JP2019507177A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019507177A5 JP2019507177A5 JP2018546518A JP2018546518A JP2019507177A5 JP 2019507177 A5 JP2019507177 A5 JP 2019507177A5 JP 2018546518 A JP2018546518 A JP 2018546518A JP 2018546518 A JP2018546518 A JP 2018546518A JP 2019507177 A5 JP2019507177 A5 JP 2019507177A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- pyrrolidine
- carbonitrile
- dihydro
- spiro
- 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
- 150000001875 compounds Chemical class 0.000 claims 19
- -1 cyano, hydroxyl Chemical group 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 230000007812 deficiency Effects 0.000 claims 7
- 208000008955 Mucolipidoses Diseases 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 208000014644 Brain disease Diseases 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 201000000915 Chronic Progressive External Ophthalmoplegia Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 2
- 208000032274 Encephalopathy Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 208000006136 Leigh Disease Diseases 0.000 claims 2
- 208000017507 Leigh syndrome Diseases 0.000 claims 2
- 108010027062 Long-Chain Acyl-CoA Dehydrogenase Proteins 0.000 claims 2
- 102000018653 Long-Chain Acyl-CoA Dehydrogenase Human genes 0.000 claims 2
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 2
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 2
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000002438 mitochondrial effect Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 2
- 208000020468 mucolipidosis III alpha/beta Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- RBNHRPZXERKDHR-KRWDZBQOSA-N (3S)-7-(4-fluorophenyl)-2-oxospiro[pyrido[2,3-b][1,4]oxazine-3,3'-pyrrolidine]-1-carbonitrile Chemical compound FC1=CC=C(C=C1)C1=CC2=C(O[C@@]3(CNCC3)C(N2C#N)=O)N=C1 RBNHRPZXERKDHR-KRWDZBQOSA-N 0.000 claims 1
- PBQINQSJWPGZAX-UHFFFAOYSA-N 1,5-dihydro-4,1-benzoxazepin-2-one Chemical compound N1C(=O)COCC2=CC=CC=C21 PBQINQSJWPGZAX-UHFFFAOYSA-N 0.000 claims 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 1
- ORNSLMJWQDGQFF-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=CC=C2NC(=O)COC2=N1 ORNSLMJWQDGQFF-UHFFFAOYSA-N 0.000 claims 1
- LMORUQRSHZOMKO-UHFFFAOYSA-N 3,4-dihydro-1h-1,5-naphthyridin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=N1 LMORUQRSHZOMKO-UHFFFAOYSA-N 0.000 claims 1
- KLPUJWLQGMDXDV-UHFFFAOYSA-N 3,4-dihydro-1h-1,6-naphthyridin-2-one Chemical compound N1=CC=C2NC(=O)CCC2=C1 KLPUJWLQGMDXDV-UHFFFAOYSA-N 0.000 claims 1
- PWCQRUXZWPUNBG-UHFFFAOYSA-N 3,4-dihydro-1h-1,7-naphthyridin-2-one Chemical compound C1=NC=C2NC(=O)CCC2=C1 PWCQRUXZWPUNBG-UHFFFAOYSA-N 0.000 claims 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 1
- 102000052553 3-Hydroxyacyl CoA Dehydrogenase Human genes 0.000 claims 1
- 108700020831 3-Hydroxyacyl-CoA Dehydrogenase Proteins 0.000 claims 1
- APYXDKYGQKKWDM-UHFFFAOYSA-N 7,8-dihydro-5h-pyrazino[2,3-b]pyrazin-6-one Chemical compound C1=CN=C2NC(=O)CNC2=N1 APYXDKYGQKKWDM-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 201000005943 Barth syndrome Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- TZEUAYCHXZDRJE-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C1=CC=C(C=C1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 TZEUAYCHXZDRJE-UHFFFAOYSA-N 0.000 claims 1
- AUYFWPWADNCLMC-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C1=CC=C(C=C1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 AUYFWPWADNCLMC-UHFFFAOYSA-N 0.000 claims 1
- AUYFWPWADNCLMC-SFHVURJKSA-N C(#N)C1=CC=C(C=C1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C1=CC=C(C=C1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 AUYFWPWADNCLMC-SFHVURJKSA-N 0.000 claims 1
