JP2018537408A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- RQCZDSOWPMKDBV-IBGZPJMESA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-(6-methylpyrimidin-4-yl)benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=NC=NC(=C1)C)(CC(C)C)C RQCZDSOWPMKDBV-IBGZPJMESA-N 0.000 claims 1
- VCBNGRWDYBWXKN-IBGZPJMESA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-[2-(difluoromethyl)pyrimidin-4-yl]benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=NC(=NC=C1)C(F)F)(CC(C)C)C VCBNGRWDYBWXKN-IBGZPJMESA-N 0.000 claims 1
- WBHCPPPSDWCQAE-FQEVSTJZSA-N 2-[(2S)-2-amino-2,4-dimethylpentoxy]-5-[2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7-yl]benzonitrile Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=CC=NC=2N1N=C(C=2)C(F)(F)F)(CC(C)C)C WBHCPPPSDWCQAE-FQEVSTJZSA-N 0.000 claims 1
- PHJCGUBYIQTZSZ-UHFFFAOYSA-N 3-(difluoromethyl)-5-[[2-(2-methylpropyl)azetidin-2-yl]methoxy]-2-pyridin-4-ylpyridine Chemical compound FC(F)C=1C(=NC=C(C1)OCC1(NCC1)CC(C)C)C1=CC=NC=C1 PHJCGUBYIQTZSZ-UHFFFAOYSA-N 0.000 claims 1
- YJBWEBYOOJGRQD-QHCPKHFHSA-N 4-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-(trifluoromethyl)phenyl]-N-(furan-2-ylmethyl)pyridin-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(NCC2=CC=CO2)=NC=C1)C(F)(F)F YJBWEBYOOJGRQD-QHCPKHFHSA-N 0.000 claims 1
- NLRFTFMASHSWIC-NRFANRHFSA-N 4-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-fluorophenyl]-6-methyl-7H-pyrrolo[3,4-b]pyridin-5-one Chemical compound N[C@](COC1=C(C=C(C=C1)C1=C2C(=NC=C1)CN(C2=O)C)F)(CC(C)C)C NLRFTFMASHSWIC-NRFANRHFSA-N 0.000 claims 1
- YDGIKDGVRAZDSF-SFHVURJKSA-N 4-[5-[(2S)-2-amino-2,4-dimethylpentoxy]-6-methylpyridin-2-yl]pyridin-2-amine Chemical compound N[C@](COC=1C=CC(=NC=1C)C1=CC(=NC=C1)N)(CC(C)C)C YDGIKDGVRAZDSF-SFHVURJKSA-N 0.000 claims 1
- QHBJYXAWUZGADH-KRWDZBQOSA-N 4-[5-[(2S)-2-amino-2,4-dimethylpentoxy]-6-methylpyridin-2-yl]pyrimidin-2-amine Chemical compound N[C@](COC=1C=CC(=NC=1C)C1=NC(=NC=C1)N)(CC(C)C)C QHBJYXAWUZGADH-KRWDZBQOSA-N 0.000 claims 1
- VQTSUAUUBDBIPE-UHFFFAOYSA-N 4-methyl-N-[1,1,1-trifluoro-4-methyl-2-[[3-methyl-5-(2-methylpyrimidin-4-yl)pyridin-2-yl]oxymethyl]pentan-2-yl]benzenesulfonamide Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(C(F)(F)F)(CC(C)C)COC1=NC=C(C=C1C)C1=NC(=NC=C1)C VQTSUAUUBDBIPE-UHFFFAOYSA-N 0.000 claims 1
- CPIXOEHRYRXGDS-SFHVURJKSA-N 5-[(2S)-2-amino-2,4-dimethylpentoxy]-2-(2-methylpyrimidin-4-yl)pyridine-4-carbonitrile Chemical compound N[C@](COC1=CN=C(C=C1C#N)C1=NC(=NC=C1)C)(CC(C)C)C CPIXOEHRYRXGDS-SFHVURJKSA-N 0.000 claims 1
- CBKXQMXUADIAMG-IBGZPJMESA-N 5-[(2S)-2-amino-2,4-dimethylpentoxy]-2-pyrazolo[1,5-a]pyrimidin-7-ylpyridine-4-carbonitrile Chemical compound N[C@](COC1=CN=C(C=C1C#N)C1=CC=NC=2N1N=CC=2)(CC(C)C)C CBKXQMXUADIAMG-IBGZPJMESA-N 0.000 claims 1
- QPJZWSYVQPLBTG-KRWDZBQOSA-N 6-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=N1)N)C(F)(F)F)(CC(C)C)C QPJZWSYVQPLBTG-KRWDZBQOSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- WKBMDESCGNLJAB-IBGZPJMESA-N BrC1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C Chemical compound BrC1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C WKBMDESCGNLJAB-IBGZPJMESA-N 0.000 claims 1
