ZA200602051B - 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors - Google Patents
4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors Download PDFInfo
- Publication number
- ZA200602051B ZA200602051B ZA200602051A ZA200602051A ZA200602051B ZA 200602051 B ZA200602051 B ZA 200602051B ZA 200602051 A ZA200602051 A ZA 200602051A ZA 200602051 A ZA200602051 A ZA 200602051A ZA 200602051 B ZA200602051 B ZA 200602051B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- amino
- phenyl
- aryl
- Prior art date
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- 150000008081 1H-pyrimidin-4-ones Chemical class 0.000 title description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title 1
- 125000001151 peptidyl group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 1003
- -1 amiro Chemical group 0.000 claims description 812
- 125000003118 aryl group Chemical group 0.000 claims description 378
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 374
- 150000001875 compounds Chemical class 0.000 claims description 305
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 301
- 125000001072 heteroaryl group Chemical group 0.000 claims description 273
- 125000005842 heteroatom Chemical group 0.000 claims description 256
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 235
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 220
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 184
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 175
- 125000003545 alkoxy group Chemical group 0.000 claims description 162
- 229910052739 hydrogen Inorganic materials 0.000 claims description 160
- 239000001257 hydrogen Substances 0.000 claims description 156
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 147
- 125000003342 alkenyl group Chemical group 0.000 claims description 141
- 125000005843 halogen group Chemical group 0.000 claims description 140
- 125000000304 alkynyl group Chemical group 0.000 claims description 134
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 126
- 125000004104 aryloxy group Chemical group 0.000 claims description 124
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 104
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 102
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims description 98
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 97
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 97
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims description 92
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 84
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 73
- 125000004429 atom Chemical group 0.000 claims description 73
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 70
- 150000002431 hydrogen Chemical class 0.000 claims description 67
- 125000000879 imine group Chemical group 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 201000010099 disease Diseases 0.000 claims description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 238000000926 separation method Methods 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 37
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 37
- 150000001345 alkine derivatives Chemical class 0.000 claims description 34
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 34
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 34
- 125000004043 oxo group Chemical group O=* 0.000 claims description 32
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 31
- 150000001336 alkenes Chemical class 0.000 claims description 29
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 125000001475 halogen functional group Chemical group 0.000 claims description 24
- 150000001299 aldehydes Chemical class 0.000 claims description 23
- 150000001408 amides Chemical class 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 21
- 125000002723 alicyclic group Chemical group 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 20
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
- 230000002401 inhibitory effect Effects 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
- 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 13
- 125000006588 heterocycloalkylene group Chemical group 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- VGPBPWRBXBKGRE-UHFFFAOYSA-N n-(oxomethylidene)hydroxylamine Chemical compound ON=C=O VGPBPWRBXBKGRE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052720 vanadium Inorganic materials 0.000 claims description 10
- 229910052727 yttrium Inorganic materials 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-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
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000004453 alkoxycarbonyl group 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
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 6
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 230000020411 cell activation Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 210000004698 lymphocyte Anatomy 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 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
- 102100029921 Dipeptidyl peptidase 1 Human genes 0.000 claims description 5
- 101710087078 Dipeptidyl peptidase 1 Proteins 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- 239000005022 packaging material Substances 0.000 claims description 5
- 150000003892 tartrate salts Chemical class 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 208000031886 HIV Infections Diseases 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 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
- 238000003860 storage Methods 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 claims description 3
- 208000037357 HIV infectious disease Diseases 0.000 claims description 3
- 206010061598 Immunodeficiency Diseases 0.000 claims description 3
- 208000029462 Immunodeficiency disease 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
