WO2006058876A1 - Verfahren zur herstellung von annelierten piperazin-2-on derivaten sowie zwischenprodukte des verfahrens - Google Patents

Verfahren zur herstellung von annelierten piperazin-2-on derivaten sowie zwischenprodukte des verfahrens Download PDF

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Publication number
WO2006058876A1
WO2006058876A1 PCT/EP2005/056291 EP2005056291W WO2006058876A1 WO 2006058876 A1 WO2006058876 A1 WO 2006058876A1 EP 2005056291 W EP2005056291 W EP 2005056291W WO 2006058876 A1 WO2006058876 A1 WO 2006058876A1
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Prior art keywords
compound
alkyl
formula
hydrogen
added
Prior art date
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PCT/EP2005/056291
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German (de)
English (en)
French (fr)
Inventor
Adil Duran
Guenter Linz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim International GmbH
Boehringer Ingelheim Pharma GmbH and Co KG
Boehringer Ingelheim Pharmaceuticals Inc
Original Assignee
Boehringer Ingelheim International GmbH
Boehringer Ingelheim Pharma GmbH and Co KG
Boehringer Ingelheim Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35923724&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2006058876(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to JP2007543838A priority Critical patent/JP5164574B2/ja
Priority to AU2005311308A priority patent/AU2005311308B2/en
Priority to KR1020077015136A priority patent/KR101362131B1/ko
Priority to PL05823799T priority patent/PL1819706T3/pl
Priority to HRP20120980TT priority patent/HRP20120980T1/hr
Priority to CN2005800406546A priority patent/CN101065381B/zh
Priority to ES05823799T priority patent/ES2395829T3/es
Priority to EP05823799A priority patent/EP1819706B1/de
Priority to MEP-2012-124A priority patent/ME01470B/me
Priority to EA200701164A priority patent/EA012624B1/ru
Priority to HK08103652.5A priority patent/HK1113489B/xx
Application filed by Boehringer Ingelheim International GmbH, Boehringer Ingelheim Pharma GmbH and Co KG, Boehringer Ingelheim Pharmaceuticals Inc filed Critical Boehringer Ingelheim International GmbH
Priority to NZ556182A priority patent/NZ556182A/en
Priority to BRPI0518601-3A priority patent/BRPI0518601A2/pt
Priority to KR1020127028659A priority patent/KR101395591B1/ko
Priority to DK05823799.1T priority patent/DK1819706T3/da
Priority to MX2007006549A priority patent/MX2007006549A/es
Priority to SI200531631T priority patent/SI1819706T1/sl
Priority to CA2588857A priority patent/CA2588857C/en
Priority to RS20120519A priority patent/RS52533B/sr
Publication of WO2006058876A1 publication Critical patent/WO2006058876A1/de
Priority to NO20072283A priority patent/NO20072283L/no
Priority to IL183568A priority patent/IL183568A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/28—Oxygen atom

