JP2017511329A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017511329A5 JP2017511329A5 JP2016560389A JP2016560389A JP2017511329A5 JP 2017511329 A5 JP2017511329 A5 JP 2017511329A5 JP 2016560389 A JP2016560389 A JP 2016560389A JP 2016560389 A JP2016560389 A JP 2016560389A JP 2017511329 A5 JP2017511329 A5 JP 2017511329A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- amine
- dimethylpentan
- methyl
- difluoromethyl
- 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
- -1 methoxy, methyl Chemical group 0.000 claims 34
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- RKAHOQATMSONTM-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C(F)F)F Chemical compound FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C(F)F)F RKAHOQATMSONTM-IBGZPJMESA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 102100038079 AP2-associated protein kinase 1 Human genes 0.000 claims 2
- PJYKLDMCKAFIQS-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=C(F)C(C)=NC=C1)C(F)F Chemical class CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=C(F)C(C)=NC=C1)C(F)F PJYKLDMCKAFIQS-IBGZPJMESA-N 0.000 claims 2
- RKBMAROJKLHAMI-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=CC(C)=NC=C1 RKBMAROJKLHAMI-IBGZPJMESA-N 0.000 claims 2
- AALSHYORLVJEBZ-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC(C)=N1 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC(C)=N1 AALSHYORLVJEBZ-SFHVURJKSA-N 0.000 claims 2
- ULGONQSWPGCYPW-IBGZPJMESA-N C[C@@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N ULGONQSWPGCYPW-IBGZPJMESA-N 0.000 claims 2
- YXRJMGXKRWHQME-SFHVURJKSA-N C[C@@](COC=1C(=CC(=NC1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC=1C(=CC(=NC1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N YXRJMGXKRWHQME-SFHVURJKSA-N 0.000 claims 2
- DCWNOICLZKGXFR-IBGZPJMESA-N FC(C1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)F)F Chemical class FC(C1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)F)F DCWNOICLZKGXFR-IBGZPJMESA-N 0.000 claims 2
- NFTPBBCMDGZSHJ-MHZLTWQESA-N FC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C Chemical compound FC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C NFTPBBCMDGZSHJ-MHZLTWQESA-N 0.000 claims 2
- 101000742699 Homo sapiens AP2-associated protein kinase 1 Proteins 0.000 claims 2
- JJNHJOVVASIHIL-INIZCTEOSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C JJNHJOVVASIHIL-INIZCTEOSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- JQZOBLFDUVUUGF-JOCHJYFZSA-N (2R)-1-(2-chloro-6-fluoro-4-quinolin-4-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@@](C)(N)COC1=C(Cl)C=C(C=C1F)C1=CC=NC2=C1C=CC=C2 JQZOBLFDUVUUGF-JOCHJYFZSA-N 0.000 claims 1
- AALSHYORLVJEBZ-GOSISDBHSA-N (2R)-1-[3-(difluoromethyl)-5-(2-methylpyrimidin-4-yl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C=1C(=NC=C(C1)C1=NC(=NC=C1)C)OC[C@@](CC(C)C)(N)C)F AALSHYORLVJEBZ-GOSISDBHSA-N 0.000 claims 1
- WIIALNVSHHTFFZ-JOCHJYFZSA-N (2R)-1-[3-(difluoromethyl)-5-(5,7-difluoroquinolin-4-yl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C=1C(=NC=C(C=1)C1=CC=NC2=CC(=CC(=C12)F)F)OC[C@@](CC(C)C)(N)C)F WIIALNVSHHTFFZ-JOCHJYFZSA-N 0.000 claims 1
- OKSLIDNQBOADCD-JOCHJYFZSA-N (2R)-1-[5-(7-chloroquinolin-4-yl)-3-(difluoromethyl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound ClC1=CC=C2C(=CC=NC2=C1)C=1C=C(C(=NC1)OC[C@@](CC(C)C)(N)C)C(F)F OKSLIDNQBOADCD-JOCHJYFZSA-N 0.000 claims 1
- QZNNODQLLRSCHN-VWLOTQADSA-N (2S)-1-(2-cyclopropyl-4-quinolin-4-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound C1(CC1)C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC2=CC=CC=C12 QZNNODQLLRSCHN-VWLOTQADSA-N 0.000 claims 1
- QJJUZJKHCZFOBJ-IBGZPJMESA-N (2S)-1-[2-(difluoromethyl)-4-(2-methylpyrimidin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC(C)=N1)C(F)F QJJUZJKHCZFOBJ-IBGZPJMESA-N 0.000 claims 1
- BIQHWJJDUAWYEN-SFHVURJKSA-N (2S)-1-[2-(difluoromethyl)-6-(2-methylpyrimidin-4-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=NC(C)=N1 BIQHWJJDUAWYEN-SFHVURJKSA-N 0.000 claims 1
- APTYRPSOZMZHRQ-QFIPXVFZSA-N (2S)-1-[2-(difluoromethyl)-6-(5,7-difluoroquinolin-4-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=NC2=CC(F)=CC(F)=C12 APTYRPSOZMZHRQ-QFIPXVFZSA-N 0.000 claims 1
- YJVNBILWESXTRQ-SFHVURJKSA-N (2S)-1-[2-(difluoromethyl)-6-(6-methylpyrimidin-4-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(C)=NC=N1 YJVNBILWESXTRQ-SFHVURJKSA-N 0.000 claims 1
- VONWNHVCOBGODO-SFHVURJKSA-N (2S)-1-[2-fluoro-4-(2-fluoropyridin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(F)C=C(C=C1)C1=CC(F)=NC=C1 VONWNHVCOBGODO-SFHVURJKSA-N 0.000 claims 1
- QYLMAGMUZOOXAT-FQEVSTJZSA-N (2S)-1-[4-(difluoromethyl)-6-(2-ethylpyridin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CCC1=NC=CC(=C1)C1=NC=C(OC[C@@](C)(N)CC(C)C)C(=C1)C(F)F QYLMAGMUZOOXAT-FQEVSTJZSA-N 0.000 claims 1
- CDMSYPKSRHQLQX-SFHVURJKSA-N (2S)-1-[4-(difluoromethyl)-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC(C)=N1)C(F)F CDMSYPKSRHQLQX-SFHVURJKSA-N 0.000 claims 1
- VQPKLYXPUPPWOJ-QFIPXVFZSA-N (2S)-1-[4-(difluoromethyl)-6-[6-(trifluoromethoxy)quinolin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)OC(F)(F)F)OC[C@](CC(C)C)(N)C)F VQPKLYXPUPPWOJ-QFIPXVFZSA-N 0.000 claims 1
- ZFBUEMDJFYDQIE-QFIPXVFZSA-N (2S)-1-[4-(difluoromethyl)-6-[6-(trifluoromethyl)quinolin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical class FC(C1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)C(F)(F)F)OC[C@](CC(C)C)(N)C)F ZFBUEMDJFYDQIE-QFIPXVFZSA-N 0.000 claims 1
- KHGSGIDZUJKCPA-QFIPXVFZSA-N (2S)-1-[6-(6-fluoroquinolin-4-yl)-2-methylpyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C)C1=CC=NC2=CC=C(F)C=C12 KHGSGIDZUJKCPA-QFIPXVFZSA-N 0.000 claims 1
- NOJOTLCVBXCQCU-QHCPKHFHSA-N (2S)-2,4-dimethyl-1-(2-methylsulfonyl-4-quinolin-4-ylphenoxy)pentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=CC=C12)S(C)(=O)=O NOJOTLCVBXCQCU-QHCPKHFHSA-N 0.000 claims 1
- PPHIUCCSQWZQGM-QFIPXVFZSA-N 4-[6-[(2S)-2-amino-2,4-dimethylpentoxy]-5-fluoropyridin-3-yl]quinoline-7-carbonitrile Chemical compound CC(C)C[C@](C)(N)COC1=C(F)C=C(C=N1)C1=CC=NC2=CC(=CC=C12)C#N PPHIUCCSQWZQGM-QFIPXVFZSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- JJNGXNQWEOMKHY-UHFFFAOYSA-N BrC1=CC(=C(OCC(CC(C)C)(C)NC(OCC2=CC=CC=C2)=O)C=C1)C Chemical compound BrC1=CC(=C(OCC(CC(C)C)(C)NC(OCC2=CC=CC=C2)=O)C=C1)C JJNGXNQWEOMKHY-UHFFFAOYSA-N 0.000 claims 1
- YRVKTWYTSXETSB-HNNXBMFYSA-N BrC1=CC(=C(OC[C@H](CC(C)C)NC(OC(C)(C)C)=O)C=C1)C1=CC=NO1 Chemical compound BrC1=CC(=C(OC[C@H](CC(C)C)NC(OC(C)(C)C)=O)C=C1)C1=CC=NO1 YRVKTWYTSXETSB-HNNXBMFYSA-N 0.000 claims 1
