PT1990343E - Azaindoles - Google Patents

Azaindoles Download PDF

Info

Publication number: PT1990343E
Authority: PT; Portugal
Prior art keywords: quot; alkyl; group; cll; aryl
Prior art date: 1999-12-24

Application number

PT08162392T

Other languages

English (en)

Portuguese (pt)

Inventor

Paul Joseph Cox

Tahir Nadeem Majid

Andrew David Morley

Shelley Amendola

Stephanie Deprets

Chris Edlin

Justine Yeun Quai Lai

Original Assignee

Aventis Pharma Ltd

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.)

1999-12-24

Filing date

2000-12-27

Publication date

2012-05-22

2000-12-27 Application filed by Aventis Pharma Ltd filed Critical Aventis Pharma Ltd

2012-05-22 Publication of PT1990343E publication Critical patent/PT1990343E/pt

Links

125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 330
239000000203 mixture Substances 0.000 claims abstract description 128
125000000217 alkyl group Chemical group 0.000 claims abstract description 72
150000003839 salts Chemical class 0.000 claims abstract description 54
125000003118 aryl group Chemical group 0.000 claims abstract description 47
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 43
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 31
125000003342 alkenyl group Chemical group 0.000 claims abstract description 24
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
125000005843 halogen group Chemical group 0.000 claims abstract description 21
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 18
239000012453 solvate Substances 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 8
125000001424 substituent group Chemical group 0.000 claims abstract description 7
125000001475 halogen functional group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
229910014033 C-OH Inorganic materials 0.000 claims abstract description 4
229910014570 C—OH Inorganic materials 0.000 claims abstract description 4
-1 cyclic acetal Chemical class 0.000 claims description 137
239000002253 acid Substances 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
125000000753 cycloalkyl group Chemical group 0.000 claims description 28
125000001041 indolyl group Chemical group 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 25
108091000080 Phosphotransferase Proteins 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 21
102000020233 phosphotransferase Human genes 0.000 claims description 21
229920006395 saturated elastomer Polymers 0.000 claims description 19
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 15
206010028980 Neoplasm Diseases 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
230000002401 inhibitory effect Effects 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
150000001204 N-oxides Chemical class 0.000 claims description 11
229910005965 SO 2 Inorganic materials 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
150000004677 hydrates Chemical class 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 8
125000003302 alkenyloxy group Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
238000002560 therapeutic procedure Methods 0.000 claims description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
AZEKOCYKHUJNKS-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxycyclobutane-1-carboxylic acid Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=1OC1(C(O)=O)CCC1 AZEKOCYKHUJNKS-UHFFFAOYSA-N 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
206010061218 Inflammation Diseases 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
125000003435 aroyl group Chemical group 0.000 claims description 4
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
230000004054 inflammatory process Effects 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000006414 CCl Chemical group ClC* 0.000 claims description 3
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000005239 aroylamino group Chemical group 0.000 claims description 3
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
208000027866 inflammatory disease Diseases 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
FTJGHPGHUSLQAK-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C#N FTJGHPGHUSLQAK-UHFFFAOYSA-N 0.000 claims description 2
UVPSSGJTBLNVRE-UHFFFAOYSA-N Moniliformin Natural products O=C1C(OC)=CC(=O)C=2C1=C1C(=O)C(OC)=CC(=O)C1=CC=2 UVPSSGJTBLNVRE-UHFFFAOYSA-N 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
KGPQKNJSZNXOPV-UHFFFAOYSA-N moniliformin Chemical compound OC1=CC(=O)C1=O KGPQKNJSZNXOPV-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims 1
210000000936 intestine Anatomy 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
102000001253 Protein Kinase Human genes 0.000 abstract description 8
108060006633 protein kinase Proteins 0.000 abstract description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 302
239000007787 solid Substances 0.000 description 193
239000000243 solution Substances 0.000 description 147
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 105
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 100
