LV12770A - Tricyclic inhibitors of poly(adp-ribose) polymerases - Google Patents

Tricyclic inhibitors of poly(adp-ribose) polymerases Download PDF

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LV12770A
LV12770A LV010115A LV010115A LV12770A LV 12770 A LV12770 A LV 12770A LV 010115 A LV010115 A LV 010115A LV 010115 A LV010115 A LV 010115A LV 12770 A LV12770 A LV 12770A
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compound
mmol
alkyl
parp
pharmaceutically acceptable
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LV12770B (lv
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Stephen Evan Webber
Stacie S Canan-Koch
Jayashree Girish Tikhe
Lars Henrik Thoresen
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Agouron Pharma
Cancer Res Campaign Tech
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
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    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • A—HUMAN NECESSITIES
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems

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Claims (21)

  1. LV 12770 IZGUDROJUMA FORMULA 1. Savienojums, kuru izvēlas no grupas, kas sastāv no:
    o
    2
  2. 2. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts saskaņā ar 1.punktu ar PARP-inhibējošo aktivitāti, kur Ki pēc PARP fermenta inhibešanas analīzes ir 100 μΜ vai mazāk.
  3. 3. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts saskaņā ar 1.punktu ar citotoksiskumu potencēšanas aktivitāti, kur PF50 pēc citotoksiskumu potencēšanas analīzes ir vismaz 1.
    3 LV 12770 Η
    Η Η
    vai šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts. 4
  4. 4. Farmaceitiska kompozīcija, kurā ietilpst: a) PARP-inhibējošo aģenta efektīvs daudzums, šis aģents ir: i) savienojums, kuru izvēlas no grupas, kas sastāv no: 0
    CHO 9 CH(OEt)2 0
    O O
    / H3C / N(C. HjC 5 LV 12770
    6
  5. 5. Savienojuma, šī savienojuma farmaceitiski pieņemama sāls, priekštečvielas, aktīva metabolīta vai solvāta saskaņā ar 1.punktu efektīva daudzuma pielietojums medikamenta iegūšanā fermenta PARP-aktivitātes inhibēšanai.
  6. 6. Pielietojums saskaņā ar 5.punktu, kas atšķiras ar to, ka ferments ir poli(ADP-ribozo)polimerāze vai tankirāze.
  7. 7. Savienojuma, šī savienojuma farmaceitiski pieņemama sāls, priekštečvielas, aktīva metabolīta vai solvāta saskaņā ar 1.punktu terapeitiski efektīva daudzuma pielietojums medikamenta iegūšanā fermenta PARP-aktivitātes inhibēšanai zīdītāju audos.
    7 LV 12770 Η Η Ν·
    Η Η Η
    Η Η Η
    Ν Η Η un ; vai ii) šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts; un b) PARP-inhibējošam aģentam farmaceitiski pieņemams nesējs.
  8. 8. Savienojuma ar formulu 8 R2 I
    kur R1 ir ūdeņraža vai halogēna atoms, ciāngrupa; iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; vai -C(0)-R10 -grupa, kur R10 ir ūdeņraža atoms, iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; vai OR100 vai NR10^110, kur R100 un Rn0 katra neatkarīgi ir ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; R2 ir ūdeņraža atoms vai alkilgrupa; R3 ir ūdeņraža atoms vai alkilgrupa; R4 ir ūdeņraža vai halogēna atoms, vai alkilgrupa; X ir skābekļa vai sēra atoms; Y ir (CR5R6)(CR7R8)„ vai N=C(R5)-grupa, kur nir 0 vai 1; R5 un R6 katra neatkarīgi ir ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; un R7 un R8 katra neatkarīgi ir ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; vai šī savienojuma farmaceitiski pieņemama sāls, priekštečvielas, aktīva metabolīta vai solvāta efektīva daudzuma pielietojums medikamenta iegūšanā fermenta PARP-aktivitātes inhibēšanai.
  9. 9 vai šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts.
    9 LV 12770 kur R1 ir halogēna atoms, ciāngrupa; iespējams aizvietota alkil-, alkenil-, alkiml-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; vai -C(0)-Rl° -grupa, kur R10 ir ūdeņraža atoms; iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; vai OR100 vai NR100R110, kur R100 un Ruo katra neatkarīgi ir Ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; R2 ir ūdeņraža atoms vai alkilgrupa; R3 ir ūdeņraža atoms vai alkilgrupa; R4 ir ūdeņraža vai halogēna atoms, vai alkilgrupa; X ir skābekļa vai sēra atoms; Y ir (CR5R6)(CR7R8)n vai N=C(R5)-gmpa, kur nir 1; R5 unR6 katra neatkarīgi ir ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; un R7 un R8 katra neatkarīgi ir ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil·, aril- vai heteroarilgrupa; un ja R1, R4, R5, R6 un R7 katra ir ūdeņraža atoms, tad R8 ir aizvietota fenilgrupa; vai šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts.