- NCZWVROOUWKLNE-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound C(#N)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N NCZWVROOUWKLNE-UHFFFAOYSA-N 0.000 claims 1
- NFLKIORMAFZRSR-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound C(#N)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N NFLKIORMAFZRSR-UHFFFAOYSA-N 0.000 claims 1
- ZRVGFQHUHDORPF-SFHVURJKSA-N C(#N)C=1C=C(C=CC=1)C1=CC2=C(N[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC2=C(N[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 ZRVGFQHUHDORPF-SFHVURJKSA-N 0.000 claims 1
- IRUHFBNMGVZHQG-UHFFFAOYSA-N C(#N)C=1C=C(C=CC=1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 IRUHFBNMGVZHQG-UHFFFAOYSA-N 0.000 claims 1
- IRUHFBNMGVZHQG-SFHVURJKSA-N C(#N)C=1C=C(C=CC=1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 IRUHFBNMGVZHQG-SFHVURJKSA-N 0.000 claims 1
- QSVFUTKXIARXKK-UHFFFAOYSA-N C(#N)C=1C=C(C=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N QSVFUTKXIARXKK-UHFFFAOYSA-N 0.000 claims 1
- IQIHWZWUMFLBRA-UHFFFAOYSA-N C(#N)C=1C=C(C=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N IQIHWZWUMFLBRA-UHFFFAOYSA-N 0.000 claims 1
- VQNIFRUAGGWIJA-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C(=O)N(C)C)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C(=O)N(C)C)=O)CC1 VQNIFRUAGGWIJA-UHFFFAOYSA-N 0.000 claims 1
- KOYWQFDRXLZVTO-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C(=O)NC)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C(=O)NC)=O)CC1 KOYWQFDRXLZVTO-UHFFFAOYSA-N 0.000 claims 1
- QZNZMTLRZYPCFT-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=C(C=CC=C2)NC(C)=O)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=C(C=CC=C2)NC(C)=O)=O)CC1 QZNZMTLRZYPCFT-UHFFFAOYSA-N 0.000 claims 1
- PAFFBWKOCGVVDK-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=CC=C(C(=O)N(C)C)C=C2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=CC=C(C(=O)N(C)C)C=C2)=O)CC1 PAFFBWKOCGVVDK-UHFFFAOYSA-N 0.000 claims 1
- KRZFFVDSKFFVRY-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=CC=C(C(=O)NC)C=C2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=CC=C(C(=O)NC)C=C2)=O)CC1 KRZFFVDSKFFVRY-UHFFFAOYSA-N 0.000 claims 1
- ZENZGXOYKNJRRS-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=CC=C(C=C2)NC(C)=O)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C2=CC=C(C=C2)NC(C)=O)=O)CC1 ZENZGXOYKNJRRS-UHFFFAOYSA-N 0.000 claims 1
- ITXOIOBLXPJETJ-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=C(C(=O)N(C)C)C=CC=2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=C(C(=O)N(C)C)C=CC=2)=O)CC1 ITXOIOBLXPJETJ-UHFFFAOYSA-N 0.000 claims 1
- NANUNTDQFUVSSF-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=C(C=CC=2)NC(C)=O)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=C(C=CC=2)NC(C)=O)=O)CC1 NANUNTDQFUVSSF-UHFFFAOYSA-N 0.000 claims 1
- JEJUHENOZQMBPN-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=C(C=CC=2)NS(=O)(=O)C2CC2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=C(C=CC=2)NS(=O)(=O)C2CC2)=O)CC1 JEJUHENOZQMBPN-UHFFFAOYSA-N 0.000 claims 1
- ORCWWINZVHVWDU-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=CC(=NC=2)C(=O)NC)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC(=CC=C3C2)C=2C=CC(=NC=2)C(=O)NC)=O)CC1 ORCWWINZVHVWDU-UHFFFAOYSA-N 0.000 claims 1
- FVPCYEDRHMZEGW-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=C(C=CC=C2)NC(C)=O)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=C(C=CC=C2)NC(C)=O)=O)CC1 FVPCYEDRHMZEGW-UHFFFAOYSA-N 0.000 claims 1
- NJKBLKFGVJBQJX-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=CC=C(C(=O)N(C)C)C=C2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=CC=C(C(=O)N(C)C)C=C2)=O)CC1 NJKBLKFGVJBQJX-UHFFFAOYSA-N 0.000 claims 1