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 86
239000000460 chlorine Substances 0.000 description 78
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
210000004027 cell Anatomy 0.000 description 56
238000000034 method Methods 0.000 description 56
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
239000011541 reaction mixture Substances 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 50
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 49
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 41
210000004072 lung Anatomy 0.000 description 41
238000003756 stirring Methods 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
238000004809 thin layer chromatography Methods 0.000 description 34
238000005481 NMR spectroscopy Methods 0.000 description 33
239000000427 antigen Substances 0.000 description 33
108091007433 antigens Proteins 0.000 description 33
102000036639 antigens Human genes 0.000 description 33
239000000377 silicon dioxide Substances 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
230000000694 effects Effects 0.000 description 30
229910052757 nitrogen Inorganic materials 0.000 description 30
238000010992 reflux Methods 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
230000008569 process Effects 0.000 description 29
125000001309 chloro group Chemical group Cl* 0.000 description 28
239000012442 inert solvent Substances 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 28
235000019341 magnesium sulphate Nutrition 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
230000005764 inhibitory process Effects 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
238000004128 high performance liquid chromatography Methods 0.000 description 25
YTWCODZNNZBQFV-KBXCAEBGSA-N (1R,2R)-2-[[4-(2-fluoro-5-propan-2-yloxyphenyl)phenoxy]methyl]cyclopropane-1-carboxylic acid Chemical compound FC1=C(C=C(C=C1)OC(C)C)C1=CC=C(C=C1)OC[C@H]1[C@@H](C1)C(=O)O YTWCODZNNZBQFV-KBXCAEBGSA-N 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
238000012360 testing method Methods 0.000 description 21
108010058846 Ovalbumin Proteins 0.000 description 20
241000700159 Rattus Species 0.000 description 20
230000000875 corresponding effect Effects 0.000 description 20
229940092253 ovalbumin Drugs 0.000 description 20
239000002585 base Substances 0.000 description 19
239000012267 brine Substances 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
241001465754 Metazoa Species 0.000 description 18
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
239000000284 extract Substances 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
108090000461 Aurora Kinase A Proteins 0.000 description 16
102100032311 Aurora kinase A Human genes 0.000 description 15
102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 description 15
108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
210000001519 tissue Anatomy 0.000 description 15
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
229940079593 drug Drugs 0.000 description 14
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
230000004044 response Effects 0.000 description 14
239000011780 sodium chloride Substances 0.000 description 14
239000000725 suspension Substances 0.000 description 14
238000003556 assay Methods 0.000 description 13
239000012634 fragment Substances 0.000 description 13
CVDGAVDNVQNYQT-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 CVDGAVDNVQNYQT-UHFFFAOYSA-N 0.000 description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
239000002609 medium Substances 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
239000012312 sodium hydride Substances 0.000 description 12
229910000104 sodium hydride Inorganic materials 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
239000006071 cream Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
108091003079 Bovine Serum Albumin Proteins 0.000 description 10
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
239000012894 fetal calf serum Substances 0.000 description 10
239000012458 free base Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
230000006978 adaptation Effects 0.000 description 9
230000029936 alkylation Effects 0.000 description 9
238000005804 alkylation reaction Methods 0.000 description 9
150000001721 carbon Chemical group 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
239000010410 layer Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
238000000746 purification Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000000758 substrate Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
229920005654 Sephadex Polymers 0.000 description 8
239000012507 Sephadex™ Substances 0.000 description 8
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 8
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 8
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 8
239000000872 buffer Substances 0.000 description 8
229910002091 carbon monoxide Inorganic materials 0.000 description 8
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
