HRP20120464T1 - Antitumorski spojevi - Google Patents

Antitumorski spojevi Download PDF

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HRP20120464T1
HRP20120464T1 HRP20120464AT HRP20120464T HRP20120464T1 HR P20120464 T1 HRP20120464 T1 HR P20120464T1 HR P20120464A T HRP20120464A T HR P20120464AT HR P20120464 T HRP20120464 T HR P20120464T HR P20120464 T1 HRP20120464 T1 HR P20120464T1
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substituted
unsubstituted
hydrogen
compound according
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Alberto@Rodr�guez@Vicente
Mar�a@@Garranzo@Garc�a@Ibarrola
Carmen@Murcia@P�rez
Francisco@S�nchez@Sancho
Mar�a@del@Carmen@Cuevas@Marchante
Cristina@Mateo@Urbano
Isabel@Dig�n@Ju�rez
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    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/51Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
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    • A61K31/365Lactones
    • A61K31/366Lactones having six-membered rings, e.g. delta-lactones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30Oxygen atoms, e.g. delta-lactones
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Abstract

Spoj opće formule I

Claims (27)

1. Spoj opće formule I [image] u kojem je Y izabran od -CHRay-, -CHRay-CHRby-, -CRay=CRby-, -C≡C-, -CHRay-CHRby-CHRCy-, -CHRay-CRby=CRCy- i -CHRay-C≡C-; svako Ray, Rby i RCy je nezavisno izabrano od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila; svako R1, R2, R3, R4 i R5 je nezavisno izabrano od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila; R6 je izabran od NR8R9 i OR10; W je izabran od O i NR7; R7 je izabran od vodika, CORa, COORa, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila, ili R7 i R5 zajedno sa odgovarajućim N atomom i C atomom za koji su vezani formiraju supstituiranu ili nesupstituiranu heterocikličnu grupu; R8 je izabran od vodika, CORa, COORa, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila; R10 je izabran od vodika, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila; svaka isprekidana linija predstavlja izbornu dodatnu vezu uz uvjet da su prisutne jedna ili više dodatnih veza, ali kada trostruka veza postoji između C atoma za koje su vezani R1 i R2, tada su R1 i R2 odsutni, i kada trostruka veza postoji između C atoma za koje su vezani R3 i R4, tada su R3 i R4 odsutni; R9 je izabran od vodika, CORa, COORa, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila; svaki R11, R12, R13, R14 i R15 nezavisno su izabrani od vodika, halogena, ORa, CORa, COORa, OCORa, OCOORa, OCONRaRb, CONRaRb, OS(O)Ra, OSO2Ra, OP(O)(Ra)ORb, OSiRaRbRC, NRaRb, NRaCORb, NRaCONRaRb, NRaS(O)Rb, NRaSO2Rb, NRaC(=NRa)NRaRb, SRa, S(O)Ra, SO2Ra, S(O)NRaRb, SO2NRaRb, S(O)ORa, SO2ORa, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila; i svaki Ra, Rb i RC nezavisno su izabrani od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila, supstituiranog ili nesupstituiranog arila i supstituirane ili nesupstituirane heterociklične grupe; ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer.
2. Spoj prema patentnom zahtjevu 1, naznačen time što su R1, R2, R3 i R4 nezavisno izabrani od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
3. Spoj prema patentnom zahtjevu 2, naznačen time što su R1, R2, R3 i R4 jednaki vodik.
4. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što su R11, R14 i R15 jednaki vodik.
5. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što je Y izabran od -CHRay-, -CRay=CRby- i -CHRay-CRby=CRCy-, i što su Ray, Rby i RCy nezavisno izabrani od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
6. Spoj prema patentnom zahtjevu 5, naznačen time što su Ray, Rby i RCy nezavisno izabrani od vodika i metila.
7. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što su R12 i R13 nezavisno izabrani od vodika, ORa, OCORa i OSiRaRbRC, i što su Ra, Rb i RC nezavisno izabrani od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
8. Spoj prema patentnom zahtjevu 7, naznačen time što je R12 izabran od vodika i ORa.
9. Spoj prema patentnom zahtjevu 7 ili 8, naznačen time što je R13 izabran od vodika, ORa i OSiRaRbRC.
10. Spoj prema bilo kojem od patentnih zahtjeva 7 do 9, naznačen time što su Ra, Rb i RC nezavisno izabrani od vodika, supstituiranog ili nesupstituiranog metila, supstituiranog ili nesupstituiranog etila, supstituiranog ili nesupstituiranog propila, supstituiranog ili nesupstituiranog izopropila, supstituiranog ili nesupstituiranog terc-butila.
11. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što je R5 izabran od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
12. Spoj prema patentnom zahtjevu 11, naznačen time što je R5 izabran od metila, izopropila i terc-butila.
13. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što, W je NR7 i R7 je kao što je definiran u patentnom zahtjevu 1.
14. Spoj prema patentnom zahtjevu 13, naznačen time što, R7 je vodik.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time što, W je NR7 i što R7 i R5 zajedno sa odgovarajućim N atomom i C atomom za koji su vezani formiraju supstituiranu ili nesupstituiranu pirolidin grupu.
16. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što, R6 je NR8R9 i što, R8 je vodik i R9 je izabran od vodika, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila.
17. Spoj prema patentnom zahtjevu 16, naznačen time što je R9 supstituirani C2-C12 alkenil koji je supstituiran na jednom ili više položaja sa halogenom, OR', =O, OCOR', OCONHR', OCONR'R', CONHR', CONR'R' i zaštićenim OH, pri čemu je svaka od R' grupa nezavisno izabrana od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog arila.
18. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što je jedna dodatna veza prisutna između C atoma za koje su vezani R1 i R2 i druga dodatna veza je prisutna između C atoma za koje su vezani R3 i R4.
19. Spoj prema patentnom zahtjevu 1, koji ima slijedeću formulu [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer.
20. Farmaceutska kompozicija koja sadrži spoj prema bilo kojem prethodnom patentnom zahtjevu, ili njegovu farmaceutski prihvatljivu sol, tautomer ili stereoizomer, i farmaceutski prihvatljiv razblaživač ili nosač.
21. Spoj ili kompozicija prema bilo kojem od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer, za upotrebu kao lijek.
22. Spoj ili kompozicija prema bilo kojem od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer, za upotrebu u liječenju kancera.
23. Spoj ili kompozicija prema bilo kojem od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer, u proizvodnji lijeka za liječenje kancera.
24. Postupak za pripremu spojeva prema formuli I [image] kao što je definirano u bilo kojem od patentnih zahtjeva 1 do 19, pri čemu su Y, W i R1, R2, R3, R4, R5, R6, R11, R12, R13, R14 i R15 također kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 19 koji sadrži spajanje fragmenata C i D [image] pri čemu, R1, R2, R3, R4, R5, R6, R11, R12, R13, R14, R15, Y i W su željene grupe ili odgovarajuća zaštitna grupa prema potrebi, i L i M su odgovarajuće reaktivne ili odlazeće grupe.
25. Postupak prema patentnom zahtjevu 24, naznačen time što je spoj formule I – bilo koji spoj definiran u patentnom zahtjevu 19.
26. Postupak za pripremu spojeva prema formuli I [image] kao što je definirano u bilo kojem od patentnih zahtjeva 1 do 19, pri čemu, Y, W i R1, R2, R3, R4, R5, R6, R11, R12, R13, R14 i R15 su također kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 19 koji sadrži spajanje fragmenata A i B [image] pri čemu, R1, R2, R3, R4, R5, R6, R11, R12, R13, R14, R15 i Y su željene grupe ili odgovarajuća zaštitna grupa prema potrebi, i J i K su odgovarajuće reaktivne ili odlazeće grupe.
27. Postupak prema patentnom zahtjevu 26, naznačen time što je spoj formule I bilo koji spoj definiran u patentnom zahtjevu 19.
HRP20120464AT 2007-12-20 2012-06-01 Antitumorski spojevi HRP20120464T1 (hr)

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EP07123882 2007-12-20
PCT/EP2008/068065 WO2009080769A1 (en) 2007-12-20 2008-12-19 Antitumoral compounds

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JP (3) JP5529038B2 (hr)
KR (3) KR101639772B1 (hr)
CN (4) CN101903337B (hr)
AT (1) ATE549313T1 (hr)
AU (2) AU2008341670B2 (hr)
BR (2) BRPI0821116B8 (hr)
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ES (3) ES2578606T3 (hr)
HK (3) HK1147990A1 (hr)
HR (2) HRP20120464T1 (hr)
IL (3) IL206396A (hr)
MX (2) MX2010006795A (hr)
MY (3) MY148651A (hr)
NZ (3) NZ586013A (hr)
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RS (2) RS53140B (hr)
RU (3) RU2528393C9 (hr)
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SI (2) SI2231590T1 (hr)
UA (3) UA104281C2 (hr)
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