ZA200201409B - Novel A-500359 derivatives. - Google Patents

Novel A-500359 derivatives. Download PDF

Info

Publication number: ZA200201409B
Authority: ZA; South Africa
Prior art keywords: group; pharmaceutically acceptable; compound; substituents; alkyl
Prior art date: 1999-08-20

Application number

ZA200201409A

Other languages

English (en)

Inventor

Hitoshi Hotoda

Masatoshi Inukai

Yukio Utsui

Masakatsu Kaneko

Yasunori Muramatsu

Satoshi Ohya

Original Assignee

Sankyo Co

Priority date (The priority date 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 date listed.)

1999-08-20

Filing date

2002-02-19

Publication date

2003-07-30

2002-02-19 Application filed by Sankyo Co filed Critical Sankyo Co

2003-07-30 Publication of ZA200201409B publication Critical patent/ZA200201409B/en

Links

-1 cyclic amine Chemical class 0.000 claims description 998
125000001424 substituent group Chemical group 0.000 claims description 199
125000000217 alkyl group Chemical group 0.000 claims description 185
150000001875 compounds Chemical class 0.000 claims description 185
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 122
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
150000002148 esters Chemical class 0.000 claims description 74
150000003839 salts Chemical class 0.000 claims description 66
125000003118 aryl group Chemical group 0.000 claims description 53
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
125000003342 alkenyl group Chemical group 0.000 claims description 49
125000003545 alkoxy group Chemical group 0.000 claims description 44
229910052757 nitrogen Inorganic materials 0.000 claims description 34
229910052717 sulfur Inorganic materials 0.000 claims description 33
125000005843 halogen group Chemical group 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
125000004430 oxygen atom Chemical group O* 0.000 claims description 30
125000004414 alkyl thio group Chemical group 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
239000011593 sulfur Substances 0.000 claims description 24
125000003277 amino group Chemical group 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
238000011282 treatment Methods 0.000 claims description 14
208000035143 Bacterial infection Diseases 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
208000022362 bacterial infectious disease Diseases 0.000 claims description 13
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
125000004434 sulfur atom Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000000464 thioxo group Chemical group S=* 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 3
239000000126 substance Substances 0.000 claims 11
201000008827 tuberculosis Diseases 0.000 claims 2
241000186359 Mycobacterium Species 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 description 45
229910052731 fluorine Inorganic materials 0.000 description 23
229910052739 hydrogen Inorganic materials 0.000 description 23
239000001257 hydrogen Substances 0.000 description 23
239000011737 fluorine Substances 0.000 description 22
125000001153 fluoro group Chemical group F* 0.000 description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
125000001309 chloro group Chemical group Cl* 0.000 description 13
150000002170 ethers Chemical class 0.000 description 12
229910052736 halogen Inorganic materials 0.000 description 12
150000002367 halogens Chemical class 0.000 description 12
229910052801 chlorine Inorganic materials 0.000 description 10
230000002349 favourable effect Effects 0.000 description 10
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
125000004185 ester group Chemical group 0.000 description 9
125000001033 ether group Chemical group 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
125000000304 alkynyl group Chemical group 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 6
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
239000011575 calcium Substances 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 4
125000006074 1-ethyl-2-butenyl group Chemical group 0.000 description 4
125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 4
125000006039 1-hexenyl group Chemical group 0.000 description 4
125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 4
125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 4
125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 4
125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 4
125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 4
125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 4
125000006023 1-pentenyl group Chemical group 0.000 description 4
125000006017 1-propenyl group Chemical group 0.000 description 4
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 4
125000006040 2-hexenyl group Chemical group 0.000 description 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 4
125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 4
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000005916 2-methylpentyl group Chemical group 0.000 description 4
125000006024 2-pentenyl group Chemical group 0.000 description 4
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 4
125000006041 3-hexenyl group Chemical group 0.000 description 4
125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
125000006042 4-hexenyl group Chemical group 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
125000006043 5-hexenyl group Chemical group 0.000 description 4
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052792 caesium Inorganic materials 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 3
125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 3
125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 description 3
125000005999 2-bromoethyl group Chemical group 0.000 description 3
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 3
125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 3
125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 3
125000005917 3-methylpentyl group Chemical group 0.000 description 3
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical group C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
238000007385 chemical modification Methods 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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 3
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000000719 pyrrolidinyl group Chemical group 0.000 description 3
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
BISOEENGZHMDEO-RLXIHFJVSA-N (2s,3s,4s)-2-[(1r)-2-amino-1-[(2s,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-n-[(3s)-2-oxoazepan-3-yl]-3,4-dihydro-2h-pyran-6-carboxamide Chemical compound O([C@@H]([C@H]([C@@H](O)C=1)O)O[C@H]([C@H]2O[C@H]([C@H](O)[C@@H]2OC)N2C(NC(=O)C=C2)=O)C(N)=O)C=1C(=O)N[C@H]1CCCCNC1=O BISOEENGZHMDEO-RLXIHFJVSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
125000003456 2,6-dinitrophenyl group Chemical group [H]C1=C([H])C(=C(*)C(=C1[H])[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
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150000004677 hydrates Chemical class 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000005990 isobenzothienyl group Chemical group 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
159000000003 magnesium salts Chemical class 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000005954 phenoxathiinyl group Chemical group 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
229960001225 rifampicin Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
239000004474 valine Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
- 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
- A61P31/08—Antibacterial agents for leprosy
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