- UXOPSHICRSEBDJ-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=CC=C(C(=O)NC)C=C2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=CC=C(C(=O)NC)C=C2)=O)CC1 UXOPSHICRSEBDJ-UHFFFAOYSA-N 0.000 claims 1
- KDQRKEGIZAUQLZ-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=CC=C(C=C2)NC(C)=O)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C2=CC=C(C=C2)NC(C)=O)=O)CC1 KDQRKEGIZAUQLZ-UHFFFAOYSA-N 0.000 claims 1
- ARMYHELMKIDFPE-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C=2C=C(C(=O)N(C)C)C=CC=2)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C=2C=C(C(=O)N(C)C)C=CC=2)=O)CC1 ARMYHELMKIDFPE-UHFFFAOYSA-N 0.000 claims 1
- XCZWEDKIKFZUBR-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C=2C=C(C=CC=2)NC(C)=O)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C=2C=C(C=CC=2)NC(C)=O)=O)CC1 XCZWEDKIKFZUBR-UHFFFAOYSA-N 0.000 claims 1
- XLGFQPFROQWIMH-UHFFFAOYSA-N C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C=2C=CC(=NC=2)C(=O)NC)=O)CC1 Chemical compound C(#N)N1CC2(C(NC3=CC=C(C=C3C2)C=2C=CC(=NC=2)C(=O)NC)=O)CC1 XLGFQPFROQWIMH-UHFFFAOYSA-N 0.000 claims 1
- NIVWWMJBYCGIDJ-UHFFFAOYSA-N C(#N)N1CC2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=C(C=CC=C1)F)=O Chemical compound C(#N)N1CC2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=C(C=CC=C1)F)=O NIVWWMJBYCGIDJ-UHFFFAOYSA-N 0.000 claims 1
- CJALBJJHSYATKP-UHFFFAOYSA-N C(#N)N1CC2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=CC=C(C=C1)F)=O Chemical compound C(#N)N1CC2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=CC=C(C=C1)F)=O CJALBJJHSYATKP-UHFFFAOYSA-N 0.000 claims 1
- GSFOZGZZBRWSKD-UHFFFAOYSA-N C(#N)N1CC2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=CC=CC=C1)=O Chemical compound C(#N)N1CC2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=CC=CC=C1)=O GSFOZGZZBRWSKD-UHFFFAOYSA-N 0.000 claims 1
- CJALBJJHSYATKP-SFHVURJKSA-N C(#N)N1C[C@@]2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=CC=C(C=C1)F)=O Chemical compound C(#N)N1C[C@@]2(CC1)C(NC1=C(O2)N=C(C=C1)C(=O)NC1=CC=C(C=C1)F)=O CJALBJJHSYATKP-SFHVURJKSA-N 0.000 claims 1
- GABPILKIYOKJHO-UHFFFAOYSA-N C(C)(C)C=1C=CC(=C(C=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)OC Chemical compound C(C)(C)C=1C=CC(=C(C=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)OC GABPILKIYOKJHO-UHFFFAOYSA-N 0.000 claims 1
- FJLKUWRZZFHSMF-UHFFFAOYSA-N C(C)(C)C=1C=CC(=C(C=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)OC Chemical compound C(C)(C)C=1C=CC(=C(C=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)OC FJLKUWRZZFHSMF-UHFFFAOYSA-N 0.000 claims 1
- NHHBGQCOLUJNKP-UHFFFAOYSA-N C(C)C1NC(C2(CCN(C2)C#N)C1)=O Chemical compound C(C)C1NC(C2(CCN(C2)C#N)C1)=O NHHBGQCOLUJNKP-UHFFFAOYSA-N 0.000 claims 1
- PPDJKDJCOKVMIU-UHFFFAOYSA-N C(C1=CC=CC=C1)C1NC(C2(CCN(C2)C#N)C1)=O Chemical compound C(C1=CC=CC=C1)C1NC(C2(CCN(C2)C#N)C1)=O PPDJKDJCOKVMIU-UHFFFAOYSA-N 0.000 claims 1
- AZURDVSNWICSLJ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N AZURDVSNWICSLJ-UHFFFAOYSA-N 0.000 claims 1
- XGZOUXDQPIRNPR-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N XGZOUXDQPIRNPR-UHFFFAOYSA-N 0.000 claims 1
- LHWGPTBOCHSNLR-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N LHWGPTBOCHSNLR-UHFFFAOYSA-N 0.000 claims 1
- ZEDBVTZEWNUZIU-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound C(C1=CC=CC=C1)OC1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N ZEDBVTZEWNUZIU-UHFFFAOYSA-N 0.000 claims 1
- BTEXBSRINXOICQ-UHFFFAOYSA-N C1(=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)C1=CC=CC=C1 BTEXBSRINXOICQ-UHFFFAOYSA-N 0.000 claims 1