- YBIVTEKYCUSQHU-SFHVURJKSA-N BrC1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)F Chemical compound BrC1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)F YBIVTEKYCUSQHU-SFHVURJKSA-N 0.000 claims 1
- WCFHRUMWKBXQBE-SFHVURJKSA-N BrC1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1F)F Chemical compound BrC1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1F)F WCFHRUMWKBXQBE-SFHVURJKSA-N 0.000 claims 1
- HEPMTGCGKVBUDH-MHZLTWQESA-N C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=C2C(=NC=C1)NC(=C2)C Chemical compound C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=C2C(=NC=C1)NC(=C2)C HEPMTGCGKVBUDH-MHZLTWQESA-N 0.000 claims 1
- UKAIKIISFDOVNA-DEOSSOPVSA-N C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C Chemical compound C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C UKAIKIISFDOVNA-DEOSSOPVSA-N 0.000 claims 1
- KQAAGMXGJSPEOA-QHCPKHFHSA-N C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C(F)(F)F Chemical compound C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C(F)(F)F KQAAGMXGJSPEOA-QHCPKHFHSA-N 0.000 claims 1
- JDULUDPUPBZBQH-VWLOTQADSA-N C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC=NC(=C1)CC Chemical compound C(#N)C1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC=NC(=C1)CC JDULUDPUPBZBQH-VWLOTQADSA-N 0.000 claims 1
- WEXNEGNHJJOXHL-VWLOTQADSA-N C(C)(=O)NC1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C Chemical compound C(C)(=O)NC1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C WEXNEGNHJJOXHL-VWLOTQADSA-N 0.000 claims 1
- URVREKSJBNYLND-QHCPKHFHSA-N C(C)(C)(C)OC(N[C@](COC1=C(C=C(C=C1)C1=NC=NC(=C1)C)C(F)(F)F)(CC(C)C)C)=O Chemical compound C(C)(C)(C)OC(N[C@](COC1=C(C=C(C=C1)C1=NC=NC(=C1)C)C(F)(F)F)(CC(C)C)C)=O URVREKSJBNYLND-QHCPKHFHSA-N 0.000 claims 1
- AITAVJSBKBFXKV-DEOSSOPVSA-N C(C)C1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F Chemical compound C(C)C1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F AITAVJSBKBFXKV-DEOSSOPVSA-N 0.000 claims 1
- KNKAABYFUJVMAY-QHCPKHFHSA-N CC(C)CC(=O)NC1=NC=CC(=C1)C1=CC(=C(OC[C@@](C)(N)CC(C)C)C=C1)C(F)(F)F Chemical compound CC(C)CC(=O)NC1=NC=CC(=C1)C1=CC(=C(OC[C@@](C)(N)CC(C)C)C=C1)C(F)(F)F KNKAABYFUJVMAY-QHCPKHFHSA-N 0.000 claims 1
- XBXLMYVIODWNQA-UHFFFAOYSA-N CC(C)CC(C(N)=O)C1=NC=CC(C(C=C2)=CC(C(F)(F)F)=C2OCC(C)(CC(C)C)N)=C1 Chemical compound CC(C)CC(C(N)=O)C1=NC=CC(C(C=C2)=CC(C(F)(F)F)=C2OCC(C)(CC(C)C)N)=C1 XBXLMYVIODWNQA-UHFFFAOYSA-N 0.000 claims 1
- GMYPQVTZBYPWLT-DEOSSOPVSA-N CC(C)C[C@@](C)(COC1=C(Cl)C=C(C=C1)B1OC(C)(C)C(C)(C)O1)NC(=O)OC(C)(C)C Chemical compound CC(C)C[C@@](C)(COC1=C(Cl)C=C(C=C1)B1OC(C)(C)C(C)(C)O1)NC(=O)OC(C)(C)C GMYPQVTZBYPWLT-DEOSSOPVSA-N 0.000 claims 1
- SRBGXLVNHFSKKZ-DEOSSOPVSA-N CC(C)C[C@@](C)(COC1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1)NC(=O)OC(C)(C)C Chemical compound CC(C)C[C@@](C)(COC1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1)NC(=O)OC(C)(C)C SRBGXLVNHFSKKZ-DEOSSOPVSA-N 0.000 claims 1
