MX2007010326A - Compuestos de imidazo(1,2-a)piridina como inhibidores de vegf-r2. - Google Patents
Compuestos de imidazo(1,2-a)piridina como inhibidores de vegf-r2.Info
- Publication number
- MX2007010326A MX2007010326A MX2007010326A MX2007010326A MX2007010326A MX 2007010326 A MX2007010326 A MX 2007010326A MX 2007010326 A MX2007010326 A MX 2007010326A MX 2007010326 A MX2007010326 A MX 2007010326A MX 2007010326 A MX2007010326 A MX 2007010326A
- Authority
- MX
- Mexico
- Prior art keywords
- pyridin
- mmol
- phenyl
- imidazo
- added
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 10
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 238000000034 method Methods 0.000 claims abstract description 109
- -1 amino, pyrrolidinyl Chemical group 0.000 claims description 295
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 197
- 229910052757 nitrogen Inorganic materials 0.000 claims description 104
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000004076 pyridyl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000002757 morpholinyl group Chemical group 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 125000000335 thiazolyl group Chemical group 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 230000033115 angiogenesis Effects 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- BGKDWGHFISLPAE-UHFFFAOYSA-N 2-[4-(7-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)phenyl]-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)CC=2C=CC(=CC=2)C=2N3C=CC(=CC3=NC=2)C=2C=CN=CC=2)=C1 BGKDWGHFISLPAE-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 4
- DIHLVQAWOPFHMC-UHFFFAOYSA-N 2-[2-fluoro-4-(7-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)phenyl]-n-(4-methyl-5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical group CC1=C(C(C)C)SC(NC(=O)CC=2C(=CC(=CC=2)C=2N3C=CC(=CC3=NC=2)C=2C=CN=CC=2)F)=N1 DIHLVQAWOPFHMC-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- SNTRBXUCDVHXOH-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-[2-fluoro-4-(7-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)phenyl]acetamide Chemical group S1C(C(C)(C)C)=NN=C1NC(=O)CC1=CC=C(C=2N3C=CC(=CC3=NC=2)C=2C=CN=CC=2)C=C1F SNTRBXUCDVHXOH-UHFFFAOYSA-N 0.000 claims 1
- XVCVNNHWLMHYCI-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]-5-(1-methylcyclopropyl)-1,3-thiazol-2-yl]-2-[2-fluoro-4-(7-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)phenyl]acetamide Chemical group S1C(C2(C)CC2)=C(CN(C)C)N=C1NC(=O)CC(C(=C1)F)=CC=C1C(N1C=C2)=CN=C1C=C2C1=CC=NC=C1 XVCVNNHWLMHYCI-UHFFFAOYSA-N 0.000 claims 1
- UGIWAEJKHMCGLS-UHFFFAOYSA-N n-[5-tert-butyl-4-(morpholin-4-ylmethyl)-1,3-thiazol-2-yl]-2-[2-fluoro-4-(7-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)phenyl]acetamide Chemical group N=1C(CN2CCOCC2)=C(C(C)(C)C)SC=1NC(=O)CC(C(=C1)F)=CC=C1C(N1C=C2)=CN=C1C=C2C1=CC=NC=C1 UGIWAEJKHMCGLS-UHFFFAOYSA-N 0.000 claims 1
- 230000005747 tumor angiogenesis Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 707
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 587
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 301
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 168
- 238000006243 chemical reaction Methods 0.000 description 165
- 239000007787 solid Substances 0.000 description 145
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 119
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 118
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 114
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
- 239000000203 mixture Substances 0.000 description 112
- 239000000243 solution Substances 0.000 description 111
- 235000019439 ethyl acetate Nutrition 0.000 description 108
- 238000002360 preparation method Methods 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 96
