JP2018529731A5 - - Google Patents
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- JP2018529731A5 JP2018529731A5 JP2018516728A JP2018516728A JP2018529731A5 JP 2018529731 A5 JP2018529731 A5 JP 2018529731A5 JP 2018516728 A JP2018516728 A JP 2018516728A JP 2018516728 A JP2018516728 A JP 2018516728A JP 2018529731 A5 JP2018529731 A5 JP 2018529731A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- amino
- amine
- dimethylpentyl
- pyridin
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- -1 methoxy, methoxymethyl Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- NCTYDBJTUKINGK-BVHINDKJSA-N 4-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-(trifluoromethyl)phenyl]-N-(oxan-3-yl)pyridin-2-amine Chemical class N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC1COCCC1)C(F)(F)F)(CC(C)C)C NCTYDBJTUKINGK-BVHINDKJSA-N 0.000 claims 3
- DIMDFUYZAOONSH-BVHINDKJSA-N 4-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-chlorophenyl]-N-(oxan-3-yl)pyridin-2-amine Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC1COCCC1)Cl)(CC(C)C)C DIMDFUYZAOONSH-BVHINDKJSA-N 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- MTVYVMWZXUVEKJ-GOSISDBHSA-N (2R)-1-(3-chloro-5-pyrazolo[1,5-a]pyrimidin-7-ylpyridin-2-yl)oxy-2,4-dimethylpentan-2-amine Chemical compound ClC=1C(=NC=C(C=1)C1=CC=NC=2N1N=CC=2)OC[C@@](CC(C)C)(N)C MTVYVMWZXUVEKJ-GOSISDBHSA-N 0.000 claims 1
- RMVAVWKUAJOXDB-JOCHJYFZSA-N (2R)-1-[5-(2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-yl)-3-methylpyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound C1(CC1)C1=NN2C(N=CC=C2C=2C=C(C(=NC=2)OC[C@@](CC(C)C)(N)C)C)=C1 RMVAVWKUAJOXDB-JOCHJYFZSA-N 0.000 claims 1
- SXPPKWGLRCJBEG-LJQANCHMSA-N (2R)-2,4-dimethyl-1-[3-methyl-5-[2-(trifluoromethyl)imidazo[1,2-b]pyridazin-8-yl]pyridin-2-yl]oxypentan-2-amine Chemical compound C[C@](COC1=NC=C(C=C1C)C=1C=2N(N=CC=1)C=C(N=2)C(F)(F)F)(CC(C)C)N SXPPKWGLRCJBEG-LJQANCHMSA-N 0.000 claims 1
- ZYXZXZOWIFUVAX-IBGZPJMESA-N (2S)-1-(2,5-difluoro-4-pyrazolo[1,5-a]pyrimidin-7-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=C(C(=C1)C1=CC=NC=2N1N=CC=2)F ZYXZXZOWIFUVAX-IBGZPJMESA-N 0.000 claims 1
- ANYGFLXRTSCXOQ-IBGZPJMESA-N (2S)-1-(2-chloro-4-imidazo[1,2-b]pyridazin-3-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound ClC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CN=C2N1N=CC=C2 ANYGFLXRTSCXOQ-IBGZPJMESA-N 0.000 claims 1
- FGXMWAMCHOWFJA-IBGZPJMESA-N (2S)-1-(2-chloro-4-pyrazolo[1,5-a]pyrimidin-7-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound ClC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC=2N1N=CC=2 FGXMWAMCHOWFJA-IBGZPJMESA-N 0.000 claims 1
- NJYNGBOJRLITFK-FQEVSTJZSA-N (2S)-1-(2-fluoro-4-pyrido[2,3-b]pyrazin-8-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC2=NC=CN=C21 NJYNGBOJRLITFK-FQEVSTJZSA-N 0.000 claims 1
- MTVYVMWZXUVEKJ-SFHVURJKSA-N (2S)-1-(3-chloro-5-pyrazolo[1,5-a]pyrimidin-7-ylpyridin-2-yl)oxy-2,4-dimethylpentan-2-amine Chemical compound ClC=1C(=NC=C(C=1)C1=CC=NC=2N1N=CC=2)OC[C@](CC(C)C)(N)C MTVYVMWZXUVEKJ-SFHVURJKSA-N 0.000 claims 1
