SI9011223B - Indenoindolne spojine - Google Patents
Indenoindolne spojine Download PDFInfo
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- SI9011223B SI9011223B SI9011223A SI9011223A SI9011223B SI 9011223 B SI9011223 B SI 9011223B SI 9011223 A SI9011223 A SI 9011223A SI 9011223 A SI9011223 A SI 9011223A SI 9011223 B SI9011223 B SI 9011223B
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- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical class C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 24
- 239000001257 hydrogen Substances 0.000 claims abstract 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 52
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 28
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 10
- 238000007126 N-alkylation reaction Methods 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- -1 radiation Substances 0.000 claims 4
- 229910021653 sulphate ion Inorganic materials 0.000 claims 4
- 150000002475 indoles Chemical class 0.000 claims 3
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims 2
- BMGLVVNENOOPFC-UHFFFAOYSA-N 5,10-dihydroindeno[1,2-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C1=CC=CC=C1C2 BMGLVVNENOOPFC-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 230000000172 allergic effect Effects 0.000 claims 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940034982 antineoplastic agent Drugs 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical class C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 claims 2
- 230000004968 inflammatory condition Effects 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000037906 ischaemic injury Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 238000010525 oxidative degradation reaction Methods 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- JDTRVJYDVHSJKB-UHFFFAOYSA-N 5,6-dihydroindeno[2,1-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CC1=CC=CC=C12 JDTRVJYDVHSJKB-UHFFFAOYSA-N 0.000 claims 1
- 208000005189 Embolism Diseases 0.000 claims 1
- 206010014523 Embolism and thrombosis Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000020335 dealkylation Effects 0.000 claims 1
- 238000006900 dealkylation reaction Methods 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006263 metalation reaction Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
- 229940067157 phenylhydrazine Drugs 0.000 claims 1
- 150000004031 phenylhydrazines Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 235000014101 wine Nutrition 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 3
- 239000003963 antioxidant agent Substances 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61P25/00—Drugs for disorders of the nervous system
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- 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]
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- A61P39/06—Free radical scavengers or antioxidants
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Claims (2)
1 PATENTNI ZAHTEVKI 1. Spojina s formulo IA ali IB
IB v kateri je R vodik, Cj-C24 alkilna skupina ali COR15, so R1, R2, R11 in R12 neodvisno izbrani izmed vodika ali Cj-C6 alkilne skupine, so R3, R1, R2 in R6 neodvisno izbrani izmed vodika, hidroksi, halogena, Cj-C6 alkilne skupine ali C^-C^ alkoksi skupine, mono- ali di-(C1-C6 alkiljamino skupine, NH2 ali NR13COR14, so R7, R8, R9 in R10 neodvisno izbrani izmed vodika, hidroksi, Cj-C6 alkilne skupine, Cj-Cg alkoksi skupine, mono- ali di-(Cj-C6 alkiljamino skupine, NH2 ali NR13COR14, so R13, R14 in R15 neodvisno izbrani izmed vodika ali Cj-C^ alkilne skupine, pod pogojema, da: i. kadar je v formuli IA R metil, potem vsaj eden od radikalov R1 do R12 ni vodik, ii. kadar je v formuli IA R vodik ali acetil in je R11 etil, potem vsaj eden od radikalov R1 do R10 ali R12 ni vodik; in njeni enantiomeri in njene soli.
2. Spojina po zahtevku 1, označena s tem, daje vsaj eden od R3, R2, R7, R9, R11 in R12 Cj-C^ alkilna skupina, prednostno metil, etil ali i-propil.
3. Spojina po zahtevku 1 ali 2, označena s tem, da je vsaj eden od R2 in R8 mono-ali di-(C1-C6 alkiljamino skupina, prednostno etil- ali dietilamino. 1 Spojina po zahtevku 1 ali 2, označena s tem, da je vsaj eden od R2 in R8 hidroksi 2 ali Cj-C6 alkoksi skupina, prednostno metoksi. 2