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 76
- 239000000047 product Substances 0.000 description 72
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 70
- 229920006395 saturated elastomer Polymers 0.000 description 67
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 59
- 235000019341 magnesium sulphate Nutrition 0.000 description 59
- 239000011541 reaction mixture Substances 0.000 description 57
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- 239000011780 sodium chloride Substances 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- 239000000725 suspension Substances 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 239000000377 silicon dioxide Substances 0.000 description 42
- 239000000741 silica gel Substances 0.000 description 41
- 229910002027 silica gel Inorganic materials 0.000 description 41
- 239000010410 layer Substances 0.000 description 39
- 238000012799 strong cation exchange Methods 0.000 description 38
- 239000003921 oil Substances 0.000 description 37
- 235000019198 oils Nutrition 0.000 description 37
- 239000002253 acid Substances 0.000 description 36
- 238000004587 chromatography analysis Methods 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 33
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 30
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 238000010992 reflux Methods 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000005843 halogen group Chemical group 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
- 239000004202 carbamide Substances 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 229940086542 triethylamine Drugs 0.000 description 17
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 16
- 235000011056 potassium acetate Nutrition 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 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 15
- 201000011510 cancer Diseases 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000012458 free base Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Substances IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000001786 isothiazolyl group Chemical group 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 235000017550 sodium carbonate Nutrition 0.000 description 9
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 9
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 8
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 8
- OXFRWJAGUOTHEH-UHFFFAOYSA-N 7-chloro-3-iodoimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C(I)=CN=C21 OXFRWJAGUOTHEH-UHFFFAOYSA-N 0.000 description 7
- NGHRUBVFDAKWBC-UHFFFAOYSA-N 7-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C=CN=C21 NGHRUBVFDAKWBC-UHFFFAOYSA-N 0.000 description 7
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- 238000010168 coupling process Methods 0.000 description 7
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- 125000001207 fluorophenyl group Chemical group 0.000 description 7
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 7
- 102000020233 phosphotransferase Human genes 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- SXJYSIBLFGQAND-UHFFFAOYSA-N 1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1 SXJYSIBLFGQAND-UHFFFAOYSA-N 0.000 description 6
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 6
- JBLWSEJYQSQFKW-UHFFFAOYSA-N 7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C=1C2=NC=CN2C=CC=1C1=CC=NC=C1 JBLWSEJYQSQFKW-UHFFFAOYSA-N 0.000 description 6
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- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 5
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- ISVFJXQITVEDSF-UHFFFAOYSA-N tert-butyl n-[2-(4-bromophenyl)sulfonylethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCS(=O)(=O)C1=CC=C(Br)C=C1 ISVFJXQITVEDSF-UHFFFAOYSA-N 0.000 description 1