- NGRBLYJMHHFRMM-UHFFFAOYSA-N C1(=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)C1=CC=CC=C1 NGRBLYJMHHFRMM-UHFFFAOYSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 101150072353 CAPN3 gene Proteins 0.000 claims 1
- KKTNBBTYQULHLY-UHFFFAOYSA-N CC1(C(NC2(CCN(C2)C#N)C(N1)=O)=O)C1=CC=CC=C1 Chemical compound CC1(C(NC2(CCN(C2)C#N)C(N1)=O)=O)C1=CC=CC=C1 KKTNBBTYQULHLY-UHFFFAOYSA-N 0.000 claims 1
- HAZYXVWGGRPZLS-UHFFFAOYSA-N CC1=NC=CC(=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CC1=NC=CC(=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N HAZYXVWGGRPZLS-UHFFFAOYSA-N 0.000 claims 1
- XRVQQNQHGBMAJC-UHFFFAOYSA-N CC1=NC=CC(=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CC1=NC=CC(=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N XRVQQNQHGBMAJC-UHFFFAOYSA-N 0.000 claims 1
- VZEBSRCABIVIFS-UHFFFAOYSA-N CC1=NNC(=C1C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)C Chemical compound CC1=NNC(=C1C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)C VZEBSRCABIVIFS-UHFFFAOYSA-N 0.000 claims 1
- WABWRXUKNDQUHV-UHFFFAOYSA-N CC1=NNC(=C1C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)C Chemical compound CC1=NNC(=C1C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)C WABWRXUKNDQUHV-UHFFFAOYSA-N 0.000 claims 1
- RVVKHNWONHKZJO-UHFFFAOYSA-N CC1=NNC2=CC(=CC=C12)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CC1=NNC2=CC(=CC=C12)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N RVVKHNWONHKZJO-UHFFFAOYSA-N 0.000 claims 1
- IPHNXWSLDIBDAI-UHFFFAOYSA-N CC1=NNC2=CC(=CC=C12)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CC1=NNC2=CC(=CC=C12)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N IPHNXWSLDIBDAI-UHFFFAOYSA-N 0.000 claims 1
- HQRBXZIPMCFPMY-UHFFFAOYSA-N CC1=NNC=C1C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CC1=NNC=C1C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N HQRBXZIPMCFPMY-UHFFFAOYSA-N 0.000 claims 1
- UBGWJHKEPWEAHM-UHFFFAOYSA-N CC1=NOC(=C1C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)C Chemical compound CC1=NOC(=C1C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)C UBGWJHKEPWEAHM-UHFFFAOYSA-N 0.000 claims 1
- QJSGPSYFYHOZNH-UHFFFAOYSA-N CC1NC(C2(CCN(C2)C#N)C1)=O Chemical compound CC1NC(C2(CCN(C2)C#N)C1)=O QJSGPSYFYHOZNH-UHFFFAOYSA-N 0.000 claims 1
- VVVXXUXVCSSAOM-UHFFFAOYSA-N CC=1C(=C2C=NNC2=CC=1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound CC=1C(=C2C=NNC2=CC=1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 VVVXXUXVCSSAOM-UHFFFAOYSA-N 0.000 claims 1
- KDZWETVEPVDWCE-UHFFFAOYSA-N CC=1C(=C2C=NNC2=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CC=1C(=C2C=NNC2=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N KDZWETVEPVDWCE-UHFFFAOYSA-N 0.000 claims 1
- KDZWETVEPVDWCE-NRFANRHFSA-N CC=1C(=C2C=NNC2=CC=1)C1=CC=C2C[C@]3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CC=1C(=C2C=NNC2=CC=1)C1=CC=C2C[C@]3(C(NC2=C1)=O)CN(CC3)C#N KDZWETVEPVDWCE-NRFANRHFSA-N 0.000 claims 1
- MICJFLCDQYNINF-UHFFFAOYSA-N CC=1C(=C2C=NNC2=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CC=1C(=C2C=NNC2=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N MICJFLCDQYNINF-UHFFFAOYSA-N 0.000 claims 1
- BXSJRMRPWOXVHC-UHFFFAOYSA-N CC=1SC2=C(N=1)C=C(C=C2)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CC=1SC2=C(N=1)C=C(C=C2)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N BXSJRMRPWOXVHC-UHFFFAOYSA-N 0.000 claims 1
- INHRDLUVKVXEFT-UHFFFAOYSA-N CC=1SC2=C(N=1)C=C(C=C2)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CC=1SC2=C(N=1)C=C(C=C2)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N INHRDLUVKVXEFT-UHFFFAOYSA-N 0.000 claims 1