- KMFWSWKDRCBYPJ-SANMLTNESA-N CC(C)C[C@@](C)(COC1=CC=C(C=C1C(F)(F)F)C1=NC(NC(=O)OC(C)C)=NC=C1)NC(=O)OC(C)(C)C Chemical compound CC(C)C[C@@](C)(COC1=CC=C(C=C1C(F)(F)F)C1=NC(NC(=O)OC(C)C)=NC=C1)NC(=O)OC(C)(C)C KMFWSWKDRCBYPJ-SANMLTNESA-N 0.000 claims 1
- VALCVENLXBCJPG-SFHVURJKSA-N CC(C)C[C@@](C)(COC1=CC=C(I)N=C1C)NC(=O)OC(C)(C)C Chemical compound CC(C)C[C@@](C)(COC1=CC=C(I)N=C1C)NC(=O)OC(C)(C)C VALCVENLXBCJPG-SFHVURJKSA-N 0.000 claims 1
- XZPFRRCTDKFOLM-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(Cl)=NC=N1)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(Cl)=NC=N1)C#N XZPFRRCTDKFOLM-SFHVURJKSA-N 0.000 claims 1
- STIBTNSZQHPXMJ-VWLOTQADSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(NC(=O)C2=NNC(=C2)C(C)C)=NC=C1)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(NC(=O)C2=NNC(=C2)C(C)C)=NC=C1)C(F)(F)F STIBTNSZQHPXMJ-VWLOTQADSA-N 0.000 claims 1
- XTEBSQGAAUIYIS-DEOSSOPVSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(NCC2=CC=CN=C2)=NC=C1)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(NCC2=CC=CN=C2)=NC=C1)C(F)(F)F XTEBSQGAAUIYIS-DEOSSOPVSA-N 0.000 claims 1
- OGAIIPYGTBOPMO-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=CC(=NC=C1)C(F)(F)F)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=CC(=NC=C1)C(F)(F)F)C(F)F OGAIIPYGTBOPMO-SFHVURJKSA-N 0.000 claims 1
- SECWLUJDTUFUCI-DEOSSOPVSA-N CC1=NC(=CC(=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F)C Chemical compound CC1=NC(=CC(=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F)C SECWLUJDTUFUCI-DEOSSOPVSA-N 0.000 claims 1
- BGZRQEFPTXZJCN-VWLOTQADSA-N CCOC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(=C1)C(F)(F)F Chemical compound CCOC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(=C1)C(F)(F)F BGZRQEFPTXZJCN-VWLOTQADSA-N 0.000 claims 1
- LZKPAXUMWMIBRS-IBGZPJMESA-N COC(=O)NC1=CC(=NC=N1)C1=C(F)C=C(OC[C@@](C)(N)CC(C)C)C(F)=C1 Chemical compound COC(=O)NC1=CC(=NC=N1)C1=C(F)C=C(OC[C@@](C)(N)CC(C)C)C(F)=C1 LZKPAXUMWMIBRS-IBGZPJMESA-N 0.000 claims 1
- SYSNYDVHFNRVOB-IBGZPJMESA-N COC(=O)NC1=NC(=CC=N1)C1=C(F)C=C(OC[C@@](C)(N)CC(C)C)C(F)=C1 Chemical compound COC(=O)NC1=NC(=CC=N1)C1=C(F)C=C(OC[C@@](C)(N)CC(C)C)C(F)=C1 SYSNYDVHFNRVOB-IBGZPJMESA-N 0.000 claims 1
- AZWVRHRVDPXEEY-VWLOTQADSA-N COC(=O)NC1=NC(=CC=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(C)=C1 Chemical compound COC(=O)NC1=NC(=CC=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(C)=C1 AZWVRHRVDPXEEY-VWLOTQADSA-N 0.000 claims 1
- CNAFHIKHNXQPGG-FQEVSTJZSA-N COC(=O)NC1=NC=CC(=C1)C1=NC(CF)=C(OC[C@@](C)(N)CC(C)C)C=C1 Chemical compound COC(=O)NC1=NC=CC(=C1)C1=NC(CF)=C(OC[C@@](C)(N)CC(C)C)C=C1 CNAFHIKHNXQPGG-FQEVSTJZSA-N 0.000 claims 1
- YIRVWHXKLZLQNU-VWLOTQADSA-N COC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(=C1)C#N Chemical compound COC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(=C1)C#N YIRVWHXKLZLQNU-VWLOTQADSA-N 0.000 claims 1