- OWZSSTHDQSTULI-QFIPXVFZSA-N C1(CC1)C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C Chemical compound C1(CC1)C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C OWZSSTHDQSTULI-QFIPXVFZSA-N 0.000 claims 1
- YUEONCDQDNXPAO-QFIPXVFZSA-N C1(CC1)C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C(F)F Chemical compound C1(CC1)C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C(F)F YUEONCDQDNXPAO-QFIPXVFZSA-N 0.000 claims 1
- PVCQHASHDIHPLR-LJQANCHMSA-N CC(C)C[C@@](N)(CF)COC1=C(N=C(C=C1)C1=CC(=NC=C1)C(F)F)C(F)F Chemical compound CC(C)C[C@@](N)(CF)COC1=C(N=C(C=C1)C1=CC(=NC=C1)C(F)F)C(F)F PVCQHASHDIHPLR-LJQANCHMSA-N 0.000 claims 1
- CVSCNGLMPXLZJZ-LJQANCHMSA-N CC(C)C[C@@](N)(CF)COC1=CN=C(C=C1C(F)F)C1=CC(C)=NC=C1 Chemical class CC(C)C[C@@](N)(CF)COC1=CN=C(C=C1C(F)F)C1=CC(C)=NC=C1 CVSCNGLMPXLZJZ-LJQANCHMSA-N 0.000 claims 1
- JBOFLATULZAPGI-INIZCTEOSA-N CC(C)C[C@H](N)COC1=C(C=C(C=C1)C1=CC(N)=NC=C1)C#N Chemical compound CC(C)C[C@H](N)COC1=C(C=C(C=C1)C1=CC(N)=NC=C1)C#N JBOFLATULZAPGI-INIZCTEOSA-N 0.000 claims 1
- STCRBGFALPZXKB-FQEVSTJZSA-N CC(C)C[C@](C)(N)COC1=C(C)C=C(C=C1)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(C=C1)C1=CC(C)=NC=C1 STCRBGFALPZXKB-FQEVSTJZSA-N 0.000 claims 1
- CNJHRPBYBRPXPD-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C)C=C(C=C1)C1=CC(F)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(C=C1)C1=CC(F)=NC=C1 CNJHRPBYBRPXPD-IBGZPJMESA-N 0.000 claims 1
- XNDCZOZTMJFJKQ-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C)C=C(C=N1)C1=CC(=NC=C1)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(C=N1)C1=CC(=NC=C1)C(F)F XNDCZOZTMJFJKQ-IBGZPJMESA-N 0.000 claims 1
- XCEFCAHRWPDBPM-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C)C=C(C=N1)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(C=N1)C1=CC(C)=NC=C1 XCEFCAHRWPDBPM-IBGZPJMESA-N 0.000 claims 1
- XWEOJBWEYOCRJM-QHCPKHFHSA-N CC(C)C[C@](C)(N)COC1=C(C)C=C(C=N1)C1=CC=NC2=CC(=CC=C12)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(C=N1)C1=CC=NC2=CC(=CC=C12)C#N XWEOJBWEYOCRJM-QHCPKHFHSA-N 0.000 claims 1
- NEWVRYGQQWTULU-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=C(C)C=C(N=C1)C1=CC=NC2=CC=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=C(C)C=C(N=C1)C1=CC=NC2=CC=CC=C12 NEWVRYGQQWTULU-QFIPXVFZSA-N 0.000 claims 1
- RBECKKYUEBWTKW-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C)N=C(C=C1)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=C(C)N=C(C=C1)C1=CC(C)=NC=C1 RBECKKYUEBWTKW-IBGZPJMESA-N 0.000 claims 1
- JUCMMQOAYJUVCF-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=C(Cl)C(F)=NC=C1)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=C(Cl)C(F)=NC=C1)C(F)(F)F JUCMMQOAYJUVCF-SFHVURJKSA-N 0.000 claims 1
- JHQIXXCRTMLJDW-FQEVSTJZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=C(F)C(C)=NC=C1)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=C(F)C(C)=NC=C1)C#N JHQIXXCRTMLJDW-FQEVSTJZSA-N 0.000 claims 1
- BTBPZGLEDPKZBT-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=C(F)C(F)=NC=C1)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=C(F)C(F)=NC=C1)C(F)(F)F BTBPZGLEDPKZBT-SFHVURJKSA-N 0.000 claims 1
- IZPCBCVMTALJQY-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(=NC=C1)C(F)F)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(=NC=C1)C(F)F)C(F)(F)F IZPCBCVMTALJQY-IBGZPJMESA-N 0.000 claims 1
- ZEGIDGUPKLLRLV-QHCPKHFHSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC2=CC=CC=C12)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC2=CC=CC=C12)C(F)(F)F ZEGIDGUPKLLRLV-QHCPKHFHSA-N 0.000 claims 1
- WKMRZAXLCSNZFP-FQEVSTJZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC=C1)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC=C1)C#N WKMRZAXLCSNZFP-FQEVSTJZSA-N 0.000 claims 1
- ZWKZNADMYDSXNL-FQEVSTJZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC=C1F)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(C)=NC=C1F)C#N ZWKZNADMYDSXNL-FQEVSTJZSA-N 0.000 claims 1
- HOWDRBOHTGWTQM-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(F)=NC=C1)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(F)=NC=C1)C#N HOWDRBOHTGWTQM-IBGZPJMESA-N 0.000 claims 1
- GFTQGQCPHUMQSI-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(F)=NC=C1Cl)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC(F)=NC=C1Cl)C(F)(F)F GFTQGQCPHUMQSI-SFHVURJKSA-N 0.000 claims 1
- OASCKTLABCKTRO-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC(=CC=C12)C(F)(F)F)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC(=CC=C12)C(F)(F)F)C(F)(F)F OASCKTLABCKTRO-QFIPXVFZSA-N 0.000 claims 1
- XYGVJFRDZWZCCC-DEOSSOPVSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC(C)=CC=C12)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC(C)=CC=C12)C#N XYGVJFRDZWZCCC-DEOSSOPVSA-N 0.000 claims 1
- PTYFBMGSODHWNP-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=C(F)C=C12)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=C(F)C=C12)C(F)(F)F PTYFBMGSODHWNP-QFIPXVFZSA-N 0.000 claims 1
- ADCMENPDHRBNNI-QHCPKHFHSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=CC=C12)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=CC=C12)C#N ADCMENPDHRBNNI-QHCPKHFHSA-N 0.000 claims 1
- XCERUKWZAADTFE-NRFANRHFSA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=NC=NC2=CC=CC=C12)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=NC=NC2=CC=CC=C12)C(F)(F)F XCERUKWZAADTFE-NRFANRHFSA-N 0.000 claims 1
- POSUBHCVLIQGIR-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=N1)C1=CC(=NC=C1)C(F)F)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=N1)C1=CC(=NC=C1)C(F)F)C#N POSUBHCVLIQGIR-IBGZPJMESA-N 0.000 claims 1
- VNNGZCQZRNCYHO-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=N1)C1=CC(=NC=C1)C(F)F)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=N1)C1=CC(=NC=C1)C(F)F)C(F)F VNNGZCQZRNCYHO-IBGZPJMESA-N 0.000 claims 1
- UMBMFKNLBDNBNH-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(C=C(C=N1)C1=CC(C)=NC=C1)C#N Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=N1)C1=CC(C)=NC=C1)C#N UMBMFKNLBDNBNH-IBGZPJMESA-N 0.000 claims 1
- OZMBCJAUHVADNN-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC2=CC(F)=CC(F)=C12)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC2=CC(F)=CC(F)=C12)C(F)F OZMBCJAUHVADNN-QFIPXVFZSA-N 0.000 claims 1
- XUPPARGHFZPHDP-NRFANRHFSA-N CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC2=CC=CC=C12)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC2=CC=CC=C12)C(F)(F)F XUPPARGHFZPHDP-NRFANRHFSA-N 0.000 claims 1
