NO308996B1 - Kondenserte pyrrolokarbazoler og anvendelse derav - Google Patents

Info

Publication number

NO308996B1

NO308996B1 NO971677A NO971677A NO308996B1 NO 308996 B1 NO308996 B1 NO 308996B1 NO 971677 A NO971677 A NO 971677A NO 971677 A NO971677 A NO 971677A NO 308996 B1 NO308996 B1 NO 308996B1

Authority

NO

Norway

Prior art keywords

carbon atoms

compound

alkyl

mmol

solution

Prior art date

1994-10-14

Links

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• QNMMYUBZGLXCCK-UHFFFAOYSA-N pyrrolo[3,2-a]carbazole Chemical class N1=C2C=CC=CC2=C2C1=C1C=CN=C1C=C2 QNMMYUBZGLXCCK-UHFFFAOYSA-N 0.000 title claims description 124
• 150000001875 compounds Chemical class 0.000 claims description 200
• 210000004027 cell Anatomy 0.000 claims description 95
• 125000004432 carbon atom Chemical group C* 0.000 claims description 84
• 238000000034 method Methods 0.000 claims description 80
• 230000000694 effects Effects 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• -1 tetrahydroquinolyl Chemical group 0.000 claims description 47
• 210000002569 neuron Anatomy 0.000 claims description 40
• 230000005764 inhibitory process Effects 0.000 claims description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
• 230000001228 trophic effect Effects 0.000 claims description 31
• 230000004083 survival effect Effects 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000002947 alkylene group Chemical group 0.000 claims description 17
• 238000004519 manufacturing process Methods 0.000 claims description 17
• 102000003923 Protein Kinase C Human genes 0.000 claims description 16
• 108090000315 Protein Kinase C Proteins 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 230000008569 process Effects 0.000 claims description 15
• 210000002932 cholinergic neuron Anatomy 0.000 claims description 14
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 12
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 230000006698 induction Effects 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 210000001044 sensory neuron Anatomy 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 102000001253 Protein Kinase Human genes 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 108060006633 protein kinase Proteins 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• 108091000080 Phosphotransferase Proteins 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 230000002708 enhancing effect Effects 0.000 claims description 4
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 102000020233 phosphotransferase Human genes 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 208000014674 injury Diseases 0.000 claims description 3
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 2
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
• 230000032683 aging Effects 0.000 claims description 2
• 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 2
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 2
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000005545 phthalimidyl group Chemical group 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000005504 styryl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000004306 triazinyl group Chemical group 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
• RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
• 230000002829 reductive effect Effects 0.000 description 54
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 50
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 49
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
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• ZMWSBJQJLMMROW-UHFFFAOYSA-N 3-bromo-5h,6h,12h,13h-indeno[2,3-a]pyrrolo[3,4-c]carbazole-7(7h)-one Chemical compound N1C2=CC=CC=C2C2=C1C(CC1=CC=C(C=C11)Br)=C1C1=C2C(=O)NC1 ZMWSBJQJLMMROW-UHFFFAOYSA-N 0.000 description 20
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