Definitions

  • the invention relates to a process for the preparation of fused piperazin-2-one derivatives of the general formula (I)
  • Pteridinone derivatives are known as agents with antiproliferative action from the prior art.
  • WO 03/020722 describes the use of Dihydropteridinonderivaten for the treatment of tumor diseases and methods for their preparation.
  • 7,8-Dihydro-5H-pteridin-6-one derivatives of the formula (I) are important intermediates in the synthesis of such active ingredients.
  • reduction methods have been applied to nitro compounds of formula (II) described below which are excessively colored Product mixtures led and complicated Aufarbeitungs- and cleaning steps required.
  • WO 96/36597 describes the catalytic hydrogenation of nitro compounds by means of noble metal catalysts with the addition of a vanadium compound, free amines but no lactams being disclosed as end products.
  • the present invention solves the above object via the synthesis method described below for compounds of formula (I).
  • the invention thus provides a process for the preparation of compounds of general formula I.
  • R is a radical selected from the group consisting of chlorine, fluorine, bromine,
  • R 2 is hydrogen or C 1 -C 3 -alkyl
  • R is hydrogen or a radical selected from the group consisting of optionally substituted C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 2 -C 12 -alkynyl and C C 6 -C 14 -aryl, or a radical selected from the group consisting of optionally substituted and / or bridged C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkenyl, C 7 -C 12 - Polycycloalkyl, C 7 -C 12 -polycycloalkenyl, C 5 -C 12 -spirocycloalkyl and saturated or unsaturated C 3 -C 12 -heterocycloalkyl containing 1 to 2 heteroatoms,
  • R 4 , R 5 are identical or different, hydrogen or optionally substituted C 1 -C 6 -alkyl, or
  • R 4 and R 5 together form a 2- to 5-membered alkyl bridge, which may contain 1 to 2 heteroatoms, or R 4 and R 3 or R 5 and R 3 together represent a saturated or unsaturated
  • R 1 -R 5 and A 1 , A 2 have the meaning indicated and R 6 is C 1 -C 4 -alkyl
  • a) in the presence of a hydrogenation catalyst is hydrogenated with hydrogen and b) a copper, iron or vanadium Compound is added, wherein the steps a) and b) can take place simultaneously or sequentially.
  • Iron or vanadium compound is further reduced to a compound of formula I.
  • the hydrogenation catalyst is selected from the group consisting of rhodium, ruthenium, iridium, platinum, palladium and nickel, preferably platinum, palladium and Raney nickel. Particularly preferred is platinum. Platinum may be in metallic or oxidized form as platinum oxide on supports such as activated carbon, silica, alumina, calcium carbonate, calcium phosphate, calcium sulfate, barium sulfate, titanium dioxide, magnesium oxide, iron oxide, lead oxide, lead sulfate or lead carbonate and optionally additionally doped with sulfur or Lead can be used. Preferred support material is activated carbon, silica or alumina.
  • Preferred copper compounds are compounds in which copper occupies the oxidation states I or II, for example the halides of copper such as CuCl, CuCl 2 , CuBr, CuBr 2 , CuI or CuSO 4 .
  • Preferred iron compounds are compounds in which iron assumes the oxidation states II or III, for example the halides of iron such as FeCl 2 , FeCl 3 , FeBr 2 , FeBr 3 , FeF 2 or other iron compounds such as FeSO 4 , FePO 4 or Fe ( acac) 2 .
  • Preferred vanadium compounds are compounds in which vanadium assumes the oxidation states 0, II, III, IV or V, for example inorganic or organic compounds or complexes such as V 2 O 3 , V 2 O 5 , V 2 O 4 , Na 4 VO 4 , NaVO 3 , NH 4 VO 3 , VOCl 2 , VOCl 3 , VOSO 4 , VCl 2 , VCl 3 , vanadium oxobis (1-phenyl-1,3-butanedionate), vanadium oxotriisopropoxide, vanadium (III) acetylacetonate [V (acac) 3 ] or vanadium (IV) oxyacetylacetonate [VO (acac) 2 ]. Particularly preferred is vanadium (IV) oxyacetylacetonate [VO (acac) 2 ].
