LV12592B - Aizvietoti 4-aminotiazola savienojumi kā ciklīnatkarīgo kināžu inhibitori - Google Patents

Aizvietoti 4-aminotiazola savienojumi kā ciklīnatkarīgo kināžu inhibitori Download PDF

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LV12592B
LV12592B LVP-00-51A LV000051A LV12592B LV 12592 B LV12592 B LV 12592B LV 000051 A LV000051 A LV 000051A LV 12592 B LV12592 B LV 12592B
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LV12592A (en
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Wesley K.M. Chong
Shao Song Chu
Rohit K. DUVADIE
Lin Li
Wei Xiao
Yi Yang
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Agouron Pharmaceuticals, Inc.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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Claims (7)

  1. LV 12592 IZGUDROJUMA FORMULA 1. Savienojums ar formulu I:
    kur R1 Ir aizvietota vai neaizvietota grupa, kuru izvēlas no: C-i-6-alkil-; Ci-6-alkenil-; Ci-6-alkinil-; Ci^-alkoksilgrupām; Ci-e-spirta; karbocikliskas vai heterocikliskas, monocikliskas vai kondensētas vai nekondensētas policikliskas cikloalkilgrupas; karbocikliskas vai heterocikliskas, monocikliskas vai kondensētas vai nekondensētas policikliskas arilgrupas; karbonilgrupas; ētera; (Ci^-alkil)-karbonil-; (Ci^-alkil)-aril-; (Ci^-alkil)-cikloalkil-; (Ci_6-alkiI)-(Ci-6-alkoksil-)-; aril-(Ci-6-alkoksil)-grūpēm; tioētera; tiol-; un sulfonilgrupām; kur ja R1 ir aizvietota grupa, katrs aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; Ci^-alkil-; Ci^-alkenil-; Ci-e-alkinil-; hidroksil-; C-i-6-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonātogrupas; fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas; sulfonamīds; ketons; aldehīds; esteris; skābekļa atoms; karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska cikloalkilgrupa; vai karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska arilgrupa; un R2 ir karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska gredzena struktūra ar aizvietotāju stāvoklī blakus pievienošanas vietai, kur gredzena struktūra iespējams papildus aizvietota un kur katrs aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; Ci-6-alkil-; Ci^-alkenil-; Ci_6-alkinil-; hidroksil-; Ci^-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonātogrupas; fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds; esteris; skābekļa atoms; karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska, cikloalkilgrupa; vai karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska, arilgrupa; vai savienojuma ar formulu I farmaceitiski pieņemams sāls vai savienojuma ar formulu I priekštečvielas forma vai farmaceitiski aktīvs metabolīts vai šī aktīva metabolīta farmaceitiski pieņemams sāls. 2
  2. 2. Savienojums vai šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai farmaceitiski aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R1 ir aizvietota grupa, katrs aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; Ci-e-alkil-; Ci^-alkenil-; Ci^-alkinil-; hidroksilgrupas; skābekļa atoms, Ci-6-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonāto-, fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds vai esteris; un R2 grupas katrs aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; Ci_6-alkil-; Ci^-alkenil-; Ci^-alkinil-; hidroksilgrupas; Ci^-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonāto-, fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds vai esteris.
  3. 3. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R1 ir aizvietota fenilgrupa.
  4. 4. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R1 ir fenilgrupa aizvietota ar alkilamino- vai piridīngrupu.
  5. 5. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R1 izvēlas no grupas, kas sastāv no: 3 LV 12592
  6. 6. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R1 ir fenilgrupa aizvietota ar iespējams aizvietotu karbonil- vai sulfonamidogrupu.
    7. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R1 izvēlas no grupas, kas sastāv no: "" “ γΌ*' , o4o -Ofo . Η}'·- kur R3 izveļas no grupas, kas sastāv no Ci-Ce-alkil-, Ci-C6-alkoksi-, aril-, ariloksi- un amīnogrupām. 4
    8. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R2ir orto-aizvietota fenil- vai tienilgrupa.
    9. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 1. punktu, kas atšķiras ar to, ka R2 ir o-halogēnfenil- vai o-dihalogēnfenilgrupa.
    10. Savienojums, šī savienojuma farmaceitiski pieņemams sāls, priekštečvielas forma vai aktīvs metabolīts saskaņā ar 9. punktu, kas atšķiras ar to, ka R2 ir o-difluorfenilgrupa.
    11. Savienojums saskaņā ar 1. punktu, kuru izvēlas no grupas, kas sastāv no:
    H
    H , un un ŠT savienojuma farmaceitiski pieņemamie sāji, priekštečvielas formas un aktīvie metabolīti. izvēlas no grupas, kas sastāv no:
