SK16352000A3 - Indolové deriváty, spôsob ich výroby, ich použitie na liečivá obsahujúce tieto zlúčeniny - Google Patents

Indolové deriváty, spôsob ich výroby, ich použitie na liečivá obsahujúce tieto zlúčeniny Download PDF

Info

Publication number: SK16352000A3
Authority: SK; Slovakia
Prior art keywords: indolyl; formula; methanone; dihydro; alkyl
Prior art date: 1998-05-04

Application number

SK1635-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Siavosh Mahboobi

Sabine Kuhr

Herwig Pongratz

Alfred Popp

Harald Hufsky

Frank-D. B�Hmer

Steffen Teller

Andrea Uecker

Thomas Beckers

Original Assignee

Zentaris Ag

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.)

1998-05-04

Filing date

1999-04-22

Publication date

2002-07-02

1998-08-25 Priority claimed from DE19838506A external-priority patent/DE19838506C2/de

1999-04-22 Application filed by Zentaris Ag filed Critical Zentaris Ag

2002-07-02 Publication of SK16352000A3 publication Critical patent/SK16352000A3/sk

Links

239000003814 drug Substances 0.000 title claims abstract description 4
150000001875 compounds Chemical class 0.000 title claims description 35
238000000034 method Methods 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 4
229940054051 antipsychotic indole derivative Drugs 0.000 title 1
150000002475 indoles Chemical class 0.000 title 1
239000003112 inhibitor Substances 0.000 claims abstract description 3
229940121358 tyrosine kinase inhibitor Drugs 0.000 claims abstract description 3
239000005483 tyrosine kinase inhibitor Substances 0.000 claims abstract description 3
-1 acyclic primary amine Chemical class 0.000 claims description 110
229910052757 nitrogen Inorganic materials 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
150000003254 radicals Chemical class 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
150000005840 aryl radicals Chemical class 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
BIKSKRPHKQWJCW-UHFFFAOYSA-N 3,4-dibromopyrrole-2,5-dione Chemical compound BrC1=C(Br)C(=O)NC1=O BIKSKRPHKQWJCW-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 5
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 4
150000001720 carbohydrates Chemical class 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
QTIQVLAVCXXZPS-UHFFFAOYSA-N 1h-indol-2-yl-(5-methoxy-1h-indol-2-yl)methanone Chemical compound C1=CC=C2NC(C(=O)C=3NC4=CC=C(C=C4C=3)OC)=CC2=C1 QTIQVLAVCXXZPS-UHFFFAOYSA-N 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
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150000001721 carbon Chemical group 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
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125000004429 atom Chemical group 0.000 claims description 2
125000000852 azido group Chemical class *N=[N+]=[N-] 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000001041 indolyl group Chemical group 0.000 claims 1
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
230000001575 pathological effect Effects 0.000 abstract description 6
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
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239000000203 mixture Substances 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
210000004027 cell Anatomy 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
229910004298 SiO 2 Inorganic materials 0.000 description 16
239000002904 solvent Substances 0.000 description 15
238000000354 decomposition reaction Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
108091008606 PDGF receptors Proteins 0.000 description 11
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000013078 crystal Substances 0.000 description 9
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238000006366 phosphorylation reaction Methods 0.000 description 8
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000001993 wax Substances 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
108091000080 Phosphotransferase Proteins 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
102000020233 phosphotransferase Human genes 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000003102 growth factor Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 4
238000003556 assay Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
230000026731 phosphorylation Effects 0.000 description 4
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230000035755 proliferation Effects 0.000 description 4
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238000003756 stirring Methods 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
102000009024 Epidermal Growth Factor Human genes 0.000 description 3
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
101100335081 Mus musculus Flt3 gene Proteins 0.000 description 3
230000004913 activation Effects 0.000 description 3
230000035578 autophosphorylation Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001514 detection method Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 3
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HYJTUULYIOBNLS-UHFFFAOYSA-N bis(1h-indol-3-yl)methanone Chemical compound C1=CC=C2C(C(C=3C4=CC=CC=C4NC=3)=O)=CNC2=C1 HYJTUULYIOBNLS-UHFFFAOYSA-N 0.000 description 2
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DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
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230000006444 vascular growth Effects 0.000 description 1

Classifications

- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
- A61P5/04—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
- 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
- C07D403/14—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 three or more hetero rings
- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems

SK1635-2000A 1998-05-04 1999-04-22 Indolové deriváty, spôsob ich výroby, ich použitie na liečivá obsahujúce tieto zlúčeniny SK16352000A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19819835		1998-05-04
DE19838506A DE19838506C2 (de)	1998-05-04	1998-08-25	Indolderivate und deren Verwendung zur Behandlung von malignen und anderen, auf pathologischen Zellproliferationen beruhenden Erkrankungen
PCT/DE1999/001214 WO1999057117A2 (fr)	1998-05-04	1999-04-22	Derives indoliques et leur utilisation pour le traitement de maladies malignes et autres induites par des proliferations cellulaires pathologiques

