JP2018537408A5 - - Google Patents
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- JP2018537408A5 JP2018537408A5 JP2018516713A JP2018516713A JP2018537408A5 JP 2018537408 A5 JP2018537408 A5 JP 2018537408A5 JP 2018516713 A JP2018516713 A JP 2018516713A JP 2018516713 A JP2018516713 A JP 2018516713A JP 2018537408 A5 JP2018537408 A5 JP 2018537408A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- amine
- amino
- methyl
- dimethylpentyl
- 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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- 239000003814 drug Substances 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- -1 (S) -methyl (4- (5-((2-amino-2,4 dimethylpentyl) oxy) -6-methylpyridin-2-yl) pyrimidin-2-yl) carbamate Chemical compound 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- KNKGQAHYNCLUIS-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-2-[[2-methyl-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxymethyl]pentan-2-amine Chemical compound FC(C(CC(C)C)(N)COC=1C(=NC(=CC=1)C1=NC(=NC=C1)C)C)(F)F KNKGQAHYNCLUIS-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 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
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- CAMODTUZESZPTO-GOSISDBHSA-N (2R)-2,4-dimethyl-1-[2-methyl-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxypentan-2-amine Chemical compound C[C@](COC=1C(=NC(=CC=1)C1=NC(=NC=C1)C)C)(CC(C)C)N CAMODTUZESZPTO-GOSISDBHSA-N 0.000 claims 1
- QWACYSBKKPMDNQ-GOSISDBHSA-N (2R)-2,4-dimethyl-1-[3-methyl-5-(2-methylpyrimidin-4-yl)pyridin-2-yl]oxypentan-2-amine Chemical compound C[C@](COC1=NC=C(C=C1C)C1=NC(=NC=C1)C)(CC(C)C)N QWACYSBKKPMDNQ-GOSISDBHSA-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
- 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
- XEZNCTPJVVSULY-SFHVURJKSA-N (2S)-1-[2,3-difluoro-4-(2-methylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1F)C1=NC(=NC=C1)C XEZNCTPJVVSULY-SFHVURJKSA-N 0.000 claims 1
- FPVSHICNSQNJBD-SFHVURJKSA-N (2S)-1-[2,5-difluoro-4-(6-methylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=C(C(=C1)C1=NC=NC(=C1)C)F FPVSHICNSQNJBD-SFHVURJKSA-N 0.000 claims 1
- GPWOFKIENUMEHE-FQEVSTJZSA-N (2S)-1-[2-(difluoromethyl)-4-(2-methoxypyridin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)OC)F GPWOFKIENUMEHE-FQEVSTJZSA-N 0.000 claims 1
- BHSGQGNMZWVVIG-IBGZPJMESA-N (2S)-1-[2-(difluoromethyl)-4-(6-methylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=NC=NC(=C1)C)F BHSGQGNMZWVVIG-IBGZPJMESA-N 0.000 claims 1
- DOIVBOYNRGAHPO-SFHVURJKSA-N (2S)-1-[2-(difluoromethyl)-6-[2-(difluoromethyl)pyrimidin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=NC(=NC=C1)C(F)F)F DOIVBOYNRGAHPO-SFHVURJKSA-N 0.000 claims 1
- RIHPQFDTJBQUJF-IBGZPJMESA-N (2S)-1-[2-(difluoromethyl)-6-[2-(fluoromethyl)pyridin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C1=C(C=CC(=N1)C1=CC(=NC=C1)CF)OC[C@](CC(C)C)(N)C)F RIHPQFDTJBQUJF-IBGZPJMESA-N 0.000 claims 1
- QKPDIUAIDJCKLY-IBGZPJMESA-N (2S)-1-[2-(fluoromethyl)-4-(2-methylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FCC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=NC(=NC=C1)C QKPDIUAIDJCKLY-IBGZPJMESA-N 0.000 claims 1
- LBHKHACLJJBTHJ-IBGZPJMESA-N (2S)-1-[2-(fluoromethyl)-6-(2-methylpyridin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FCC1=C(C=CC(=N1)C1=CC(=NC=C1)C)OC[C@](CC(C)C)(N)C LBHKHACLJJBTHJ-IBGZPJMESA-N 0.000 claims 1
- VPMWROAPRPMVDL-SFHVURJKSA-N (2S)-1-[2-(fluoromethyl)-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FCC1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=NC(=NC=C1)C VPMWROAPRPMVDL-SFHVURJKSA-N 0.000 claims 1