- BHTCEAANCMHFIL-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC2=CC=CC=C12)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC2=CC=CC=C12)C(F)F BHTCEAANCMHFIL-QFIPXVFZSA-N 0.000 claims 1
- PDOZMUWETOUCIO-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CN=NC(C)=C1)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CN=NC(C)=C1)C(F)F PDOZMUWETOUCIO-SFHVURJKSA-N 0.000 claims 1
- YIALBHYBYYNMRD-NRFANRHFSA-N CC(C)C[C@](C)(N)COC1=C(Cl)C=C(N=C1)C1=CC=NC2=CC(=CC=C12)C(F)(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(Cl)C=C(N=C1)C1=CC=NC2=CC(=CC=C12)C(F)(F)F YIALBHYBYYNMRD-NRFANRHFSA-N 0.000 claims 1
- MMYXQNLVBPFLSL-NRFANRHFSA-N CC(C)C[C@](C)(N)COC1=C(Cl)C=C(N=C1)C1=CC=NC2=CC=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=C(Cl)C=C(N=C1)C1=CC=NC2=CC=CC=C12 MMYXQNLVBPFLSL-NRFANRHFSA-N 0.000 claims 1
- OAWXJOFGASPGQX-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(Cl)N=C(C=C1)C1=CC(=NC=C1)C(F)F Chemical compound CC(C)C[C@](C)(N)COC1=C(Cl)N=C(C=C1)C1=CC(=NC=C1)C(F)F OAWXJOFGASPGQX-SFHVURJKSA-N 0.000 claims 1
- YQIQWANGWUKJKT-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(F)C=C(C=C1)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=C(F)C=C(C=C1)C1=CC(C)=NC=C1 YQIQWANGWUKJKT-IBGZPJMESA-N 0.000 claims 1
- HOIUMPKLMLSLGO-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=C(F)C(Cl)=NC=C1)C(F)F Chemical class CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=C(F)C(Cl)=NC=C1)C(F)F HOIUMPKLMLSLGO-SFHVURJKSA-N 0.000 claims 1
- NCAHZTSVEOYGOW-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NC2=CC(F)=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NC2=CC(F)=CC=C12 NCAHZTSVEOYGOW-QFIPXVFZSA-N 0.000 claims 1
- KQUJMVTULOTQPQ-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NC2=CC=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NC2=CC=CC=C12 KQUJMVTULOTQPQ-QFIPXVFZSA-N 0.000 claims 1
- XESNTGKRAJJPIU-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CN=NC(C)=C1 Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CN=NC(C)=C1 XESNTGKRAJJPIU-SFHVURJKSA-N 0.000 claims 1
- SAXBECZYTDBRKR-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=CC=C(N=C1C)C1=CC=NC2=CC=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C)C1=CC=NC2=CC=CC=C12 SAXBECZYTDBRKR-QFIPXVFZSA-N 0.000 claims 1
- ZVUKEHVADHPZQR-NRFANRHFSA-N CC(C)C[C@](C)(N)COC1=CC=C(N=C1Cl)C1=CC=NC2=CC(F)=CC(F)=C12 Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1Cl)C1=CC=NC2=CC(F)=CC(F)=C12 ZVUKEHVADHPZQR-NRFANRHFSA-N 0.000 claims 1
- SWKIRCKOMQZZFW-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=C(F)C(Cl)=NC=C1 Chemical class CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=C(F)C(Cl)=NC=C1 SWKIRCKOMQZZFW-SFHVURJKSA-N 0.000 claims 1
- QHPJIUARPKBLQQ-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=CC(Cl)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=CC(Cl)=NC=C1 QHPJIUARPKBLQQ-SFHVURJKSA-N 0.000 claims 1
- CIHFEDCEWSFTAE-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=CN=C(C=C1C)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=CN=C(C=C1C)C1=CC(C)=NC=C1 CIHFEDCEWSFTAE-IBGZPJMESA-N 0.000 claims 1
- UXXJSPPSOKNICG-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C#N)C1=CC=NC2=CC(F)=CC(F)=C12 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C#N)C1=CC=NC2=CC(F)=CC(F)=C12 UXXJSPPSOKNICG-QFIPXVFZSA-N 0.000 claims 1
- VTQAPSZSIXWNQK-QHCPKHFHSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC2=CC(C)=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC2=CC(C)=CC=C12 VTQAPSZSIXWNQK-QHCPKHFHSA-N 0.000 claims 1
- WIIALNVSHHTFFZ-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC2=CC(F)=CC(F)=C12 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC2=CC(F)=CC(F)=C12 WIIALNVSHHTFFZ-QFIPXVFZSA-N 0.000 claims 1
- NNXIZBKMOATQJI-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC2=CC=C(F)C=C12 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC2=CC=C(F)C=C12 NNXIZBKMOATQJI-QFIPXVFZSA-N 0.000 claims 1
- CAILPJJGCANYGD-QFIPXVFZSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C)C1=CC=NC2=CC(Cl)=CC=C12 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C)C1=CC=NC2=CC(Cl)=CC=C12 CAILPJJGCANYGD-QFIPXVFZSA-N 0.000 claims 1
- FXCDGLZLXUIWGE-NRFANRHFSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1Cl)C1=CC=NC2=CC=C(F)C=C12 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1Cl)C1=CC=NC2=CC=C(F)C=C12 FXCDGLZLXUIWGE-NRFANRHFSA-N 0.000 claims 1
- QKEUFTAZOLHEAI-FQEVSTJZSA-N COC(=O)NC1=NC=CC(=C1)C1=CC(=C(OC[C@@](C)(N)CC(C)C)C=C1)C(F)(F)F Chemical compound COC(=O)NC1=NC=CC(=C1)C1=CC(=C(OC[C@@](C)(N)CC(C)C)C=C1)C(F)(F)F QKEUFTAZOLHEAI-FQEVSTJZSA-N 0.000 claims 1
- ZKULRVLUDZUZOJ-IBGZPJMESA-N COC1=C(C=CN=C1)C1=CC(=C(OC[C@@](C)(N)CC(C)C)C=C1)C(F)(F)F Chemical compound COC1=C(C=CN=C1)C1=CC(=C(OC[C@@](C)(N)CC(C)C)C=C1)C(F)(F)F ZKULRVLUDZUZOJ-IBGZPJMESA-N 0.000 claims 1
- ZHGKDOYOHZJUPD-IBGZPJMESA-N COC1=C(OC[C@@](C)(N)CC(C)C)N=CC(=C1)C1=CC(C)=NC=C1 Chemical compound COC1=C(OC[C@@](C)(N)CC(C)C)N=CC(=C1)C1=CC(C)=NC=C1 ZHGKDOYOHZJUPD-IBGZPJMESA-N 0.000 claims 1
- YKGQUBOYHDWACY-KRWDZBQOSA-N COC1=NC=CC(=C1)C1=CC(C#N)=C(OC[C@@H](N)CC(C)C)C=C1 Chemical compound COC1=NC=CC(=C1)C1=CC(C#N)=C(OC[C@@H](N)CC(C)C)C=C1 YKGQUBOYHDWACY-KRWDZBQOSA-N 0.000 claims 1
- GNLDTFQXTMVJHS-QFIPXVFZSA-N COC=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C Chemical compound COC=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C GNLDTFQXTMVJHS-QFIPXVFZSA-N 0.000 claims 1
- IAOYSFIEUUJVEC-FQEVSTJZSA-N C[C@@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)C)S(=O)(=O)C)(CC(C)C)N Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)C)S(=O)(=O)C)(CC(C)C)N IAOYSFIEUUJVEC-FQEVSTJZSA-N 0.000 claims 1
- WLAZWTACSHXEGN-QFIPXVFZSA-N C[C@@](COC1=C(C=C(C=C1)C1=CC=NC2=CC=CC=C12)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=CC=NC2=CC=CC=C12)C(F)(F)F)(CC(C)C)N WLAZWTACSHXEGN-QFIPXVFZSA-N 0.000 claims 1
- UJFBQMHGCCSHRP-SFHVURJKSA-N C[C@@](COC1=C(C=C(C=C1)C1=CC=NC=C1)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=CC=NC=C1)C(F)(F)F)(CC(C)C)N UJFBQMHGCCSHRP-SFHVURJKSA-N 0.000 claims 1
- MYJMDFXSTDDBGP-HKBQPEDESA-N C[C@@](COC1=CC=C(C2=CC=CC=C12)C1=CC=NC2=CC=CC=C12)(CC(C)C)NC(OC(C)(C)C)=O Chemical compound C[C@@](COC1=CC=C(C2=CC=CC=C12)C1=CC=NC2=CC=CC=C12)(CC(C)C)NC(OC(C)(C)C)=O MYJMDFXSTDDBGP-HKBQPEDESA-N 0.000 claims 1
- DPRYJZGDMSIMLY-NRFANRHFSA-N C[C@@](COC1=NC=C(C=C1C(F)(F)F)C1=CC=NC2=CC=CC=C12)(CC(C)C)N Chemical compound C[C@@](COC1=NC=C(C=C1C(F)(F)F)C1=CC=NC2=CC=CC=C12)(CC(C)C)N DPRYJZGDMSIMLY-NRFANRHFSA-N 0.000 claims 1