5. Spojina po kateremkoli od predhodnih zahtevkov, označena s tem, da so R, R1, R2, R4, R6 in R10 vodik.
6. Spojina po zahtevku 1, označena s tem, da je cis-4b,5,9b,10-tetrahidroindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-6,8-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-5,8-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-4b,6,8,9b-tetrametilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-izopropilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-metoksi-5-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-metoksiindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-10,10-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-9b-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-4b,9b-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-4b,5,9b-trimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-2-metoksi-l,3-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-2-metoksi-l,3-dimetil-8-izopropilindeno[l,2-b]indol cis-4b,5,9b, 10-tetrahidro-4b-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-2-hidroksi-l,3-dimetil-8-izopropilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-2-hidroksi-l,3-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-4b,8,9b-trimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-izopropil-4b,9b-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-izopropil-4b-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-2,8-dimetoksi-l,3-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-4b,5,8,9b-tetrametilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-terc.butilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-metoksi-7,9-dimetilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-metoksi-6-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-dietilamino-5-etilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-2-dietilaminoindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-terc.butil-4b-metilindeno[l,2-b]indol cis-4b,5,9b,10-tetrahidro-8-fluoroindeno[l,2,-b]indol cis-5,5a,6,10b-tetrahidroindeno[2,l-b]indol eis-5,5a,6,10b-tetrahidro-9-metoksiindeno[2,l-b]indol ali cis-5,5a,6,10b-tetrahidro-9-izopropilindeno[2,l-b]indol. 3
7. Spojina po zahtevku 1, označena s tem, daje cis-5,5a,6,10b-tetrahidro-9-metoksi-7-metilindeno[2,l,-b]indol cis-4b,5,9b,10-tetrahidro-4,6-dimetil-8-metoksiindeno[l,2-b]indol ali cis-4b,5,9b,10-tetrahidro-8-metoksi-4b,6,9b-trimetilindeno[l,2-b]indol. 8. cis-5,5a,6,10b-Tetrahidro-9-metoksi-7-metilindeno[2,l -bjindol, njegovi enantiomeri in njegove soli.
9. Spojina s formulo LA ali IB
v kateri je R vodik, Cj-C^ alkilna skupina ali COR15, so R1, R2, R11 in R12 neodvisno izbrani izmed vodika ali Cj-Cg alkilne skupine, so R3, R4, R5 in R6 neodvisno izbrani izmed vodika, hidroksi, halogena, Cj-C^ alkilne skupine, C -C6 alkoksi skupine, mono- ali di-(C -C6 alkiljamino skupine, NH2 ali NR13COR14, so R7, R8, R9 in R10 neodvisno izbrani izmed vodika, hidroksi, Cj-C6 alkilne skupine, C^Cg alkoksi skupine ali mono- ali di-(C1-C6 alkiljamino skupine, NH2 ali NR13COR14, so R13, R14 in R15 neodvisno izbrani izmed vodika ali Cj-C6 alkilne skupine, pod pogojem, da kadar je R COR13, potem je vsaj eden od R3 do R10 hidroksi ali mono- ali di-(Cj-C6 alkiljamino skupina, njeni enantiomeri in njene farmacevtsko sprejemljive soli za uporabo v postopku zdravljenja, ki se izvaja na človeškem ali živalskem telesu.
10. Spojina po zahtevku 9 za uporabo v zdravljenju ishemskih ali reperfuzijskih poškodb, tromboze in embolije. 4
11. Spojina po zahtevku 9 za uporabo v zdravljenju ali preprečevanju neoplazem.
12. Spojina po zahtevku 9 za uporabo v zdravljenju Parkinsonove bolezni, Alzheimerjeve bolezni ali staranja.
13. Spojina po zahtevku 9 za uporabo v zdravljenju ateroskleroze.
14. Spojina po zahtevku 9 za uporabo v zdravljenju alergijskih/vnetnih stanj, kot je bronhialna astma in revmatoidni artritis.
15. Spojina po zahtevku 9 za uporabo v zdravljenju poškodb povzročenih s kemikalijami, sevanjem, antineoplastičnimi ali imunosupresivnimi sredstvi.
16. Spojina po kateremkoli od zahtevkov 9 -15, označena s tem, daje formula LA ali IB kot je definirana v kateremkoli od zahtevkov 1 -8.
17. Farmacevtski sestavek, označen s tem, da obsega aktivno sestavino, ki je spojina, kot je definirana v kateremkoli od zahtevkov 1-6, njen enaniomer ali njena farmacevtsko sprejemljiva sol, skupaj s farmacevtsko sprejemljivim nosilcem.
18. Uporaba spojine s formulo IA ali IB, kot je definirana v kateremkoli od zahtevkov 1 do 8, v izdelavi zdravila za zdravljenje ishemskih ali reperfuzijskih poškodb, tromboze, embolije, ateroskleroze, Parkinsonove bolezni, Alzheimerjeve bolezni, staranja, neoplazem, alergijskih ali vnetnih stanj, kot je bronhialna astma in revmatoidni artritis in poškodb, povzročenih s kemikalijami, sevanjem, antineoplastičnimi ali imunosupresivnimi sredstvi.