ZA200201409A 1999-08-20 2002-02-19 Novel A-500359 derivatives. ZA200201409B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP23393499		1999-08-20

Publications (1)

Publication Number	Publication Date
ZA200201409B true ZA200201409B (en)	2003-07-30

Family

ID=16962911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200201409A ZA200201409B (en)	1999-08-20	2002-02-19	Novel A-500359 derivatives.

Country Status (24)

Country	Link
US (1)	US7157442B2 (de)
EP (1)	EP1209166B1 (de)
KR (1)	KR100787849B1 (de)
CN (1)	CN1176936C (de)
AT (1)	ATE263183T1 (de)
AU (1)	AU763492B2 (de)
BR (1)	BR0013435A (de)
CA (1)	CA2382654C (de)
CZ (1)	CZ2002682A3 (de)
DE (1)	DE60009517T2 (de)
DK (1)	DK1209166T3 (de)
ES (1)	ES2216933T3 (de)
HU (1)	HUP0204217A3 (de)
IL (2)	IL148196A0 (de)
MX (1)	MXPA02001817A (de)
NO (1)	NO323556B1 (de)
NZ (1)	NZ517315A (de)
PL (1)	PL353494A1 (de)
PT (1)	PT1209166E (de)
RU (1)	RU2227799C2 (de)
TR (1)	TR200200485T2 (de)
TW (1)	TWI245047B (de)
WO (1)	WO2001014399A1 (de)
ZA (1)	ZA200201409B (de)

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BR9911965A (pt) *	1998-07-09	2001-05-29	Sankyo Co	Composto, derivado de éster, éter ou n-alquilcarbamoìla farmaceuticamente aceitáveis, composição farmacêutica, uso de um composto, processo para o tratamento ou prevenção de uma infecção bacteriana, streptomices griseus, derivado de amida, processo para preparar um composto, e, cepa de streptomyces griseus
CN101404986B (zh) *	2002-05-17	2011-09-28	赛奎拉公司	用于诊断和治疗感染性疾病的组合物和制药方法
US20040033986A1 (en) *	2002-05-17	2004-02-19	Protopopova Marina Nikolaevna	Anti tubercular drug: compositions and methods
US7456222B2 (en) *	2002-05-17	2008-11-25	Sequella, Inc.	Anti tubercular drug: compositions and methods
EP1670314A4 (de) *	2003-09-05	2009-02-25	Sequella Inc	Verfahren und zusammensetzungen enthaltend diamine als neue therapeutika für tuberkulose
US20090281054A1 (en) *	2008-05-06	2009-11-12	Venkata Reddy	Compositions and methods comprising capuramycin analogues
KR101104505B1 (ko) *	2010-01-30	2012-01-12	김근섭	호스 연결용 원클릭 피팅
WO2015027137A1 (en) *	2013-08-23	2015-02-26	University Of Tennessee Research Foundation	Improved synthesis of capuramycin and its analogues
WO2022006231A1 (en) *	2020-06-30	2022-01-06	University Of Tennessee Research Foundation	Dpagt1 inhibitors of capuramycin analogues and their antimigratory activities of solid tumors