231100000673 dose–response relationship Toxicity 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
230000014509 gene expression Effects 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
210000000440 neutrophil Anatomy 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 7
108090000695 Cytokines Proteins 0.000 description 7
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 7
102000000551 Syk Kinase Human genes 0.000 description 7
108010016672 Syk Kinase Proteins 0.000 description 7
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 7
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
210000003979 eosinophil Anatomy 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000001914 filtration Methods 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
229910052736 halogen Inorganic materials 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 6
102000004127 Cytokines Human genes 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
IQFYYKKMVGJFEH-UDIABACLSA-N [14C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1 Chemical compound [14C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-UDIABACLSA-N 0.000 description 6
208000010668 atopic eczema Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
210000003630 histaminocyte Anatomy 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
125000002346 iodo group Chemical group I* 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
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230000003449 preventive effect Effects 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000005554 pyridyloxy group Chemical group 0.000 description 1
BQMPGKPTOHKYHS-UHFFFAOYSA-N pyrrole-2-carbonitrile Natural products N#CC1=CC=CN1 BQMPGKPTOHKYHS-UHFFFAOYSA-N 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
238000011002 quantification Methods 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
238000007420 radioactive assay Methods 0.000 description 1
238000011552 rat model Methods 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
238000003757 reverse transcription PCR Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
201000005404 rubella Diseases 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000005204 segregation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000007781 signaling event Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000020347 spindle assembly Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
102000009076 src-Family Kinases Human genes 0.000 description 1
108010087686 src-Family Kinases Proteins 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
201000004595 synovitis Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
SKJFKFSWFAPTSH-UHFFFAOYSA-N tert-butyl 3-bromo-5-[(2-methylpropan-2-yl)oxycarbonylamino]indole-1-carboxylate Chemical compound CC(C)(C)OC(=O)NC1=CC=C2N(C(=O)OC(C)(C)C)C=C(Br)C2=C1 SKJFKFSWFAPTSH-UHFFFAOYSA-N 0.000 description 1
JYVIXXYTWJADKB-UHFFFAOYSA-N tert-butyl 3-bromo-6-methoxy-5-phenylmethoxyindole-1-carboxylate Chemical compound COC1=CC=2N(C(=O)OC(C)(C)C)C=C(Br)C=2C=C1OCC1=CC=CC=C1 JYVIXXYTWJADKB-UHFFFAOYSA-N 0.000 description 1
BRPGFFZFIUSCME-UHFFFAOYSA-N tert-butyl 5-methoxy-3-[4-methoxy-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]indole-1-carboxylate Chemical compound C12=CC(OC)=CC=C2N(C(=O)OC(C)(C)C)C=C1C1=CC2=C(OC)C=CN=C2N1S(=O)(=O)C1=CC=C(C)C=C1 BRPGFFZFIUSCME-UHFFFAOYSA-N 0.000 description 1
KVELIXMOCRPWAV-UHFFFAOYSA-N tert-butyl-[2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-2,3-dihydroindol-1-yl]ethoxy]-dimethylsilane Chemical compound C1=CN=C2NC(C3CN(CCO[Si](C)(C)C(C)(C)C)C4=CC=C(C=C43)OC)=CC2=N1 KVELIXMOCRPWAV-UHFFFAOYSA-N 0.000 description 1
RZMPCCIQPRHXCC-UHFFFAOYSA-N tert-butyl-[3-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propoxy]-dimethylsilane Chemical compound C1=CN=C2NC(C3=CN(CCCO[Si](C)(C)C(C)(C)C)C4=CC=C(C=C43)OC)=CC2=N1 RZMPCCIQPRHXCC-UHFFFAOYSA-N 0.000 description 1
IJAGVSQDJDQRIM-UHFFFAOYSA-N tert-butyl-dimethyl-[3-[3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propoxy]silane Chemical compound C12=CC=CC=C2N(CCCO[Si](C)(C)C(C)(C)C)C=C1C1=CC2=NC=CN=C2N1 IJAGVSQDJDQRIM-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
PXSQLMPCRDHKPE-UHFFFAOYSA-N trimethyl-[5-[1-methyl-3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]indol-5-yl]tetrazol-1-yl]stannane Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC=C2C=C1C1=CN(C)C2=CC=C(C=3N(N=NN=3)[Sn](C)(C)C)C=C12 PXSQLMPCRDHKPE-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000005748 tumor development Effects 0.000 description 1
150000003668 tyrosines Chemical class 0.000 description 1
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
210000005253 yeast cell Anatomy 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/437—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 five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
- 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
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