- CNVMYEBGXAXTTF-UHFFFAOYSA-N tert-butyl n-[2-[3-[[2-(4-bromo-2-fluorophenyl)acetyl]amino]phenyl]propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)C1=CC=CC(NC(=O)CC=2C(=CC(Br)=CC=2)F)=C1 CNVMYEBGXAXTTF-UHFFFAOYSA-N 0.000 description 1
- TWLJXJVGIXSKFX-UHFFFAOYSA-N tert-butyl n-[4-(hydroxymethyl)-5-(1-methylcyclopropyl)-1,3-thiazol-2-yl]carbamate Chemical compound S1C(NC(=O)OC(C)(C)C)=NC(CO)=C1C1(C)CC1 TWLJXJVGIXSKFX-UHFFFAOYSA-N 0.000 description 1
- PWNSTTFBSWIZSQ-UHFFFAOYSA-N tert-butyl n-[4-[(dimethylamino)methyl]-5-(1-methylcyclopropyl)-1,3-thiazol-2-yl]carbamate Chemical compound N1=C(NC(=O)OC(C)(C)C)SC(C2(C)CC2)=C1CN(C)C PWNSTTFBSWIZSQ-UHFFFAOYSA-N 0.000 description 1
- RZFJKHLFPCKXDX-UHFFFAOYSA-N tert-butyl n-[[4-(7-chloroimidazo[1,2-a]pyridin-3-yl)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C1=CN=C2N1C=CC(Cl)=C2 RZFJKHLFPCKXDX-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- VSLIUWLPFRVCDL-UHFFFAOYSA-N zolimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN(C=CC=C2)C2=N1 VSLIUWLPFRVCDL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/4375—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 six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65598105P | 2005-02-24 | 2005-02-24 | |
| PCT/US2006/006283 WO2006091671A1 (en) | 2005-02-24 | 2006-02-23 | Imidazo (1, 2-a) pyridine compounds as vegf-r2 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007010326A true MX2007010326A (es) | 2007-10-16 |
Family
ID=36587138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007010326A MX2007010326A (es) | 2005-02-24 | 2006-02-23 | Compuestos de imidazo(1,2-a)piridina como inhibidores de vegf-r2. |
Country Status (33)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101679408B (zh) * | 2006-12-22 | 2016-04-27 | Astex治疗学有限公司 | 作为fgfr抑制剂的双环杂环化合物 |
| JP5442449B2 (ja) | 2006-12-22 | 2014-03-12 | アステックス、セラピューティックス、リミテッド | 新規化合物 |
| US8131527B1 (en) | 2006-12-22 | 2012-03-06 | Astex Therapeutics Ltd. | FGFR pharmacophore compounds |
| WO2008112164A2 (en) | 2007-03-08 | 2008-09-18 | The Board Of Trustees Of The Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| GB0720038D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New compounds |
| GB0720041D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New Compounds |
| EA201000615A1 (ru) | 2007-10-17 | 2010-12-30 | Новартис Аг | Производные имидазо[1,2-а]пиридина, применимые в качестве ингибиторов апк (активиноподобной киназы) |
| GB0810902D0 (en) * | 2008-06-13 | 2008-07-23 | Astex Therapeutics Ltd | New compounds |
| WO2010028175A1 (en) | 2008-09-08 | 2010-03-11 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase activity and methods of use thereof |
| JP2012506856A (ja) | 2008-10-28 | 2012-03-22 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼのモジュレーターおよびその使用方法 |
| JO3265B1 (ar) | 2008-12-09 | 2018-09-16 | Novartis Ag | مثبطات بيريديلوكسى اندولات vegf-r2 واستخدامها لعلاج المرض |
| US8278302B2 (en) | 2009-04-08 | 2012-10-02 | Boehringer Ingelheim International Gmbh | Substituted piperidines as CCR3 antagonists |
| GB0906470D0 (en) | 2009-04-15 | 2009-05-20 | Astex Therapeutics Ltd | New compounds |
| GB0906472D0 (en) | 2009-04-15 | 2009-05-20 | Astex Therapeutics Ltd | New compounds |
| TW201124391A (en) | 2009-10-20 | 2011-07-16 | Lundbeck & Co As H | 2-substituted-ethynylthiazole derivatives and uses of same |
| GB201009731D0 (en) | 2010-06-10 | 2010-07-21 | Pulmagen Therapeutics Inflamma | Kinase inhibitors |
| UA109290C2 (uk) | 2010-10-07 | 2015-08-10 | Спільні кристали і солі інгібіторів ccr3 | |
| WO2012149106A1 (en) | 2011-04-29 | 2012-11-01 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
| AR090566A1 (es) | 2012-04-02 | 2014-11-19 | Boehringer Ingelheim Int | Proceso para la produccion de inhibidores de crr |