- FJSLWMPTBQKJHB-FQEVSTJZSA-N (2S)-1-(4-imidazo[1,2-b]pyridazin-3-yl-2-methylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound N=1C=C(N2N=CC=CC2=1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C FJSLWMPTBQKJHB-FQEVSTJZSA-N 0.000 claims 1
- TWWRDFYLSWJKOB-IBGZPJMESA-N (2S)-1-(4-imidazo[1,2-b]pyridazin-8-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound N=1C=CN2N=CC=C(C2=1)C1=CC=C(OC[C@](CC(C)C)(N)C)C=C1 TWWRDFYLSWJKOB-IBGZPJMESA-N 0.000 claims 1
- CKJNGEJAQQWVOA-FQEVSTJZSA-N (2S)-1-[2-(difluoromethyl)-4-pyrazolo[1,5-a]pyrimidin-7-ylphenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=NN12)C(F)F CKJNGEJAQQWVOA-FQEVSTJZSA-N 0.000 claims 1
- JMNAAPWZVDJIPG-FQEVSTJZSA-N (2S)-1-[2-(difluoromethyl)-6-(2-methylimidazo[1,2-b]pyridazin-8-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NN2C=C(C)N=C12 JMNAAPWZVDJIPG-FQEVSTJZSA-N 0.000 claims 1
- ZNVJOUYPQVPULC-IBGZPJMESA-N (2S)-1-[2-chloro-4-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound ClC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=C2C(=NC=C1)NN=C2 ZNVJOUYPQVPULC-IBGZPJMESA-N 0.000 claims 1
- GRDOMDXTCHEOSF-NRFANRHFSA-N (2S)-1-[2-chloro-4-(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(Cl)C=C(C=C1)C1=CC(C)=NC2=CC(C)=NN12 GRDOMDXTCHEOSF-NRFANRHFSA-N 0.000 claims 1
- GERJDYOHZAGTPG-QFIPXVFZSA-N (2S)-1-[2-chloro-4-(2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound ClC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC=2N1N=C(C=2)C1CC1 GERJDYOHZAGTPG-QFIPXVFZSA-N 0.000 claims 1
- CRAIJRBCVVXBGM-FQEVSTJZSA-N (2S)-1-[2-chloro-4-(2-methyl-1H-imidazo[4,5-b]pyridin-7-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound ClC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=C2C(=NC=C1)NC(=N2)C CRAIJRBCVVXBGM-FQEVSTJZSA-N 0.000 claims 1
- YQVLFMSBAWJDQO-IBGZPJMESA-N (2S)-1-[2-chloro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound ClC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C=1C2=C(N=CN=1)NC=C2 YQVLFMSBAWJDQO-IBGZPJMESA-N 0.000 claims 1
- UTNYUBVFTFRKNV-FQEVSTJZSA-N (2S)-1-[2-fluoro-4-(1-methylpyrazolo[3,4-b]pyridin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=C2C(=NC=C1)N(N=C2)C UTNYUBVFTFRKNV-FQEVSTJZSA-N 0.000 claims 1
- MNZRGDCNGYBNMW-IBGZPJMESA-N (2S)-1-[2-fluoro-4-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=C2C(=NC=C1)NN=C2 MNZRGDCNGYBNMW-IBGZPJMESA-N 0.000 claims 1
- OHBXLPKLTNQFAG-FQEVSTJZSA-N (2S)-1-[2-fluoro-4-(1H-pyrrolo[3,2-b]pyridin-7-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=C2C(=NC=C1)C=CN2 OHBXLPKLTNQFAG-FQEVSTJZSA-N 0.000 claims 1
- MCNMBNDAUSHJAO-FQEVSTJZSA-N (2S)-1-[2-fluoro-4-(2-methylimidazo[1,2-b]pyridazin-8-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C=1C=2N(N=CC=1)C=C(N=2)C MCNMBNDAUSHJAO-FQEVSTJZSA-N 0.000 claims 1
- FEPDNETVHUTNKO-IBGZPJMESA-N (2S)-1-[2-fluoro-4-[2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC=2N1N=C(C=2)C(F)(F)F FEPDNETVHUTNKO-IBGZPJMESA-N 0.000 claims 1