- PSPYAPHQKNAPFI-DEOSSOPVSA-N COC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(=C1)C(F)(F)F Chemical compound COC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(=C1)C(F)(F)F PSPYAPHQKNAPFI-DEOSSOPVSA-N 0.000 claims 1
- AMFMYUMFPDUDSR-DEOSSOPVSA-N COC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(Cl)=C1 Chemical compound COC(=O)NC1=NC=CC(=N1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(Cl)=C1 AMFMYUMFPDUDSR-DEOSSOPVSA-N 0.000 claims 1
- KWFAECYQXWPSHL-DEOSSOPVSA-N COC(=O)NC1=NN=CC(=C1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(Cl)=C1 Chemical compound COC(=O)NC1=NN=CC(=C1)C1=CC=C(OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C)C(Cl)=C1 KWFAECYQXWPSHL-DEOSSOPVSA-N 0.000 claims 1
- UUXQIVZZDGHWGV-VWLOTQADSA-N COC1=NC=CC(=C1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C Chemical compound COC1=NC=CC(=C1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C UUXQIVZZDGHWGV-VWLOTQADSA-N 0.000 claims 1
- JBSIDAOHQJUDKU-QHCPKHFHSA-N C[C@@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)C(F)(F)F)C)(CC(C)C)NC(OC(C)(C)C)=O Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)C(F)(F)F)C)(CC(C)C)NC(OC(C)(C)C)=O JBSIDAOHQJUDKU-QHCPKHFHSA-N 0.000 claims 1
- NUQKSHNJZFWRGH-QHCPKHFHSA-N C[C@@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)C)C(F)(F)F)(CC(C)C)NC(OC(C)(C)C)=O Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)C)C(F)(F)F)(CC(C)C)NC(OC(C)(C)C)=O NUQKSHNJZFWRGH-QHCPKHFHSA-N 0.000 claims 1
- YIYOTINRWMDGRF-DEOSSOPVSA-N C[C@@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)C)C)(CC(C)C)NC(OC(C)(C)C)=O Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)C)C)(CC(C)C)NC(OC(C)(C)C)=O YIYOTINRWMDGRF-DEOSSOPVSA-N 0.000 claims 1
- BXGSILHFQCMUMQ-DEOSSOPVSA-N C[C@@](COC1=C(C=C(C=C1)C1=NC=NC(=C1)C)C)(CC(C)C)NC(OC(C)(C)C)=O Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=NC=NC(=C1)C)C)(CC(C)C)NC(OC(C)(C)C)=O BXGSILHFQCMUMQ-DEOSSOPVSA-N 0.000 claims 1
- KGTXKCSZUJPTDB-FQEVSTJZSA-N C[C@@](COC1=C(C=C(C=C1)C=1C=2N(N=CC=1)C=C(N=2)C)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC1=C(C=C(C=C1)C=1C=2N(N=CC=1)C=C(N=2)C)C(F)(F)F)(CC(C)C)N KGTXKCSZUJPTDB-FQEVSTJZSA-N 0.000 claims 1
- ROAUYVKHNZPXAW-QHCPKHFHSA-N ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C Chemical compound ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C ROAUYVKHNZPXAW-QHCPKHFHSA-N 0.000 claims 1
- GOTOOCRVDFHYIV-QFIPXVFZSA-N ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C(F)(F)F Chemical compound ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)C(F)(F)F GOTOOCRVDFHYIV-QFIPXVFZSA-N 0.000 claims 1
- DNBFQCHMKIRYSA-QFIPXVFZSA-N ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)Cl Chemical compound ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC(=NC=C1)Cl DNBFQCHMKIRYSA-QFIPXVFZSA-N 0.000 claims 1
- NXZVHVWAAHWQPA-QHCPKHFHSA-N ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC=NC(=C1)C Chemical compound ClC1=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=CC(=C1)C1=NC=NC(=C1)C NXZVHVWAAHWQPA-QHCPKHFHSA-N 0.000 claims 1