  • the copper, iron or vanadium compound can optionally be used either directly at the beginning of the hydrogenation or after formation of the intermediate of the formula (III).
  • a solvent selected from the group consisting of: dipolar, aprotic solvents, for example dimethylformamide, dimethylacetamide, N-methylpyrrolidinone, dimethyl sulfoxide or sulfolane; Alcohols, for example Methanol, ethanol, 1-propanol, 2-propanol, the various isomeric alcohols of butane and pentane; Ethers, for example diethyl ether, methyl tert-butyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dioxane or dimethoxyethane; Esters, for example ethyl acetate, 2-propyl acetate or 1-butyl acetate; Ketones, for example acetone, methyl ethyl ketone or methyl isobutyl ketone; Carboxylic acids, for example acetic acid; Apolar solvents, for example tolu, acetic acid; Apolar solvents, for example
  • reaction temperature is between 0 ° C and 150 ° C, preferably between 20 ° C and 100 ° C.
  • Another object of the invention is a compound of formula (III)
  • R 1 to R 5 may have the meaning indicated.
  • the work-up of the reactions is carried out by customary methods, for example via extractive purification steps or precipitation and crystallization procedures.
  • the compounds according to the invention may be in the form of the individual optical isomers, mixtures of the individual enantiomers, diastereomers or racemates, in Form of tautomers and in the form of the free bases or the corresponding acid addition salts with acids - such as acid addition salts with hydrohalic acids, for example hydrochloric or hydrobromic acid, or organic acids, such as oxalic, fumaric, diglycol or methanesulfonic acid present.
  • alkyl groups and alkyl groups which are part of other groups are preferably 1 to 6, more preferably 1 to 4 carbon atoms, for example: methyl, ethyl, propyl, butyl, pentyl, hexyl, Heptyl, octyl, nonyl, decyl and dodecyl.
  • propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and dodecyl include all of the possible isomeric forms.
  • propyl includes the two isomeric radicals n-propyl and iso-propyl, the term butyl n-butyl, iso-butyl, sec. Butyl and tert. Butyl, called pentyl, iso-pentyl, neopentyl, etc.
  • alkyl groups it is optionally possible for one or more hydrogen atoms to be replaced by other radicals.
  • these alkyl groups may be substituted by fluorine.
  • all hydrogen atoms of the alkyl group may also be replaced.
  • alkyl bridge Branched and unbranched alkyl groups having 2 to 5 carbon atoms, for example ethylene, propylene, isopropylene, n-butylene, isobutyl, sec-butyl and tert-butyl, etc., are referred to as alkyl bridge, unless stated otherwise. Particular preference is given to ethylene, propylene and butylene bridges. In the abovementioned alkyl bridges, optionally 1 to 2 C atoms may be replaced by one or more heteroatoms selected from the group consisting of oxygen, nitrogen or sulfur.
  • Alkenyl groups include branched and unbranched alkylene groups having 2 to 12 carbon atoms, preferably 2 to 6 carbon atoms, more preferably 2 to 3 carbon atoms, as far as they are concerned have at least one double bond. Examples which may be mentioned are: ethenyl, propenyl, butenyl, pentenyl, etc. Unless stated otherwise, all of the possible isomeric forms are included among the abovementioned designations propenyl, butenyl, etc.
  • butenyl includes 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, and 1 -Ethyl-l -Ethenyl.
  • one or more hydrogen atoms in the abovementioned alkenyl groups may optionally be replaced by other radicals.
  • these alkyl groups may be substituted by the halogen atoms fluorine.
  • all hydrogen atoms of the alkenyl group may also be replaced.
  • Alkynyl groups are branched and unbranched alkynyl groups having 2 to 12 carbon atoms, provided they have at least one triple bond, for example ethynyl, propargyl, butynyl, pentynyl, hexynyl, etc., preferably ethynyl or propynyl.
  • one or more hydrogen atoms in the abovementioned alkynyl groups may optionally be replaced by other radicals.
  • these alkyl groups may be fluorine-substituted.
