ZA200206576B - Cell division inhibitors and process for producing the same. - Google Patents
Cell division inhibitors and process for producing the same. Download PDFInfo
- Publication number
- ZA200206576B ZA200206576B ZA200206576A ZA200206576A ZA200206576B ZA 200206576 B ZA200206576 B ZA 200206576B ZA 200206576 A ZA200206576 A ZA 200206576A ZA 200206576 A ZA200206576 A ZA 200206576A ZA 200206576 B ZA200206576 B ZA 200206576B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbon
- substituted
- alkyl
- alkenyl
- alkoxy
- Prior art date
Links
- 230000032823 cell division Effects 0.000 title claims description 41
- 239000003112 inhibitor Substances 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 26
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- 101710088194 Dehydrogenase Proteins 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 239000002246 antineoplastic agent Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 102000004190 Enzymes Human genes 0.000 claims description 12
- 108090000790 Enzymes Proteins 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 8
- 241000972623 Streptomyces albulus Species 0.000 claims description 7
- 238000001727 in vivo Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 description 17
- GWMHBVLPNWHWGW-CNYBTUBUSA-N (3s,6z)-3-benzyl-6-[[5-(2-methylbut-3-en-2-yl)-1h-imidazol-4-yl]methylidene]piperazine-2,5-dione Chemical compound N1C=NC(\C=C/2C(N[C@@H](CC=3C=CC=CC=3)C(=O)N\2)=O)=C1C(C)(C=C)C GWMHBVLPNWHWGW-CNYBTUBUSA-N 0.000 description 16
- -1 5-methylhexyl Chemical group 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 108010054981 dehydrophenylahistin Proteins 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 9
- 230000000259 anti-tumor effect Effects 0.000 description 8
- 230000022131 cell cycle Effects 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 108010016626 Dipeptides Proteins 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- RXGJTUSBYWCRBK-UHFFFAOYSA-M 5-methylphenazinium methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=NC2=C1 RXGJTUSBYWCRBK-UHFFFAOYSA-M 0.000 description 4
- 241000186361 Actinobacteria <class> Species 0.000 description 4
- FBWADIKARMIWNM-UHFFFAOYSA-N N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1N=C1C=CC(=O)C=C1 FBWADIKARMIWNM-UHFFFAOYSA-N 0.000 description 4
- LCIIOYPBHIZBOD-JMVBYTIWSA-N albonoursin Chemical compound N1C(=O)C(=C/C(C)C)/NC(=O)\C1=C\C1=CC=CC=C1 LCIIOYPBHIZBOD-JMVBYTIWSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- LCIIOYPBHIZBOD-UHFFFAOYSA-N albonoursin Natural products N1C(=O)C(=CC(C)C)NC(=O)C1=CC1=CC=CC=C1 LCIIOYPBHIZBOD-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- FVTCRASFADXXNN-UHFFFAOYSA-N flavin mononucleotide Natural products OP(=O)(O)OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-UHFFFAOYSA-N 0.000 description 3
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 3
- 229940013640 flavin mononucleotide Drugs 0.000 description 3
- 239000011768 flavin mononucleotide Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000030103 pronuclear fusion Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- MMXZSJMASHPLLR-UHFFFAOYSA-N pyrroloquinoline quinone Chemical compound C12=C(C(O)=O)C=C(C(O)=O)N=C2C(=O)C(=O)C2=C1NC(C(=O)O)=C2 MMXZSJMASHPLLR-UHFFFAOYSA-N 0.000 description 3
- 235000019231 riboflavin-5'-phosphate Nutrition 0.000 description 3
