SI9011223B - Indenoindolne spojine - Google Patents

Indenoindolne spojine Download PDF

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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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tetrahydro
formula
indole
cis
hydrogen
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Malcolm Sainsbury
Howard G. Shertzer
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University Of Bath
University Of Cincinnati
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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
SI9011223A 1989-06-22 1990-06-22 Indenoindolne spojine SI9011223B (sl)

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SE8902274A SE8902274D0 (sv) 1989-06-22 1989-06-22 Indenoidole compounds ii
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AU8713291A (en) * 1990-10-16 1992-05-20 University Of Bath Indenoindole compounds
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
BR9915900A (pt) * 1998-12-04 2001-08-21 American Home Prod Composto, composição farmacêutica, e, processo para tratar ou inibir distúrbios associados com contração da musculatura lisa.
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
MX2008000462A (es) 2005-07-14 2008-03-10 Irm Llc Compuestos heterotetraciclicos como mimeticos de tpo.
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
MX363405B (es) * 2011-06-16 2019-03-22 Katholieke Univ Leuven K U Leuven R&D Derivados de indanona, sales farmaceuticamente aceptables o isomeros opticos de los mismos, metodo de preparacion de los mismos, y composiciones farmaceuticas que contienen los mismos como ingrediente activo para prevención o tratamiento de enfermedades virales.
WO2014092514A1 (ko) 2012-12-14 2014-06-19 한국화학연구원 신규한 화합물, 이의 약학적으로 허용가능한 염 또는 이의 광학 이성질체, 이의 제조방법 및 이를 유효성분으로 함유하는 바이러스성 질환의 예방 또는 치료용 약학적 조성물

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LT3675B (en) 1996-01-25
DK0409410T3 (da) 1996-04-29
CN1051554A (zh) 1991-05-22
PT94468A (pt) 1991-02-08
PT94468B (pt) 1997-12-31
FI915999A0 (fi) 1991-12-19
IS3590A7 (is) 1990-12-23
YU122390A (sh) 1992-09-07
AU644084B2 (en) 1993-12-02
EP0409410B1 (en) 1996-03-20
NO177932C (no) 1995-12-20
DE69025998T2 (de) 1996-08-08
IE902247A1 (en) 1991-01-16
NO915049L (no) 1992-02-21
DD297960A5 (de) 1992-01-30
ATE135688T1 (de) 1996-04-15
DZ1428A1 (fr) 2004-09-13
KR920702679A (ko) 1992-10-06
NZ234175A (en) 1992-12-23
FI100800B (fi) 1998-02-27
JP3064411B2 (ja) 2000-07-12
LTIP912A (en) 1995-03-27
ZA904827B (en) 1991-04-24
WO1990015799A1 (en) 1990-12-27
IL94830A (en) 1996-07-23
HRP920903A2 (hr) 1994-04-30
PL285752A1 (en) 1991-03-11
HUT59097A (en) 1992-04-28
RU2104270C1 (ru) 1998-02-10
GR3019779T3 (en) 1996-07-31
CA2060897A1 (en) 1990-12-23
MX21244A (es) 1994-03-31
HU904825D0 (en) 1992-03-30
SE8902274D0 (sv) 1989-06-22
AU5836990A (en) 1991-01-08
IE74682B1 (en) 1997-07-30
NO177932B (no) 1995-09-11
LV10253B (en) 1995-04-20
HRP920903B1 (en) 1998-06-30
DE69025998D1 (de) 1996-04-25
SI9011223A (en) 1997-10-31
MY107311A (en) 1995-11-30
PL167761B1 (pl) 1995-10-31
EP0409410A1 (en) 1991-01-23
LV10253A (lv) 1994-10-20
ES2084660T3 (es) 1996-05-16
RO111573B1 (ro) 1996-11-29
CN1033029C (zh) 1996-10-16
IL94830A0 (en) 1991-04-15
BG60317B2 (bg) 1994-07-25
NO915049D0 (no) 1991-12-20
IE902247L (en) 1990-12-22
JPH04505923A (ja) 1992-10-15

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