JP2007513058A - ジペプチジルぺプチダーゼ阻害剤 - Google Patents
ジペプチジルぺプチダーゼ阻害剤 Download PDFInfo
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- JP2007513058A JP2007513058A JP2006526185A JP2006526185A JP2007513058A JP 2007513058 A JP2007513058 A JP 2007513058A JP 2006526185 A JP2006526185 A JP 2006526185A JP 2006526185 A JP2006526185 A JP 2006526185A JP 2007513058 A JP2007513058 A JP 2007513058A
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- JP
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- Prior art keywords
- alkyl
- group
- phenyl
- cycloalkyl
- aryl
- Prior art date
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- 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 title description 6
- 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 title description 6
- 229940122344 Peptidase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 248
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims abstract description 125
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims abstract description 111
- 238000000034 method Methods 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 1016
- -1 cyano, thio Chemical group 0.000 claims description 543
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 439
- 125000001072 heteroaryl group Chemical group 0.000 claims description 360
- 125000005842 heteroatom Chemical group 0.000 claims description 358
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 348
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 318
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 297
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 292
- 125000003118 aryl group Chemical group 0.000 claims description 245
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 237
- 229910052739 hydrogen Inorganic materials 0.000 claims description 183
- 239000001257 hydrogen Substances 0.000 claims description 183
- 125000003545 alkoxy group Chemical group 0.000 claims description 176
- 125000004104 aryloxy group Chemical group 0.000 claims description 175
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 173
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 159
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 146
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 141
- 125000003342 alkenyl group Chemical group 0.000 claims description 133
- 125000000304 alkynyl group Chemical group 0.000 claims description 133
- 125000005843 halogen group Chemical group 0.000 claims description 132
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 130
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 88
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 80
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 68
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 68
- 125000004429 atom Chemical group 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 201000010099 disease Diseases 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 35
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 35
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 35
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000879 imine group Chemical group 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 26
- 238000001727 in vivo Methods 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 18
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 125000005647 linker group Chemical group 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 208000024891 symptom Diseases 0.000 claims description 11
- 230000007170 pathology Effects 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 102000004169 proteins and genes Human genes 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000005022 packaging material Substances 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000031886 HIV Infections Diseases 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 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 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 238000001361 intraarterial administration Methods 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000007912 intraperitoneal administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 238000001959 radiotherapy Methods 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 226
- 150000002431 hydrogen Chemical class 0.000 claims 58
- 125000001475 halogen functional group Chemical group 0.000 claims 17
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 150000003335 secondary amines Chemical class 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000000676 alkoxyimino group Chemical group 0.000 claims 3
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 3
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000012669 liquid formulation Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims 1
- WAUGGYPDCQZJKK-UHFFFAOYSA-N 1h-pyrrol-3-amine Chemical compound NC=1C=CNC=1 WAUGGYPDCQZJKK-UHFFFAOYSA-N 0.000 claims 1
- BCVJWRGLEYIGPL-UHFFFAOYSA-N 2-[(2-chloro-6-oxopyridin-1-yl)methyl]benzonitrile Chemical compound ClC1=CC=CC(=O)N1CC1=CC=CC=C1C#N BCVJWRGLEYIGPL-UHFFFAOYSA-N 0.000 claims 1