Publications (1)

Publication Number	Publication Date
SK16352000A3 true SK16352000A3 (sk)	2002-07-02

Family

ID=26045937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1635-2000A SK16352000A3 (sk)	1998-05-04	1999-04-22	Indolové deriváty, spôsob ich výroby, ich použitie na liečivá obsahujúce tieto zlúčeniny

Country Status (22)

Country	Link
US (2)	US6407102B1 (fr)
EP (1)	EP1109785B1 (fr)
JP (1)	JP2002514572A (fr)
CN (1)	CN1151127C (fr)
AT (1)	ATE230394T1 (fr)
AU (1)	AU752464B2 (fr)
BG (1)	BG104996A (fr)
BR (1)	BR9911017A (fr)
CA (1)	CA2330756C (fr)
CZ (1)	CZ20003960A3 (fr)
DE (1)	DE59903921D1 (fr)
DK (1)	DK1109785T3 (fr)
ES (1)	ES2190221T3 (fr)
HK (1)	HK1038354A1 (fr)
HU (1)	HUP0102563A3 (fr)
IL (1)	IL139056A0 (fr)
NO (1)	NO317261B1 (fr)
NZ (1)	NZ507735A (fr)
PL (1)	PL346840A1 (fr)
SK (1)	SK16352000A3 (fr)
TR (1)	TR200003206T2 (fr)
WO (1)	WO1999057117A2 (fr)

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TWI490219B (zh)	2009-06-29	2015-07-01	Incyte Corp	作為ｐｉ３ｋ抑制劑之嘧啶酮
CN101704828A (zh) *	2009-11-04	2010-05-12	中国科学院昆明植物研究所	山橙素类双吲哚化合物,其药物组合物及其制备方法和用途
AR079529A1 (es) *	2009-12-18	2012-02-01	Incyte Corp	Derivados arilo y heteroarilo sustituidos y fundidos como inhibidores de la pi3k
US8759359B2 (en) *	2009-12-18	2014-06-24	Incyte Corporation	Substituted heteroaryl fused derivatives as PI3K inhibitors
EP2558463A1 (fr)	2010-04-14	2013-02-20	Incyte Corporation	Dérivés condensés en tant qu'inhibiteurs de i3
WO2011163195A1 (fr)	2010-06-21	2011-12-29	Incyte Corporation	Dérivés condensés de pyrrole en tant qu'inhibiteurs de pi3k
TW201249844A (en)	2010-12-20	2012-12-16	Incyte Corp	N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
WO2012125629A1 (fr)	2011-03-14	2012-09-20	Incyte Corporation	Dérivés diamino-pyrimidines et diamino-pyridines substituées en tant qu'inhibiteurs de pi3k
US9126948B2 (en)	2011-03-25	2015-09-08	Incyte Holdings Corporation	Pyrimidine-4,6-diamine derivatives as PI3K inhibitors
TWI543980B (zh)	2011-09-02	2016-08-01	英塞特控股公司	作為ｐｉ３ｋ抑制劑之雜環基胺
AR090548A1 (es)	2012-04-02	2014-11-19	Incyte Corp	Azaheterociclobencilaminas biciclicas como inhibidores de pi3k
US10077277B2 (en)	2014-06-11	2018-09-18	Incyte Corporation	Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
LT3831833T (lt)	2015-02-27	2023-02-27	Incyte Holdings Corporation	Pi3k inhibitoriaus gamybos būdai
WO2016183060A1 (fr)	2015-05-11	2016-11-17	Incyte Corporation	Procédé de synthèse d'un inhibiteur de phospho-inositide 3-kinases
US9988401B2 (en)	2015-05-11	2018-06-05	Incyte Corporation	Crystalline forms of a PI3K inhibitor
CN106317169B (zh) *	2015-06-23	2019-07-02	首都医科大学	双吲哚-二肽衍生物,其合成,抗血栓活性和制备抗血栓剂的应用
WO2018024172A1 (fr) *	2016-08-05	2018-02-08	The University Of Hong Kong	Complexes de platine et leurs procédés d'utilisation
KR20210142154A (ko)	2019-03-21	2021-11-24	옹쎄오	암 치료를 위한 키나제 억제제와 조합된 dbait 분자
WO2020245208A1 (fr)	2019-06-04	2020-12-10	INSERM (Institut National de la Santé et de la Recherche Médicale)	Utilisation de cd9 en tant que biomarqueur et en tant que biocible dans la glomérulonéphrite ou la glomérulosclérose
US20220401436A1 (en)	2019-11-08	2022-12-22	INSERM (Institute National de la Santé et de la Recherche Médicale)	Methods for the treatment of cancers that have acquired resistance to kinase inhibitors
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1999
- 1999-04-22 TR TR2000/03206T patent/TR200003206T2/xx unknown
- 1999-04-22 SK SK1635-2000A patent/SK16352000A3/sk unknown
- 1999-04-22 IL IL13905699A patent/IL139056A0/xx not_active IP Right Cessation
- 1999-04-22 PL PL99346840A patent/PL346840A1/xx not_active Application Discontinuation
- 1999-04-22 HU HU0102563A patent/HUP0102563A3/hu unknown
- 1999-04-22 WO PCT/DE1999/001214 patent/WO1999057117A2/fr not_active Application Discontinuation
- 1999-04-22 BR BR9911017-2A patent/BR9911017A/pt not_active IP Right Cessation
- 1999-04-22 CA CA002330756A patent/CA2330756C/fr not_active Expired - Fee Related
- 1999-04-22 ES ES99927711T patent/ES2190221T3/es not_active Expired - Lifetime
- 1999-04-22 CZ CZ20003960A patent/CZ20003960A3/cs unknown
- 1999-04-22 EP EP99927711A patent/EP1109785B1/fr not_active Expired - Lifetime
- 1999-04-22 AT AT99927711T patent/ATE230394T1/de not_active IP Right Cessation
- 1999-04-22 AU AU44975/99A patent/AU752464B2/en not_active Ceased
- 1999-04-22 JP JP2000547087A patent/JP2002514572A/ja not_active Withdrawn
- 1999-04-22 DK DK99927711T patent/DK1109785T3/da active
- 1999-04-22 DE DE59903921T patent/DE59903921D1/de not_active Expired - Fee Related
- 1999-04-22 CN CNB998058033A patent/CN1151127C/zh not_active Expired - Fee Related
- 1999-05-04 US US09/305,115 patent/US6407102B1/en not_active Expired - Fee Related
2000
- 2000-10-24 NZ NZ507735A patent/NZ507735A/xx unknown
- 2000-10-27 NO NO20005448A patent/NO317261B1/no unknown
- 2000-11-28 BG BG104996A patent/BG104996A/xx unknown
2001
- 2001-12-27 HK HK01109122A patent/HK1038354A1/xx not_active IP Right Cessation
2002
- 2002-05-03 US US10/137,653 patent/US6812243B2/en not_active Expired - Fee Related