  • all hydrogen atoms of the alkynyl group may also be replaced.
  • aryl denotes an aromatic ring system having 6 to 14 carbon atoms, preferably 6 or 10 carbon atoms, preferably phenyl, which, unless otherwise stated, may carry, for example, one or more of the following substituents: OH, NO 2 , CN, OMe, -OCHF 2, -OCF 3, halogen, preferably fluorine or chlorine, C 1 -C 10 alkyl, C 1 -C preferably 5 alkyl, preferably C 1 - C 3 alkyl, more preferably methyl or ethyl, -OC 1 C 3 alkyl, preferably -O-methyl or -O-ethyl, -COOH, -COO-C 1 -C 4 -alkyl, preferably -O-methyl or -O-ethyl, -CONH 2 .
  • Cycloalkyl radicals having 3 to 12 carbon atoms are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, preferably cyclopropyl, cyclopentyl or cyclohexyl, where any of the abovementioned cycloalkyl radicals may optionally further carry one or more substituents, for example: OH, NO 2 , CN, OMe, -OCHF 2 , - OCF 3 or halogen, preferably fluorine or chlorine, C 1 -C 10 -alkyl, preferably C 1 -C 5 -alkyl, preferably C 1 -C 3 -alkyl, more preferably methyl or ethyl, -OC 1 -C 3 -alkyl, preferably -O-methyl or -O-ethyl, -COOH, -COO-
  • Cycloalkenyl radicals are cycloalkyl radicals having 3 to 12 carbon atoms which have at least one double bond, for example cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl or cycloheptenyl, preferably cyclopropenyl, cyclopentenyl or cyclohexenyl, where each of the abovementioned cycloalkenyl radicals may optionally also carry one or more substituents.
  • heterocycloalkyl radicals are, unless otherwise described in the definitions, 3 to 12-membered, preferably 5-, 6- or 7-membered, saturated or unsaturated heterocycles which may contain nitrogen, oxygen or sulfur as heteroatoms, for example tetrahydrofuran, tetrahydrofuranone, ⁇ Butylrolactone, ⁇ -pyran, ⁇ -pyran, dioxolane, tetrahydropyran, dioxane, dihydrothiophene, thiolane, dithiolane, pyrroline, pyrrolidine, pyrazoline, pyrazolidine, imidazoline, imidazolidine, tetrazole, piperidine, pyridazine, pyrimidine, pyrazine, piperazine, triazine, tetrazine , Morpholine, thiomorpholine, diazepane, oxazine, tetrahydro-oxazin
  • polycycloalkenyl radicals optionally bridged or / and substituted, 8-membered bi-, tri-, tetra- or pentacyclic cycloalkenyl radicals, preferably bicycloalkenyl or tricycloalkenyl radicals, if they have at least one double bond, for example norbornene.
  • spiroalkyl radicals optionally substituted spirocyclic C 5 -C 12 alkyl radicals are referred to.
  • the halogen is generally fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.
  • the substituent R 1 may be a radical selected from the group consisting of chlorine, fluorine, bromine, methanesulfonyl, ethanesulfonyl, trifluoromethanesulfonyl and para-toluenesulfonyl, preferably chlorine.
  • the substituent R 2 may be hydrogen or C 1 -C 3 -alkyl, preferably hydrogen.
  • the substituent R 3 may be hydrogen, or a radical selected from the group consisting of optionally substituted C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, and C 6 -C 14 aryl , preferably phenyl, or a radical selected from the group consisting of optionally substituted and / or bridged C 3 -C 12 cycloalkyl, preferably
  • Cyclopentyl, C 3 -C 12 cycloalkenyl, C 7 -C 12 polycycloalkyl, C 7 -C 12 polycycloalkenyl, C 5 -C 12 spirocycloalkyl, and saturated or unsaturated C 3 -C 12 heterocycloalkyl containing 1 to 2 heteroatoms contains mean.
  • R 4 , R 5 are identical or different and may be hydrogen, or optionally substituted C 1 -C 6 -alkyl, or R 4 and R 5 together form a 2- to 5-membered alkyl bridge which may contain 1 to 2 heteroatoms, or R 4 and R 3 or R 5 and R 3 together form a saturated or unsaturated C 3 -C 4 alkyl bridge, the optionally contain 1 heteroatom, mean.
  • R 6 may be a C 1 -C 4 alkyl, preferably methyl or ethyl.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/EP2005/056291 2004-12-02 2005-11-29 Verfahren zur herstellung von annelierten piperazin-2-on derivaten sowie zwischenprodukte des verfahrens Ceased WO2006058876A1 (de)