- MUBLYAYJEWYQBK-QHCPKHFHSA-N ClC1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C#N Chemical compound ClC1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C#N MUBLYAYJEWYQBK-QHCPKHFHSA-N 0.000 claims 1
- QECUFHZZBXEITL-QFIPXVFZSA-N ClC1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F Chemical compound ClC1=CC(=NC=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F QECUFHZZBXEITL-QFIPXVFZSA-N 0.000 claims 1
- OJAKVICODSDBNP-QHCPKHFHSA-N ClC1=NC=CC(=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C#N Chemical compound ClC1=NC=CC(=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C#N OJAKVICODSDBNP-QHCPKHFHSA-N 0.000 claims 1
- DCPBIRRYZYKVLY-QFIPXVFZSA-N ClC1=NC=CC(=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F Chemical compound ClC1=NC=CC(=N1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F DCPBIRRYZYKVLY-QFIPXVFZSA-N 0.000 claims 1
- PGLHOMQXJZWBRS-QFIPXVFZSA-N ClC1=NC=CC(=N1)C1=CC=C(C(=N1)C)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O Chemical compound ClC1=NC=CC(=N1)C1=CC=C(C(=N1)C)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O PGLHOMQXJZWBRS-QFIPXVFZSA-N 0.000 claims 1
- PUMNLDADMRYMKA-QHCPKHFHSA-N FC1=NC=CC(=C1)C1=NC=C(C(=C1)C)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O Chemical compound FC1=NC=CC(=C1)C1=NC=C(C(=C1)C)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O PUMNLDADMRYMKA-QHCPKHFHSA-N 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- CJUDEYLRRWEPHI-UCSBTNPJSA-N N-[4-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-(trifluoromethyl)phenyl]pyridin-2-yl]-3-methylpentanamide Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(CC(CC)C)=O)C(F)(F)F)(CC(C)C)C CJUDEYLRRWEPHI-UCSBTNPJSA-N 0.000 claims 1
- YNTLLTJBHMDFGR-QHCPKHFHSA-N N-[4-[4-[(2S)-2-amino-2,4-dimethylpentoxy]-3-(trifluoromethyl)phenyl]pyridin-2-yl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(NC(=O)C2=NOC(C)=C2)=NC=C1)C(F)(F)F YNTLLTJBHMDFGR-QHCPKHFHSA-N 0.000 claims 1
- ISFHPNHSGNEPIB-QHCPKHFHSA-N NC1=NC=CC(=C1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F Chemical compound NC1=NC=CC(=C1)C1=CC(=C(OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C=C1)C(F)(F)F ISFHPNHSGNEPIB-QHCPKHFHSA-N 0.000 claims 1
- KNIFCKHVVQVHPJ-GOSISDBHSA-N N[C@@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)Cl)(CC(C)C)C Chemical compound N[C@@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)Cl)(CC(C)C)C KNIFCKHVVQVHPJ-GOSISDBHSA-N 0.000 claims 1
- IHZJPJROWHPTCL-GOSISDBHSA-N N[C@@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)F)(CC(C)C)C Chemical compound N[C@@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)F)(CC(C)C)C IHZJPJROWHPTCL-GOSISDBHSA-N 0.000 claims 1
- HQYXPHDJALHZOC-VWLOTQADSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC1=CC2=C(OCO2)C=C1)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC1=CC2=C(OCO2)C=C1)C(F)(F)F)(CC(C)C)C HQYXPHDJALHZOC-VWLOTQADSA-N 0.000 claims 1
