ES2406107T3 - Compuestos antitumorales - Google Patents
Compuestos antitumorales Download PDFInfo
- Publication number
- ES2406107T3 ES2406107T3 ES08861840T ES08861840T ES2406107T3 ES 2406107 T3 ES2406107 T3 ES 2406107T3 ES 08861840 T ES08861840 T ES 08861840T ES 08861840 T ES08861840 T ES 08861840T ES 2406107 T3 ES2406107 T3 ES 2406107T3
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- alkyl
- hydrogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 85
- 230000000259 anti-tumor effect Effects 0.000 title description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 42
- 125000006239 protecting group Chemical group 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 11
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
- 238000011282 treatment Methods 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- -1 2-quinoxalinyl BE-22179 Chemical compound 0.000 description 172
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
- 239000011347 resin Substances 0.000 description 28
- 229920005989 resin Polymers 0.000 description 28
- 108090000765 processed proteins & peptides Proteins 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- WCHAVJJXSIQEMZ-DOZAELEDSA-N 3-hydroxy-n-[(1r,7r,11r,14s,20r,24r)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-3,6,10,13,16,19,23,26-octaoxo-28,29-dithia-2,5,9,12,15,18,22,25-octazabicyclo[12.12.3]nonacosan-20-yl]quinoline-2-carboxam Chemical compound O=C([C@@H]1SSC[C@H](N(C(=O)CNC2=O)C)C(=O)N(C)[C@H](C(NC[C@H](C(=O)NCC(=O)N1C)NC(=O)C=1C(=CC3=CC=CC=C3N=1)O)=O)CSC)N(C)[C@@H](CSC)C(=O)NC[C@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O WCHAVJJXSIQEMZ-DOZAELEDSA-N 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 12
- 108010070024 azathiocoraline Proteins 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 10
- 125000001118 alkylidene group Chemical group 0.000 description 10
- 229940125782 compound 2 Drugs 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 230000001472 cytotoxic effect Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000003643 water by type Substances 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 7
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 7
- 125000005493 quinolyl group Chemical group 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007821 HATU Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 5
- 238000001802 infusion Methods 0.000 description 5
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 5
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
- GULVULFEAVZHHC-UHFFFAOYSA-N Triostin-A Natural products CN1C(=O)C(C)NC(=O)C(NC(=O)C=2N=C3C=CC=CC3=NC=2)COC(=O)C(C(C)C)N(C)C(=O)C(N(C(=O)C(C)NC2=O)C)CSSCC1C(=O)N(C)C(C(C)C)C(=O)OCC2NC(=O)C1=CN=C(C=CC=C2)C2=N1 GULVULFEAVZHHC-UHFFFAOYSA-N 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- GULVULFEAVZHHC-SZZROTLHSA-N n-[(1s,4s,7r,11s,14s,17s,20r,24s)-2,4,12,15,17,25-hexamethyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@H]1CSSC[C@@H](N(C(=O)[C@H](C)NC2=O)C)C(=O)N(C)[C@H](C(OC[C@H](C(=O)N[C@@H](C)C(=O)N1C)NC(=O)C=1N=C3C=CC=CC3=NC=1)=O)C(C)C)N(C)[C@@H](C(C)C)C(=O)OC[C@H]2NC(=O)C1=CN=C(C=CC=C2)C2=N1 GULVULFEAVZHHC-SZZROTLHSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- UPGGKUQISSWRJJ-ZRBWWFCKSA-N 3-hydroxy-n-[(1r,7s,11s,14r,20s,24s)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-3,6,10,13,16,19,23,26-octaoxo-9,22,28,29-tetrathia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-20-yl]quinoline-2-carb Chemical compound O=C([C@@H]1CSSC[C@H](N(C(=O)CNC2=O)C)C(=O)N(C)[C@H](C(SC[C@H](C(=O)NCC(=O)N1C)NC(=O)C=1C(=CC3=CC=CC=C3N=1)O)=O)CSC)N(C)[C@@H](CSC)C(=O)SC[C@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O UPGGKUQISSWRJJ-ZRBWWFCKSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- JMFVWNKPLURQMI-UHFFFAOYSA-N cyclopentyl carbamate Chemical compound NC(=O)OC1CCCC1 JMFVWNKPLURQMI-UHFFFAOYSA-N 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000005956 isoquinolyl group Chemical group 0.000 description 3
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 3
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
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- 230000002441 reversible effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MVWPBNQGEGBGRF-LJQANCHMSA-N (2r)-3-(9h-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC=C2C(COC(=O)NC[C@@H](NC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 MVWPBNQGEGBGRF-LJQANCHMSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 2
