DE102005019181A1 - Peptid-Deformylase (PDF) Inhibitoren 1 - Google Patents
Peptid-Deformylase (PDF) Inhibitoren 1 Download PDFInfo
- Publication number
- DE102005019181A1 DE102005019181A1 DE102005019181A DE102005019181A DE102005019181A1 DE 102005019181 A1 DE102005019181 A1 DE 102005019181A1 DE 102005019181 A DE102005019181 A DE 102005019181A DE 102005019181 A DE102005019181 A DE 102005019181A DE 102005019181 A1 DE102005019181 A1 DE 102005019181A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- atom
- hetero
- compound
- groups
- 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.)
- Withdrawn
Links
- -1 indene compound Chemical class 0.000 title claims abstract description 44
- 108010026809 Peptide deformylase Proteins 0.000 title claims abstract description 15
- 230000000694 effects Effects 0.000 title claims abstract description 6
- 102000005741 Metalloproteases Human genes 0.000 title claims description 4
- 108010006035 Metalloproteases Proteins 0.000 title claims description 4
- 230000001404 mediated effect Effects 0.000 title claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000000081 peptide deformylase inhibitor Substances 0.000 title abstract description 3
- 201000010099 disease Diseases 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 4
- 239000002671 adjuvant Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 230000006806 disease prevention Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 abstract description 3
- 125000005842 heteroatom Chemical group 0.000 abstract 10
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 1
- 101710170181 Metalloproteinase inhibitor Proteins 0.000 abstract 1
- 238000004166 bioassay Methods 0.000 abstract 1
- 239000012876 carrier material Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 229940126170 metalloproteinase inhibitor Drugs 0.000 abstract 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 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 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007901 soft capsule Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 description 1
- MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical compound CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- REBWSFKBXIVNRQ-UHFFFAOYSA-N 2-(furan-3-yl)furan Chemical group C1=COC(C2=COC=C2)=C1 REBWSFKBXIVNRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108010077805 Bacterial Proteins Proteins 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005354 acylalkyl group Chemical group 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical group [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005015 aryl alkynyl group Chemical group 0.000 description 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000037358 bacterial metabolism Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005312 heteroarylalkynyl group Chemical group 0.000 description 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005019181A DE102005019181A1 (de) | 2005-04-25 | 2005-04-25 | Peptid-Deformylase (PDF) Inhibitoren 1 |
| CN2006800139164A CN101163703B (zh) | 2005-04-25 | 2006-04-24 | 用作肽脱甲酰基酶（pdf）抑制剂的咪唑并[1,2-a]吡啶衍生物 |
| PCT/EP2006/003767 WO2006114263A1 (en) | 2005-04-25 | 2006-04-24 | Imidazo [1, 2-a] pyridine derivatives useful as peptide deformylase (pdf) inhibitors |
| RU2007143512/04A RU2420526C2 (ru) | 2005-04-25 | 2006-04-24 | ИМИДАЗО[1,2-a]ПИРИДИНОВЫЕ ПРОИЗВОДНЫЕ, КОТОРЫЕ МОЖНО ИСПОЛЬЗОВАТЬ В КАЧЕСТВЕ ИНГИБИТОРОВ ПЕПТИДДЕФОРМИЛАЗЫ (ПДФ) |