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JPS60259190A (ja) *	1984-06-06	1985-12-21	Kanto Ishi Pharma Co Ltd	新抗生物質カプラマイシン及びその製造法
US5034381A (en) *	1988-01-07	1991-07-23	Ciba-Geigy Corporation	2-(substituted amino) adenosines as antihypertensives
JPH05148293A (ja) *	1991-11-28	1993-06-15	Mect Corp	新規カプラマイシン誘導体およびその製造方法
GB9307043D0 (en)	1993-04-05	1993-05-26	Norsk Hydro As	Chemical compounds
BR9911965A (pt)	1998-07-09	2001-05-29	Sankyo Co	Composto, derivado de éster, éter ou n-alquilcarbamoìla farmaceuticamente aceitáveis, composição farmacêutica, uso de um composto, processo para o tratamento ou prevenção de uma infecção bacteriana, streptomices griseus, derivado de amida, processo para preparar um composto, e, cepa de streptomyces griseus
JP4428762B2 (ja)	1998-07-09	2010-03-10	セケラインコーポレイテッド	抗生物質ａ−５００３５９及び誘導体
JP2000072774A (ja) *	1998-08-25	2000-03-07	Sankyo Co Ltd	ラクトン誘導体
JP4531167B2 (ja)	1998-09-24	2010-08-25	セケラインコーポレイテッド	新規抗細菌化合物
JP4960548B2 (ja) *	2000-01-07	2012-06-27	セケラインコーポレイテッド	新規抗細菌化合物の用途
JP5022539B2 (ja)	2000-01-07	2012-09-12	セケラインコーポレイテッド	抗生物質ａ−５００３５９及び誘導体を含有する抗菌剤

2000
- 2000-08-17 TW TW089116650A patent/TWI245047B/zh not_active IP Right Cessation
- 2000-08-18 AU AU65955/00A patent/AU763492B2/en not_active Ceased
- 2000-08-18 PL PL00353494A patent/PL353494A1/xx not_active IP Right Cessation
- 2000-08-18 CN CNB008146535A patent/CN1176936C/zh not_active Expired - Fee Related
- 2000-08-18 BR BR0013435-0A patent/BR0013435A/pt not_active Application Discontinuation
- 2000-08-18 DE DE2000609517 patent/DE60009517T2/de not_active Expired - Lifetime
- 2000-08-18 WO PCT/JP2000/005538 patent/WO2001014399A1/ja not_active Ceased
- 2000-08-18 AT AT00953494T patent/ATE263183T1/de active
- 2000-08-18 IL IL14819600A patent/IL148196A0/xx active IP Right Grant
- 2000-08-18 KR KR1020027002090A patent/KR100787849B1/ko not_active Expired - Fee Related
- 2000-08-18 ES ES00953494T patent/ES2216933T3/es not_active Expired - Lifetime
- 2000-08-18 RU RU2002104359/04A patent/RU2227799C2/ru not_active IP Right Cessation
- 2000-08-18 NZ NZ517315A patent/NZ517315A/xx not_active IP Right Cessation
- 2000-08-18 HU HU0204217A patent/HUP0204217A3/hu unknown
- 2000-08-18 PT PT00953494T patent/PT1209166E/pt unknown
- 2000-08-18 TR TR2002/00485T patent/TR200200485T2/xx unknown
- 2000-08-18 MX MXPA02001817A patent/MXPA02001817A/es active IP Right Grant
- 2000-08-18 CA CA002382654A patent/CA2382654C/en not_active Expired - Fee Related
- 2000-08-18 CZ CZ2002682A patent/CZ2002682A3/cs unknown
- 2000-08-18 DK DK00953494T patent/DK1209166T3/da active
- 2000-08-18 EP EP00953494A patent/EP1209166B1/de not_active Expired - Lifetime
2002
- 2002-02-17 IL IL148196A patent/IL148196A/en not_active IP Right Cessation
- 2002-02-19 NO NO20020804A patent/NO323556B1/no not_active IP Right Cessation
- 2002-02-19 ZA ZA200201409A patent/ZA200201409B/en unknown
- 2002-02-19 US US10/080,191 patent/US7157442B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US7157442B2 (en)	2007-01-02
WO2001014399A1 (fr)	2001-03-01
ES2216933T3 (es)	2004-11-01
CZ2002682A3 (cs)	2002-06-12
MXPA02001817A (es)	2002-08-12
EP1209166A4 (de)	2002-10-09
CA2382654A1 (en)	2001-03-01
NO20020804D0 (no)	2002-02-19
TR200200485T2 (tr)	2002-06-21
PT1209166E (pt)	2004-06-30
KR20020092901A (ko)	2002-12-12
EP1209166A1 (de)	2002-05-29
BR0013435A (pt)	2002-07-16
DK1209166T3 (da)	2004-07-26
DE60009517D1 (de)	2004-05-06
DE60009517T2 (de)	2005-01-13
RU2227799C2 (ru)	2004-04-27
IL148196A0 (en)	2002-09-12
IL148196A (en)	2008-06-05
ATE263183T1 (de)	2004-04-15
KR100787849B1 (ko)	2007-12-27
CN1176936C (zh)	2004-11-24
NO20020804L (no)	2002-04-19
HK1044951A1 (en)	2002-11-08
CN1382152A (zh)	2002-11-27
AU763492B2 (en)	2003-07-24
EP1209166B1 (de)	2004-03-31
US20030171330A1 (en)	2003-09-11
HUP0204217A2 (en)	2003-03-28
PL353494A1 (en)	2003-11-17
AU6595500A (en)	2001-03-19
NO323556B1 (no)	2007-06-11
HUP0204217A3 (en)	2005-11-28
TWI245047B (en)	2005-12-11
NZ517315A (en)	2004-02-27
CA2382654C (en)	2009-01-13