- NDKDFTQNXLHCGO-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)acetic acid Chemical compound C1=CC=C2C(COC(=O)NCC(=O)O)C3=CC=CC=C3C2=C1 NDKDFTQNXLHCGO-UHFFFAOYSA-N 0.000 description 2
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- MIMWGQNUOCPPOL-XEQGPDGQSA-N 3-hydroxy-n-[(1r,7r,11r,14s,20r,24r)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-20-yl]quinoline-2-ca Chemical compound O=C([C@@H]1SSC[C@H](N(C(=O)CNC2=O)C)C(=O)N(C)[C@H](C(OC[C@H](C(=O)NCC(=O)N1C)NC(=O)C=1C(=CC3=CC=CC=C3N=1)O)=O)CSC)N(C)[C@@H](CSC)C(=O)OC[C@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O MIMWGQNUOCPPOL-XEQGPDGQSA-N 0.000 description 2
- QLOZXPNJEDVFIH-ZRTHHSRSSA-N 3-hydroxy-n-[(1r,7s,14r,20s)-7-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-dimethylidene-3,6,10,13,16,19,23,26-octaoxo-9,22,28,29-tetrathia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-20-yl]quinoline-2-carboxamide Chemical compound CN([C@H]1CSSC[C@@H](C(N(C)C(=C)C(=O)SC2)=O)N(C(CNC(=O)[C@H](NC(=O)C=3C(=CC4=CC=CC=C4N=3)O)CSC(=O)C(=C)N(C)C1=O)=O)C)C(=O)CNC(=O)[C@@H]2NC(=O)C1=NC2=CC=CC=C2C=C1O QLOZXPNJEDVFIH-ZRTHHSRSSA-N 0.000 description 2
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910014299 N-Si Inorganic materials 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- MUEWAZLLNCYKKG-UHFFFAOYSA-N trimethylsilyl N-(9H-fluoren-1-ylmethyl)carbamate Chemical compound C[Si](C)(C)OC(NCC1=CC=CC=2C3=CC=CC=C3CC1=2)=O MUEWAZLLNCYKKG-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- REHCLTYQNDLJHW-UHFFFAOYSA-N tritylsulfanyloxymethyl benzoate Chemical compound C(C1=CC=CC=C1)(=O)OCOSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 REHCLTYQNDLJHW-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07380361 | 2007-12-14 | ||
| EP07380361 | 2007-12-14 | ||
| PCT/EP2008/067189 WO2009077401A1 (en) | 2007-12-14 | 2008-12-10 | Antitumoral compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2406107T3 true ES2406107T3 (es) | 2013-06-05 |
Family
ID=40290734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08861840T Active ES2406107T3 (es) | 2007-12-14 | 2008-12-10 | Compuestos antitumorales |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8748388B2 (enExample) |
| EP (1) | EP2231695B1 (enExample) |
| JP (1) | JP5577256B2 (enExample) |
| CN (1) | CN101932592B (enExample) |
| AU (1) | AU2008337605B2 (enExample) |
| CA (1) | CA2708080C (enExample) |
| ES (1) | ES2406107T3 (enExample) |
| WO (1) | WO2009077401A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110027417A1 (en) | 2009-07-31 | 2011-02-03 | Patrick Joseph Corrigan | Process for Dusting Animal Food |
| US10370409B2 (en) * | 2011-10-25 | 2019-08-06 | The Scripps Research Institute | Synthesis of libraries of peptide tertiary amides |
| JOP20190254A1 (ar) | 2017-04-27 | 2019-10-27 | Pharma Mar Sa | مركبات مضادة للأورام |
| CN111777668B (zh) * | 2020-07-28 | 2022-02-25 | 安徽工程大学 | 一种基于海洋环肽Samoamide A的改造多肽、合成方法及应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5681813A (en) * | 1994-04-06 | 1997-10-28 | Pharma Mar, S.A. | Thiodepsipeptide isolated from a marine actinomycete |
| KR20030088423A (ko) * | 2000-12-21 | 2003-11-19 | 더 스크립스 리서치 인스티튜트 | 티오코르알린 및 ｂｅ-22179의 동족체 |
-
2008
- 2008-12-10 AU AU2008337605A patent/AU2008337605B2/en not_active Ceased
- 2008-12-10 JP JP2010537432A patent/JP5577256B2/ja not_active Expired - Fee Related
- 2008-12-10 ES ES08861840T patent/ES2406107T3/es active Active
- 2008-12-10 US US12/746,957 patent/US8748388B2/en not_active Expired - Fee Related
- 2008-12-10 CN CN200880126032.9A patent/CN101932592B/zh not_active Expired - Fee Related
- 2008-12-10 WO PCT/EP2008/067189 patent/WO2009077401A1/en not_active Ceased
- 2008-12-10 CA CA2708080A patent/CA2708080C/en not_active Expired - Fee Related
- 2008-12-10 EP EP08861840A patent/EP2231695B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101932592A (zh) | 2010-12-29 |
| JP2011506393A (ja) | 2011-03-03 |
| US8748388B2 (en) | 2014-06-10 |
| WO2009077401A1 (en) | 2009-06-25 |
| JP5577256B2 (ja) | 2014-08-20 |
| AU2008337605B2 (en) | 2013-08-29 |
| US20110207674A2 (en) | 2011-08-25 |
| CA2708080A1 (en) | 2009-06-25 |
| EP2231695B1 (en) | 2013-02-13 |
| HK1149022A1 (en) | 2011-09-23 |
| CA2708080C (en) | 2016-06-14 |
| AU2008337605A1 (en) | 2009-06-25 |
| CN101932592B (zh) | 2014-02-26 |
| EP2231695A1 (en) | 2010-09-29 |
| US20100292163A1 (en) | 2010-11-18 |
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