| US11/912,555 US20090215816A1 (en) | 2005-04-25 | 2006-04-24 | Imidazo(1,2-a)Pyridine Derivatives Useful as Peptide Deformylase (PDF) Inhibitors |
| US11/912,325 US7662833B2 (en) | 2005-04-25 | 2006-04-24 | Imidazo [1,2-A] pyridine derivatives useful as peptide deformylase (PDF) inhibitors |
| EP06742663A EP1877408A1 (en) | 2005-04-25 | 2006-04-24 | Imidazo [1, 2-a]pyridine derivatives useful as peptide deformylase (pdf) inhibitors |
| MX2007013225A MX2007013225A (es) | 2005-04-25 | 2006-04-24 | Derivados de imidazo-[1,2-a]-piridina utiles como inhibidores de desformilasa peptidica (pdf). |
| JP2008508134A JP2008538778A (ja) | 2005-04-25 | 2006-04-24 | ペプチド脱ホルミル酵素（ｐｄｆ）阻害剤として有用なイミダゾ［１，２−ａ］ピリジン誘導体 |
| KR1020077024438A KR20080002867A (ko) | 2005-04-25 | 2006-04-24 | 펩티드 데포르밀라제 (ｐｄｆ) 억제제로서 유용한이미다조[1,2-ａ]피리딘 유도체 |
| BRPI0609946-7A BRPI0609946A2 (pt) | 2005-04-25 | 2006-04-24 | derivados de imidazo [1,2-a] piridina úteis como inibidores de peptìdio deformilase (pdf) |
| AU2006239548A AU2006239548B8 (en) | 2005-04-25 | 2006-04-24 | Imidazo [1, 2-A] pyridine derivatives useful as peptide deformylase (PDF) inhibitors |
| CA002605925A CA2605925A1 (en) | 2005-04-25 | 2006-04-24 | Imidazo [1, 2-a] pyridine derivatives useful as peptide deformylase (pdf) inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005019181A DE102005019181A1 (de) | 2005-04-25 | 2005-04-25 | Peptid-Deformylase (PDF) Inhibitoren 1 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005019181A1 true DE102005019181A1 (de) | 2006-10-26 |
Family
ID=36692610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005019181A Withdrawn DE102005019181A1 (de) | 2005-04-25 | 2005-04-25 | Peptid-Deformylase (PDF) Inhibitoren 1 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7662833B2 (https=) |
| EP (1) | EP1877408A1 (https=) |
| JP (1) | JP2008538778A (https=) |
| KR (1) | KR20080002867A (https=) |
| CN (1) | CN101163703B (https=) |
| AU (1) | AU2006239548B8 (https=) |
| BR (1) | BRPI0609946A2 (https=) |
| CA (1) | CA2605925A1 (https=) |
| DE (1) | DE102005019181A1 (https=) |
| MX (1) | MX2007013225A (https=) |
| RU (1) | RU2420526C2 (https=) |
| WO (1) | WO2006114263A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010032195A1 (en) * | 2008-09-16 | 2010-03-25 | Csir | Imidazopyridines and imidazopyrimidines as hiv-i reverse transcriptase inhibitors |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008068392A1 (fr) * | 2006-12-07 | 2008-06-12 | Commissariat A L'energie Atomique | Nouveaux derives fluorophores imidazo [1,2-a] pyridin-3-yl-amine et leur procede de preparation |
| CN101855222A (zh) * | 2007-05-10 | 2010-10-06 | 通用电气健康护理有限公司 | 对大麻素cb2受体具有活性的咪唑并(1,2-a)吡啶和相关化合物 |
| DE102007040336A1 (de) | 2007-08-27 | 2009-03-05 | Johann Wolfgang Goethe-Universität Frankfurt am Main | Neue Inhibitoren der 5-Lipoxygenase und deren Verwendungen |
| FR2925903B1 (fr) * | 2008-01-02 | 2011-01-21 | Sanofi Aventis | DERIVES 6-HETEROCYCLIQUE-IMIDAZO°1,2-a!PYRIDINE-2- CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| CN101729939B (zh) * | 2008-10-31 | 2012-12-05 | 中兴通讯股份有限公司 | 无源光网络带宽分配方法及系统 |
| WO2011041713A2 (en) * | 2009-10-02 | 2011-04-07 | Glaxosmithkline Llc | Piperazinyl antiviral agents |
| EP2601194B1 (en) | 2010-08-03 | 2016-05-25 | Merck Sharp & Dohme Corp. | Fused-imidazoyl compounds useful as antimicrobial agents |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| CN103957910A (zh) * | 2011-10-21 | 2014-07-30 | 葛兰素史克有限责任公司 | 增加先天免疫反应的化合物和方法 |
