UA76410C2 - Azaindols, pharmaceutical composition on their basis - Google Patents

Azaindols, pharmaceutical composition on their basis Download PDF

Info

Publication number: UA76410C2
Authority: UA; Ukraine
Prior art keywords: group; compound according; vya; iia; optionally substituted
Prior art date: 1999-12-24

Application number

UA2002076056A

Other languages

English (en)

Ukrainian (uk)

Inventor

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

2006-08-15

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

2000-12-27 Priority claimed from PCT/GB2000/004993 external-priority patent/WO2001047922A2/en

2006-08-15 Publication of UA76410C2 publication Critical patent/UA76410C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 352
239000000203 mixture Substances 0.000 claims abstract description 127
125000000217 alkyl group Chemical group 0.000 claims abstract description 117
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 85
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 68
150000003839 salts Chemical class 0.000 claims abstract description 67
125000003118 aryl group Chemical group 0.000 claims abstract description 64
229940002612 prodrug Drugs 0.000 claims abstract description 49
239000000651 prodrug Substances 0.000 claims abstract description 49
125000005843 halogen group Chemical group 0.000 claims abstract description 33
125000003342 alkenyl group Chemical group 0.000 claims abstract description 26
239000012453 solvate Substances 0.000 claims abstract description 26
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 24
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 20
125000001424 substituent group Chemical group 0.000 claims abstract description 11
125000002252 acyl group Chemical group 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
229910014033 C-OH Inorganic materials 0.000 claims abstract description 3
229910014570 C—OH Inorganic materials 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 282
-1 atom halogen Chemical class 0.000 claims description 207
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 127
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 115
239000002253 acid Substances 0.000 claims description 83
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 77
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 72
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 54
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
150000004677 hydrates Chemical class 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
125000003107 substituted aryl group Chemical group 0.000 claims description 18
108091000080 Phosphotransferase Proteins 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
102000020233 phosphotransferase Human genes 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000001041 indolyl group Chemical group 0.000 claims description 14
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 13
125000003831 tetrazolyl group Chemical group 0.000 claims description 12
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
125000005530 alkylenedioxy group Chemical group 0.000 claims description 9
125000000168 pyrrolyl group Chemical group 0.000 claims description 9
125000003302 alkenyloxy group Chemical group 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
206010028980 Neoplasm Diseases 0.000 claims description 7
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical group CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 claims description 7
125000003367 polycyclic group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims 2
208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
201000004681 Psoriasis Diseases 0.000 claims 1
206010003246 arthritis Diseases 0.000 claims 1
208000006673 asthma Diseases 0.000 claims 1
125000000524 functional group Chemical group 0.000 claims 1
229940043355 kinase inhibitor Drugs 0.000 claims 1
239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
102000001253 Protein Kinase Human genes 0.000 abstract description 10
108060006633 protein kinase Proteins 0.000 abstract description 10
239000001257 hydrogen Substances 0.000 abstract description 4
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
125000001475 halogen functional group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 366
239000007787 solid Substances 0.000 description 296
238000001819 mass spectrum Methods 0.000 description 229
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
239000000243 solution Substances 0.000 description 158
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 119
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 82
ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 64
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 60
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
238000003756 stirring Methods 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 50
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 39
238000004809 thin layer chromatography Methods 0.000 description 38
239000000377 silicon dioxide Substances 0.000 description 37
238000003818 flash chromatography Methods 0.000 description 36
239000011734 sodium Substances 0.000 description 35
IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
238000004128 high performance liquid chromatography Methods 0.000 description 34
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 31
229910052943 magnesium sulfate Inorganic materials 0.000 description 31
235000019341 magnesium sulphate Nutrition 0.000 description 31
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 30
235000012239 silicon dioxide Nutrition 0.000 description 30
239000000126 substance Substances 0.000 description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
239000012299 nitrogen atmosphere Substances 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000012442 inert solvent Substances 0.000 description 26
239000012267 brine Substances 0.000 description 25
229910052799 carbon Inorganic materials 0.000 description 25
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
150000001721 carbon Chemical group 0.000 description 21
239000000284 extract Substances 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
150000001732 carboxylic acid derivatives Chemical class 0.000 description 19
239000012634 fragment Substances 0.000 description 19
239000010410 layer Substances 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 18
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 17
229960000583 acetic acid Drugs 0.000 description 17
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 17
125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 17
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
239000012044 organic layer Substances 0.000 description 16
235000019260 propionic acid Nutrition 0.000 description 16
229940086542 triethylamine Drugs 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 15
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 14
238000005481 NMR spectroscopy Methods 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
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
239000000725 suspension Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
239000012312 sodium hydride Substances 0.000 description 12
229910000104 sodium hydride Inorganic materials 0.000 description 12
239000002904 solvent Substances 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
239000004146 Propane-1,2-diol Substances 0.000 description 11
239000002585 base Substances 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
229960004063 propylene glycol Drugs 0.000 description 11
235000013772 propylene glycol Nutrition 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
239000007858 starting material Substances 0.000 description 11
CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 10
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 10
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 10
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
239000011572 manganese Substances 0.000 description 10
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 10
238000000746 purification Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 9
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 9
230000029936 alkylation Effects 0.000 description 9
238000005804 alkylation reaction Methods 0.000 description 9
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 9
239000012458 free base Substances 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
235000010469 Glycine max Nutrition 0.000 description 8
241000764773 Inna Species 0.000 description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
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 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
150000001408 amides Chemical class 0.000 description 7
239000011575 calcium Substances 0.000 description 7
239000006071 cream Substances 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
CZFFYXFWPCJEGW-UHFFFAOYSA-N 5-methoxy-1h-indole-3-carbonitrile Chemical compound COC1=CC=C2NC=C(C#N)C2=C1 CZFFYXFWPCJEGW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
244000068988 Glycine max Species 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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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
VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 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)