- OFMWMZVLUNNWMK-FQEVSTJZSA-N C[C@@](COC=1C(=CC(=NC1C)C1=CC(=NC=C1)C)C)(CC(C)C)N Chemical compound C[C@@](COC=1C(=CC(=NC1C)C1=CC(=NC=C1)C)C)(CC(C)C)N OFMWMZVLUNNWMK-FQEVSTJZSA-N 0.000 claims 1
- YXRJMGXKRWHQME-GOSISDBHSA-N C[C@](COC=1C(=CC(=NC=1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N Chemical compound C[C@](COC=1C(=CC(=NC=1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N YXRJMGXKRWHQME-GOSISDBHSA-N 0.000 claims 1
- XUPPARGHFZPHDP-OAQYLSRUSA-N C[C@](COC=1C=NC(=CC=1C(F)(F)F)C1=CC=NC2=CC=CC=C12)(CC(C)C)N Chemical compound C[C@](COC=1C=NC(=CC=1C(F)(F)F)C1=CC=NC2=CC=CC=C12)(CC(C)C)N XUPPARGHFZPHDP-OAQYLSRUSA-N 0.000 claims 1
- BHOKOGJZOVMLHI-SFHVURJKSA-N ClC1=C(C=CC(=N1)C1=CC(=NC=C1)C)OC[C@](CC(C)C)(N)C Chemical compound ClC1=C(C=CC(=N1)C1=CC(=NC=C1)C)OC[C@](CC(C)C)(N)C BHOKOGJZOVMLHI-SFHVURJKSA-N 0.000 claims 1
- RVJJUOGIXQTZRV-SANMLTNESA-N ClC1=C(C=NC(=C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O Chemical compound ClC1=C(C=NC(=C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O RVJJUOGIXQTZRV-SANMLTNESA-N 0.000 claims 1
- SDPZRFIRDDBFJR-NRFANRHFSA-N ClC1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)Cl)OC[C@](CC(C)C)(N)C Chemical compound ClC1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)Cl)OC[C@](CC(C)C)(N)C SDPZRFIRDDBFJR-NRFANRHFSA-N 0.000 claims 1
- JUSKTTQYHPHBQN-SANMLTNESA-N ClC1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)F)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O Chemical compound ClC1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)F)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O JUSKTTQYHPHBQN-SANMLTNESA-N 0.000 claims 1
- NZYDJZSDSQDTKX-QFIPXVFZSA-N ClC1=CC(=NC=C1OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C1=CC=NC=C1 Chemical compound ClC1=CC(=NC=C1OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C1=CC=NC=C1 NZYDJZSDSQDTKX-QFIPXVFZSA-N 0.000 claims 1
- BGQQCWHNIRQURN-IBGZPJMESA-N ClC1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)C Chemical compound ClC1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)C BGQQCWHNIRQURN-IBGZPJMESA-N 0.000 claims 1
- XWZJJCICBZFART-SFHVURJKSA-N ClC1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1)C Chemical compound ClC1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1)C XWZJJCICBZFART-SFHVURJKSA-N 0.000 claims 1
- OSVUOYZAHGVSAY-MHZLTWQESA-N ClC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C Chemical compound ClC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C OSVUOYZAHGVSAY-MHZLTWQESA-N 0.000 claims 1
- VQBFWTSZIQXWTK-QFIPXVFZSA-N ClC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound ClC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F VQBFWTSZIQXWTK-QFIPXVFZSA-N 0.000 claims 1
- OKSLIDNQBOADCD-QFIPXVFZSA-N ClC1=CC=C2C(=CC=NC2=C1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C(F)F Chemical compound ClC1=CC=C2C(=CC=NC2=C1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C(F)F OKSLIDNQBOADCD-QFIPXVFZSA-N 0.000 claims 1
- DFOZFPXLACXZBX-NRFANRHFSA-N ClC1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=CC=NC2=CC(=CC=C12)F Chemical compound ClC1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=CC=NC2=CC(=CC=C12)F DFOZFPXLACXZBX-NRFANRHFSA-N 0.000 claims 1
- QBWQGOBPRRMHEI-NRFANRHFSA-N ClC1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=CC=NC2=CC=CC=C12 Chemical compound ClC1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=CC=NC2=CC=CC=C12 QBWQGOBPRRMHEI-NRFANRHFSA-N 0.000 claims 1
- TZOZJFWDYLPJED-SFHVURJKSA-N ClC1=NC=C(C(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C)F Chemical compound ClC1=NC=C(C(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C)F TZOZJFWDYLPJED-SFHVURJKSA-N 0.000 claims 1
- SISQPPCZDPNKAD-GOSISDBHSA-N ClC1=NC=C(C(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C)F Chemical class ClC1=NC=C(C(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C)F SISQPPCZDPNKAD-GOSISDBHSA-N 0.000 claims 1
- CAHWFUWISRRLIM-SFHVURJKSA-N ClC1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C(F)F Chemical compound ClC1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C(F)F CAHWFUWISRRLIM-SFHVURJKSA-N 0.000 claims 1
- QHPJIUARPKBLQQ-GOSISDBHSA-N ClC1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C Chemical compound ClC1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C QHPJIUARPKBLQQ-GOSISDBHSA-N 0.000 claims 1
- IQJQVNJMMUZATP-QFIPXVFZSA-N ClC1=NC=CC(=C1)C1=NC=C(C(=C1)Cl)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O Chemical compound ClC1=NC=CC(=C1)C1=NC=C(C(=C1)Cl)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O IQJQVNJMMUZATP-QFIPXVFZSA-N 0.000 claims 1
- ZCHJRHXGHGSPDX-SFHVURJKSA-N ClC1=NC=CC(=C1)C=1C=NC(=C(C1)C(F)F)OC[C@](CC(C)C)(N)C Chemical compound ClC1=NC=CC(=C1)C=1C=NC(=C(C1)C(F)F)OC[C@](CC(C)C)(N)C ZCHJRHXGHGSPDX-SFHVURJKSA-N 0.000 claims 1
- NZFQPJZRKOFDHS-QHCPKHFHSA-N ClC1=NC=CC(=C1F)C1=NC(=C(C=C1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C Chemical compound ClC1=NC=CC(=C1F)C1=NC(=C(C=C1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C NZFQPJZRKOFDHS-QHCPKHFHSA-N 0.000 claims 1
- SWKIRCKOMQZZFW-GOSISDBHSA-N ClC1=NC=CC(=C1F)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C Chemical class ClC1=NC=CC(=C1F)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C SWKIRCKOMQZZFW-GOSISDBHSA-N 0.000 claims 1
- VHXNBVOHECAUTO-SANMLTNESA-N ClC=1C(=NC=C(C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O Chemical compound ClC=1C(=NC=C(C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O VHXNBVOHECAUTO-SANMLTNESA-N 0.000 claims 1
- IGJJATQUVSNMJD-NRFANRHFSA-N ClC=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C Chemical compound ClC=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C IGJJATQUVSNMJD-NRFANRHFSA-N 0.000 claims 1
- ASPJNLYWGAKLTB-KRWDZBQOSA-N ClC=1C(=NC=C(C1)C1=NC(=NC=C1)C)OC[C@](CC(C)C)(N)C Chemical compound ClC=1C(=NC=C(C1)C1=NC(=NC=C1)C)OC[C@](CC(C)C)(N)C ASPJNLYWGAKLTB-KRWDZBQOSA-N 0.000 claims 1
- FXRWQJAEZHTNFX-SFHVURJKSA-N ClC=1C=C(C=NC1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1)C Chemical compound ClC=1C=C(C=NC1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1)C FXRWQJAEZHTNFX-SFHVURJKSA-N 0.000 claims 1
- GRLYYFXNPFAHQW-MHZLTWQESA-N ClC=1C=C2C(=CC=NC2=CC1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C Chemical compound ClC=1C=C2C(=CC=NC2=CC1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C GRLYYFXNPFAHQW-MHZLTWQESA-N 0.000 claims 1