| KR101650539B1 (ko) | 2014-10-15 | 2016-08-26 | 장준구 | 다각도로 발광하는 led패키지 |
| CN107245050B (zh) * | 2016-12-05 | 2019-10-25 | 徐州医科大学 | 香草醛异羟肟酸类衍生物及其应用 |
| EP3750878B1 (en) * | 2019-06-14 | 2025-05-14 | Vivoryon Therapeutics N.V. | Heteroaromatic inhibitors of astacin proteinases |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052016A1 (en) * | 1980-11-11 | 1982-05-19 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds, compositions containing same and processes for preparing same |
| DE10050663A1 (de) * | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| DE10150172A1 (de) * | 2001-10-11 | 2003-04-30 | Morphochem Ag | Neue Verbindungen, die Protein Tyrosin Phosphatase 1B (PTP-1B) inhibieren |
| EP1364952A1 (en) * | 2001-02-08 | 2003-11-26 | Eisai Co., Ltd. | Bicyclic nitrogenous fused-ring compound |
| US20040127719A1 (en) * | 2002-03-08 | 2004-07-01 | Kexin Yang | Alpha-isocyanocarboxylate solid support templates, method of preparation and for using the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU176214B (en) * | 1977-05-18 | 1981-01-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives |
| JPS61218589A (ja) * | 1985-03-26 | 1986-09-29 | Eisai Co Ltd | ５―（６―イミダゾ〔１，２―ａ〕ピリジニル）ピリジン誘導体 |
| JPH0717971A (ja) * | 1993-07-02 | 1995-01-20 | Takeda Chem Ind Ltd | イミダゾール誘導体、その製造法及び用途 |
| DE69729007T2 (de) * | 1996-08-07 | 2005-04-07 | Darwin Discovery Ltd., Slough | Hydroxamsäure- und carbonsäure-derivate mit mmp und tnf hemmender wirkung |
| AR029916A1 (es) * | 2000-05-05 | 2003-07-23 | Smithkline Beecham Corp | N-formil-n-hidroxi-ariloxi alquilaminas y metodos para tratar infecciones bacterianas |
| UY27813A1 (es) * | 2002-05-31 | 2003-12-31 | Smithkline Beecham Corp | Inhibidores de la peptido-desformilasa |
| AU2003296960A1 (en) * | 2002-12-11 | 2004-06-30 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
-
2005
- 2005-04-25 DE DE102005019181A patent/DE102005019181A1/de not_active Withdrawn
-
2006
- 2006-04-24 KR KR1020077024438A patent/KR20080002867A/ko not_active Ceased
- 2006-04-24 BR BRPI0609946-7A patent/BRPI0609946A2/pt not_active IP Right Cessation
- 2006-04-24 MX MX2007013225A patent/MX2007013225A/es active IP Right Grant
- 2006-04-24 CN CN2006800139164A patent/CN101163703B/zh not_active Expired - Fee Related
- 2006-04-24 EP EP06742663A patent/EP1877408A1/en not_active Withdrawn
- 2006-04-24 RU RU2007143512/04A patent/RU2420526C2/ru not_active IP Right Cessation
- 2006-04-24 AU AU2006239548A patent/AU2006239548B8/en not_active Ceased
- 2006-04-24 JP JP2008508134A patent/JP2008538778A/ja active Pending
- 2006-04-24 US US11/912,325 patent/US7662833B2/en not_active Expired - Fee Related
- 2006-04-24 CA CA002605925A patent/CA2605925A1/en not_active Abandoned
- 2006-04-24 US US11/912,555 patent/US20090215816A1/en not_active Abandoned
- 2006-04-24 WO PCT/EP2006/003767 patent/WO2006114263A1/en not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052016A1 (en) * | 1980-11-11 | 1982-05-19 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds, compositions containing same and processes for preparing same |
| DE10050663A1 (de) * | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| EP1364952A1 (en) * | 2001-02-08 | 2003-11-26 | Eisai Co., Ltd. | Bicyclic nitrogenous fused-ring compound |
| DE10150172A1 (de) * | 2001-10-11 | 2003-04-30 | Morphochem Ag | Neue Verbindungen, die Protein Tyrosin Phosphatase 1B (PTP-1B) inhibieren |