- YIRILFGNIIUPJM-SFHVURJKSA-N (2S)-1-[2-(fluoromethyl)-6-(6-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FCC1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=NC=NC(=C1)C YIRILFGNIIUPJM-SFHVURJKSA-N 0.000 claims 1
- LMXADOVWTGSOCY-IBGZPJMESA-N (2S)-1-[2-(fluoromethyl)-6-[2-(fluoromethyl)pyridin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(CF)N=C(C=C1)C1=CC(CF)=NC=C1 LMXADOVWTGSOCY-IBGZPJMESA-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
- 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
- MAQRLFVZVXAJPA-SFHVURJKSA-N (2S)-1-[2-fluoro-4-(2-methylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=NC(=NC=C1)C MAQRLFVZVXAJPA-SFHVURJKSA-N 0.000 claims 1
- SOVPNJLVDSVFLN-FQEVSTJZSA-N (2S)-1-[2-fluoro-4-(2-propan-2-ylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=NC(=NC=C1)C(C)C SOVPNJLVDSVFLN-FQEVSTJZSA-N 0.000 claims 1
- RXFKHOFNIOSORD-KRWDZBQOSA-N (2S)-1-[2-fluoro-4-[2-(trifluoromethyl)pyrimidin-4-yl]phenoxy]-2,4-dimethylpentan-2-amine Chemical compound FC1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=NC(=NC=C1)C(F)(F)F RXFKHOFNIOSORD-KRWDZBQOSA-N 0.000 claims 1
- MUBBONNTSFEQLW-KRWDZBQOSA-N (2S)-1-[3-chloro-5-(6-methylpyrimidin-4-yl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound ClC=1C(=NC=C(C=1)C1=NC=NC(=C1)C)OC[C@](CC(C)C)(N)C MUBBONNTSFEQLW-KRWDZBQOSA-N 0.000 claims 1
- OCHIFWUMTRVTJX-KRWDZBQOSA-N (2S)-1-[4-(2-chloropyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound ClC1=NC=CC(=N1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F OCHIFWUMTRVTJX-KRWDZBQOSA-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
- 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
- GJWIQWWUGFKKNE-KRWDZBQOSA-N (2S)-1-[4-(6-chloropyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(Cl)=NC=N1)C(F)(F)F GJWIQWWUGFKKNE-KRWDZBQOSA-N 0.000 claims 1
- AJVXVKZDDMKCHR-SFHVURJKSA-N (2S)-1-[4-(difluoromethyl)-6-(6-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C1=C(C=NC(=C1)C1=NC=NC(=C1)C)OC[C@](CC(C)C)(N)C)F AJVXVKZDDMKCHR-SFHVURJKSA-N 0.000 claims 1
- NEYPKSYHXQDKLY-IBGZPJMESA-N (2S)-1-[4-[2-(difluoromethyl)pyridin-4-yl]-2,5-difluorophenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(F)C=C(C(F)=C1)C1=CC(=NC=C1)C(F)F NEYPKSYHXQDKLY-IBGZPJMESA-N 0.000 claims 1
- JJNGSZHKSVGEOE-IBGZPJMESA-N (2S)-1-[5-(6-ethylpyrimidin-4-yl)-3-methylpyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound C(C)C1=CC(=NC=N1)C=1C=C(C(=NC=1)OC[C@](CC(C)C)(N)C)C JJNGSZHKSVGEOE-IBGZPJMESA-N 0.000 claims 1
- QZIRMGCMBPRJPN-IBGZPJMESA-N (2S)-1-[6-[2-(difluoromethyl)pyridin-4-yl]-2-(fluoromethyl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(CF)N=C(C=C1)C1=CC(=NC=C1)C(F)F QZIRMGCMBPRJPN-IBGZPJMESA-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
- 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
- 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
- CAMODTUZESZPTO-SFHVURJKSA-N (2S)-2,4-dimethyl-1-[2-methyl-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxypentan-2-amine Chemical compound C[C@@](COC=1C(=NC(=CC=1)C1=NC(=NC=C1)C)C)(CC(C)C)N CAMODTUZESZPTO-SFHVURJKSA-N 0.000 claims 1
- NQSHPCVRRMFJCB-SFHVURJKSA-N (2S)-2,4-dimethyl-1-[2-methyl-6-[2-(trifluoromethyl)pyridin-4-yl]pyridin-3-yl]oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C)N=C(C=C1)C1=CC(=NC=C1)C(F)(F)F NQSHPCVRRMFJCB-SFHVURJKSA-N 0.000 claims 1
- QWACYSBKKPMDNQ-SFHVURJKSA-N (2S)-2,4-dimethyl-1-[3-methyl-5-(2-methylpyrimidin-4-yl)pyridin-2-yl]oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C)C1=CC=NC(C)=N1 QWACYSBKKPMDNQ-SFHVURJKSA-N 0.000 claims 1
- XWVLXABIHUJMKI-SFHVURJKSA-N (2S)-2,4-dimethyl-1-[3-methyl-5-(6-methylpyrimidin-4-yl)pyridin-2-yl]oxypentan-2-amine Chemical compound C[C@@](COC1=NC=C(C=C1C)C1=NC=NC(=C1)C)(CC(C)C)N XWVLXABIHUJMKI-SFHVURJKSA-N 0.000 claims 1