- XPOLLNPFTKCWJA-UHFFFAOYSA-N 2-[(3-bromo-6-chloro-2-oxopyridin-1-yl)methyl]benzonitrile Chemical compound ClC1=CC=C(Br)C(=O)N1CC1=CC=CC=C1C#N XPOLLNPFTKCWJA-UHFFFAOYSA-N 0.000 claims 1
- XPPWZDVPECIYRM-MRXNPFEDSA-N 2-[[2-[(3r)-3-aminopiperidin-1-yl]-6-oxopyridin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C1=CC=CC(=O)N1CC1=CC=CC=C1C#N XPPWZDVPECIYRM-MRXNPFEDSA-N 0.000 claims 1
- RAYCWFYYKVPFPX-LJQANCHMSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-2-oxo-3-prop-1-ynylpyridin-1-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)C(C#CC)=CC=C1N1CCC[C@@H](N)C1 RAYCWFYYKVPFPX-LJQANCHMSA-N 0.000 claims 1
- RDKRSCXDUPITRO-HXUWFJFHSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-2-oxo-3-pyridin-3-ylpyridin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC=C1C1=CC=CN=C1 RDKRSCXDUPITRO-HXUWFJFHSA-N 0.000 claims 1
- XYWQXVRTTZQMPU-OAHLLOKOSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-bromo-2-oxopyridin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C1=CC=C(Br)C(=O)N1CC1=CC=CC=C1C#N XYWQXVRTTZQMPU-OAHLLOKOSA-N 0.000 claims 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 206010061598 Immunodeficiency Diseases 0.000 claims 1
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- NINIDFKCEFEMDL-RNFDNDRNSA-N Sulfur-36 Chemical compound [36S] NINIDFKCEFEMDL-RNFDNDRNSA-N 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 208000015322 bone marrow disease Diseases 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000597 dioxinyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 230000007813 immunodeficiency Effects 0.000 claims 1
- 238000007913 intrathecal administration Methods 0.000 claims 1
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- 210000000214 mouth Anatomy 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 50
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 48
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Classifications
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- 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
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Landscapes
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| US50148603P | 2003-09-08 | 2003-09-08 | |
| PCT/US2004/028678 WO2005030751A2 (en) | 2003-09-08 | 2004-09-02 | Dipeptidyl peptidase inhibitors |
Publications (2)
| Publication Number | Publication Date |
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| JP2007513058A true JP2007513058A (ja) | 2007-05-24 |
| JP2007513058A5 JP2007513058A5 (enExample) | 2007-10-18 |
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| JP2006526185A Pending JP2007513058A (ja) | 2003-09-08 | 2004-09-02 | ジペプチジルぺプチダーゼ阻害剤 |
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| Country | Link |
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| US (1) | US20050065144A1 (enExample) |
| EP (1) | EP1697342A2 (enExample) |
| JP (1) | JP2007513058A (enExample) |
| WO (1) | WO2005030751A2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2017528486A (ja) * | 2014-09-17 | 2017-09-28 | ヴァーセオン コーポレイション | セリンプロテアーゼ阻害剤としてのピラゾリル置換ピリドン化合物 |
| US10532995B2 (en) | 2015-02-27 | 2020-01-14 | Verseon Corporation | Substituted pyrazole compounds as serine protease inhibitors |
| US10653674B2 (en) | 2010-03-30 | 2020-05-19 | Verseon Corporation | Multisubstituted aromatic compounds as inhibitors of thrombin |
| JP2022533526A (ja) * | 2019-05-15 | 2022-07-25 | レオ ファーマ アクティーゼルスカブ | 皮膚エリテマトーデスの治療 |
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| JP3909056B2 (ja) | 2001-06-27 | 2007-04-25 | スミスクライン ビーチャム コーポレーション | ジペプチジルペプチダーゼ阻害剤としてのフルオロピロリジン類 |
| PL377847A1 (pl) | 2003-01-14 | 2006-02-20 | Arena Pharmaceuticals Inc. | 1,2,3-Tripodstawione pochodne arylowe i heteroarylowe jako modulatory metabolizmu oraz profilaktyka i leczenie związanych z nim zaburzeń takich jak cukrzyca i hiperglikemia |
| WO2004087053A2 (en) | 2003-03-25 | 2004-10-14 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
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| US10653674B2 (en) | 2010-03-30 | 2020-05-19 | Verseon Corporation | Multisubstituted aromatic compounds as inhibitors of thrombin |
| JP2017528486A (ja) * | 2014-09-17 | 2017-09-28 | ヴァーセオン コーポレイション | セリンプロテアーゼ阻害剤としてのピラゾリル置換ピリドン化合物 |
| JP2020143112A (ja) * | 2014-09-17 | 2020-09-10 | ヴァーセオン コーポレイション | セリンプロテアーゼ阻害剤としてのピラゾリル置換ピリドン化合物 |
| US10532995B2 (en) | 2015-02-27 | 2020-01-14 | Verseon Corporation | Substituted pyrazole compounds as serine protease inhibitors |
| JP2022533526A (ja) * | 2019-05-15 | 2022-07-25 | レオ ファーマ アクティーゼルスカブ | 皮膚エリテマトーデスの治療 |
| JP2025114800A (ja) * | 2019-05-15 | 2025-08-05 | レオ ファーマ アクティーゼルスカブ | 皮膚エリテマトーデスの治療 |
| JP7734587B2 (ja) | 2019-05-15 | 2025-09-05 | レオ ファーマ アクティーゼルスカブ | 皮膚エリテマトーデスの治療 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050065144A1 (en) | 2005-03-24 |
| WO2005030751A3 (en) | 2005-11-17 |
| EP1697342A2 (en) | 2006-09-06 |
| WO2005030751A2 (en) | 2005-04-07 |
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