DK175507B1 - N-substituerede staurosporinderivater og salte deraf, fremgangsmåde til fremstilling deraf, farmaceutisk præparat med indhold deraf samt anvendelse af de N-substituerede staurosporinderivater til fremstilling af farmaceutiske præparater - Google Patents

Info

Publication number

DK175507B1

DK175507B1 DK198803248A DK324888A DK175507B1 DK 175507 B1 DK175507 B1 DK 175507B1 DK 198803248 A DK198803248 A DK 198803248A DK 324888 A DK324888 A DK 324888A DK 175507 B1 DK175507 B1 DK 175507B1

Authority

DK

Denmark

Prior art keywords

alkyl

formula

group

acid

staurosporine

Prior art date

1987-06-15

Links

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• Global Dossier
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• 150000003839 salts Chemical class 0.000 title claims abstract description 63
• HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical class C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 title claims abstract description 55
• 238000002360 preparation method Methods 0.000 title claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
• 238000000034 method Methods 0.000 title description 20
• 230000008569 process Effects 0.000 title description 9
• 239000000825 pharmaceutical preparation Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 75
• HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 claims abstract description 53
• 125000002252 acyl group Chemical group 0.000 claims abstract description 52
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 36
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
• -1 methylenedioxy Chemical group 0.000 claims description 114
• 125000000217 alkyl group Chemical group 0.000 claims description 79
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
• 239000002253 acid Substances 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 239000013543 active substance Substances 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
• 239000003153 chemical reaction reagent Substances 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• 125000002015 acyclic group Chemical group 0.000 claims description 12
• 125000005493 quinolyl group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 125000005907 alkyl ester group Chemical group 0.000 claims description 7
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 239000003638 chemical reducing agent Substances 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 3
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
• HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
• 229940125782 compound 2 Drugs 0.000 claims 1
• 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 1
• 102000003923 Protein Kinase C Human genes 0.000 abstract description 8
• 108090000315 Protein Kinase C Proteins 0.000 abstract description 8
• 230000010933 acylation Effects 0.000 abstract description 3
• 238000005917 acylation reaction Methods 0.000 abstract description 3
• 230000029936 alkylation Effects 0.000 abstract description 2
• 238000005804 alkylation reaction Methods 0.000 abstract description 2
• 229940124639 Selective inhibitor Drugs 0.000 abstract 1
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 107
• 239000000243 solution Substances 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• 239000011541 reaction mixture Substances 0.000 description 52
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 42
• 239000000203 mixture Substances 0.000 description 40
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
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• 239000003480 eluent Substances 0.000 description 24
• 239000012043 crude product Substances 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
• 235000019341 magnesium sulphate Nutrition 0.000 description 22
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• 239000000047 product Substances 0.000 description 20
• 235000017557 sodium bicarbonate Nutrition 0.000 description 19
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• 125000003277 amino group Chemical group 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• 229910052739 hydrogen Inorganic materials 0.000 description 16
• 239000001257 hydrogen Substances 0.000 description 16
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 14
• 125000000623 heterocyclic group Chemical group 0.000 description 14
• 229920002472 Starch Polymers 0.000 description 13
• 150000007513 acids Chemical class 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 12
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 229910052757 nitrogen Chemical group 0.000 description 12
• 125000002837 carbocyclic group Chemical group 0.000 description 11
• 229910052740 iodine Inorganic materials 0.000 description 11
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
• 150000001721 carbon Chemical group 0.000 description 10
• 229910052801 chlorine Inorganic materials 0.000 description 10
• 238000000354 decomposition reaction Methods 0.000 description 10
• FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 10
• CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• 239000001301 oxygen Substances 0.000 description 9
• 239000011593 sulfur Chemical group 0.000 description 9
• 239000000454 talc Substances 0.000 description 9
• 229910052623 talc Inorganic materials 0.000 description 9
• 235000012222 talc Nutrition 0.000 description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
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• 229940100445 wheat starch Drugs 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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• 239000002585 base Substances 0.000 description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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• 125000006239 protecting group Chemical group 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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