19. Postopek za pripravo spojine s formulo IA ali IB, kot je definirana v kateremkoli od zahtevkov 1 do 8, označen s tem, da obsega: a. redukcijo 5,10-dihidroindeno[l,2-b]indola (DHII):
XI 5 kjer so R, R1, R2, R3, R4, Rs, R6, R7, R8, R9 in R10 kot je definirano v formuli IA, pri čemer, po potrebi, pred redukcijo izvedemo N-alkiliranje izo-DHII, ali kateri sledi N-alkiliranje izo-THII z R-halogenidom ali R-sulfatom, kjer je R kot je definirano v formuli I; b. Fischerjevo indolizacijo fenilhidrazina s formulo II in 2-substituiranega 1-indanona s formulo III, kateri sledi redukcija indoleninov (IV)
kjer so R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 in Ru kot je definirano v formuli IA in kateri, po potrebi, sledi N-alkiliranje z R-halogenidom ali R-sulfatom, kjer je R kot je definirano v formuli IA; 6
kjer so R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, Ru in R12 kot je definirano v formuli IA in kateri, po potrebi, sledi N-alkiliranje z R-halogenidom ali R-sulfatom, kjer je R kot je definirano v formuli IA; d. redukcijo 5,6-dihidroindeno[2,l-b]indola (izo-DHII), pri čemer, po potrebi, pred redukcijo izvedemo N-alkiliranje izo-DHII, ali kateri sledi N-alkiliranje izo-THII z R-halogenidom ali R-sulfatom, kjer je R kot je definirano v formuli I; e. za 10b-substituirane-5,5a,6,10b-tetrahidroindeno[2,l-b]indole (IX) in analoge, uporabo indan-2-onov (XII), ki imajo substituentno skupino na C-3, po Fischerjevi indolizaciji s fenilhidrazini s formulo (II), čemur sledi reakcija intermediata VIII z reducirnim sredstvom;
IX vin kjer so R1, R2, R3, R4, R5, R6, R7, R8, R9, RU) in R11 kot je definirano pod formulo IB ali čemur, po potrebi, sledi N-alkiliranje z R-halogenidom ali R-sulfatom, kjer je R kot je definirano za formulo IB; f. za 5a,10b-substituirane-5,5a,6,10b-tetrahidroindeno[2,l-b]indole in analoge reakcijo indoleninov s formulo VIII z litijevimi alkili R12Li
kjer so R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 in R12 kot je definirano pod formulo IB, ali kateri, po potrebi, sledi N-alkiliranje z R-halogenidom ali R-sulfatom, kjer je R kot je definirano v formuli IB; g. za 5-alkil-THII ali 6-alkil-izo-THII, kjer so R, R1, R2, R3, R4, R5, R6, R7, R8, R9 in R10 kot je definirano v formuli I, N-alkiliranje ustreznega THII ali izo-THII z R-halogenidom ali R-sulfatom; h. za 5-alkil-THII ali 6-alkil-izo-THII, kjer so R, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 kot je definirano v formuli I, redukcijo ustreznega 5-acil-THII ali 6-acil-izo-THII; i. za THII ali izo-THII, kjer so R3 - R6 in/ali R7 - R10 definirani kot mono- ali di-(Cj-C6 alkiljamino skupina in so R, R1, R2, R11 in R12 definirani kot v formuli I, redukcijo ustreznih 5-acil-THII ali 6-acil-izo-THII nitro komponent, kateri sledi N-alkiliranje in, po izbiri, kisla hidroliza; j. za THII ali izo-THII, kjer so R3 - R6 in/ali R7 - R10 definirani kot hidroksi in so R, R1, R2, R11 in R12 kot je definirano v formuli I, etersko dealkiliranje ustreznih alkoksi substituiranih THII ali izo-THII spojin; 8 k. za THII ali izo-THII, kjer je R12 nižja alkilna skupina in so R, R1 - R11 kot je definirano v formuli (I), sekvenco metalacije ustreznega 4b-nesubstituiranega analoga, kateri sledi alkiliranje z R12-halogenidom ali R12-sulfatom in končna hidroliza.
20. Sestavek, označen s tem, za obsega spojino, ki je občutljiva za oksidativno razgradnjo in spojino s formulo LA. ali IB
IB R R v kateri je R vodik, Cj-C24 alkilna skupina ali COR15, so R1, R2, R11 in R12 neodvisno izbrani izmed vodika ali Cj-C6 alkilne skupine, so R3, R4, R5 in R6 neodvisno izbrani izmed vodika, hidroksi, halogena, Cj-C6-alkilne skupine, Cj-C6 alkoksi skupine, mono- ali di-(Cj-C6 alkiljamino skupine, NH2 ali NR13COR14, so R7, R8, R9 in R10 neodvisno izbrani izmed vodika, hidroksi, Cj-C6 alkilne skupine, C -C6 alkoksi skupine ali mono- ali di-(Cj-C6 alkiljamino skupine, NH2 ali NRl3COR14, so R13, R14 in R15 neodvisno izbrani izmed vodika ali C -C6 alkilne skupine, pod pogojem, da kadar je R COR15, potem je vsaj eden od R3 do R10 hidroksi ali mono- ali di-(Cj-C6 alkiljamino skupina, ali njene enantiomere in njene soli.
