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AR068056A1 - DERIVATIVES OF N, N'-2, 4 - DIANILINOPIRIMIDINAS, ITS PREPARATION, ITS USE AS MEDICINES, PHARMACEUTICAL COMPOSITIONS AND ESPECIALLY AS IKK INHIBITORS. - Google Patents

DERIVATIVES OF N, N'-2, 4 - DIANILINOPIRIMIDINAS, ITS PREPARATION, ITS USE AS MEDICINES, PHARMACEUTICAL COMPOSITIONS AND ESPECIALLY AS IKK INHIBITORS.

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Publication number
AR068056A1
AR068056A1 ARP080103453A ARP080103453A AR068056A1 AR 068056 A1 AR068056 A1 AR 068056A1 AR P080103453 A ARP080103453 A AR P080103453A AR P080103453 A ARP080103453 A AR P080103453A AR 068056 A1 AR068056 A1 AR 068056A1
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Argentina
Prior art keywords
alkyl
radicals
optionally substituted
radical
different
Prior art date
Application number
ARP080103453A
Other languages
Spanish (es)
Inventor
Bernard Tonnerre
Monsif Bouaboula
Original Assignee
Sanofi Aventis
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Publication date
Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR068056A1 publication Critical patent/AR068056A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • A—HUMAN NECESSITIES
    • 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]
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Productos de formula (1), su uso como medicamentos, principalmente como inhibidores de IKK, composiciones farmacéuticas que los comprenden y un método para su preparacion. Reivindicacion 1: Productos de formula (1) en la que R2, R3 y R4, idénticos o diferentes, son tales que uno representa un átomo de halogeno o CF3 y los otros dos, idénticos o diferentes, representan un átomo de hidrogeno o un átomo de halogeno o un radical alquilo o un radical alcoxi, sustituidos opcionalmente con uno o varios átomos de halogeno; R5 representa un átomo de hidrogeno o un átomo de halogeno; Z representa CO o SO2; el ciclo con N (en la formula (1)), o sea, que está sustituido en el mismo átomo de carbono con R1 y R6, que contiene 4 a 7 eslabones, estando saturado y pudiendo además contener un puente carbonado constituido por 1 a 3 carbonos, entendiéndose que R1 y R6 representan una de las 5 alternativas siguientes i) a v): i) R1 representa -X1-R7, representando X1, -(CH2)m- y R7 representa un ciclo heterocicloalquilo, arilo o heteroarilo, todos sustituidos opcionalmente; y R6 representa el átomo de hidrogeno o los radicales hidroxilo, -(CH2)mOH, -CO-NRaRb, -CH2-NRaRb, -CO2H, y -CO2alq; ii) R1 representa -X2-R7, representando X2 ,-O-; -O-(CH2)m-; -CH(OH)-(CH2)n-; -CO-; -CO-NRc-; -CO-NRc-O-; -CH(NRaRb)-; -C=NOH-; -CN-NH2-; -(CH2)n1-NRc-(CH2)n2-; y R7 representa un ciclo heterocicloalquilo, arilo o heteroarilo, todos sustituidos opcionalmente; y R6 representa hidrogeno; iii) R1 representa -NRc-W representando W el átomo de hidrogeno o un radical alquilo que contiene de 1 a 4 átomos de carbono, lineal o ramificado a partir de 3 átomos de carbono sustituido opcionalmente con un radical elegido entre -PO(OEt)2, -OH, -Oalq, -CF3, -CO-NR8R9 y SO2-alq; y R6 representa hidrogeno; entendiéndose que cuando W representa un átomo de hidrogeno entonces Z representa CO; iv) R1 representa -CH2-NRc-W representando W el átomo de hidrogeno o un radical alquilo que contiene de 1 a 4 átomos de carbono, lineal o ramificado a partir de 3 átomos de carbono, y sustituido opcionalmente con un radical elegido entre -PO(OEt)2, -OH, -OEt, -CF3, -CON(alq)2 y SO2-alq ; y R6 representa hidrogeno; v) R1 representa -CO-N(Rc)-OR'c y R6 representa hidrogeno; representando n, n1 y n2, idénticos o diferentes, un numero entero de 0 a 3; m representa un numero entero de 1 a 3; Rc y R'c, idénticos o diferentes, representan el átomo de hidrogeno o un radical alquilo que contiene de 1 a 4 átomos de carbono, sustituido opcionalmente con uno o varios átomos de halogeno; NRaRb es tal, que bien Ra y Rb, idénticos o diferentes, representan el átomo de hidrogeno o un radical alquilo que contiene de 1 a 4 átomos de carbono o un radical cicloalquilo, estando estos radicales alquilo y cicloalquilo sustituidos opcionalmente con uno o varios átomos de halogeno, un