- GWMHBVLPNWHWGW-DFSFMLJYSA-N (3r,6z)-3-benzyl-6-[[5-(2-methylbut-3-en-2-yl)-1h-imidazol-4-yl]methylidene]piperazine-2,5-dione Chemical compound N1C=NC(\C=C/2C(N[C@H](CC=3C=CC=CC=3)C(=O)N\2)=O)=C1C(C)(C=C)C GWMHBVLPNWHWGW-DFSFMLJYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- CJVYYDCBKKKIPD-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N(C)C CJVYYDCBKKKIPD-UHFFFAOYSA-N 0.000 description 2
- MNIQECRMTVGZBM-UHFFFAOYSA-N 3-(1-methylpyrrolidin-2-yl)pyridine;7h-purin-6-amine Chemical compound NC1=NC=NC2=C1NC=N2.CN1CCCC1C1=CC=CN=C1 MNIQECRMTVGZBM-UHFFFAOYSA-N 0.000 description 2
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 2
- 241000122818 Aspergillus ustus Species 0.000 description 2
- 102000018832 Cytochromes Human genes 0.000 description 2
- 108010052832 Cytochromes Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000257465 Echinoidea Species 0.000 description 2
- XLRHXNIVIZZOON-WFUPGROFSA-L Flavin adenine dinucleotide disodium Chemical compound [Na+].[Na+].C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1COP([O-])(=O)OP([O-])(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 XLRHXNIVIZZOON-WFUPGROFSA-L 0.000 description 2
- VWWQXMAJTJZDQX-UHFFFAOYSA-N Flavine adenine dinucleotide Natural products C1=NC2=C(N)N=CN=C2N1C(C(O)C1O)OC1COP(O)(=O)OP(O)(=O)OCC(O)C(O)C(O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- 102000004243 Tubulin Human genes 0.000 description 2
- 108090000704 Tubulin Proteins 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000001641 gel filtration chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000001161 mammalian embryo Anatomy 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 241001446247 uncultured actinomycete Species 0.000 description 2
- HLXXMJDWTBXTOR-STQMWFEESA-N (3s,6s)-3-benzyl-6-(1h-imidazol-5-ylmethyl)piperazine-2,5-dione Chemical group C([C@@H]1NC([C@@H](NC1=O)CC=1NC=NC=1)=O)C1=CC=CC=C1 HLXXMJDWTBXTOR-STQMWFEESA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- OVRMIHWMEMVKJA-UHFFFAOYSA-N 3-benzylidene-6-(1h-imidazol-5-ylmethylidene)piperazine-2,5-dione Chemical compound O=C1NC(=CC=2N=CNC=2)C(=O)NC1=CC1=CC=CC=C1 OVRMIHWMEMVKJA-UHFFFAOYSA-N 0.000 description 1
- ATLALIOIRJKBST-UHFFFAOYSA-N 3-benzylidene-6-[(5-butyl-1h-imidazol-4-yl)methylidene]piperazine-2,5-dione Chemical compound N1C=NC(C=C2C(NC(=CC=3C=CC=CC=3)C(=O)N2)=O)=C1CCCC ATLALIOIRJKBST-UHFFFAOYSA-N 0.000 description 1
- BASBUEKYPASYGU-UHFFFAOYSA-N 3-benzylidene-6-[(5-ethyl-1h-imidazol-4-yl)methylidene]piperazine-2,5-dione Chemical compound N1C=NC(C=C2C(NC(=CC=3C=CC=CC=3)C(=O)N2)=O)=C1CC BASBUEKYPASYGU-UHFFFAOYSA-N 0.000 description 1
- DGYUPUJNJNIPTA-UHFFFAOYSA-N 3-benzylidene-6-[(5-methyl-1h-imidazol-4-yl)methylidene]piperazine-2,5-dione Chemical compound N1C=NC(C=C2C(NC(=CC=3C=CC=CC=3)C(=O)N2)=O)=C1C DGYUPUJNJNIPTA-UHFFFAOYSA-N 0.000 description 1
- JJDZJEFHAQKYGU-UHFFFAOYSA-N 3-benzylidene-6-[(5-pentyl-1h-imidazol-4-yl)methylidene]piperazine-2,5-dione Chemical compound N1C=NC(C=C2C(NC(=CC=3C=CC=CC=3)C(=O)N2)=O)=C1CCCCC JJDZJEFHAQKYGU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229940123587 Cell cycle inhibitor Drugs 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000008574 D-amino acids Chemical class 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- GKZIWHRNKRBEOH-HOTGVXAUSA-N Phe-Phe Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)C1=CC=CC=C1 GKZIWHRNKRBEOH-HOTGVXAUSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 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 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