- PUQWOBSWNJVTHJ-QFIPXVFZSA-N ClC=1C=C2C(=CC=NC2=CC1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound ClC=1C=C2C(=CC=NC2=CC1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F PUQWOBSWNJVTHJ-QFIPXVFZSA-N 0.000 claims 1
- UNOJLQKTJVHDKW-QFIPXVFZSA-N ClC=1C=C2C(=CC=NC2=CC1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C Chemical compound ClC=1C=C2C(=CC=NC2=CC1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C UNOJLQKTJVHDKW-QFIPXVFZSA-N 0.000 claims 1
- CQKGLFXBOCVPLN-IBGZPJMESA-N FC(C1=C(C=CC(=N1)C1=CC(=NC=C1)C)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C1=C(C=CC(=N1)C1=CC(=NC=C1)C)OC[C@](CC(C)C)(N)C)F CQKGLFXBOCVPLN-IBGZPJMESA-N 0.000 claims 1
- HXCGSQCIKQWJGY-QFIPXVFZSA-N FC(C1=C(C=NC(=C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C1=C(C=NC(=C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@](CC(C)C)(N)C)F HXCGSQCIKQWJGY-QFIPXVFZSA-N 0.000 claims 1
- LQBIZVPAGIHQBS-QFIPXVFZSA-N FC(C1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)F)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)F)OC[C@](CC(C)C)(N)C)F LQBIZVPAGIHQBS-QFIPXVFZSA-N 0.000 claims 1
- NGBWQVJCOYTGOR-FQEVSTJZSA-N FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C(F)F)F Chemical compound FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C(F)F)F NGBWQVJCOYTGOR-FQEVSTJZSA-N 0.000 claims 1
- LLASSJMOZUBNPF-FQEVSTJZSA-N FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C)F Chemical compound FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC(=NC=C1)C)F LLASSJMOZUBNPF-FQEVSTJZSA-N 0.000 claims 1
- CSISHGRVGRXVKC-QHCPKHFHSA-N FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC2=CC=C(C=C12)F)F Chemical compound FC(C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC2=CC=C(C=C12)F)F CSISHGRVGRXVKC-QHCPKHFHSA-N 0.000 claims 1
- DCWNOICLZKGXFR-LJQANCHMSA-N FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)F)F Chemical class FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)F)F DCWNOICLZKGXFR-LJQANCHMSA-N 0.000 claims 1
- QYLMAGMUZOOXAT-HXUWFJFHSA-N FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)C)C1=CC(=NC=C1)CC)F Chemical compound FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)C)C1=CC(=NC=C1)CC)F QYLMAGMUZOOXAT-HXUWFJFHSA-N 0.000 claims 1
- XSNBBAWHAMAEDA-LJQANCHMSA-N FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)C)C1=CC(=NC=C1F)C)F Chemical class FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)C)C1=CC(=NC=C1F)C)F XSNBBAWHAMAEDA-LJQANCHMSA-N 0.000 claims 1
- CVSCNGLMPXLZJZ-IBGZPJMESA-N FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)CF)C1=CC(=NC=C1)C)F Chemical class FC(C1=CC(=NC=C1OC[C@@](CC(C)C)(N)CF)C1=CC(=NC=C1)C)F CVSCNGLMPXLZJZ-IBGZPJMESA-N 0.000 claims 1
- XSNBBAWHAMAEDA-IBGZPJMESA-N FC(C1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1F)C)F Chemical class FC(C1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1F)C)F XSNBBAWHAMAEDA-IBGZPJMESA-N 0.000 claims 1
- ZZHJITDYMFEKBO-QFIPXVFZSA-N FC(C1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=CC=NC2=CC=C(C=C12)F)F Chemical compound FC(C1=NC(=CC=C1OC[C@](CC(C)C)(N)C)C1=CC=NC2=CC=C(C=C12)F)F ZZHJITDYMFEKBO-QFIPXVFZSA-N 0.000 claims 1
- OPLYCHUBAPFARE-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)OC(F)(F)F)F Chemical compound FC(C1=NC=CC(=C1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)OC(F)(F)F)F OPLYCHUBAPFARE-IBGZPJMESA-N 0.000 claims 1
- RKAHOQATMSONTM-LJQANCHMSA-N FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@@](CC(C)C)(N)C)C(F)F)F Chemical compound FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@@](CC(C)C)(N)C)C(F)F)F RKAHOQATMSONTM-LJQANCHMSA-N 0.000 claims 1
- PVCQHASHDIHPLR-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@@](CC(C)C)(N)CF)C(F)F)F Chemical compound FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@@](CC(C)C)(N)CF)C(F)F)F PVCQHASHDIHPLR-IBGZPJMESA-N 0.000 claims 1
- HVHRHDHQHUAOQI-LJQANCHMSA-N FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C)F Chemical compound FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)C)F HVHRHDHQHUAOQI-LJQANCHMSA-N 0.000 claims 1
- AFMUKAVRUCBENP-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)CF)F Chemical compound FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@@](CC(C)C)(N)CF)F AFMUKAVRUCBENP-IBGZPJMESA-N 0.000 claims 1
- HVHRHDHQHUAOQI-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@](CC(C)C)(N)C)F HVHRHDHQHUAOQI-IBGZPJMESA-N 0.000 claims 1
- AFMUKAVRUCBENP-LJQANCHMSA-N FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@](CC(C)C)(N)CF)F Chemical compound FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C(F)F)OC[C@](CC(C)C)(N)CF)F AFMUKAVRUCBENP-LJQANCHMSA-N 0.000 claims 1
- VYPORTDNBOGDIG-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)C)OC[C@](CC(C)C)(N)C)F VYPORTDNBOGDIG-IBGZPJMESA-N 0.000 claims 1
- FOYCJWNMPKZNFD-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)OC)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C1=NC=CC(=C1)C1=NC=C(C(=C1)OC)OC[C@](CC(C)C)(N)C)F FOYCJWNMPKZNFD-IBGZPJMESA-N 0.000 claims 1
- CACPZHJCOBROER-QFIPXVFZSA-N FC(C=1C(=NC=C(C1)C1=CC=NC2=CC(=CC=C12)C(F)(F)F)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C=1C(=NC=C(C1)C1=CC=NC2=CC(=CC=C12)C(F)(F)F)OC[C@](CC(C)C)(N)C)F CACPZHJCOBROER-QFIPXVFZSA-N 0.000 claims 1
- FEGPESNEZYWGEQ-QFIPXVFZSA-N FC(C=1C(=NC=C(C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C=1C(=NC=C(C1)C1=CC=NC2=CC(=CC=C12)F)OC[C@](CC(C)C)(N)C)F FEGPESNEZYWGEQ-QFIPXVFZSA-N 0.000 claims 1
- VZSXUICSTBAKTM-JOCHJYFZSA-N FC(C=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@@](CC(C)C)(N)C)F Chemical compound FC(C=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@@](CC(C)C)(N)C)F VZSXUICSTBAKTM-JOCHJYFZSA-N 0.000 claims 1
- VZSXUICSTBAKTM-QFIPXVFZSA-N FC(C=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C)F Chemical compound FC(C=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C)F VZSXUICSTBAKTM-QFIPXVFZSA-N 0.000 claims 1
- FMRXHOYDWMZVGT-IBGZPJMESA-N FC1=C(C(=CC(=N1)C1=CC(=NC=C1)C)C)OC[C@](CC(C)C)(N)C Chemical compound FC1=C(C(=CC(=N1)C1=CC(=NC=C1)C)C)OC[C@](CC(C)C)(N)C FMRXHOYDWMZVGT-IBGZPJMESA-N 0.000 claims 1
- CTUGJRNJERMRLI-QFIPXVFZSA-N FC1=C2C(=CC=NC2=CC(=C1)F)C1=CC(=C(C=N1)OC[C@](CC(C)C)(N)C)C Chemical compound FC1=C2C(=CC=NC2=CC(=C1)F)C1=CC(=C(C=N1)OC[C@](CC(C)C)(N)C)C CTUGJRNJERMRLI-QFIPXVFZSA-N 0.000 claims 1
- HJBSVLDJABXCTF-QFIPXVFZSA-N FC1=C2C(=CC=NC2=CC(=C1)F)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound FC1=C2C(=CC=NC2=CC(=C1)F)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F HJBSVLDJABXCTF-QFIPXVFZSA-N 0.000 claims 1