radical hidroxilo o un radical NH2, NH-alquilo o N(alquilo)2; bien Ra y Rb forman con el átomo de nitrogeno al que están unidos una amina cíclica que puede contener opcionalmente uno o dos heteroátomos distintos elegidos entre: O, S, N o NR10, estando la amina cíclica así formada sustituida opcionalmente con uno o varios radicales idénticos o diferentes, elegidos entre los átomos de halogeno y los radicales alquilo ellos mismos sustituidos opcionalmente con uno o varios átomos de halogeno estando todos los radicales heterocicloalquilo, arilo y heteroarilo sustituidos opcionalmente con uno o varios radicales, idénticos o diferentes, elegidos entre los átomos de halogeno; los radicales hidroxilo; ciano; NR8R9 ; y los radicales alquilo, cicloalquilo, alcoxi, fenilo, heterocicloalquilo y heteroarilo, ellos mismos sustituidos opcionalmente con uno o varios radicales idénticos o diferentes elegidos entre los átomos de halogeno y los radicales hidroxilo, alcoxi, alquilo, hidroxialquilo, alcoxialquilo, CN, CF3, OCF3, o NRaRb; NR8R9 es tal que bien R8 y R9, idénticos o diferentes, son tales que R8 representa el átomo de hidrogeno o un radical alquilo que contiene de 1 a 4 átomos de carbono o un radical cicloalquilo, estando estos radicales alquilo y cicloalquilo sustituidos opcionalmente con uno o varios átomos de halogeno, un radical hidroxilo o un radical NH2, NH-alquilo o N(alquilo)2; y R9 representa el átomo de hidrogeno y los radicales alquilo, cicloalquilo o heterocicloalquilo ellos mismos sustituidos opcionalmente con uno o varios radicales idénticos o diferentes, elegidos entre los átomos de halogeno y los radicales hidroxilo, alcoxi, NH2, NH-alquilo, N(alquilo)2, estando los radicales alquilo que representa R9 además sustituidos opcionalmente con un radical fenilo, heterocicloalquilo o heteroarilo ellos mismos sustituidos opcionalmente con uno o varios radicales elegidos entre los átomos de halogeno y los radicales hidroxilo, alcoxi, alquilo, hidroxialquilo, alcoxialquilo, CN, CF3, OCF3, NH2, NHalq o N(alq)2; bien R8 y R9 forman con el átomo de nitrogeno al que están unidos una amina cíclica que puede contener opcionalmente uno o dos heteroátomos distintos elegidos entre O, S, N o NR10, estando la amina cíclica así formada ella misma sustituida opcionalmente con uno o varios radicales idénticos o diferentes, elegidos entre los átomos de halogeno y los radicales alquilo ellos mismos sustituidos opcionalmente con uno o varios átomos de halogeno; todos los radicales heterocicloalquilo y heteroarilo anteriores sustituidos opcionalmente como se ha indicado anteriormente, estando constituidos por 4 a 10 eslabones y con 1 a 3 heteroátomos elegido(s) entre O, S, N y NR10; R10 representa un átomo de hidrogeno o un radical alquilo, estando dichos productos de formula (1) en todas las formas isomeras posibles racémicos, enantiomeros y diastereoisomeros, así como las sales de adicion con los ácidos minerales y orgánicos de dichos productos de formula (1).Products of formula (1), their use as medicaments, mainly as IKK inhibitors, pharmaceutical compositions comprising them and a method for their preparation. Claim 1: Products of formula (1) wherein R2, R3 and R4, identical or different, are such that one represents a halogen atom or CF3 and the other two, identical or different, represent a hydrogen atom or an atom halogen or an alkyl radical or an alkoxy radical, optionally substituted with one or more halogen atoms; R5 represents a hydrogen atom or a halogen atom; Z represents CO or SO2; the cycle with N (in formula (1)), that is, which is substituted on the same carbon atom with R1 and R6, which contains 4 to 7 links, being saturated and may also contain a carbon bridge consisting of 1 to 3 carbons, it being understood that R1 and R6 represent one of the following 5 alternatives i) av): i) R1 represents -X1-R7, representing X1, - (CH2) m- and R7 represents a heterocycloalkyl, aryl or heteroaryl cycle, all optionally substituted; and R6 represents the hydrogen atom or hydroxyl radicals, - (CH2) mOH, -CO-NRaRb, -CH2-NRaRb, -CO2H, and -CO2alq; ii) R1 represents -X2-R7, representing X2, -O-; -O- (CH2) m-; -CH (OH) - (CH2) n-; -CO-; -CO-NRc-; -CO-NRc-O-; -CH (NRaRb) -; -C = NOH-; -CN-NH2-; - (CH2) n1-NRc- (CH2) n2-; and R7 represents a heterocycloalkyl, aryl or heteroaryl cycle, all optionally substituted; and R6 represents hydrogen; iii) R1 represents -NRc-W representing W the hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms, linear or branched from 3 carbon atoms optionally substituted with a radical chosen from -PO (OEt) 2, -OH, -Oalq, -CF3, -CO-NR8R9 and SO2-alq; and R6 represents hydrogen; it being understood that when W represents a hydrogen atom then Z represents CO; iv) R1 represents -CH2-NRc-W representing W the hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms, linear or branched from 3 carbon atoms, and optionally substituted with a radical chosen from - PO (OEt) 2, -OH, -OEt, -CF3, -CON (alq) 2 and SO2-alq; and R6 represents hydrogen; v) R1 represents -CO-N (Rc) -OR'c and R6 represents hydrogen; representing n, n1 and n2, identical or different, an integer from 0 to 3; m represents an integer from 1 to 3; Rc and R'c, identical or different, represent the hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms, optionally substituted with one or more halogen atoms; NRaRb is such that either Ra and Rb, identical or different, represent the hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms or a cycloalkyl radical, these alkyl and cycloalkyl radicals being optionally substituted with one or more atoms of halogen, a hydroxyl radical or an NH2, NH-alkyl or N (alkyl) 2 radical; either Ra and Rb form with the nitrogen atom to which they are attached a cyclic amine that may optionally contain one or two different heteroatoms chosen from: O, S, N or NR10, the cyclic amine thus formed being optionally substituted with one or more radicals identical or different, chosen from halogen atoms and alkyl radicals themselves optionally substituted with one or more halogen atoms, all heterocycloalkyl, aryl and heteroaryl radicals being optionally substituted with one or more radicals, identical or different, chosen between atoms halogen; hydroxyl radicals; cyano; NR8R9; and the alkyl, cycloalkyl, alkoxy, phenyl, heterocycloalkyl and heteroaryl radicals, themselves optionally substituted with one or more identical or different radicals chosen from the halogen atoms and the hydroxyl, alkoxy, alkyl, hydroxyalkyl, alkoxyalkyl radicals, CN, CF3, OCF3, or NRaRb; NR8R9 is such that either R8 and R9, identical or different, are such that R8 represents the hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms or a cycloalkyl radical, these alkyl and cycloalkyl radicals being optionally substituted with one or several halogen atoms, a hydroxyl radical or an NH2, NH-alkyl or N (alkyl) 2 radical; and R9 represents the hydrogen atom and the alkyl, cycloalkyl or heterocycloalkyl radicals themselves optionally substituted with one or more identical or different radicals, chosen from the halogen atoms and the hydroxyl, alkoxy, NH2, NH-alkyl, N (alkyl) radicals ) 2, the alkyl radicals representing R9 being further optionally substituted with a phenyl, heterocycloalkyl or heteroaryl radical themselves optionally substituted with one or more radicals chosen from halogen atoms and hydroxyl, alkoxy, alkyl, hydroxyalkyl, alkoxyalkyl radicals, CN , CF3, OCF3, NH2, NHalq or N (alq) 2; either R8 and R9 form with the nitrogen atom to which they are attached a cyclic amine that may optionally contain one or two different heteroatoms chosen from O, S, N or NR10, the cyclic amine thus formed itself being optionally substituted with one or more identical or different radicals, chosen from the halogen atoms and the alkyl radicals themselves optionally substituted with one or more halogen atoms; all the above heterocycloalkyl and heteroaryl radicals optionally substituted as indicated above, consisting of 4 to 10 links and with 1 to 3 heteroatoms chosen from O, S, N and NR10; R10 represents a hydrogen atom or an alkyl radical, said products of formula (1) being in all possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as the addition salts with mineral and organic acids of said products of formula (1 ).