- 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
- 210000004292 cytoskeleton Anatomy 0.000 description 1
- 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 1
- 230000007547 defect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004503 fine granule Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 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 1
- 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 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 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 1
- 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 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 108010073025 phenylalanylphenylalanine Proteins 0.000 description 1
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000009370 | 2000-01-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200206576B true ZA200206576B (en) | 2003-05-12 |
Family
ID=18537534
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200206576A ZA200206576B (en) | 2000-01-18 | 2002-08-16 | Cell division inhibitors and process for producing the same. |
Country Status (12)
Country | Link |
---|---|
US (2) | US6972289B1 (ja) |
EP (1) | EP1264831A4 (ja) |
JP (1) | JP4810043B2 (ja) |
KR (1) | KR100831400B1 (ja) |
AU (2) | AU782917C (ja) |
BR (2) | BR0017067A (ja) |
CA (1) | CA2403790C (ja) |
IL (2) | IL150430A0 (ja) |
MX (1) | MXPA02006826A (ja) |
NZ (1) | NZ519989A (ja) |
WO (1) | WO2001053290A1 (ja) |
ZA (1) | ZA200206576B (ja) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2205323T3 (es) | 1997-06-09 | 2004-05-01 | Hitachi, Ltd. | Procedimiento de docdificacion de secuencias de imagenes. |
US7026322B2 (en) | 1998-11-12 | 2006-04-11 | Nereus Pharmaceuticals, Inc. | Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds |
IL150430A0 (en) * | 2000-01-18 | 2002-12-01 | Nereus Pharmaceuticals Inc | Cell division inhibitors and process for producing the same |
EP1529044B1 (en) * | 2002-08-02 | 2007-10-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
US7919497B2 (en) * | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
CN101633655B (zh) * | 2002-08-02 | 2014-04-30 | 大连万春药业有限公司 | 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成 |
US7935704B2 (en) | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
RU2005119172A (ru) * | 2002-12-18 | 2006-01-20 | Пфайзер Продактс Инк. (Us) | Производные 4-анилинхиназолина для лечения патологического роста клеток |
GR1004602B (el) * | 2003-07-03 | 2004-06-18 | Μεθοδοι παρασκευης παραγωγων δεϋδρο-δικετοπιπεραζινων | |
CN1934101B (zh) * | 2004-02-04 | 2011-10-12 | 尼瑞斯药品公司 | 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成 |
KR101228104B1 (ko) * | 2004-02-04 | 2013-02-01 | 니리어스 파마슈티컬즈, 인코퍼레이션 | 데하이드로페닐아히스틴 및 그의 동족체, 및 이들의합성방법 |
WO2006105051A2 (en) * | 2005-03-29 | 2006-10-05 | Nereus Pharmaceuticals, Inc. | Synthesis of diketopiperazines |
AR058408A1 (es) * | 2006-01-02 | 2008-01-30 | Basf Ag | Compuestos de piperazina con accion herbicida |
JP5015174B2 (ja) * | 2006-01-05 | 2012-08-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草作用を有するピペラジン化合物 |
US8129527B2 (en) | 2006-11-03 | 2012-03-06 | Nereus Pharmacuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