Publication	Publication Date	Title
ZA200201409B (en)	2003-07-30	Novel A-500359 derivatives.
JP3808095B2 (ja)	2006-08-09	四環式誘導体、製造方法および用途
FI88163C (fi)	1993-04-13	Foerfarande foer framstaellning av farmaceutiskt anvaendbara pyrazolo/3,4-d/pyrimidiner
ZA200207956B (en)	2003-07-16	8-quinolinxanthine and 8-isoquinolinxanthine derivatives as PDE 5 inhibitors.
EP1660475B1 (de)	2008-05-28	Pyrimidylpyrrolderivate, die als kinaseinhibitoren wirken
KR20090101278A (ko)	2009-09-24	누클레오시다제 및 포스포릴라제 억제제의 아제티딘 유사체
PE20081377A1 (es)	2008-09-18	Compuestos de tiazol pirazolopirimidina
NO20082338L (no)	2008-06-25	Pyrimidinderivater for behandling av avvikende cellevekst
RU2005116239A (ru)	2006-01-27	Замещенный 4-амино-1-(пиридилметил)пиперидин в качестве антагонистов мускариновых рецепторов
CA2412164A1 (en)	2001-12-27	Amidine derivatives as selective antagonists of nmda receptors
CN102816165A (zh)	2012-12-12	氨基-氮杂-金刚烷衍生物和使用方法
US20050043323A1 (en)	2005-02-24	Pyrimidylpyrrole derivatives active as kinase inhibitors
ZA200100200B (en)	2002-06-26	Novel antibacterial compounds
JP4162840B2 (ja)	2008-10-08	新規ａ−５００３５９誘導体
JP4658438B2 (ja)	2011-03-23	新規ａ−５００３５９誘導体を含有する抗菌剤
AU2019235042B2 (en)	2021-03-04	Substituted pyridopyrrolopyrimidine ribonucleosides for therapeutic uses
CA2287465A1 (en)	1998-10-22	6,7-disubstituted-4-aminopyrido[2,3-d]pyrimidine compounds
NZ584037A (en)	2012-08-31	Formulation containing cyclin-dependent kinase inhibiting compound and method of treating tumors using the same
NZ337125A (en)	2001-06-29	5,6,7-trisubstituted-4-amino-pyrido[2,3-d]pyrimidine compounds useful for inhibiting adenosine kinase
HK1044951B (en)	2004-08-13	Novel a-500359 derivatives
RU2415852C2 (ru)	2011-04-10	Производные пиразолиламинопиридина, пригодные в качестве ингибиторов киназы
TH82131A (th)	2007-01-04	ไธอีโน [2,3-ดี] พัยริมิดีนที่มีฤทธิ์แอโกนิสท์ของ lh และ fsh รวมกัน
BR0014668A (pt)	2002-06-18	Derivados de piperidina como inibidores de reabsorção de serotonina
CZ350899A3 (cs)	2000-04-12	5,6,7-trisubstituované-4-aminopyrido-[2,3- D]pyrimidinové sloučeniny