- LEDLHCXWMUVUFY-QFIPXVFZSA-N FC1=C2C(=CC=NC2=CC(=C1)F)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C Chemical compound FC1=C2C(=CC=NC2=CC(=C1)F)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C LEDLHCXWMUVUFY-QFIPXVFZSA-N 0.000 claims 1
- SUUWMCAOZYIVCT-NRFANRHFSA-N FC1=C2C(=CC=NC2=CC(=C1)F)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C(F)(F)F Chemical compound FC1=C2C(=CC=NC2=CC(=C1)F)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C(F)(F)F SUUWMCAOZYIVCT-NRFANRHFSA-N 0.000 claims 1
- UFJRTEOIZHMRHA-QFIPXVFZSA-N FC1=CC=C2C(=CC=NC2=C1)C1=CC=C(C(=N1)C)OC[C@](CC(C)C)(N)C Chemical compound FC1=CC=C2C(=CC=NC2=C1)C1=CC=C(C(=N1)C)OC[C@](CC(C)C)(N)C UFJRTEOIZHMRHA-QFIPXVFZSA-N 0.000 claims 1
- KGGRQHXUHUQTBJ-QFIPXVFZSA-N FC1=CC=C2C(=CC=NC2=C1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C Chemical compound FC1=CC=C2C(=CC=NC2=C1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C KGGRQHXUHUQTBJ-QFIPXVFZSA-N 0.000 claims 1
- WYFYLJMUQWYKNM-SFHVURJKSA-N FC1=NC=CC(=C1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound FC1=NC=CC(=C1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F WYFYLJMUQWYKNM-SFHVURJKSA-N 0.000 claims 1
- GAZUFNTUTKTHDN-IBGZPJMESA-N FC1=NC=CC(=C1C)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound FC1=NC=CC(=C1C)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F GAZUFNTUTKTHDN-IBGZPJMESA-N 0.000 claims 1
- KCHNAXACULVLBP-NRFANRHFSA-N FC=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C Chemical compound FC=1C(=NC=C(C1)C1=CC=NC2=CC=CC=C12)OC[C@](CC(C)C)(N)C KCHNAXACULVLBP-NRFANRHFSA-N 0.000 claims 1
- PPHVWFRCKAYPEU-SFHVURJKSA-N FC=1C=C(C=NC=1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1)C Chemical compound FC=1C=C(C=NC=1OC[C@](CC(C)C)(N)C)C1=CC(=NC=C1)C PPHVWFRCKAYPEU-SFHVURJKSA-N 0.000 claims 1
- MSDPFDQNEGSXTB-MHZLTWQESA-N FC=1C=C2C(=CC=NC2=CC1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C Chemical compound FC=1C=C2C(=CC=NC2=CC1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C MSDPFDQNEGSXTB-MHZLTWQESA-N 0.000 claims 1
- DIESDROGZNCYLM-QFIPXVFZSA-N FC=1C=C2C(=CC=NC2=CC1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C Chemical compound FC=1C=C2C(=CC=NC2=CC1)C=1C=C(C(=NC1)OC[C@](CC(C)C)(N)C)C DIESDROGZNCYLM-QFIPXVFZSA-N 0.000 claims 1
- OIQWKZIEKGGAEW-SFHVURJKSA-N FC=1C=NC=CC1C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound FC=1C=NC=CC1C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F OIQWKZIEKGGAEW-SFHVURJKSA-N 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- WJLQUMMDKPAJCH-NRFANRHFSA-N N1=CC=C(C2=CN=CC=C12)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound N1=CC=C(C2=CN=CC=C12)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F WJLQUMMDKPAJCH-NRFANRHFSA-N 0.000 claims 1
- QGEJTLQFMDSDBM-FQEVSTJZSA-N N1C=CC=2C1=NC=CC=2C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound N1C=CC=2C1=NC=CC=2C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F QGEJTLQFMDSDBM-FQEVSTJZSA-N 0.000 claims 1
- TZAOHCCGAGVZHV-INIZCTEOSA-N N[C@H](COC1=C(C#N)C=C(C=C1)C1=CC(=NC=C1)C(F)(F)F)CC(C)C Chemical compound N[C@H](COC1=C(C#N)C=C(C=C1)C1=CC(=NC=C1)C(F)(F)F)CC(C)C TZAOHCCGAGVZHV-INIZCTEOSA-N 0.000 claims 1
- BSOULHYZJJKVGA-SFHVURJKSA-N N[C@H](COC1=C(C#N)C=C(C=C1)C1=CC(=NC=C1)C)CC(C)C Chemical compound N[C@H](COC1=C(C#N)C=C(C=C1)C1=CC(=NC=C1)C)CC(C)C BSOULHYZJJKVGA-SFHVURJKSA-N 0.000 claims 1
- HTMZSVARGJGKLE-SFHVURJKSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C#N)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C#N)CC(C)C HTMZSVARGJGKLE-SFHVURJKSA-N 0.000 claims 1
- LAHYYLXFCBPDDW-INIZCTEOSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C(F)(F)F)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C(F)(F)F)CC(C)C LAHYYLXFCBPDDW-INIZCTEOSA-N 0.000 claims 1
- UZGBIRGBWRCWKF-SFHVURJKSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C)CC(C)C UZGBIRGBWRCWKF-SFHVURJKSA-N 0.000 claims 1
- DPKIBVXNSRPEDN-INIZCTEOSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)Cl)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)Cl)CC(C)C DPKIBVXNSRPEDN-INIZCTEOSA-N 0.000 claims 1
- WSZZLVNYBNWVDL-INIZCTEOSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)OC(F)(F)F)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)OC(F)(F)F)CC(C)C WSZZLVNYBNWVDL-INIZCTEOSA-N 0.000 claims 1
- DKKCUFUUVDZUCP-KRWDZBQOSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)OC)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)OC)CC(C)C DKKCUFUUVDZUCP-KRWDZBQOSA-N 0.000 claims 1
- XYXJLVVKIBEGES-HNNXBMFYSA-N N[C@H](COC1=C(C=C(C=C1C(F)(F)F)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1C(F)(F)F)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C XYXJLVVKIBEGES-HNNXBMFYSA-N 0.000 claims 1
- AKUJIVTZSHCXRK-HNNXBMFYSA-N N[C@H](COC1=C(C=C(C=C1F)C1=CC(=NC=C1)NC(C)=O)Cl)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1F)C1=CC(=NC=C1)NC(C)=O)Cl)CC(C)C AKUJIVTZSHCXRK-HNNXBMFYSA-N 0.000 claims 1
- WEWDGPNKOHRMCP-HNNXBMFYSA-N N[C@H](COC1=C(C=C(C=C1F)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1F)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C WEWDGPNKOHRMCP-HNNXBMFYSA-N 0.000 claims 1
- KCBBDWLXBHSCCC-AWEZNQCLSA-N N[C@H](COC1=CC(=C(C=C1F)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C Chemical compound N[C@H](COC1=CC(=C(C=C1F)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C KCBBDWLXBHSCCC-AWEZNQCLSA-N 0.000 claims 1
- VWSITUXKTVTAKL-FQEVSTJZSA-N N[C@](COC1=C(C#N)C=C(C=C1)C1=CC(=NC=C1)C(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=CC(=NC=C1)C(F)F)(CC(C)C)C VWSITUXKTVTAKL-FQEVSTJZSA-N 0.000 claims 1
- JZGADLVQVYPSLJ-QFIPXVFZSA-N N[C@](COC1=C(C#N)C=C(C=C1)C1=CC=NC2=CC=CN=C12)(CC(C)C)C Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=CC=NC2=CC=CN=C12)(CC(C)C)C JZGADLVQVYPSLJ-QFIPXVFZSA-N 0.000 claims 1
- UMKJJTLACIYHLQ-QFIPXVFZSA-N N[C@](COC1=C(C#N)C=C(C=C1)C1=CC=NC2=CC=NC=C12)(CC(C)C)C Chemical compound N[C@](COC1=C(C#N)C=C(C=C1)C1=CC=NC2=CC=NC=C12)(CC(C)C)C UMKJJTLACIYHLQ-QFIPXVFZSA-N 0.000 claims 1
- OWFLPJCMBWRINU-NRFANRHFSA-N N[C@](COC1=C(C#N)C=C(C=N1)C1=CC=NC2=CC=NC=C12)(CC(C)C)C Chemical compound N[C@](COC1=C(C#N)C=C(C=N1)C1=CC=NC2=CC=NC=C12)(CC(C)C)C OWFLPJCMBWRINU-NRFANRHFSA-N 0.000 claims 1
- KYMVFHAFTDDWKW-NRFANRHFSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C#N)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C#N)(CC(C)C)C KYMVFHAFTDDWKW-NRFANRHFSA-N 0.000 claims 1
- JRJSMTAUWDJJIH-FQEVSTJZSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C(F)(F)F)(CC(C)C)C JRJSMTAUWDJJIH-FQEVSTJZSA-N 0.000 claims 1