    12. Savienojums saskaņa ar 1. punktu, kuru 5 LV 12592
    un ŠT savienojuma farmaceitiski pieņemamie sāļi, priekštečvielas formas un aktīvie metabolīti.
    6
    νη2 ΊΡ^Ρ
    un un šī savienojuma farmaceitiski pieņemamie sāļi, priekštečvielas formas un aktīvie metabolīti.
    14. Farmaceitiska kompozīcija, kurā ietilpst: (a) šūnu cikla kontrolējoša (regulējoša) aģenta daudzums, kas ir efektīvs CDK4 vai CDK4/ciklīna kompleksa inhibēšanai, pie kam šo šūnu cikla kontrolējošo (regulējošo) aģentu izvēlas no grupas, kas sastāv no (I) savienojuma ar formulu I: kur
  7. 7 LV 12592 R1 ir aizvietota vai neaizvietota grupa, kuru izvēlas no: Ci_6-alkil-; Ci-e-alkenil-; Ci-6-alkinil-; Ci^-alkoksilgrupām; Ci^-spirta; karbocikliskas vai heterocikliskas, monocikliskas vai kondensētas vai nekondensētas poiicikliskas cikloalkilgrupas; karbocikliskas vai heterocikliskas, monocikliskas vai kondensētas vai nekondensētas poiicikliskas arilgrupas; karbonilgrupas; ētera; (C1_6-alkil)-karbonil-; (Ci-6-alkil)-aril-; (Ci^-alkil)-cikloalkil·; (Ci_6-alkil)-(Ci_6-alkoksil-)-; aril-(Ci-e-alkoksil)-grupām; tioētera; tiol-; un sulfonilgnjpām; kur ja R1 ir aizvietota grupa, katrs aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; Ci-e-alkil-; Ci^-alkenil-; C-i-e-alkinil-; hidroksil-; C1-6-alkoksil-; amino-; nltro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonātogrupas; fosfīn-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds; esteris; skābekļa atoms; karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska, cikloalkilgrupa; vai karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska arilgrupa; un R2 ir karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska gredzena struktūra ar aizvietotāju stāvoklī blakus pievienošanas vietai, kur gredzena struktūra iespējams papildus aizvietota un kur katrs aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; Ci^-alkil-; Ci-6-alkenil-; Ci-6-alkinil-; hidroksil-; Ci-e-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonātogrupas; fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds; esteris; skābekļa atoms; karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska, cikloalkilgrupa; vai karbocikliska vai heterocikliska, monocikliska vai kondensēta vai nekondensēta policikliska arilgrupa; (II) savienojuma ar formulu I farmaceitiski pieņemama sāls; un (III) savienojuma ar formulu I priekštečvielas formas vai farmaceitiski aktīva metabolīta vai šī aktīva metabolīta farmaceitiski pieņemama sāls; un b) farmaceitiski pieņemams nesējs. 15. Šūnu cikla kontrolējoša aģenta, kuru izvēlas no grupas, kas sastāv no: savienojumu ar formulu I: 8
    kur R1 ir aizvietota vai neaizvietota grupa, kuru izvēlas no: C-i-e-alkil-; Ci-e-alkenil-; C^-alkinil-; C^-alkoksilgrupām; Ci-e-spirta; karbocikliskas vai heterocikliskas, monocikliskas vai kondensētas vai nekondensētas policikliskas, cikloalkilgrupas; karbocikliskas vai heterocikliskas, monocikliskas vai kondensētas vai nekondensētas policikliskas arilgrupas; karbonilgrupas; ētera; (Ci_6-alkil)-karbonil-; (Ci_6-alkil)-aril-; (C^-alkil)-cikloalkil-; (C^-alkilHCi-e-alkoksil-)-; ariKC^-alkoksiO-grupām; tioētera; tiol-; un sulfonilgrupām; kur ja R1 ir aizvietota grupa, katrs aizvietotājs neatkarīgi ir halogēna atoms; halbgēnalkil-; Ci_6-alkil-; Ci-e-alkenil-; Ci_6-alkinil-; hidroksil-; skābekļa atoms; Ci-e-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonātogrupas; fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds vai esteris; un R2 ir karbocikliska vai heterocikliska, monociliska vai kondensēta vai nekondensēta policikliska gredzena struktūra ar aizvietotāju stāvoklī blakus pievienošanas vietai, kur gredzena struktūra iespējams papildus aizvietota un kur katrs R2-grupas aizvietotājs neatkarīgi ir halogēna atoms; halogēnalkil-; C-i-6-alkil-; Ci-6-alkenil-; Ci.6-alkinil-; hidroksil-; C-i-6-alkoksil-; amino-; nitro-; tiolgrupas; tioēteris; imino-; ciān-; amido-; fosfonātogrupas; fosfin-; karboksil-; tiokarbonil-; sulfonilgrupas, sulfonamīds; ketons; aldehīds vai esteris; savienojumu ar formulu I farmaceitiski pieņemamiem sāļiem; un savienojumu ar formulu I priekštečvielas formām un farmaceitiski aktīviem metabolītiem un priekštečvielas formas un farmaceitiski aktīva metabolīta farmaceitiski pieņemamiem sāļiem, pielietojums medikamenta iegūšanā slimības vai traucējuma ārstēšanai, kas saistīta ar CDK4 vai CDK/ciklīna kompleksa inhibēšanu.
LVP-00-51A 1997-10-27 2000-05-03 Aizvietoti 4-aminotiazola savienojumi kā ciklīnatkarīgo kināžu inhibitori LV12592B (lv)

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PCT/US1998/022809 WO1999021845A2 (en) 1997-10-27 1998-10-27 4-aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases

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