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CN1151127C (zh)	2004-05-26
NO20005448D0 (no)	2000-10-27
IL139056A0 (en)	2001-11-25
US6812243B2 (en)	2004-11-02
US6407102B1 (en)	2002-06-18
JP2002514572A (ja)	2002-05-21
TR200003206T2 (tr)	2001-07-23
ES2190221T3 (es)	2003-07-16
ATE230394T1 (de)	2003-01-15
BG104996A (en)	2001-07-31
BR9911017A (pt)	2001-02-06
US20030008898A1 (en)	2003-01-09
WO1999057117A2 (fr)	1999-11-11
AU4497599A (en)	1999-11-23
NZ507735A (en)	2003-04-29
HUP0102563A2 (hu)	2001-11-28
HK1038354A1 (en)	2002-03-15
NO20005448L (no)	2000-10-27
WO1999057117A3 (fr)	2001-04-12
PL346840A1 (en)	2002-02-25
NO317261B1 (no)	2004-09-27
CN1310705A (zh)	2001-08-29
CA2330756A1 (fr)	1999-11-11
EP1109785A2 (fr)	2001-06-27
CA2330756C (fr)	2007-10-02
AU752464B2 (en)	2002-09-19
EP1109785B1 (fr)	2003-01-02
CZ20003960A3 (cs)	2002-04-17
HUP0102563A3 (en)	2003-04-28
DK1109785T3 (da)	2003-04-22
DE59903921D1 (de)	2003-02-06

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SK16352000A3 (sk)	2002-07-02	Indolové deriváty, spôsob ich výroby, ich použitie na liečivá obsahujúce tieto zlúčeniny
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AU2005202387B2 (en)	2009-03-26	Indolylmaleimide derivatives as protein kinase C inhibitors
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US20040053949A1 (en)	2004-03-18	Indolylmaleimide derivatives
JP2019520412A (ja)	2019-07-18	哺乳動物のチロシンキナーゼｒｏｒ１活性の阻害剤として有用な２−フェニルイミダゾ［４，５−ｂ］ピリジン−７−アミン誘導体
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KR20110082094A (ko)	2011-07-15	６-시클로아미노-３-（１ｈ-피롤로［２,３-ｂ］피리딘-４-일）이미다조［1,２-ｂ］피리다진 유도체, 그의 제법 및 그의 치료적 용도
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WO2020173328A1 (fr)	2020-09-03	Dérivé de pyrrole et son procédé de préparation et son application
KR20010043288A (ko)	2001-05-25	인돌 유도체 및 병리학적 세포 증식으로 인한 악성 질환과기타 질환의 치료에 있어서 이의 용도
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MXPA00010739A (en)	2001-09-07	Indole derivatives and their use in the treatment of malignant and other diseases caused by pathological cell proliferation
CA2496859A1 (fr)	1999-11-11	Derives indoliques et leur utilisation pour le traitement de maladies malignes et autres induites par des proliferations cellulaires pathologiques