- YGRDQPIAALDLEG-NRFANRHFSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)C(F)F)(CC(C)C)C YGRDQPIAALDLEG-NRFANRHFSA-N 0.000 claims 1
- GRSIRCARZOBGMU-FQEVSTJZSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)F)(CC(C)C)C GRSIRCARZOBGMU-FQEVSTJZSA-N 0.000 claims 1
- ITANMUHQSHOARC-FQEVSTJZSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)OC(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)OC(F)(F)F)(CC(C)C)C ITANMUHQSHOARC-FQEVSTJZSA-N 0.000 claims 1
- UIQAYSMUZYPFQZ-NRFANRHFSA-N N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1CO)NC(C)=O)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC(=NC=C1CO)NC(C)=O)C(F)(F)F)(CC(C)C)C UIQAYSMUZYPFQZ-NRFANRHFSA-N 0.000 claims 1
- UPNVJHYDVZFZBM-FQEVSTJZSA-N N[C@](COC1=C(C=C(C=C1)C1=CC=NC(=C1C(=O)O)C)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC=NC(=C1C(=O)O)C)C(F)(F)F)(CC(C)C)C UPNVJHYDVZFZBM-FQEVSTJZSA-N 0.000 claims 1
- CBNLXZBTQVYRAC-QHCPKHFHSA-N N[C@](COC1=C(C=C(C=C1)C1=CC=NC2=CC(=CC=C12)C#N)C(F)(F)F)(CC(C)C)C Chemical compound N[C@](COC1=C(C=C(C=C1)C1=CC=NC2=CC(=CC=C12)C#N)C(F)(F)F)(CC(C)C)C CBNLXZBTQVYRAC-QHCPKHFHSA-N 0.000 claims 1
- OLZRNCKDWRCSFH-SFHVURJKSA-N N[C@](COC=1C=CC(=NC1C)C1=C(C(=NC=C1)N)F)(CC(C)C)C Chemical compound N[C@](COC=1C=CC(=NC1C)C1=C(C(=NC=C1)N)F)(CC(C)C)C OLZRNCKDWRCSFH-SFHVURJKSA-N 0.000 claims 1
- ZOPYQNXBXPYOBE-SFHVURJKSA-N O1CCC(=CC1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F Chemical compound O1CCC(=CC1)C1=CC(=C(OC[C@](CC(C)C)(N)C)C=C1)C(F)(F)F ZOPYQNXBXPYOBE-SFHVURJKSA-N 0.000 claims 1
- YBETWJGSSWPXMC-SFHVURJKSA-N O1N=CC=C1C1=C(OC[C@H](CC(C)C)N)C=CC(=C1)C1=CC(=NC=C1)C Chemical compound O1N=CC=C1C1=C(OC[C@H](CC(C)C)N)C=CC(=C1)C1=CC(=NC=C1)C YBETWJGSSWPXMC-SFHVURJKSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- WQGZXRBBTKWGLG-MHZLTWQESA-N tert-butyl N-[(2S)-1-[6-(5,7-difluoroquinolin-4-yl)-4-methylpyridin-3-yl]oxy-2,4-dimethylpentan-2-yl]carbamate Chemical compound CC(C)C[C@@](C)(COC1=CN=C(C=C1C)C1=C2C(F)=CC(F)=CC2=NC=C1)NC(=O)OC(C)(C)C WQGZXRBBTKWGLG-MHZLTWQESA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461973942P | 2014-04-02 | 2014-04-02 | |
| US61/973,942 | 2014-04-02 | ||
| US201462061591P | 2014-10-08 | 2014-10-08 | |
| US62/061,591 | 2014-10-08 | ||
| PCT/US2015/023805 WO2015153720A1 (en) | 2014-04-02 | 2015-04-01 | Biaryl kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017511329A JP2017511329A (ja) | 2017-04-20 |
| JP2017511329A5 true JP2017511329A5 (enExample) | 2018-03-15 |
| JP6411541B2 JP6411541B2 (ja) | 2018-10-24 |
Family
ID=52988448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016560389A Active JP6411541B2 (ja) | 2014-04-02 | 2015-04-01 | ビアリールキナーゼ阻害剤 |
Country Status (27)
| Country | Link |
|---|---|
| US (7) | US9902722B2 (enExample) |
| EP (1) | EP3126351B1 (enExample) |
| JP (1) | JP6411541B2 (enExample) |
| KR (1) | KR102379518B1 (enExample) |
| CN (1) | CN106458994B (enExample) |
| AU (1) | AU2015240869B2 (enExample) |
| BR (1) | BR112016022298B1 (enExample) |
| CA (1) | CA2944466C (enExample) |
| CL (1) | CL2016002502A1 (enExample) |
| CY (1) | CY1120988T1 (enExample) |
| DK (1) | DK3126351T3 (enExample) |
| EA (1) | EA028942B1 (enExample) |
| ES (1) | ES2700549T3 (enExample) |
| HR (1) | HRP20181899T1 (enExample) |
| HU (1) | HUE041457T2 (enExample) |
| IL (1) | IL248086B (enExample) |
| LT (1) | LT3126351T (enExample) |
| MX (1) | MX2016012829A (enExample) |
| PE (1) | PE20170004A1 (enExample) |
| PL (1) | PL3126351T3 (enExample) |
| PT (1) | PT3126351T (enExample) |
| RS (1) | RS58062B1 (enExample) |
| SG (1) | SG11201608195QA (enExample) |
| SI (1) | SI3126351T1 (enExample) |
| SM (1) | SMT201800665T1 (enExample) |
| WO (1) | WO2015153720A1 (enExample) |
| ZA (1) | ZA201606767B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3019475A1 (en) | 2013-07-08 | 2016-05-18 | Bristol-Myers Squibb Company | Aryl amide kinase inhibitors |
| EP3054955B1 (en) | 2013-10-11 | 2018-05-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| EP3105218B1 (en) | 2014-02-13 | 2019-09-25 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| JP6602779B2 (ja) | 2014-02-13 | 2019-11-06 | インサイト・コーポレイション | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
| SI3126351T1 (sl) * | 2014-04-02 | 2018-11-30 | Bristol-Myers Squibb Company | Biaril kinazni inhibitorji |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| US9695167B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted triazolo[1,5-a]pyridines and triazolo[1,5-a]pyrazines as LSD1 inhibitors |
| WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| ES2740224T3 (es) * | 2015-04-10 | 2020-02-05 | Bristol Myers Squibb Co | 6H-isocromeno[3,4-c]piridinas y benzo[c][1,7]naftiridin-6-(5H)-onas como inhibidores de la cinasa asociada a adaptador 1 (AAK1) |
| MY189367A (en) | 2015-08-12 | 2022-02-08 | Incyte Corp | Salts of an lsd1 inhibitor |
| EP3356330B1 (en) | 2015-10-01 | 2019-11-20 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| KR102704295B1 (ko) * | 2015-10-01 | 2024-09-05 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| JP7190906B2 (ja) | 2017-01-24 | 2022-12-16 | 住友化学株式会社 | 縮合複素環化合物及びそれを含有する組成物 |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| TW202120495A (zh) * | 2019-08-02 | 2021-06-01 | 美商愛彼特生物製藥股份有限公司 | 經取代環丙基—２，２＇—聯嘧啶基化合物、其類似物及其使用方法 |
| AU2021258128A1 (en) | 2020-04-21 | 2022-11-03 | Lexicon Pharmaceuticals, Inc. | 4-(3-(pyridin-3-yl)pyrazolo(1,5-a)pyrimidin-5-yl)piperazine for use in the the treatment of COV-229E or COV-OC43 coronaviruses infections |
| AU2021259419A1 (en) * | 2020-04-21 | 2022-11-10 | Lexicon Pharmaceuticals, Inc. | AAK1 inhibitors for use in treating viral infections |
| CN115697968B (zh) * | 2020-05-28 | 2024-03-29 | 杭州中美华东制药有限公司 | (s)-2-氨基-3-(4-(2,3-二甲基吡啶-4-基)苯基丙酸甲酯及其盐的制备方法 |
| TW202210461A (zh) * | 2020-05-28 | 2022-03-16 | 中國大陸商杭州中美華東製藥有限公司 | 一種（ｓ）—２—胺基—３—（４—（２，３—二甲基吡啶—４—基）苯基）丙酸甲酯二酸鹽的製備方法 |
| JP2024527618A (ja) * | 2021-07-15 | 2024-07-25 | シーザン ハイスーク ファーマシューティカル カンパニー リミテッド | Ａａｋ１阻害剤及びその用途 |
| CN115872927A (zh) * | 2021-09-30 | 2023-03-31 | 武汉人福创新药物研发中心有限公司 | Aak1抑制剂及其用途 |
| CA3244394A1 (en) * | 2022-03-01 | 2023-09-07 | Lexicon Pharmaceuticals, Inc. | METHODS AND COMPOUNDS USEFUL IN THE SYNTHESIS OF AN AAK1 INHIBITOR |
| EP4486723A1 (en) | 2022-03-01 | 2025-01-08 | 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 |
| WO2023183443A1 (en) | 2022-03-23 | 2023-09-28 | Teva Pharmaceuticals International Gmbh | Solid state forms of lx9211 and salts thereof |