Priority Applications (21)

Application Number Priority Date Filing Date Title
RS20120519A RS52533B (sr) 2004-12-02 2005-11-29 Postupak za dobijanje kondenzovanih derivata piperazin-2-ona, kao i međuproizvodi ovog postupka
NZ556182A NZ556182A (en) 2004-12-02 2005-11-29 Method for producing pteridine and annelated piperazin-2-one derivatives and intermediates of said method
KR1020077015136A KR101362131B1 (ko) 2004-12-02 2005-11-29 고리화된 피페라진-2-온 유도체의 제조 방법 및 상기방법의 중간체
PL05823799T PL1819706T3 (pl) 2004-12-02 2005-11-29 Sposób wytwarzania skondensowanych pochodnych piperazyn-2-onu oraz produkty pośrednie tego sposobu
HRP20120980TT HRP20120980T1 (hr) 2004-12-02 2005-11-29 Postupak proizvodnje derivata aneliranih piperazin-2-ona kao i međuprodukti iz spomenutog postupka
CN2005800406546A CN101065381B (zh) 2004-12-02 2005-11-29 稠合的哌嗪-2-酮衍生物的制备方法及所述方法的中间体
ES05823799T ES2395829T3 (es) 2004-12-02 2005-11-29 Procedimiento para preparar derivados condensados de piperazin-2-ona, así como productos intermedios del procedimiento
EP05823799A EP1819706B1 (de) 2004-12-02 2005-11-29 Verfahren zur herstellung von annelierten piperazin-2-on derivaten sowie zwischenprodukte des verfahrens
MEP-2012-124A ME01470B (me) 2004-12-02 2005-11-29 Postupak za dobijanje anelacijskih piperazin-2-on derivata i intermedijera navedenog postupka
AU2005311308A AU2005311308B2 (en) 2004-12-02 2005-11-29 Method for producing annelated piperazin-2-one derivatives and intermediates of said method
HK08103652.5A HK1113489B (en) 2004-12-02 2005-11-29 Method for producing annelated piperazin-2-one derivatives and intermediates of said method
JP2007543838A JP5164574B2 (ja) 2004-12-02 2005-11-29 環付加ピペラジン−２−オン誘導体の製造方法及び前記方法の中間体
KR1020127028659A KR101395591B1 (ko) 2004-12-02 2005-11-29 고리화된 피페라진-2-온 유도체의 제조 방법 및 상기 방법의 중간체
EA200701164A EA012624B1 (ru) 2004-12-02 2005-11-29 Способ получения аннелированных производных пиперазин-2-она и соответствующие промежуточные продукты
BRPI0518601-3A BRPI0518601A2 (pt) 2004-12-02 2005-11-29 processo para preparaÇço de derivados de piperazin-2-ona anelados bem como produtos intermediÁrios do processo
DK05823799.1T DK1819706T3 (da) 2004-12-02 2005-11-29 Fremgangsmåde til fremstilling af annelerede piperazin-2-on-derivater samt mellemprodukter af fremgangsmåden
MX2007006549A MX2007006549A (es) 2004-12-02 2005-11-29 Procedimiento para preparar derivados condensados de piperazin-2-ona, asi como productos intermedios del procedimiento.
SI200531631T SI1819706T1 (sl) 2004-12-02 2005-11-29 Postopek za pripravo aneliranih derivatov piperazin-2-ona in intermediati postopka
CA2588857A CA2588857C (en) 2004-12-02 2005-11-29 Method for producing annelated piperazin-2-one derivatives and intermediates of said method
NO20072283A NO20072283L (no) 2004-12-02 2007-05-03 Fremgangsmate for fremstilling av annelerte piperazin-2-on derivater samt mellomprodukter i samme
IL183568A IL183568A (en) 2004-12-02 2007-05-31 Process for making 7,8-dihydro-5 h-patridine-6-onh

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004058337A DE102004058337A1 (de) 2004-12-02 2004-12-02 Verfahren zur Herstellung von annelierten Piperazin-2-on Derivaten
DE102004058337.4 2004-12-02

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WO2006058876A1 true WO2006058876A1 (de) 2006-06-08

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PCT/EP2005/056291 Ceased WO2006058876A1 (de) 2004-12-02 2005-11-29 Verfahren zur herstellung von annelierten piperazin-2-on derivaten sowie zwischenprodukte des verfahrens