- KBZFWOCHVZRANF-IBGZPJMESA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=N1)NC(OC)=O)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=N1)NC(OC)=O)C(F)(F)F)(CC(C)C)C KBZFWOCHVZRANF-IBGZPJMESA-N 0.000 claims 1
- XHPGNKKCONUHAQ-KRWDZBQOSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(NC=N1)=O)Cl)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(NC=N1)=O)Cl)(CC(C)C)C XHPGNKKCONUHAQ-KRWDZBQOSA-N 0.000 claims 1
- FCDGECJJXGLBJX-KRWDZBQOSA-N N[C@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)O)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=NC(=NC=C1)O)C(F)(F)F)(CC(C)C)C FCDGECJJXGLBJX-KRWDZBQOSA-N 0.000 claims 1
- CEQCSEJIBMRNEN-FQEVSTJZSA-N N[C@](COC1=C(C=C(C=C1)C=1C=C(N=NC=1)NC(OC)=O)C#N)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C=1C=C(N=NC=1)NC(OC)=O)C#N)(CC(C)C)C CEQCSEJIBMRNEN-FQEVSTJZSA-N 0.000 claims 1
- LWCUISZWGAZAMB-IBGZPJMESA-N N[C@](COC1=C(C=C(C=N1)C1=CC(=NC=N1)NC(OC)=O)C)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=N1)C1=CC(=NC=N1)NC(OC)=O)C)(CC(C)C)C LWCUISZWGAZAMB-IBGZPJMESA-N 0.000 claims 1
- LJEWKSGYSPHRRA-SFHVURJKSA-N N[C@](COC1=C(C=C(C=N1)C1=CC(=NC=N1)NC(OC)=O)Cl)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=N1)C1=CC(=NC=N1)NC(OC)=O)Cl)(CC(C)C)C LJEWKSGYSPHRRA-SFHVURJKSA-N 0.000 claims 1
- JPFXZFOXTVGRDA-IBGZPJMESA-N N[C@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)C)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)C)(CC(C)C)C JPFXZFOXTVGRDA-IBGZPJMESA-N 0.000 claims 1
- KNIFCKHVVQVHPJ-SFHVURJKSA-N N[C@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)Cl)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)Cl)(CC(C)C)C KNIFCKHVVQVHPJ-SFHVURJKSA-N 0.000 claims 1
- RATCBMQFWBQWKS-IBGZPJMESA-N N[C@](COC1=CC(=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)C)(CC(C)C)C Chemical compound N[C@](COC1=CC(=C(C=N1)C1=NC(=NC=C1)NC(OC)=O)C)(CC(C)C)C RATCBMQFWBQWKS-IBGZPJMESA-N 0.000 claims 1
- CCRNDRCUVGXVOY-IBGZPJMESA-N N[C@](COC=1C=CC(=NC=1C(F)F)C1=NC(=NC=C1)NC(OC)=O)(CC(C)C)C Chemical compound N[C@](COC=1C=CC(=NC=1C(F)F)C1=NC(=NC=C1)NC(OC)=O)(CC(C)C)C CCRNDRCUVGXVOY-IBGZPJMESA-N 0.000 claims 1
- OIXMDUVCOSGJOR-IBGZPJMESA-N N[C@](COC=1C=CC(=NC=1CF)C1=NC(=NC=C1)NC(OC)=O)(CC(C)C)C Chemical compound N[C@](COC=1C=CC(=NC=1CF)C1=NC(=NC=C1)NC(OC)=O)(CC(C)C)C OIXMDUVCOSGJOR-IBGZPJMESA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- MCUCUABNLZIHDX-UHFFFAOYSA-N methyl N-[4-[5-[2-amino-4-methyl-2-(trifluoromethyl)pentoxy]-6-methylpyridin-2-yl]pyridin-2-yl]carbamate Chemical compound NC(COC=1C=CC(=NC=1C)C1=CC(=NC=C1)NC(OC)=O)(CC(C)C)C(F)(F)F MCUCUABNLZIHDX-UHFFFAOYSA-N 0.000 claims 1
- JLSFIEDKSVOGGY-VWLOTQADSA-N methyl N-[6-[4-[(2S)-2,4-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentoxy]-3-methylphenyl]pyrimidin-4-yl]carbamate Chemical compound CC1=C(C=CC(=C1)C2=CC(=NC=N2)NC(=O)OC)OC[C@](C)(CC(C)C)NC(=O)OC(C)(C)C JLSFIEDKSVOGGY-VWLOTQADSA-N 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3170/DEL/2015 | 2015-10-01 | ||
| IN3170DE2015 | 2015-10-01 | ||