DE502008000206D1 (de) * | 2007-06-12 | 2009-12-31 | Basf Se | Piperazinverbindungen mit herbizider wirkung |
JP2010529169A (ja) * | 2007-06-12 | 2010-08-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草作用を有するピペラジン化合物 |
KR20100018066A (ko) * | 2007-06-12 | 2010-02-16 | 바스프 에스이 | 제초적 활성 조성물 |
WO2010012649A1 (de) * | 2008-07-29 | 2010-02-04 | Basf Se | Piperazinverbindungen mit herbizider wirkung |
BRPI0916949A2 (pt) | 2008-08-13 | 2015-08-18 | Basf Se | Processo para a preparação de derivados de piperazinadiona, e, uso dos compostos. |
CN102171203A (zh) * | 2008-10-02 | 2011-08-31 | 巴斯夫欧洲公司 | 具有除草作用的哌嗪化合物 |
EP3265091A4 (en) | 2015-03-06 | 2018-08-01 | Beyondspring Pharmaceuticals Inc. | Method of treating a brain tumor |
JP6769982B2 (ja) | 2015-03-06 | 2020-10-14 | ビヨンドスプリング ファーマシューティカルズ,インコーポレイテッド | Ras変異と関連するがんの治療方法 |
SG10202108194XA (en) | 2015-07-13 | 2021-09-29 | Beyondspring Pharmaceuticals Inc | Plinabulin compositions |
MX2018009413A (es) | 2016-02-08 | 2019-05-15 | Beyondspring Pharmaceuticals Inc | Composiciones que contienen tucaresol o sus analogos. |
KR20230018545A (ko) | 2016-06-06 | 2023-02-07 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 호중구감소증을 줄이는 조성물 및 방법 |
US10851086B2 (en) | 2016-08-12 | 2020-12-01 | Marine Biomedical Research Institute Of Qingdao Co., Ltd. | Polycrystalline form of dehydrophenylahistin-like compound, and manufacturing and purification method and application thereof |
CN106565686B (zh) * | 2016-10-11 | 2019-03-01 | 深圳海王医药科技研究院有限公司 | 微管蛋白抑制剂 |
US11633393B2 (en) | 2017-01-06 | 2023-04-25 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
SG11201907023UA (en) | 2017-02-01 | 2019-08-27 | Beyondspring Pharmaceuticals Inc | Method of reducing neutropenia |
WO2019147615A1 (en) | 2018-01-24 | 2019-08-01 | Beyondspring Pharmaceuticals, Inc. | Composition and method for reducing thrombocytopenia via the administration of plinabulin |
KR20220117501A (ko) | 2021-02-17 | 2022-08-24 | 주식회사 티제이 | 카드리더기 모듈의 슬림화장치 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0725858A (ja) * | 1993-07-13 | 1995-01-27 | Otsuka Pharmaceut Co Ltd | ピペラジン誘導体 |
GB9402809D0 (en) * | 1994-02-14 | 1994-04-06 | Xenova Ltd | Pharmaceutical compounds |
GB9402807D0 (en) * | 1994-02-14 | 1994-04-06 | Xenova Ltd | Pharmaceutical compounds |
GB9426224D0 (en) * | 1994-12-23 | 1995-02-22 | Xenova Ltd | Pharmaceutical compounds |
JP3131574B2 (ja) * | 1996-09-04 | 2001-02-05 | 新日本製鐵株式会社 | 新規抗腫瘍物質、該物質を製造するための微生物及び方法、並びに該物質を有効成分とする細胞周期阻害剤及び抗腫瘍剤 |
US6069146A (en) * | 1998-03-25 | 2000-05-30 | The Regents Of The University Of California | Halimide, a cytotoxic marine natural product, and derivatives thereof |
US6358957B1 (en) * | 1998-11-12 | 2002-03-19 | Nereus Pharmaceuticals, Inc. | Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds |
IL150430A0 (en) * | 2000-01-18 | 2002-12-01 | Nereus Pharmaceuticals Inc | Cell division inhibitors and process for producing the same |
EP1529044B1 (en) * | 2002-08-02 | 2007-10-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
US7919497B2 (en) * | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
-
2000
- 2000-09-29 IL IL15043000A patent/IL150430A0/xx active IP Right Grant
- 2000-09-29 AU AU74511/00A patent/AU782917C/en not_active Expired
- 2000-09-29 BR BR0017067-4A patent/BR0017067A/pt not_active IP Right Cessation