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US (9) US7238807B2 (enExample)
EP (2) EP2436685B1 (enExample)
JP (1) JP5164574B2 (enExample)
KR (2) KR101362131B1 (enExample)
CN (3) CN102070637B (enExample)
AR (1) AR053100A1 (enExample)
AU (1) AU2005311308B2 (enExample)
BR (1) BRPI0518601A2 (enExample)
CA (1) CA2588857C (enExample)
CL (1) CL2013002895A1 (enExample)
CY (1) CY1113625T1 (enExample)
DE (1) DE102004058337A1 (enExample)
DK (2) DK1819706T3 (enExample)
EA (1) EA012624B1 (enExample)
ES (2) ES2548680T3 (enExample)
HR (1) HRP20120980T1 (enExample)
HU (1) HUE027689T2 (enExample)
IL (1) IL183568A (enExample)
ME (1) ME01470B (enExample)
MX (1) MX2007006549A (enExample)
MY (1) MY147459A (enExample)
NO (1) NO20072283L (enExample)
NZ (1) NZ556182A (enExample)
PE (2) PE20090488A1 (enExample)
PL (2) PL1819706T3 (enExample)
PT (1) PT1819706E (enExample)
RS (1) RS52533B (enExample)
SG (2) SG141461A1 (enExample)
SI (1) SI1819706T1 (enExample)
TW (1) TWI362391B (enExample)
UA (1) UA89390C2 (enExample)
UY (1) UY29233A1 (enExample)
WO (1) WO2006058876A1 (enExample)
ZA (1) ZA200703368B (enExample)

Cited By (6)

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EP2100894A1 (en) 2008-03-12 2009-09-16 4Sc Ag Pyridopyrimidines used as Plk1 (polo-like kinase) inhibitors
US7622463B2 (en) 2006-02-14 2009-11-24 Vertex Pharmaceuticals Incorporated Dihydrodiazepines useful as inhibitors of protein kinases
US7799781B2 (en) 2007-02-01 2010-09-21 Astrazeneca Ab 5,6,7,8-tetrahydropteridine derivatives as HSP90 inhibitors
WO2011036566A1 (en) 2009-09-25 2011-03-31 Vertex Pharmaceuticals Incorporated Methods for preparing pyrimidine derivatives useful as protein kinase inhibitors
WO2011035534A1 (zh) 2009-09-22 2011-03-31 江苏恒瑞医药股份有限公司 二氢喋啶酮类衍生物、其制备方法及其在医药上的应用
WO2011038185A2 (en) 2009-09-25 2011-03-31 Vertex Pharmaceuticals Incorporated Methods for preparing pyrimidine derivatives useful as protein kinase inhibitors

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US6861422B2 (en) * 2003-02-26 2005-03-01 Boehringer Ingelheim Pharma Gmbh & Co. Kg Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions
DE102004029784A1 (de) * 2004-06-21 2006-01-05 Boehringer Ingelheim Pharma Gmbh & Co. Kg Neue 2-Benzylaminodihydropteridinone, Verfahren zur deren Herstellung und deren Verwendung als Arzneimittel
DE102004033670A1 (de) 2004-07-09 2006-02-02 Boehringer Ingelheim Pharma Gmbh & Co. Kg Neue Pyridodihydropyrazinone, Verfahren zu Ihrer Herstellung und Ihre Verwendung als Arzneimittel
US20060058311A1 (en) * 2004-08-14 2006-03-16 Boehringer Ingelheim International Gmbh Combinations for the treatment of diseases involving cell proliferation
US7728134B2 (en) * 2004-08-14 2010-06-01 Boehringer Ingelheim International Gmbh Hydrates and polymorphs of 4[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide, process for their manufacture and their use as medicament
US20060035903A1 (en) * 2004-08-14 2006-02-16 Boehringer Ingelheim International Gmbh Storage stable perfusion solution for dihydropteridinones
US7759485B2 (en) * 2004-08-14 2010-07-20 Boehringer Ingelheim International Gmbh Process for the manufacture of dihydropteridinones
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