21. Sestavek po zahtevku 17, označen s tem, da je spojina s formulo IA ali IB kot je definirana v kateremkoli od zahtevkov 1-8.
22. Postopek stabilizacije spojine, ki je občutljiva za oksidativno razgradnjo, označen s tem, da občutljivo spojino vzpostavimo v stik s spojino s formulo IA ali IB, kot je definirana v zahtevku 20 ali 21. Za: 1. UNIVERSITY OF ΒΑΤΗ
2. L dNCINNATI
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8902274A SE8902274D0 (sv) | 1989-06-22 | 1989-06-22 | Indenoidole compounds ii |
| YU122390A YU122390A (sh) | 1989-06-22 | 1990-06-22 | Indenoindolova jedinjenja ii |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9011223A SI9011223A (en) | 1997-10-31 |
| SI9011223B true SI9011223B (sl) | 1998-08-31 |
Family
ID=20376370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9011223A SI9011223B (sl) | 1989-06-22 | 1990-06-22 | Indenoindolne spojine |
Country Status (34)
| Country | Link |
|---|---|
| EP (1) | EP0409410B1 (sl) |
| JP (1) | JP3064411B2 (sl) |
| KR (1) | KR920702679A (sl) |
| CN (1) | CN1033029C (sl) |
| AT (1) | ATE135688T1 (sl) |
| BG (1) | BG60317B2 (sl) |
| CA (1) | CA2060897A1 (sl) |
| DD (1) | DD297960A5 (sl) |
| DE (1) | DE69025998T2 (sl) |
| DK (1) | DK0409410T3 (sl) |
| DZ (1) | DZ1428A1 (sl) |
| ES (1) | ES2084660T3 (sl) |
| FI (1) | FI100800B (sl) |
| GR (1) | GR3019779T3 (sl) |
| HR (1) | HRP920903B1 (sl) |
| HU (1) | HUT59097A (sl) |
| IE (1) | IE74682B1 (sl) |
| IL (1) | IL94830A (sl) |
| IS (1) | IS3590A7 (sl) |
| LT (1) | LT3675B (sl) |
| LV (1) | LV10253B (sl) |
| MX (1) | MX21244A (sl) |
| MY (1) | MY107311A (sl) |
| NO (1) | NO177932C (sl) |
| NZ (1) | NZ234175A (sl) |
| PL (1) | PL167761B1 (sl) |
| PT (1) | PT94468B (sl) |
| RO (1) | RO111573B1 (sl) |
| RU (1) | RU2104270C1 (sl) |
| SE (1) | SE8902274D0 (sl) |
| SI (1) | SI9011223B (sl) |
| WO (1) | WO1990015799A1 (sl) |
| YU (1) | YU122390A (sl) |
| ZA (1) | ZA904827B (sl) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU9301104D0 (en) * | 1990-10-16 | 1993-07-28 | Univ Bath | Method for producing tetrahydro-indeno-indole derivatves and pharmaceutical preparatives containing it |
| JPH0656669A (ja) * | 1992-06-11 | 1994-03-01 | Asahi Breweries Ltd | 活性酸素消去作用を持つプテリン誘導体製剤 |
| SE9302431D0 (sv) * | 1993-07-16 | 1993-07-16 | Ab Astra | Use of indenoindole compounds |
| AU675141B2 (en) * | 1993-07-20 | 1997-01-23 | Adir Et Compagnie | (Thia)cycloalkyl(b)indoles, process for preparing them and pharmaceutical compositions containing them |
| CA2350590A1 (en) * | 1998-12-04 | 2000-06-15 | John A. Butera | Substituted benzofuranoindoles and indenoindoles as novel potassium channel openers |
| US6288099B1 (en) | 1998-12-04 | 2001-09-11 | American Home Products Corporation | Substituted benzofuranoindoles and indenoindoles as novel potassium channel openers |
| FR2826009B1 (fr) * | 2001-06-13 | 2003-08-15 | Servier Lab | Nouveaux derives d'indenoindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| BRPI0613460A2 (pt) | 2005-07-14 | 2011-01-11 | Irm Llc | compostos e composições como inibidores de proteìna cinase |