| JP2026505877A (ja) * | 2022-11-02 | 2026-02-19 | ソウルブレイン シーオー．， エルティーディー． | 電解液添加剤、これを含む電池用電解液及びこれを含む二次電池 |
| 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 |
| WO2024125668A1 (zh) * | 2022-12-13 | 2024-06-20 | 上海海雁医药科技有限公司 | 杂环取代的五并六元杂芳基衍生物、其药物组合物及应用与制备方法 |
| WO2024153067A1 (zh) * | 2023-01-16 | 2024-07-25 | 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 |
| CN118772152B (zh) * | 2023-04-07 | 2026-01-02 | 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 |
| KR20250167096A (ko) | 2023-04-07 | 2025-11-28 | 앨리콘 파머슈티컬 컴퍼니 리미티드 | Aak1 억제제인 질소 함유 헤테로고리계 화합물 |
| 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 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5464764A (en) | 1989-08-22 | 1995-11-07 | University Of Utah Research Foundation | Positive-negative selection methods and vectors |
| WO1993004169A1 (en) | 1991-08-20 | 1993-03-04 | Genpharm International, Inc. | Gene targeting in animal cells using isogenic dna constructs |
| US20030187026A1 (en) * | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| EP1560824A1 (en) * | 2002-11-05 | 2005-08-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of jak and other protein kinases |
| JP2007526324A (ja) * | 2004-03-02 | 2007-09-13 | スミスクライン・ビーチャム・コーポレイション | Ａｋｔ活性のある阻害剤 |
| WO2007120593A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | Anilino-pyrimidine phenyl and benzothiophene analogs |
| AU2008210455A1 (en) * | 2007-01-31 | 2008-08-07 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as kinase inhibitors |
| DK2822555T3 (en) * | 2012-03-09 | 2018-02-05 | Lexicon Pharmaceuticals Inc | Inhibition of adapter-associated kinase 1 for the treatment of pain |
| 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 |
| EP3019475A1 (en) | 2013-07-08 | 2016-05-18 | 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 |
| ES2693771T3 (es) | 2014-01-29 | 2018-12-13 | Bristol-Myers Squibb Company | Inhibidores de aril lactama quinasa |
| MX2016009352A (es) | 2014-01-31 | 2016-10-13 | Bristol Myers Squibb Co | Inhibidores de quinasa a base de quinolina. |
| SI3126351T1 (sl) * | 2014-04-02 | 2018-11-30 | Bristol-Myers Squibb Company | Biaril kinazni inhibitorji |
| WO2016053794A1 (en) | 2014-09-30 | 2016-04-07 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| ES2740224T3 (es) | 2015-04-10 | 2020-02-05 | Bristol Myers Squibb Co | 6H-isocromeno[3,4-c]piridinas y benzo[c][1,7]naftiridin-6-(5H)-onas como inhibidores de la cinasa asociada a adaptador 1 (AAK1) |
| KR102704295B1 (ko) * | 2015-10-01 | 2024-09-05 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| EP3356330B1 (en) | 2015-10-01 | 2019-11-20 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| WO2020010295A1 (en) | 2018-07-06 | 2020-01-09 | Liqui-Box Corporation | Dispensing probe for dispensing flowable material |
-
2015
- 2015-04-01 SI SI201530425T patent/SI3126351T1/sl unknown
- 2015-04-01 JP JP2016560389A patent/JP6411541B2/ja active Active
- 2015-04-01 CN CN201580029294.3A patent/CN106458994B/zh active Active
- 2015-04-01 MX MX2016012829A patent/MX2016012829A/es active IP Right Grant
- 2015-04-01 EP EP15717342.8A patent/EP3126351B1/en active Active
- 2015-04-01 US US15/300,618 patent/US9902722B2/en active Active
- 2015-04-01 SM SM20180665T patent/SMT201800665T1/it unknown
- 2015-04-01 LT LTEP15717342.8T patent/LT3126351T/lt unknown
- 2015-04-01 EA EA201691916A patent/EA028942B1/ru not_active IP Right Cessation
- 2015-04-01 PT PT15717342T patent/PT3126351T/pt unknown
- 2015-04-01 KR KR1020167030237A patent/KR102379518B1/ko active Active
- 2015-04-01 RS RS20181374A patent/RS58062B1/sr unknown
- 2015-04-01 BR BR112016022298-9A patent/BR112016022298B1/pt active IP Right Grant
- 2015-04-01 HU HUE15717342A patent/HUE041457T2/hu unknown
- 2015-04-01 PL PL15717342T patent/PL3126351T3/pl unknown
- 2015-04-01 PE PE2016001842A patent/PE20170004A1/es unknown
- 2015-04-01 HR HRP20181899TT patent/HRP20181899T1/hr unknown
- 2015-04-01 CA CA2944466A patent/CA2944466C/en active Active
- 2015-04-01 ES ES15717342T patent/ES2700549T3/es active Active
- 2015-04-01 WO PCT/US2015/023805 patent/WO2015153720A1/en not_active Ceased
- 2015-04-01 AU AU2015240869A patent/AU2015240869B2/en active Active
- 2015-04-01 SG SG11201608195QA patent/SG11201608195QA/en unknown
- 2015-04-01 DK DK15717342.8T patent/DK3126351T3/en active
-
2016
- 2016-09-27 IL IL248086A patent/IL248086B/en active IP Right Grant
- 2016-09-30 ZA ZA2016/06767A patent/ZA201606767B/en unknown
- 2016-09-30 CL CL2016002502A patent/CL2016002502A1/es unknown
-
2018
- 2018-01-09 US US15/865,848 patent/US10155760B2/en active Active
- 2018-10-23 US US16/168,533 patent/US10351563B2/en active Active
- 2018-12-10 CY CY181101318T patent/CY1120988T1/el unknown
-
2019
- 2019-06-18 US US16/443,929 patent/US10723734B2/en active Active
-
2020
- 2020-06-26 US US16/913,064 patent/US10981910B2/en active Active
-
2021
- 2021-03-05 US US17/192,985 patent/US12065437B2/en active Active
-
2024
- 2024-07-11 US US18/769,916 patent/US20240360131A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017511329A5 (enExample) | ||
| JP2018537408A5 (enExample) | ||
| NZ609955A (en) | Sgc stimulators | |
| ES2675760T3 (es) | Compuestos terapéuticamente activos y métodos de uso de los mismos | |
| JP5367707B2 (ja) | Ｄｈｏｄｈ阻害剤としてのアザビフェニルアミノ安息香酸誘導体 | |
| JP2016523977A5 (enExample) | ||
| JP2016525076A5 (enExample) | ||
| NZ604004A (en) | Pyridone and aza-pyridone compounds and methods of use | |
| RU2015100942A (ru) | Производное пиперидинилпиразолпиридина | |
| RU2018138050A (ru) | Производные тиазолопиридина как агонисты gpr119 | |
| JP2016525075A5 (enExample) | ||
| JP2020502111A5 (enExample) | ||
| US10376510B2 (en) | 2,4- or 4,6-diaminopyrimidine compounds as IDH2 mutants inhibitors for the treatment of cancer | |
| JP2015172062A5 (enExample) | ||
| JP2022500402A5 (enExample) | ||
| JP2015503571A5 (enExample) | ||
| HRP20180546T1 (hr) | Supstituirani benzilindazoli za uporabu kao inhibitori bub1 kinaze za liječenje hiperproliferativnih bolesti | |
| JP2017530962A5 (enExample) | ||
| JP2011503230A5 (enExample) | ||
| RU2019121871A (ru) | Новые производные фенилпропионовой кислоты и их применение | |
| RU2014124953A (ru) | Производные аминопиридина в качестве модуляторов богатой лейцином повторной киназы 2 (lrrk2) | |
| JP2016522232A5 (enExample) | ||
| JP2012525395A5 (enExample) | ||
| JP2013543480A5 (enExample) | ||
| CA2624602A1 (en) | Process for preparing 6-substituted-7-azaindoles |