- CHODUQRWFPOFGC-QFIPXVFZSA-N (2S)-1-[4-(2-cyclopropylimidazo[1,2-b]pyridazin-8-yl)-2-fluorophenoxy]-2,4-dimethylpentan-2-amine Chemical compound C1(CC1)C=1N=C2N(N=CC=C2C2=CC(=C(OC[C@](CC(C)C)(N)C)C=C2)F)C=1 CHODUQRWFPOFGC-QFIPXVFZSA-N 0.000 claims 1
- WJONEHJTOSHKEQ-QFIPXVFZSA-N (2S)-1-[4-(2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-yl)-2-(trifluoromethyl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound C1(CC1)C1=NN2C(N=CC=C2C2=CC(=C(OC[C@](CC(C)C)(N)C)C=C2)C(F)(F)F)=C1 WJONEHJTOSHKEQ-QFIPXVFZSA-N 0.000 claims 1
- CTSQZQWPLDEIPE-SFHVURJKSA-N (2S)-1-[4-(3,5-dimethyl-1H-pyrazol-4-yl)-2-fluorophenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC1=NNC(=C1C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)F)C CTSQZQWPLDEIPE-SFHVURJKSA-N 0.000 claims 1
- IESWZJXLGRDUCU-QFIPXVFZSA-N (2S)-1-[4-(6-chloro-2-cyclopropylimidazo[1,2-b]pyridazin-8-yl)-2-(trifluoromethyl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound ClC=1C=C(C=2N(N=1)C=C(N=2)C1CC1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F IESWZJXLGRDUCU-QFIPXVFZSA-N 0.000 claims 1
- VKVCEBPZCYNFNC-QFIPXVFZSA-N (2S)-1-[4-[2-(methoxymethyl)-1H-imidazo[4,5-b]pyridin-7-yl]-2-methylphenoxy]-2,4-dimethylpentan-2-amine Chemical compound COCC1=NC=2C(=NC=CC=2C2=CC(=C(OC[C@](CC(C)C)(N)C)C=C2)C)N1 VKVCEBPZCYNFNC-QFIPXVFZSA-N 0.000 claims 1
- DNAVSXQDIBKRCV-IBGZPJMESA-N (2S)-1-[4-imidazo[1,2-b]pyridazin-8-yl-2-(trifluoromethyl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound N=1C=CN2N=CC=C(C2=1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F DNAVSXQDIBKRCV-IBGZPJMESA-N 0.000 claims 1
- BTWIQOATDPCMFG-FQEVSTJZSA-N (2S)-2,4-dimethyl-1-(2-methyl-4-pyrazolo[1,5-a]pyrimidin-7-ylphenoxy)pentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(C=C1)C1=CC=NC2=CC=NN12 BTWIQOATDPCMFG-FQEVSTJZSA-N 0.000 claims 1
- UQSOEMDTCKSGQH-IBGZPJMESA-N (2S)-2,4-dimethyl-1-(2-methyl-6-pyrazolo[1,5-a]pyrimidin-7-ylpyridin-3-yl)oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C)C1=CC=NC2=CC=NN12 UQSOEMDTCKSGQH-IBGZPJMESA-N 0.000 claims 1
- RWZWMJUGARVMDE-IBGZPJMESA-N (2S)-2,4-dimethyl-1-(3-methyl-5-pyrazolo[1,5-a]pyrimidin-7-ylpyridin-2-yl)oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C)C1=CC=NC2=CC=NN12 RWZWMJUGARVMDE-IBGZPJMESA-N 0.000 claims 1
- WLERMVGQYROBCE-INIZCTEOSA-N (2S)-2,4-dimethyl-1-[(5-methyl-2-pyridin-4-yl-1,3-thiazol-4-yl)oxy]pentan-2-amine Chemical compound C[C@@](COC=1N=C(SC=1C)C1=CC=NC=C1)(CC(C)C)N WLERMVGQYROBCE-INIZCTEOSA-N 0.000 claims 1
- WQXXHBWRQWTLGW-QFIPXVFZSA-N (2S)-2,4-dimethyl-1-[2-methyl-4-(1-methylpyrrolo[3,2-b]pyridin-7-yl)phenoxy]pentan-2-amine Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=C2C(=NC=C1)C=CN2C)C)(CC(C)C)N WQXXHBWRQWTLGW-QFIPXVFZSA-N 0.000 claims 1
- ZWBXNHSDBLFMPD-FQEVSTJZSA-N (2S)-2,4-dimethyl-1-[2-methyl-4-[2-(trifluoromethyl)imidazo[1,2-b]pyridazin-8-yl]phenoxy]pentan-2-amine Chemical compound C[C@@](COC1=C(C=C(C=C1)C=1C=2N(N=CC=1)C=C(N=2)C(F)(F)F)C)(CC(C)C)N ZWBXNHSDBLFMPD-FQEVSTJZSA-N 0.000 claims 1