| DE102006047231B4 (de) * | 2006-10-04 | 2009-02-12 | Hemmerling, Hans-Jörg, Dr. | Substituierte Indeno[1,2-b]indolderivate als neue Hemmstoffe der Protein Kinase CK2 und ihre Verwendung als Tumor Therapeutika, Cytostatika und Diagnostika |
| CA3124852A1 (en) * | 2011-06-16 | 2012-12-20 | Korea Research Institute Of Chemical Technology | Indanone derivatives, pharmaceutically acceptable salts or optical isomers thereof, preparation method for same, and pharmaceutical compositions containing same as active ingredient for preventing or treating viral diseases |
| KR101630243B1 (ko) | 2012-12-14 | 2016-06-15 | 한국화학연구원 | 신규한 화합물, 이의 약학적으로 허용가능한 염 또는 이의 광학 이성질체, 이의 제조방법 및 이를 유효성분으로 함유하는 바이러스성 질환의 예방 또는 치료용 약학적 조성물 |
| AU2021260048B2 (en) | 2020-04-20 | 2024-04-18 | Katholieke Universiteit Leuven | Antiviral 1,3-di-oxo-indene compounds |
| KR20260004471A (ko) | 2020-04-20 | 2026-01-08 | 노파르티스 아게 | 항바이러스 1,3-다이-옥소-인덴 화합물 |
-
1989
- 1989-06-22 SE SE8902274A patent/SE8902274D0/xx unknown
-
1990
- 1990-06-13 IS IS3590A patent/IS3590A7/is unknown
- 1990-06-20 WO PCT/GB1990/000949 patent/WO1990015799A1/en not_active Ceased
- 1990-06-20 CA CA002060897A patent/CA2060897A1/en not_active Abandoned
- 1990-06-20 JP JP2508940A patent/JP3064411B2/ja not_active Expired - Fee Related
- 1990-06-20 DK DK90306718.9T patent/DK0409410T3/da active
- 1990-06-20 MX MX21244A patent/MX21244A/es unknown
- 1990-06-20 DE DE69025998T patent/DE69025998T2/de not_active Expired - Fee Related
- 1990-06-20 RU SU5010937A patent/RU2104270C1/ru active
- 1990-06-20 RO RO149127A patent/RO111573B1/ro unknown
- 1990-06-20 EP EP90306718A patent/EP0409410B1/en not_active Expired - Lifetime
- 1990-06-20 AT AT90306718T patent/ATE135688T1/de active
- 1990-06-20 ES ES90306718T patent/ES2084660T3/es not_active Expired - Lifetime
- 1990-06-20 DZ DZ900114A patent/DZ1428A1/fr active
- 1990-06-20 HU HU904825A patent/HUT59097A/hu unknown
- 1990-06-20 PL PL90285752A patent/PL167761B1/pl unknown
- 1990-06-20 IE IE224790A patent/IE74682B1/en not_active IP Right Cessation
- 1990-06-21 NZ NZ234175A patent/NZ234175A/xx unknown
- 1990-06-21 ZA ZA904827A patent/ZA904827B/xx unknown
- 1990-06-21 IL IL9483090A patent/IL94830A/en not_active IP Right Cessation
- 1990-06-21 MY MYPI90001050A patent/MY107311A/en unknown
- 1990-06-21 DD DD90341939A patent/DD297960A5/de not_active IP Right Cessation
- 1990-06-22 SI SI9011223A patent/SI9011223B/sl unknown
- 1990-06-22 CN CN90104933A patent/CN1033029C/zh not_active Expired - Fee Related
- 1990-06-22 YU YU122390A patent/YU122390A/sh unknown
- 1990-06-22 PT PT94468A patent/PT94468B/pt not_active IP Right Cessation
-
1991
- 1991-12-19 FI FI915999A patent/FI100800B/fi active
- 1991-12-20 NO NO915049A patent/NO177932C/no unknown
- 1991-12-20 BG BG095667A patent/BG60317B2/bg unknown
- 1991-12-23 KR KR1019910701951A patent/KR920702679A/ko not_active Ceased
-
1992
- 1992-10-02 HR HRP-1223/90A patent/HRP920903B1/xx not_active IP Right Cessation
-
1993
- 1993-06-14 LV LVP-93-568A patent/LV10253B/xx unknown
- 1993-08-30 LT LTIP912A patent/LT3675B/lt not_active IP Right Cessation
-
1996
- 1996-04-29 GR GR960401159T patent/GR3019779T3/el unknown
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