| US10213421B2 (en) | 2012-04-04 | 2019-02-26 | Alkahest, Inc. | Pharmaceutical formulations comprising CCR3 antagonists |
| JP6430383B2 (ja) * | 2012-09-28 | 2018-11-28 | ヴァンダービルト ユニバーシティーＶａｎｄｅｒｂｉｌｔ Ｕｎｉｖｅｒｓｉｔｙ | 選択的ｂｍｐ阻害剤としての縮合複素環化合物 |
| CN104822679B (zh) * | 2012-11-29 | 2016-10-19 | 霍夫曼-拉罗奇有限公司 | 咪唑并吡啶衍生物 |
| KR20150135332A (ko) | 2013-03-14 | 2015-12-02 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 | 미토콘드리아 알데히드 탈수소효소-2 조절인자들 및 이들의 사용 방법 |
| AU2014365823B2 (en) | 2013-12-16 | 2019-05-02 | Abs Development 1, Inc. | P2X3 and/or P2X2/3 compounds and methods |
| CN103772308B (zh) * | 2013-12-31 | 2015-11-18 | 北京颖泰嘉和生物科技股份有限公司 | 5-氨基-3-(1-乙基-1-甲基丙基)异噁唑中间体的制备方法和异噁草胺的制备方法 |
| US9988371B2 (en) | 2014-06-03 | 2018-06-05 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Benzimidazole analogues and related methods |
| DK3169671T3 (da) | 2014-07-17 | 2019-09-23 | Sunshine Lake Pharma Co Ltd | 1-(5-(tert.-butyl)isoxazol-3-yl)-3-(4-((phenyl)ethynyl)phenyl)ureaderivater og relaterede forbindelser som flt3-inhibitorer til behandling af kræft |
| CN104163790B (zh) * | 2014-08-19 | 2016-02-10 | 贵州威顿晶磷电子材料股份有限公司 | 一种2-氨基-4-甲基-5溴吡啶的制备工艺 |
| US10829484B2 (en) | 2015-07-28 | 2020-11-10 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| AU2016315881B2 (en) | 2015-09-03 | 2019-09-19 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of DYRK1A and uses thereof |
| US10160747B2 (en) * | 2016-03-16 | 2018-12-25 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US12528810B2 (en) | 2018-03-01 | 2026-01-20 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of DYRK/CLK and uses thereof |
| WO2019178383A1 (en) | 2018-03-14 | 2019-09-19 | Vanderbilt University | Inhibition of bmp signaling, compounds, compositions and uses thereof |
| WO2019245590A1 (en) | 2018-06-18 | 2019-12-26 | Avista Pharma Solutions, Inc. | Chemical compounds |
| TW202043205A (zh) | 2018-12-31 | 2020-12-01 | 美商拜歐米富士恩有限公司 | Menin-mll相互作用之抑制劑 |
| WO2020142557A1 (en) | 2018-12-31 | 2020-07-09 | Biomea Fusion, Llc | Irreversible inhibitors of menin-mll interaction |
| WO2020144375A1 (en) | 2019-01-11 | 2020-07-16 | Grünenthal GmbH | Substituted pyrrolidine amides iii |
| US11512088B2 (en) * | 2019-01-30 | 2022-11-29 | Avista Pharma Solutions, Inc. | Synthetic process and intermediates |
| CA3128024A1 (en) | 2019-01-30 | 2020-08-06 | Avista Pharma Solutions, Inc. | Chemical compounds |
| US12365685B2 (en) | 2019-02-18 | 2025-07-22 | Shenzhen Targetrx, Inc. | Substituted fused aromatic ring derivative, composition and use thereof |
| EP3990458A4 (en) * | 2019-06-25 | 2025-01-08 | Sinopsee Therapeutics | LINKS TO THE TREATMENT OF CANCER |
| CN112778294A (zh) * | 2021-01-07 | 2021-05-11 | 苏州安睿药业有限公司 | 5-氨基异噁唑衍生物及其在制备多激酶抑制剂中的应用 |
| JP7891524B2 (ja) | 2021-08-11 | 2026-07-16 | バイオメア フュージョン，インコーポレイテッド | 真性糖尿病に対するメニン－ｍｌｌ相互作用の共有結合性阻害剤 |
| MX2024002189A (es) | 2021-08-20 | 2024-06-11 | Biomea Fusion Inc | Forma cristalina de n-[4-[4-(4-morfolinil)-7h-pirrolo[2,3-d]pirimi din-6-il]fenil]-4-[[3(r)-[(1-oxo)-2-propen-1-il)amino]-1-piperidi nil]metil]-2-piridinacarboxamida, un inhibidor irreversible de menina-mll para el tratamiento del cancer. |
| WO2024155719A1 (en) | 2023-01-18 | 2024-07-25 | Biomea Fusion, Inc. | Crystalline forms of n-[4-[4-(4-morpholinyl)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-4-[[3(r)-[(l-oxo-2-propen-l-yl)amino]-l-piperidinyl]methyl]-2- pyridinecarboxamide as a covalentinhibitor of menin-mll interaction |
| WO2025038525A1 (en) * | 2023-08-11 | 2025-02-20 | Bioventures, Llc | Fms-like tyrosine kinase 3 (flt3) inhibitors for treating cell proliferative diseases or conditions |
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| EP0888310B1 (en) | 1996-03-15 | 2005-09-07 | AstraZeneca AB | Cinnoline derivatives and use as medicine |