- HVEDZNKVDAPADE-IBGZPJMESA-N (2S)-2,4-dimethyl-1-[4-(1H-pyrazolo[3,4-b]pyridin-4-yl)-2-(trifluoromethyl)phenoxy]pentan-2-amine Chemical compound N1N=CC=2C1=NC=CC=2C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F HVEDZNKVDAPADE-IBGZPJMESA-N 0.000 claims 1
- BSJBZGWVXKFQGU-FQEVSTJZSA-N (2S)-2,4-dimethyl-1-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-2-(trifluoromethyl)phenoxy]pentan-2-amine Chemical compound N1C=CC2=NC=CC(=C21)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F BSJBZGWVXKFQGU-FQEVSTJZSA-N 0.000 claims 1
- IBXFJMPAXJNQCV-FQEVSTJZSA-N (2S)-2,4-dimethyl-1-[4-(2-methylthieno[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]pentan-2-amine Chemical compound C[C@@](COC1=C(C=C(C=C1)C=1C2=C(N=C(N=1)C)SC=C2)C(F)(F)F)(CC(C)C)N IBXFJMPAXJNQCV-FQEVSTJZSA-N 0.000 claims 1
- SOABFCCGKNWHQM-IBGZPJMESA-N (2S)-2,4-dimethyl-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]pentan-2-amine Chemical compound N1=CN=C(C2=C1NC=C2)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F SOABFCCGKNWHQM-IBGZPJMESA-N 0.000 claims 1
- NMIHYGDPGMTIIF-IBGZPJMESA-N (2S)-2,4-dimethyl-1-[4-[2-(trifluoromethyl)imidazo[1,2-b]pyridazin-8-yl]phenoxy]pentan-2-amine Chemical compound C[C@@](COC1=CC=C(C=C1)C=1C=2N(N=CC=1)C=C(N=2)C(F)(F)F)(CC(C)C)N NMIHYGDPGMTIIF-IBGZPJMESA-N 0.000 claims 1
- BKEAKMLRGWILBU-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-2-[(2-methyl-6-pyrazolo[1,5-a]pyrimidin-7-ylpyridin-3-yl)oxymethyl]pentan-2-amine Chemical compound CC(C)CC(N)(COC1=CC=C(N=C1C)C1=CC=NC2=CC=NN12)C(F)(F)F BKEAKMLRGWILBU-UHFFFAOYSA-N 0.000 claims 1
- RNGRHWGXQHPBJQ-UHFFFAOYSA-N 1-[[3-methyl-5-(2-methylpyrimidin-4-yl)pyridin-2-yl]oxymethyl]cyclobutan-1-amine Chemical compound CC1=CC(=CN=C1OCC1(N)CCC1)C1=CC=NC(C)=N1 RNGRHWGXQHPBJQ-UHFFFAOYSA-N 0.000 claims 1
- UBDPSUOTKUCDID-QFIPXVFZSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(1-methylpyrrolo[3,2-b]pyridin-7-yl)benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=C2C(=NC=C1)C=CN2C)(CC(C)C)C UBDPSUOTKUCDID-QFIPXVFZSA-N 0.000 claims 1
- HCJNGNVCUVTDCV-NRFANRHFSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(1H-pyrrolo[3,2-b]pyridin-7-yl)benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=C2C(=NC=C1)C=CN2)(CC(C)C)C HCJNGNVCUVTDCV-NRFANRHFSA-N 0.000 claims 1
- FPLVYIFLTVDSGC-QHCPKHFHSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(2,3-dimethylpyrido[2,3-b]pyrazin-8-yl)benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=CC=NC2=NC(=C(N=C21)C)C)(CC(C)C)C FPLVYIFLTVDSGC-QHCPKHFHSA-N 0.000 claims 1
- YHZIXFGUUNVDLL-QFIPXVFZSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)benzonitrile Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC2=CC(C)=NN12)C#N YHZIXFGUUNVDLL-QFIPXVFZSA-N 0.000 claims 1
- TWOWABBZIUZTDH-FQEVSTJZSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(2-amino-1H-imidazo[4,5-b]pyridin-7-yl)benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=C2C(=NC=C1)NC(=N2)N)(CC(C)C)C TWOWABBZIUZTDH-FQEVSTJZSA-N 0.000 claims 1