- IJPSSWRNIYOXIB-NRFANRHFSA-N (2S)-2,4-dimethyl-1-[4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(trifluoromethyl)phenoxy]pentan-2-amine Chemical class C[C@@](COC1=C(C=C(C=C1)C1=C2C(=NC=C1)NC(=C2)C)C(F)(F)F)(CC(C)C)N IJPSSWRNIYOXIB-NRFANRHFSA-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
- 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
- XVOACXYWAZTIKQ-SFHVURJKSA-N (2S)-2,4-dimethyl-1-[4-methyl-6-(6-methylpyrimidin-4-yl)pyridin-3-yl]oxypentan-2-amine Chemical compound C[C@@](COC=1C=NC(=CC=1C)C1=NC=NC(=C1)C)(CC(C)C)N XVOACXYWAZTIKQ-SFHVURJKSA-N 0.000 claims 1
- GQTXVEHCJGYSSS-SFHVURJKSA-N (2S)-2,4-dimethyl-1-[4-methyl-6-[2-(trifluoromethyl)pyridin-4-yl]pyridin-3-yl]oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CN=C(C=C1C)C1=CC(=NC=C1)C(F)(F)F GQTXVEHCJGYSSS-SFHVURJKSA-N 0.000 claims 1
- SJTIZWLIWYTKLZ-FQEVSTJZSA-N (2S)-2,4-dimethyl-1-[5-(2-methylpyrimidin-4-yl)-3-(1,3-oxazol-5-yl)pyridin-2-yl]oxypentan-2-amine Chemical compound C[C@@](COC1=NC=C(C=C1C1=CN=CO1)C1=NC(=NC=C1)C)(CC(C)C)N SJTIZWLIWYTKLZ-FQEVSTJZSA-N 0.000 claims 1
- LNUMKTDWDOCBHB-KRWDZBQOSA-N (2S)-2,4-dimethyl-1-[6-(2-methylpyrimidin-4-yl)-2-(trifluoromethyl)pyridin-3-yl]oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)(F)F)C1=CC=NC(C)=N1 LNUMKTDWDOCBHB-KRWDZBQOSA-N 0.000 claims 1
- VJWWCIIQNAXBRB-FQEVSTJZSA-N (2S)-2,4-dimethyl-1-[6-(2-methylpyrimidin-4-yl)-4-(1,3-oxazol-5-yl)pyridin-3-yl]oxypentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC(C)=N1)C1=CN=CO1 VJWWCIIQNAXBRB-FQEVSTJZSA-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
- WORQUKLLAQUYNS-UHFFFAOYSA-N 1-[2-chloro-4-(2-propan-2-ylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)CC(C)(N)COc1ccc(cc1Cl)-c1ccnc(n1)C(C)C WORQUKLLAQUYNS-UHFFFAOYSA-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
- OLVLZGMMYLQFMV-IBGZPJMESA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(2-methoxypyridin-4-yl)pyridine-3-carbonitrile Chemical compound COC1=NC=CC(=C1)C1=CC(C#N)=C(OC[C@@](C)(N)CC(C)C)N=C1 OLVLZGMMYLQFMV-IBGZPJMESA-N 0.000 claims 1
- HPIVVEODRVNBIU-NRFANRHFSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(2-methylimidazo[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)C)(CC(C)C)C HPIVVEODRVNBIU-NRFANRHFSA-N 0.000 claims 1
- ILIXSERZCVATSL-QHCPKHFHSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(6-chloro-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=C(C=1)Cl)C=C(N=2)C1CC1)(CC(C)C)C ILIXSERZCVATSL-QHCPKHFHSA-N 0.000 claims 1
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| WO2017059080A1 (en) | 2015-10-01 | 2017-04-06 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| WO2018116139A1 (en) | 2016-12-19 | 2018-06-28 | Novartis Ag | New picolinic acid derivatives and their use as intermediates |
| CN115484951A (zh) * | 2020-04-21 | 2022-12-16 | 莱西肯医药有限公司 | 用于治疗病毒感染的aak1抑制剂 |
| CN111995583A (zh) * | 2020-08-18 | 2020-11-27 | 上海毕得医药科技有限公司 | 一种1,5-二甲基嘧啶-2(1h)-酮的合成方法 |
| EP4371980A4 (en) | 2021-07-15 | 2024-12-11 | Xizang Haisco Pharmaceutical Co., Ltd. | AAK1 INHIBITOR AND USE THEREOF |
| CN119095826A (zh) | 2022-03-01 | 2024-12-06 | 莱西肯医药有限公司 | 用于合成aak1抑制剂的方法和化合物 |
| AU2023229156A1 (en) | 2022-03-01 | 2024-08-15 | Lexicon Pharmaceuticals, Inc. | Solid forms of (s)-l-((2',6-bis(difluoromethyl)-[2,4'-bipyridin]-5-yl)oxy)-2,4-dimethylpentan-2-amine and salts thereof |
| TW202423433A (zh) * | 2022-11-10 | 2024-06-16 | 大陸商西藏海思科製藥有限公司 | 含aak1抑制劑的藥物组合物 |
| CN120641406A (zh) * | 2023-01-16 | 2025-09-12 | 上海海雁医药科技有限公司 | 杂环取代的含氮杂环衍生物、其药物组合物及应用与制备方法 |
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