- 2000-09-29 EP EP00963011A patent/EP1264831A4/en not_active Withdrawn
- 2000-09-29 CA CA2403790A patent/CA2403790C/en not_active Expired - Lifetime
- 2000-09-29 WO PCT/JP2000/006807 patent/WO2001053290A1/ja active IP Right Grant
- 2000-09-29 BR BRPI0017067A patent/BRPI0017067B8/pt unknown
- 2000-09-29 JP JP2001553764A patent/JP4810043B2/ja not_active Expired - Lifetime
- 2000-09-29 US US10/181,786 patent/US6972289B1/en not_active Expired - Lifetime
- 2000-09-29 KR KR1020027009268A patent/KR100831400B1/ko active IP Right Grant
- 2000-09-29 NZ NZ519989A patent/NZ519989A/en not_active IP Right Cessation
- 2000-09-29 MX MXPA02006826A patent/MXPA02006826A/es active IP Right Grant
-
2002
- 2002-06-26 IL IL150430A patent/IL150430A/en unknown
- 2002-08-16 ZA ZA200206576A patent/ZA200206576B/en unknown
-
2005
- 2005-11-17 US US11/281,773 patent/US20060079534A1/en not_active Abandoned
- 2005-12-07 AU AU2005242133A patent/AU2005242133B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US20060079534A1 (en) | 2006-04-13 |
US6972289B1 (en) | 2005-12-06 |
CA2403790C (en) | 2011-09-27 |
AU7451100A (en) | 2001-07-31 |
KR20020082484A (ko) | 2002-10-31 |
BRPI0017067B8 (pt) | 2021-05-25 |
BRPI0017067B1 (pt) | 2019-08-27 |
AU782917B2 (en) | 2005-09-08 |
CA2403790A1 (en) | 2001-07-26 |
EP1264831A1 (en) | 2002-12-11 |
IL150430A (en) | 2011-03-31 |
KR100831400B1 (ko) | 2008-05-21 |
EP1264831A4 (en) | 2005-11-23 |
WO2001053290A1 (fr) | 2001-07-26 |
MXPA02006826A (es) | 2004-04-05 |
AU2005242133B2 (en) | 2009-09-03 |
BR0017067A (pt) | 2002-10-22 |
JP4810043B2 (ja) | 2011-11-09 |
AU782917C (en) | 2006-11-23 |
IL150430A0 (en) | 2002-12-01 |
AU2005242133A1 (en) | 2006-01-05 |
NZ519989A (en) | 2004-05-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200206576B (en) | Cell division inhibitors and process for producing the same. | |
KR100240143B1 (ko) | 뉴로펩티드 y 수용체 길항제를 포함하는 화장품 조성물 | |
CN103403000B (zh) | 固体形式的促旋酶抑制剂(r)‑1‑乙基‑3‑[6‑氟‑5‑[2‑(1‑羟基‑1‑甲基‑乙基)嘧啶‑5‑基]‑7‑(四氢呋喃‑2‑基)‑1氢‑苯并咪唑‑2‑基]脲 | |
CN101304743B (zh) | 刺激神经形成和抑制神经元变性的方法和组合物 | |
CA2086142A1 (en) | Prolyl endopeptidase inhibitor | |
US8344017B2 (en) | Anti-hepatitis C virus agents and anti-HIV agents | |
WO2000044335A2 (en) | Uridyl peptide antibiotic (upa) derivatives, their synthesis and use | |
CN111153948B (zh) | 动孢菌素类化合物及其用途 | |
JPH0586374B2 (ja) | ||
EP3301096A1 (en) | Bis-indole derivatives for use in the treatment of bacterial infections | |
US4576948A (en) | Composition and method for inhibiting terminal deoxyribonucleotidyl transferase activity | |
EP0369503B1 (en) | Method for the control of pneumocystis carinii | |
JPH01240196A (ja) | 新規グリコペプチド系抗生物質pa−45052 | |
US20040266873A1 (en) | 1-butane acid derivatives pharmaceutical compositions containing said derivatives and the use thereof | |
KR100327155B1 (ko) | 화합물 kr-15012를 함유하는 항암제 | |
JPH09295980A (ja) | 新規マクロライド系化合物0406 | |
Cain | Studies related to the biogenesis of bicyclomycin | |
JPS58500947A (ja) | 末端デオキシリボヌクレオチジルトランスフエラ−ゼ活性を抑制する組成物及び方法 | |
JPH0770098A (ja) | 生理活性ペプチド系化合物 | |
JP2001226355A (ja) | 新規な1−ヒドロキシキノリノン誘導体 | |
JPH07278055A (ja) | 抗菌性物質be−40665類 | |
IL109227A (en) | Lustrodoxin H, pharmaceutical preparations containing it and processes for its preparation | |
FR2550536A1 (fr) | Desacetyl-ravidomycine, son procede de production et son application en therapeutique |