- GPHQKOCUIQONQZ-QHCPKHFHSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(2-cyclopropylimidazo[1,2-b]pyridazin-8-yl)benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C=1C=2N(N=CC=1)C=C(N=2)C1CC1)(CC(C)C)C GPHQKOCUIQONQZ-QHCPKHFHSA-N 0.000 claims 1
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| US5464764A (en) | 1989-08-22 | 1995-11-07 | University Of Utah Research Foundation | Positive-negative selection methods and vectors |
| AU2515992A (en) | 1991-08-20 | 1993-03-16 | Genpharm International, Inc. | Gene targeting in animal cells using isogenic dna constructs |
| AU2003286895A1 (en) | 2002-11-05 | 2004-06-07 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of jak and other protein kinases |
| MX2008013203A (es) * | 2006-04-12 | 2008-10-22 | Wyeth Corp | Analogos de anilino-pirimidina fenilo y benzotiofeno. |
| KR101641596B1 (ko) | 2007-11-15 | 2016-07-21 | 엠에스디 이탈리아 에스.알.엘. | Ｐａｒｐ 억제제로서의 피리다지논 유도체 |
| CN106359439B (zh) * | 2012-02-29 | 2018-10-30 | 明治制果药业株式会社 | 包括新型亚氨基吡啶衍生物的有害物防治组合物 |
| US8703953B2 (en) | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| HUE036040T2 (hu) | 2012-03-09 | 2018-06-28 | Lexicon Pharmaceuticals Inc | Adaptor-asszociált kináz 1 gátlása fájdalom kezelésére |
| US8901305B2 (en) * | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| US9708337B2 (en) | 2013-02-22 | 2017-07-18 | Bristol-Myers Squibb Company | Aryl amide-based kinase inhibitors |
| EP3019475A1 (en) | 2013-07-08 | 2016-05-18 | Bristol-Myers Squibb Company | Aryl amide kinase inhibitors |
| EP3044226B1 (en) | 2013-09-11 | 2017-09-06 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| KR20160058863A (ko) * | 2013-09-19 | 2016-05-25 | 바스프 에스이 | Ｎ-아실이미노 헤테로시클릭 화합물 |
| CA2937529A1 (en) | 2014-01-29 | 2015-08-06 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| MX2016009352A (es) | 2014-01-31 | 2016-10-13 | Bristol Myers Squibb Co | Inhibidores de quinasa a base de quinolina. |
| KR102379518B1 (ko) * | 2014-04-02 | 2022-03-25 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| US20170239249A1 (en) | 2014-09-30 | 2017-08-24 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| WO2016164295A2 (en) | 2015-04-10 | 2016-10-13 | Bristol-Myers Squibb Company | Fused pyridines as kinase inhibitors |
| US10246469B2 (en) | 2015-10-01 | 2019-04-02 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| WO2017059085A1 (en) | 2015-10-01 | 2017-04-06 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
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- 2016-09-29 CN CN201680070096.6A patent/CN108290843B/zh active Active
- 2016-09-29 KR KR1020187011873A patent/KR102707968B1/ko active Active
- 2016-09-29 EP EP16781938.2A patent/EP3356330B1/en active Active
- 2016-09-29 ES ES16781938T patent/ES2767776T3/es active Active
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