    9. Savienojums ar formulu
  10. 10. Savienojums ar formulu
    kur p ir 2; R11 ir ūdeņraža atoms vai alkilgrupa; R12 ir halogēna atoms vai iespējams aizvietota aril-, alkil-, alkenil-, alkinil- vai acilgrupa -C(0)-R10, kur R10 ir ūdeņraža atoms; iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; vai OR100 vai NR^R110-grupa, kur R100 un R110 katra neatkarīgi ir ūdeņraža atoms vai iespējams aizvietota alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa; 10 R13 ir ūdeņraža atoms vai alkilgrupa; un R14 ir ūdeņraža vai halogēna atoms; vai šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts. 11. Savienojums ar formulu H
    kur R15 ir ūdeņraža vai halogēna atoms, vai alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa neaizvietota vai aizvietota ar vienu vai vairākiem aizvietotājiem, kurus izvēlas no halogēna atoma, oksi-, nitro-, aminogrupām un alkil- un arilgrupas neaizvietotas vai aizvietotas ar vienu vai vairākiem aizvietotājiem, kurus izvēlas no halogēna atoma, oksi-, nitro-, aminogrupām; R16 ir ūdeņraža vai halogēna atoms, ciāngrupa, vai alkil-, alkenil-, alkinil-, cikloalkil-, heterocikloalkil-, aril- vai heteroarilgrupa neaizvietota vai aizvietota ar vienu vai vairākiem aizvietotājiem, kurus izvēlas no halogēna atoma, oksi-, nitro-, aminogrupām un alkil- un arilgrupas neaizvietotas vai aizvietotas ar vienu vai vairākiem aizvietotājiem, kurus izvēlas no halogēna atoma, oksi-, nitro-, aminogrupām; R17 ir ūdeņraža atoms vai alkilgrupa; un R ir ūdeņraža vai halogēna atoms, vai alkilgrupa; kur R15 R16, R17 un R18 nav ūdeņraža atomi vienlaicīgi; vai šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts.
  11. 11 LV 12770 Η
    >
    Η
    \ Η
    12
  12. 12. Savienojums, kuru izvēlas no grupas, kas sastāv no:
  13. 13. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts saskaņā ar 9.punktu ar PARP-inhibējošo aktivitāti, kur Ki pēc PARP fermenta inhibēšanas analīzes ir 100 μΜ vai mazāk. 18
  14. 14. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts saskaņā ar 9.punktu ar citotoksiskumu potencēšanas aktivitāti, kur PF50 pēc citotoksiskumu potencēšanas analīzes ir vismaz 1.
    14 X 2
  15. 15. Farmaceitiska kompozīcija, kurā ietilpst a) PARP-inhibējošo aģenta efektīvs daudzums, šis aģents ir savienojums saskaņā ar 9.punktu vai šī savienojuma farmaceitiski pieņemams sāls, priekštečviela, aktīvs metabolīts vai solvāts; un b) PARP-inhibējošam aģentam farmaceitiski pieņemams nesējs.
    15 LV 12770
    16
    17
    LV 12770
  16. 16. Savienojuma, šī savienojuma farmaceitiski pieņemama sāls, priekštečvielas, aktīva metabolīta vai solvāta saskaņā ar 9.punktu efektīva daudzuma pielietojums medikamenta iegūšanā fermenta PARP-aktivitātes inhibēšanai.
  17. 17. Pielietojums saskaņā ar 16.punktu, kas atšķiras ar to, ka ferments ir poli(ADP-ribozo)-polimerāze vai tankirāze.
  18. 18. Savienojuma, šī savienojuma farmaceitiski pieņemama sāls, priekštečvielas, aktīva metabolīta vai solvāta saskaņā ar 9.punktu terapeitiski efektīva daudzuma pielietojums medikamenta iegūšanā fermenta PARP-aktivitātes inhibēšanai zīdītāju audos.
  19. 19. Savienojuma, šī savienojuma farmaceitiski pieņemama sāls, priekštečvielas, aktīva metabolīta vai solvāta saskaņā ar 12.punktu efektīva daudzuma pielietojums medikamenta iegūšanā fermenta PARP-aktivitātes inhibēšanai. 19 LV 12770
  20. 20. Savienojums saskaņā ar 12. punktu ar strucruru
    \ vai šī savienojuma farmaceitiski pieņemams sāls.
  21. 21. Farmaceitiska kompozīcija saskaņa ar 15. punktu, kas atšķirasarto,ka PARP-inhibējošais aģents ir o
    H \ vai ši aģenta farmaceitiski pieņemams sāls.
LV010115A 1999-01-11 2001-08-01 Poli(adp-ribozo) polimerazu tricikliskie inhibitori LV12770B (lv)

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US11543199P 1999-01-11 1999-01-11
PCT/US2000/000411 WO2000042040A1 (en) 1999-01-11 2000-01-10 Tricyclic inhibitors of poly(adp-ribose) polymerases

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