| PCT/US2016/054471 WO2017059085A1 (en) | 2015-10-01 | 2016-09-29 | Biaryl kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018537408A JP2018537408A (ja) | 2018-12-20 |
| JP2018537408A5 true JP2018537408A5 (OSRAM) | 2019-11-07 |
| JP6785302B2 JP6785302B2 (ja) | 2020-11-18 |
Family
ID=57190217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018516713A Active JP6785302B2 (ja) | 2015-10-01 | 2016-09-29 | ビアリールキナーゼ阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10544120B2 (OSRAM) |
| EP (1) | EP3356340B1 (OSRAM) |
| JP (1) | JP6785302B2 (OSRAM) |
| KR (1) | KR102704295B1 (OSRAM) |
| CN (2) | CN108368084B (OSRAM) |
| ES (1) | ES2765730T3 (OSRAM) |
| WO (1) | WO2017059085A1 (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102379518B1 (ko) | 2014-04-02 | 2022-03-25 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| ES2767776T3 (es) | 2015-10-01 | 2020-06-18 | Bristol Myers Squibb Co | Inhibidores de biaril cinasa |
| US10544120B2 (en) | 2015-10-01 | 2020-01-28 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| EP3555048B1 (en) | 2016-12-19 | 2021-07-07 | Novartis AG | New picolinic acid derivatives and their use as intermediates |
| US11730723B2 (en) * | 2020-04-21 | 2023-08-22 | Lexicon Pharmaceuticals, Inc. | Compounds and methods for treating viral infections |
| 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 |
| CN117715899A (zh) * | 2021-07-15 | 2024-03-15 | 西藏海思科制药有限公司 | Aak1抑制剂及其用途 |
| US12344596B2 (en) | 2022-03-01 | 2025-07-01 | Lexicon Pharmaceuticals, Inc. | Solid forms of (S)-1-((2′,6-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)-2,4-dimethylpentan-2-amine and salts thereof |
| WO2023167806A1 (en) * | 2022-03-01 | 2023-09-07 | Lexicon Pharmaceuticals, Inc. | Methods and compounds useful in the sythesis of an aak1 inhibitor |
| CN120202001A (zh) * | 2022-11-10 | 2025-06-24 | 西藏海思科制药有限公司 | 一种含aak1抑制剂的药物组合物 |
| 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 |
| WO2024207945A1 (zh) * | 2023-04-07 | 2024-10-10 | 艾立康药业股份有限公司 | 作为aak1抑制剂的氮杂环类化合物 |
| CN118772152A (zh) * | 2023-04-07 | 2024-10-15 | 艾立康药业股份有限公司 | 作为aak1抑制剂的氮杂环类化合物 |
| WO2025092928A1 (zh) * | 2023-11-02 | 2025-05-08 | 西藏海思科制药有限公司 | 一种可抑制连接蛋白相关激酶1的化合物、制备及其用途 |
| KR20250158680A (ko) | 2024-04-29 | 2025-11-06 | 심플렉스 주식회사 | 신규한 헤테로아릴 유도체 및 이의 aak1 억제 용도 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003286895A1 (en) | 2002-11-05 | 2004-06-07 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of jak and other protein kinases |
| AR093195A1 (es) * | 2012-02-29 | 2015-05-27 | Meiji Seika Pharma Co Ltd | Composicion para el control de plagas que incluye un derivado de iminopiridina |
| HUE036040T2 (hu) | 2012-03-09 | 2018-06-28 | Lexicon Pharmaceuticals Inc | Adaptor-asszociált kináz 1 gátlása fájdalom kezelésére |
| US8703953B2 (en) * | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| US8901305B2 (en) * | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| JP2016509066A (ja) | 2013-02-22 | 2016-03-24 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アダプター関連キナーゼ１（ａａｋ１）の阻害剤としての５ｈ−クロメノ［３，４−ｃ］ピリジン |