ARP080103453A 2007-08-09 2008-08-07 DERIVATIVES OF N, N'-2, 4 - DIANILINOPIRIMIDINAS, ITS PREPARATION, ITS USE AS MEDICINES, PHARMACEUTICAL COMPOSITIONS AND ESPECIALLY AS IKK INHIBITORS. AR068056A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0705790A FR2919869B1 (en) 2007-08-09 2007-08-09 NOVEL N, N'-2,4-DIANILINOPYRIMIDINE DERIVATIVES, THEIR PREPARATION AS MEDICAMENTS, PHARMACEUTICAL COMPOSITIONS AND IN PARTICULAR AS INHIBITORS OF IKK

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AR068056A1 true AR068056A1 (en) 2009-11-04

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AR (1) AR068056A1 (en)
FR (1) FR2919869B1 (en)
TW (1) TW200916457A (en)
UY (1) UY31278A1 (en)
WO (1) WO2009056693A1 (en)

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WO2011107494A1 (en) 2010-03-03 2011-09-09 Sanofi Novel aromatic glycoside derivatives, medicaments containing said compounds, and the use thereof
US8927547B2 (en) 2010-05-21 2015-01-06 Noviga Research Ab Pyrimidine derivatives
TW201215388A (en) 2010-07-05 2012-04-16 Sanofi Sa (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201221505A (en) 2010-07-05 2012-06-01 Sanofi Sa Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
TW201215387A (en) 2010-07-05 2012-04-16 Sanofi Aventis Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
US9006241B2 (en) 2011-03-24 2015-04-14 Noviga Research Ab Pyrimidine derivatives
PH12016502453B1 (en) 2014-06-19 2022-11-23 Takeda Pharmaceuticals Co Heteroaryl compounds for kinase inhibition
KR20200144579A (en) 2018-05-14 2020-12-29 어리어드 파마슈티칼스, 인코포레이티드 Pharmaceutical salts of pyrimidine derivatives and methods of treatment of disorders
SG11202101417XA (en) * 2018-08-14 2021-03-30 Mei Pharma Inc Treatment of relapsed follicular lymphoma
AU2020397059A1 (en) 2019-12-06 2022-07-21 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
CN117794920A (en) 2021-06-04 2024-03-29 沃泰克斯药物股份有限公司 N-(Hydroxyalkyl(hetero)aryl)tetrahydrofurancarboxamide as a sodium channel modulator
CN114621206B (en) * 2022-03-24 2023-11-24 安徽医科大学 A 5-substituted pyrimidinediamine derivative and its preparation method and application

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GB0004888D0 (en) * 2000-03-01 2000-04-19 Astrazeneca Uk Ltd Chemical compounds
CN105348203B (en) * 2005-06-08 2018-09-18 里格尔药品股份有限公司 Inhibit the composition and method of JAK approach
EP1904479A2 (en) * 2005-07-11 2008-04-02 Sanofi-Aventis Novel 2,4-dianilinopyrimidine derivatives, the preparation thereof, their use as medicaments, pharmaceutical compositions and, in particular, as ikk inhibitors

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TW200916457A (en) 2009-04-16
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FR2919869A1 (en) 2009-02-13
WO2009056693A1 (en) 2009-05-07

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