PT08162392T 1999-12-24 2000-12-27 Azaindoles PT1990343E (pt)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9930698.7A GB9930698D0 (en)	1999-12-24	1999-12-24	Chemical compounds
US21581800P	2000-07-05	2000-07-05

Publications (1)

Publication Number	Publication Date
PT1990343E true PT1990343E (pt)	2012-05-22

Family

ID=10867079

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
PT08162392T PT1990343E (pt)	1999-12-24	2000-12-27	Azaindoles
PT00985695T PT1263759E (pt)	1999-12-24	2000-12-27	Azaindoles

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
PT00985695T PT1263759E (pt)	1999-12-24	2000-12-27	Azaindoles

Country Status (12)

Country	Link
JP (1)	JP4871474B2 (sr)
AT (2)	ATE552258T1 (sr)
DE (1)	DE60044946D1 (sr)
DK (2)	DK1263759T3 (sr)
ES (2)	ES2382759T3 (sr)
GB (1)	GB9930698D0 (sr)
ME (1)	MEP49908A (sr)
PL (1)	PL218884B1 (sr)
PT (2)	PT1990343E (sr)
RS (2)	RS20100123A (sr)
UA (1)	UA76410C2 (sr)
ZA (1)	ZA200204126B (sr)

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Publication number	Priority date	Publication date	Assignee	Title
GB0422057D0 (en) *	2004-10-05	2004-11-03	Astrazeneca Ab	Novel compounds
ES2408318T3 (es) *	2005-12-23	2013-06-20	Glaxosmithkline Llc	Inhibidores de azaindol de las cinasas Aurora
CL2007002617A1 (es) *	2006-09-11	2008-05-16	Sanofi Aventis	Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto.
JP5274805B2 (ja) *	2006-09-20	2013-08-28	三菱化学株式会社	フッ素化芳香族化合物の製造方法
ES2464458T3 (es) *	2008-12-05	2014-06-02	F. Hoffmann-La Roche Ag	Pirrolopirazinil-ureas como inhibidores de quinasas
US8816085B2 (en) *	2009-08-26	2014-08-26	Takeda Gmbh	Methylpyrrolopyridinecarboxamides
JP2016514113A (ja) *	2013-03-14	2016-05-19	アッヴィ・インコーポレイテッド	ピロロ［２，３−ｂ］ピリジンｃｄｋ９キナーゼ阻害剤

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DE69728688T2 (de) *	1996-11-19	2004-08-19	Amgen Inc., Thousand Oaks	Aryl und heteroaryl substituierte kondensierte pyrrole als entzündunghemmende mittel
WO1998047899A1 (en) *	1997-04-24	1998-10-29	Ortho-Mcneil Corporation, Inc.	Substituted pyrrolopyridines useful in the treatment of inflammatory diseases
CA2306870A1 (en) *	1997-10-20	1999-04-29	David Michael Goldstein	Bicyclic kinase inhibitors

1999
- 1999-12-24 GB GBGB9930698.7A patent/GB9930698D0/en not_active Ceased
2000
- 2000-12-27 AT AT08162392T patent/ATE552258T1/de active
- 2000-12-27 RS RSP-2010/0123A patent/RS20100123A/sr unknown
- 2000-12-27 RS YUP-462/02A patent/RS51303B/sr unknown
- 2000-12-27 ES ES08162392T patent/ES2382759T3/es not_active Expired - Lifetime
- 2000-12-27 JP JP2001549392A patent/JP4871474B2/ja not_active Expired - Fee Related
- 2000-12-27 AT AT00985695T patent/ATE480537T1/de active
- 2000-12-27 UA UA2002076056A patent/UA76410C2/uk unknown
- 2000-12-27 PT PT08162392T patent/PT1990343E/pt unknown
- 2000-12-27 PT PT00985695T patent/PT1263759E/pt unknown
- 2000-12-27 ES ES00985695T patent/ES2348861T3/es not_active Expired - Lifetime
- 2000-12-27 DK DK00985695.6T patent/DK1263759T3/da active
- 2000-12-27 ME MEP-499/08A patent/MEP49908A/xx unknown
- 2000-12-27 PL PL386205A patent/PL218884B1/pl unknown
- 2000-12-27 DE DE60044946T patent/DE60044946D1/de not_active Expired - Lifetime
- 2000-12-27 DK DK08162392.8T patent/DK1990343T3/da active
2002
- 2002-05-23 ZA ZA200204126A patent/ZA200204126B/xx unknown

Also Published As

Publication number	Publication date
MEP49908A (en)	2011-02-10
RS20100123A (sr)	2010-12-31
YU46202A (sh)	2005-06-10
GB9930698D0 (en)	2000-02-16
DE60044946D1 (de)	2010-10-21
UA76410C2 (en)	2006-08-15
ES2348861T3 (es)	2010-12-16
DK1263759T3 (da)	2011-01-10
JP2003519144A (ja)	2003-06-17
ATE552258T1 (de)	2012-04-15
ZA200204126B (en)	2003-08-25
DK1990343T3 (da)	2012-07-23
JP4871474B2 (ja)	2012-02-08
ATE480537T1 (de)	2010-09-15
PT1263759E (pt)	2010-11-02
ES2382759T3 (es)	2012-06-13
PL218884B1 (pl)	2015-02-27
RS51303B (sr)	2010-12-31

Publication	Publication Date	Title
EP1990343B1 (en)	2012-04-04	Azaindoles
KR100915289B1 (ko)	2009-09-03	아자인돌
ES2382759T3 (es)	2012-06-13	Azaindoles