| AU744939B2 (en) | 1997-09-26 | 2002-03-07 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
| CA2374737C (en) | 1999-07-09 | 2008-02-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel process for synthesis of heteroaryl-substituted urea compounds |
| US6492529B1 (en) * | 2000-01-18 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Bis pyrazole-1H-pyrazole intermediates and their synthesis |
| ES2284887T3 (es) | 2001-07-11 | 2007-11-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Metodos para tratar enfermedades transmitidas por citocinas. |
| JP2003313126A (ja) * | 2002-04-23 | 2003-11-06 | Sankyo Co Ltd | イミダゾピリジン誘導体を有効成分とする医薬 |
| US7125888B2 (en) * | 2002-05-02 | 2006-10-24 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| AU2003298942A1 (en) * | 2002-12-11 | 2004-06-30 | Merck And Co., Inc. | Tyrosine kinase inhibitors |
| US7550470B2 (en) | 2002-12-11 | 2009-06-23 | Merck & Co. Inc. | Substituted pyrazolo[1,5-A]pyrimidines as tyrosine kinase inhibitors |
| WO2005016928A1 (ja) | 2003-08-15 | 2005-02-24 | Banyu Pharmaceutical Co., Ltd. | イミダゾピリジン誘導体 |
-
2006
- 2006-02-22 DO DO2006000051A patent/DOP2006000051A/es unknown
- 2006-02-23 PE PE2006000219A patent/PE20061098A1/es not_active Application Discontinuation
- 2006-02-23 DE DE602006018615T patent/DE602006018615D1/de not_active Expired - Lifetime
- 2006-02-23 BR BRPI0609047-8A patent/BRPI0609047A2/pt not_active IP Right Cessation
- 2006-02-23 AR ARP060100668A patent/AR056186A1/es not_active Application Discontinuation
- 2006-02-23 NZ NZ584753A patent/NZ584753A/en not_active IP Right Cessation
- 2006-02-23 ES ES06735794T patent/ES2354716T3/es not_active Expired - Lifetime
- 2006-02-23 MX MX2007010326A patent/MX2007010326A/es active IP Right Grant
- 2006-02-23 AU AU2006216710A patent/AU2006216710B2/en not_active Ceased
- 2006-02-23 HR HR20100677T patent/HRP20100677T1/hr unknown
- 2006-02-23 EA EA200701802A patent/EA011691B1/ru not_active IP Right Cessation
- 2006-02-23 WO PCT/US2006/006283 patent/WO2006091671A1/en not_active Ceased
- 2006-02-23 CA CA2599124A patent/CA2599124C/en not_active Expired - Fee Related
- 2006-02-23 EP EP06735794A patent/EP1904494B1/en not_active Expired - Lifetime
- 2006-02-23 PL PL06735794T patent/PL1904494T3/pl unknown
- 2006-02-23 AT AT06735794T patent/ATE490254T1/de active
- 2006-02-23 NZ NZ560402A patent/NZ560402A/en not_active IP Right Cessation
- 2006-02-23 KR KR1020077019338A patent/KR100904938B1/ko not_active Expired - Fee Related
- 2006-02-23 SI SI200630871T patent/SI1904494T1/sl unknown
- 2006-02-23 CN CN2006800060044A patent/CN101128461B/zh not_active Expired - Fee Related
- 2006-02-23 US US11/816,416 patent/US7666879B2/en not_active Expired - Fee Related
- 2006-02-23 PT PT06735794T patent/PT1904494E/pt unknown
- 2006-02-23 JP JP2007557126A patent/JP5055136B2/ja not_active Expired - Fee Related
- 2006-02-23 UA UAA200709559A patent/UA91535C2/ru unknown
- 2006-02-23 TW TW095106022A patent/TW200640924A/zh unknown
- 2006-02-23 DK DK06735794.7T patent/DK1904494T3/da active
- 2006-02-23 RS RS20110042A patent/RS51590B/sr unknown
-
2007
- 2007-07-19 IL IL184717A patent/IL184717A/en not_active IP Right Cessation
- 2007-08-22 CR CR9331A patent/CR9331A/es not_active Application Discontinuation
- 2007-08-23 ZA ZA200707136A patent/ZA200707136B/xx unknown
- 2007-08-23 TN TNP2007000323A patent/TNSN07323A1/en unknown
- 2007-09-13 NO NO20074666A patent/NO20074666L/no not_active Application Discontinuation
- 2007-09-24 MA MA30233A patent/MA29433B1/fr unknown
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2011
- 2011-02-03 CY CY20111100115T patent/CY1111154T1/el unknown
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