| US20040127719A1 (en) * | 2002-03-08 | 2004-07-01 | Kexin Yang | Alpha-isocyanocarboxylate solid support templates, method of preparation and for using the same |
Non-Patent Citations (4)
| Title |
|---|
| J.J. Chen et al.: Synlett 2001, 8, 1263-5, zitiert als Chemical Abstract, recherchiert in STN (HCAPLUS), Accession No. 2001:585625 |
| J.J. Chen et al.: Synlett 2001, 8, 1263-5, zitiertals Chemical Abstract, recherchiert in STN (HCAPLUS), Accession No. 2001:585625 * |
| JP 11343289 A, zitiert als Patent Abstract * |
| JP 11-343289 A, zitiert als Patent Abstract |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010032195A1 (en) * | 2008-09-16 | 2010-03-25 | Csir | Imidazopyridines and imidazopyrimidines as hiv-i reverse transcriptase inhibitors |
| US8501767B2 (en) | 2008-09-16 | 2013-08-06 | Csir | Imidazopyridines and imidazopyrimidines as HIV-1 reverse transcriptase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| US7662833B2 (en) | 2010-02-16 |
| RU2007143512A (ru) | 2009-06-10 |
| AU2006239548B8 (en) | 2010-08-26 |
| JP2008538778A (ja) | 2008-11-06 |
| KR20080002867A (ko) | 2008-01-04 |
| CA2605925A1 (en) | 2006-11-02 |
| BRPI0609946A2 (pt) | 2010-05-11 |
| EP1877408A1 (en) | 2008-01-16 |
| US20080188515A1 (en) | 2008-08-07 |
| RU2420526C2 (ru) | 2011-06-10 |
| AU2006239548A1 (en) | 2006-11-02 |
| CN101163703A (zh) | 2008-04-16 |
| WO2006114263A1 (en) | 2006-11-02 |
| MX2007013225A (es) | 2007-12-12 |
| AU2006239548B2 (en) | 2010-04-29 |
| CN101163703B (zh) | 2010-12-15 |
| US20090215816A1 (en) | 2009-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1521769B1 (de) | Tubulysinkonjugate | |
| EP1523493B1 (de) | Neue tubulysinanaloga | |
| DE102004041163A1 (de) | Neue Verbindungen mit antibakterieller Aktivität | |
| DE10316081A1 (de) | Neue Verbindungen mit antibakterieller Aktivität | |
| DE3875361T2 (de) | Thiazolidin-derivate. | |
| DE102005019181A1 (de) | Peptid-Deformylase (PDF) Inhibitoren 1 | |
| DE102005017116A1 (de) | Hemmstoffe für Inhibitoren von Apoptose Proteinen (IAP) | |
| EP2098226A1 (de) | AKAP-PKA-Interaktionshemmer zur Anwendung in der Behandlung von Herzkrankheiten | |
| WO2004005269A1 (de) | Verfahren zur herstellung von substituierten thiazol-2-ylmethylestern | |
| DE10320453A1 (de) | Neue Bioisostere von Actinonin | |
| EP1581165B1 (de) | Verbindungen, die faktor viia inhibieren | |
| EP1521750A1 (de) | Neue makrocyclen zur behandlung von krebserkrankungen | |
| DE102005026231A1 (de) | Peptid-Deformylase (PDF) Inhibitoren 3 | |
| EP1470143B1 (de) | Verbindungen, die faktor xa-aktiv t inhibieren | |
| DE10247233A1 (de) | Neue Verbindungen, die Topoisomerase IV inhibieren | |
| EP1893574A2 (en) | Peptide deformylase (pdf) inhibitors 4 | |
| DE10327472A1 (de) | Neue Makrocyclen zur Behandlung von Krebserkrankungen | |
| EP1877407A1 (en) | Imidazo(1,2-a)pyridine derivatives useful as peptide deformylase (pdf) inhibitors | |
| DE10230874A1 (de) | Neue Tubulysinanaloga | |
| DE10342292A1 (de) | Neue Makrolid Antibiotika | |
| DE102007013812A1 (de) | Neue Inhibitoren van Aspartylproteasen | |
| DE102006028649A1 (de) | Neue Verbindungen mit antibakterieller Aktivität | |
| DE60211665T2 (de) | Diamide, die tryptase und faktor-xa-aktivität hemmen | |
| DE102006062278A1 (de) | Neues Verfahren zur stereoselektiven Herstellung von 2.4-disubstiluierten γ-Aminosäuren und deren Nutzung in der Totalsynthese von cytotoxischen Substanzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20121101 |