| WO2015006100A1 (en) | 2013-07-08 | 2015-01-15 | Bristol-Myers Squibb Company | Aryl amide kinase inhibitors |
| WO2015038112A1 (en) | 2013-09-11 | 2015-03-19 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| EP3046919B1 (en) * | 2013-09-19 | 2019-08-07 | Basf Se | N-acylimino heterocyclic compounds |
| EP3099300B1 (en) | 2014-01-29 | 2018-09-05 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| ES2701903T3 (es) | 2014-01-31 | 2019-02-26 | Bristol Myers Squibb Co | Inhibidores de cinasa a base de quinolina |
| KR102379518B1 (ko) * | 2014-04-02 | 2022-03-25 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| EP3200797A1 (en) | 2014-09-30 | 2017-08-09 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| EP3292124B1 (en) | 2015-04-10 | 2019-05-22 | Bristol-Myers Squibb Company | 6h-isochromeno[3,4-c]pyridines and benzo[c][1,7]naphthyridin-6-(5h)-ones as adaptor associated kinase 1 (aak1) inhibitors |
| ES2767776T3 (es) | 2015-10-01 | 2020-06-18 | Bristol Myers Squibb Co | Inhibidores de biaril cinasa |
| US10544120B2 (en) | 2015-10-01 | 2020-01-28 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
-
2016
- 2016-09-29 US US15/763,280 patent/US10544120B2/en active Active
- 2016-09-29 JP JP2018516713A patent/JP6785302B2/ja active Active
- 2016-09-29 CN CN201680070440.1A patent/CN108368084B/zh active Active
- 2016-09-29 WO PCT/US2016/054471 patent/WO2017059085A1/en not_active Ceased
- 2016-09-29 EP EP16785279.7A patent/EP3356340B1/en active Active
- 2016-09-29 KR KR1020187011874A patent/KR102704295B1/ko active Active
- 2016-09-29 CN CN202010986635.9A patent/CN112142655A/zh active Pending
- 2016-09-29 ES ES16785279T patent/ES2765730T3/es active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018537408A5 (OSRAM) | ||
| JP2017511329A5 (OSRAM) | ||
| RU2018138050A (ru) | Производные тиазолопиридина как агонисты gpr119 | |
| JP2018529731A5 (OSRAM) | ||
| NZ604004A (en) | Pyridone and aza-pyridone compounds and methods of use | |
| JP2016522232A5 (OSRAM) | ||
| HRP20160635T1 (hr) | Inhibitori pirimidina pde10 | |
| JP2012525395A5 (OSRAM) | ||
| HRP20211957T1 (hr) | Analozi 1,4-disupstituiranog piridazina i postupci za liječenje stanja povezanih s nedostatkom smn | |
| JP2008519765A5 (OSRAM) | ||
| US10376510B2 (en) | 2,4- or 4,6-diaminopyrimidine compounds as IDH2 mutants inhibitors for the treatment of cancer | |
| JP2019526550A5 (OSRAM) | ||
| RU2015100942A (ru) | Производное пиперидинилпиразолпиридина | |
| JP2016523977A5 (OSRAM) | ||
| JP2019534324A5 (OSRAM) | ||
| JP2016525076A5 (OSRAM) | ||
| JP2013522354A5 (OSRAM) | ||
| SI3183247T1 (en) | Aminopyrimidinyl compounds as inhibitors of JAK | |
| JP2019514878A5 (OSRAM) | ||
| JP2016530274A5 (OSRAM) | ||
| JP2016529292A5 (OSRAM) | ||
| TW202024089A (zh) | 三唑并－嘧啶化合物及其用途 | |
| EP4529956A3 (en) | Dosage form compositions comprising an inhibitor of bruton s tyrosine kinase | |
| RU2013136542A (ru) | Конденсированные производные аминодигидротиазина | |
| JP2019503337A5 (OSRAM) |