- 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
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 3
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 3
- 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 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 230000007813 immunodeficiency Effects 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- BFXPUIUKFVPUKI-UHFFFAOYSA-N 2,5-dichloro-1h-pyrimidin-6-one Chemical compound ClC1=NC=C(Cl)C(=O)N1 BFXPUIUKFVPUKI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229940099990 ogen Drugs 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
- 239000007787 solid Substances 0.000 claims description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000004452 carbocyclyl group Chemical group 0.000 claims 14
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- SVJKMLBXJJZCHN-UHFFFAOYSA-N 4-(aminomethyl)benzenesulfonamide;propanoic acid Chemical group CCC(O)=O.NCC1=CC=C(S(N)(=O)=O)C=C1 SVJKMLBXJJZCHN-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000000597 dioxinyl group Chemical group 0.000 claims 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
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- ROWSWSYVRWESPI-MRXNPFEDSA-N 2-[[2-[(3r)-3-aminopiperidin-1-yl]-5-bromo-4-tert-butyl-6-oxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)C(Br)=C(C(C)(C)C)N=C1N1CCC[C@@H](N)C1 ROWSWSYVRWESPI-MRXNPFEDSA-N 0.000 claims 1
- YEBKYXHNDLEMKJ-CQSZACIVSA-N 2-[[2-[(3r)-3-aminopiperidin-1-yl]-5-fluoro-6-oxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C1=NC=C(F)C(=O)N1CC1=CC=CC=C1C#N YEBKYXHNDLEMKJ-CQSZACIVSA-N 0.000 claims 1
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- FHTLMXYURUPWJB-UHFFFAOYSA-N 2-chloro-5-fluoro-1h-pyrimidin-6-one Chemical compound FC1=CN=C(Cl)NC1=O FHTLMXYURUPWJB-UHFFFAOYSA-N 0.000 claims 1
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- LKDWQHQNDDNHSC-UHFFFAOYSA-N 5-phenyl-1,2,4-dithiazol-3-one Chemical compound S1SC(=O)N=C1C1=CC=CC=C1 LKDWQHQNDDNHSC-UHFFFAOYSA-N 0.000 claims 1
- 108091000069 Cystinyl Aminopeptidase Proteins 0.000 claims 1
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- KOBHCUDVWOTEKO-VKHMYHEASA-N Nomega-hydroxy-nor-l-arginine Chemical compound OC(=O)[C@@H](N)CCNC(=N)NO KOBHCUDVWOTEKO-VKHMYHEASA-N 0.000 claims 1
- 101150049278 US20 gene Proteins 0.000 claims 1
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- PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 claims 1
- OQCUGPQOZNYIMV-UHFFFAOYSA-N pyrrolidin-3-ylmethanamine Chemical compound NCC1CCNC1 OQCUGPQOZNYIMV-UHFFFAOYSA-N 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
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- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 description 32
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- 238000011282 treatment Methods 0.000 description 11
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Classifications
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
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- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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-
2004
- 2004-08-12 ZA ZA200602051A patent/ZA200602051B/en unknown
- 2004-08-12 WO PCT/US2004/026265 patent/WO2005016911A1/en active Application Filing
- 2004-08-12 US US10/917,955 patent/US7470700B2/en not_active Expired - Fee Related
- 2004-08-12 MX MXPA06001601A patent/MXPA06001601A/es unknown
- 2004-08-12 KR KR1020067003037A patent/KR20060041309A/ko not_active Application Discontinuation
- 2004-08-12 US US10/918,318 patent/US20050065148A1/en not_active Abandoned
- 2004-08-12 CN CNA2004800300053A patent/CN1867560A/zh active Pending
- 2004-08-12 US US10/918,317 patent/US7790736B2/en not_active Expired - Fee Related
- 2004-08-12 US US10/918,327 patent/US7723344B2/en not_active Expired - Fee Related
- 2004-08-12 CA CA002535619A patent/CA2535619A1/en not_active Abandoned
- 2004-08-12 BR BRPI0413452-4A patent/BRPI0413452A/pt not_active IP Right Cessation
- 2004-08-12 AU AU2004265341A patent/AU2004265341A1/en not_active Abandoned
- 2004-08-12 EP EP04254864A patent/EP1506967B1/en not_active Expired - Lifetime
- 2004-08-12 US US10/918,326 patent/US7579357B2/en not_active Expired - Fee Related
- 2004-08-12 US US10/918,186 patent/US20050070531A1/en not_active Abandoned
- 2004-08-12 RU RU2006107553/04A patent/RU2006107553A/ru not_active Application Discontinuation
- 2004-08-12 DE DE602004010206T patent/DE602004010206T2/de not_active Expired - Lifetime
- 2004-08-13 JP JP2004263071A patent/JP4854943B2/ja not_active Expired - Fee Related
- 2004-08-13 TW TW093124384A patent/TW200524895A/zh unknown
- 2004-08-17 AR ARP040102936A patent/AR045455A1/es unknown
-
2006
- 2006-01-31 IL IL173490A patent/IL173490A0/en unknown
- 2006-03-10 NO NO20061157A patent/NO20061157L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1506967B1 (en) | 2007-11-21 |
| WO2005016911A1 (en) | 2005-02-24 |
| NO20061157L (no) | 2006-05-11 |
| US7790736B2 (en) | 2010-09-07 |
| US20050070530A1 (en) | 2005-03-31 |
| TW200524895A (en) | 2005-08-01 |
| KR20060041309A (ko) | 2006-05-11 |
| US20050075330A1 (en) | 2005-04-07 |
| JP2005060401A (ja) | 2005-03-10 |
| CA2535619A1 (en) | 2005-02-24 |
| US20050065148A1 (en) | 2005-03-24 |
| AU2004265341A1 (en) | 2005-02-24 |
| AR045455A1 (es) | 2005-10-26 |
| MXPA06001601A (es) | 2006-08-25 |
| DE602004010206T2 (de) | 2008-10-09 |
| US7470700B2 (en) | 2008-12-30 |
| CN1867560A (zh) | 2006-11-22 |
| US7723344B2 (en) | 2010-05-25 |
| JP4854943B2 (ja) | 2012-01-18 |
| US20050070706A1 (en) | 2005-03-31 |
| US7579357B2 (en) | 2009-08-25 |
| US20050070531A1 (en) | 2005-03-31 |
| EP1506967A1 (en) | 2005-02-16 |
| DE602004010206D1 (de) | 2008-01-03 |
| IL173490A0 (en) | 2006-06-11 |
| BRPI0413452A (pt) | 2006-10-17 |
| RU2006107553A (ru) | 2007-09-20 |
| US20050070535A1 (en) | 2005-03-31 |
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