWHQGQE-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-7,8,9,9a-tetrahydro-6h-pyrido[1,2-a]pyrazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2CCCCC2C1=O JLLTWIATWHQGQE-UHFFFAOYSA-N 0.000 claims description 2
- QRRFFIMDQTVVLL-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-7,8-dihydro-6h-pyrazolo[1,2-a][1,2,4]triazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2CCCN2C1=O QRRFFIMDQTVVLL-UHFFFAOYSA-N 0.000 claims description 2
- DELIRVZXUUZZKZ-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-8h-pyrimido[1,6-c]pyrimidin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CC2=CC=NCN2C1=O DELIRVZXUUZZKZ-UHFFFAOYSA-N 0.000 claims description 2
- IMDRCKNBUIPNAO-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-[1,2,4]triazino[1,2-a][1,2,4]triazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2C=CN=CN2C1=O IMDRCKNBUIPNAO-UHFFFAOYSA-N 0.000 claims description 2
- SEIMGQRTYVPTSU-UHFFFAOYSA-N 2-[[2-(aminomethyl)phenyl]methyl]-3-(3-aminopiperidin-1-yl)-[1,2,4]triazino[2,1-a][1,2,4]triazin-1-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=CN2C=NC=CN2C1=O SEIMGQRTYVPTSU-UHFFFAOYSA-N 0.000 claims description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims description 2
- UCKRBOSSBCWZAH-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-(3-aminopiperidin-1-yl)-4a,5,6,7-tetrahydropyrrolo[2,1-f][1,2,4]triazin-4-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=NN2CCCC2C1=O UCKRBOSSBCWZAH-UHFFFAOYSA-N 0.000 claims description 2
- GNNAPWNNIAMWMP-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-(3-aminopiperidin-1-yl)-6,7,9,9a-tetrahydro-[1,4]oxazino[4,3-a][1,3,5]triazin-4-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=NC2COCCN2C1=O GNNAPWNNIAMWMP-UHFFFAOYSA-N 0.000 claims description 2
- MXMQQWUVQOPJAI-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-(3-aminopiperidin-1-yl)-6,7,9,9a-tetrahydro-[1,4]thiazino[4,3-a][1,3,5]triazin-4-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=NC2CSCCN2C1=O MXMQQWUVQOPJAI-UHFFFAOYSA-N 0.000 claims description 2
- BFDNISCXKJPKSN-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-(3-aminopiperidin-1-yl)-6h-pyrazino[1,2-a][1,3,5]triazin-4-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=NC2=CN=CCN2C1=O BFDNISCXKJPKSN-UHFFFAOYSA-N 0.000 claims description 2
- PZBKCHWKTOIPMJ-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-(3-aminopiperidin-1-yl)-6h-pyrimido[1,2-a][1,3,5]triazin-4-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=NC2=NC=CCN2C1=O PZBKCHWKTOIPMJ-UHFFFAOYSA-N 0.000 claims description 2
- XASWLWPYYSZOCQ-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-(3-aminopiperidin-1-yl)-6h-pyrimido[1,6-a][1,3,5]triazin-4-one Chemical compound NCC1=CC=CC=C1CN1C(N2CC(N)CCC2)=NC2=CC=NCN2C1=O XASWLWPYYSZOCQ-UHFFFAOYSA-N 0.000 claims description 2
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63824804P | 2004-12-21 | 2004-12-21 | |
| PCT/US2005/045769 WO2006068978A2 (en) | 2004-12-21 | 2005-12-16 | Dipeptidyl peptidase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008524331A true JP2008524331A (ja) | 2008-07-10 |
| JP2008524331A5 JP2008524331A5 (https=) | 2009-02-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2007548348A Pending JP2008524331A (ja) | 2004-12-21 | 2005-12-16 | ジペプチジルペプチダーゼ阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US7872124B2 (https=) |
| EP (2) | EP2805953B1 (https=) |
| JP (1) | JP2008524331A (https=) |
| WO (1) | WO2006068978A2 (https=) |
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| JP2013516391A (ja) * | 2009-12-30 | 2013-05-13 | シャンハイ フォチョン ファーマシューティカル カンパニー リミテッド | ジペプチジルペプチダーゼ阻害剤 |
| JP2020500841A (ja) * | 2016-10-28 | 2020-01-16 | ハー・ルンドベック・アクチエゼルスカベット | イミダゾピラジノンの投与を含む併用療法 |
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- 2005-12-16 WO PCT/US2005/045769 patent/WO2006068978A2/en not_active Ceased
- 2005-12-16 US US11/305,818 patent/US7872124B2/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2013516391A (ja) * | 2009-12-30 | 2013-05-13 | シャンハイ フォチョン ファーマシューティカル カンパニー リミテッド | ジペプチジルペプチダーゼ阻害剤 |
| JP2020500841A (ja) * | 2016-10-28 | 2020-01-16 | ハー・ルンドベック・アクチエゼルスカベット | イミダゾピラジノンの投与を含む併用療法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006068978A3 (en) | 2007-02-22 |
| US8093382B2 (en) | 2012-01-10 |
| EP1828192A2 (en) | 2007-09-05 |
| WO2006068978A2 (en) | 2006-06-29 |
| US20060135767A1 (en) | 2006-06-22 |
| US7872124B2 (en) | 2011-01-18 |
| EP2805953B1 (en) | 2016-03-09 |
| EP1828192B1 (en) | 2014-12-03 |
| US20110087022A1 (en) | 2011-04-14 |
| EP2805953A1 (en) | 2014-11-26 |
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