UA2002076056A 1999-12-24 2000-12-27 Azaindols, pharmaceutical composition on their basis UA76410C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9930698.7A GB9930698D0 (en)	1999-12-24	1999-12-24	Chemical compounds
PCT/GB2000/004993 WO2001047922A2 (en)	1999-12-24	2000-12-27	Azaindoles

Publications (1)

Publication Number	Publication Date
UA76410C2 true UA76410C2 (en)	2006-08-15

Family

ID=10867079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002076056A UA76410C2 (en)	1999-12-24	2000-12-27	Azaindols, pharmaceutical composition on their basis

Country Status (12)

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

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0422057D0 (en) *	2004-10-05	2004-11-03	Astrazeneca Ab	Novel compounds
WO2007076348A2 (en) *	2005-12-23	2007-07-05	Smithkline Beecham Corporation	Azaindole inhibitors of aurora kinases
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
JP2013503132A (ja) *	2009-08-26	2013-01-31	ニコメッドゲゼルシャフトミットベシュレンクテルハフツング	メチルピロロピリジンカルボキサミド
MX2015012899A (es) *	2013-03-14	2016-06-02	Abbvie Inc	Pirrolo [2,3-b] piridina como inhibidores de quinasa cdk9.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUP9903330A2 (hu) *	1996-11-19	2000-03-28	Amgen Inc.	Gyulladásgátló hatású, aril- és heteroaril csoporttal szubsztituált kondenzált pirrolszármazékok, valamint ezeket tartalmazó gyógyászati készítmények
WO1998047899A1 (en) *	1997-04-24	1998-10-29	Ortho-Mcneil Corporation, Inc.	Substituted pyrrolopyridines useful in the treatment of inflammatory diseases
HRP20000209A2 (en) *	1997-10-20	2001-04-30	Hoffmann La Roche	Bicyclic kinase inhibitors

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

Also Published As

Publication number	Publication date
JP4871474B2 (ja)	2012-02-08
ES2382759T3 (es)	2012-06-13
MEP49908A (en)	2011-02-10
ATE480537T1 (de)	2010-09-15
ES2348861T3 (es)	2010-12-16
YU46202A (sh)	2005-06-10
RS51303B (sr)	2010-12-31
PT1263759E (pt)	2010-11-02
RS20100123A (sr)	2010-12-31
DK1263759T3 (da)	2011-01-10
DE60044946D1 (de)	2010-10-21
JP2003519144A (ja)	2003-06-17
GB9930698D0 (en)	2000-02-16
ATE552258T1 (de)	2012-04-15
PT1990343E (pt)	2012-05-22
DK1990343T3 (da)	2012-07-23
ZA200204126B (en)	2003-08-25
PL218884B1 (pl)	2015-02-27

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