- YWFISXVUTQAJDH-UHFFFAOYSA-N CN1C(=CC=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1C(=CC=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N YWFISXVUTQAJDH-UHFFFAOYSA-N 0.000 claims 1
- NQYVJFHVXAXVMA-UHFFFAOYSA-N CN1C(=CC=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1C(=CC=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N NQYVJFHVXAXVMA-UHFFFAOYSA-N 0.000 claims 1
- FCNZSNJQHGUSHC-UHFFFAOYSA-N CN1C=C(C=CC1=O)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1C=C(C=CC1=O)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N FCNZSNJQHGUSHC-UHFFFAOYSA-N 0.000 claims 1
- FHAQTIUAPGEIQK-UHFFFAOYSA-N CN1C=C(C=CC1=O)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1C=C(C=CC1=O)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N FHAQTIUAPGEIQK-UHFFFAOYSA-N 0.000 claims 1
- MWXKHXQNOSGJFK-UHFFFAOYSA-N CN1CCN(CC1)C(=O)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1CCN(CC1)C(=O)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N MWXKHXQNOSGJFK-UHFFFAOYSA-N 0.000 claims 1
- WBLRNMBMQAHBIL-UHFFFAOYSA-N CN1CCN(CC1)C(=O)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1CCN(CC1)C(=O)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N WBLRNMBMQAHBIL-UHFFFAOYSA-N 0.000 claims 1
- IJQAIBWZZQEOLL-UHFFFAOYSA-N CN1CCN(CC1)C(=O)C=1C=C(C=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1CCN(CC1)C(=O)C=1C=C(C=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N IJQAIBWZZQEOLL-UHFFFAOYSA-N 0.000 claims 1
- ODYUKQYCIUSFGA-UHFFFAOYSA-N CN1CCN(CC1)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N ODYUKQYCIUSFGA-UHFFFAOYSA-N 0.000 claims 1
- ODYUKQYCIUSFGA-DEOSSOPVSA-N CN1CCN(CC1)C1=CC=C(C=C1)C1=CC=C2C[C@]3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)C1=CC=C2C[C@]3(C(NC2=C1)=O)CN(CC3)C#N ODYUKQYCIUSFGA-DEOSSOPVSA-N 0.000 claims 1
- CFCHWWXDCMMRTQ-UHFFFAOYSA-N CN1CCN(CC1)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N CFCHWWXDCMMRTQ-UHFFFAOYSA-N 0.000 claims 1
- SWYLXPPAIGBSJD-UHFFFAOYSA-N CN1N=CC(=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1N=CC(=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N SWYLXPPAIGBSJD-UHFFFAOYSA-N 0.000 claims 1
- UQCRBDYQYSOBLZ-UHFFFAOYSA-N CN1N=CC(=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1N=CC(=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N UQCRBDYQYSOBLZ-UHFFFAOYSA-N 0.000 claims 1
- VUVFSJXKHQAFBX-UHFFFAOYSA-N CN1N=CC(=C1C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1)C Chemical compound CN1N=CC(=C1C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1)C VUVFSJXKHQAFBX-UHFFFAOYSA-N 0.000 claims 1
- QJGVWJHPIXHZOH-UHFFFAOYSA-N CN1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound CN1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 QJGVWJHPIXHZOH-UHFFFAOYSA-N 0.000 claims 1
- QJGVWJHPIXHZOH-IBGZPJMESA-N CN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound CN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 QJGVWJHPIXHZOH-IBGZPJMESA-N 0.000 claims 1
- QJGVWJHPIXHZOH-LJQANCHMSA-N CN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound CN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@]3(CN(CC3)C#N)C(N2)=O)N=C1 QJGVWJHPIXHZOH-LJQANCHMSA-N 0.000 claims 1
- SCKVIGBOAAMNEG-UHFFFAOYSA-N CN1N=CC2=CC(=CC=C12)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1N=CC2=CC(=CC=C12)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N SCKVIGBOAAMNEG-UHFFFAOYSA-N 0.000 claims 1
- GUMBIBQYIWPWMC-UHFFFAOYSA-N CN1N=CC2=CC(=CC=C12)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1N=CC2=CC(=CC=C12)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N GUMBIBQYIWPWMC-UHFFFAOYSA-N 0.000 claims 1
- OZHVYCLOYQETBT-UHFFFAOYSA-N CN1N=CC=C1C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound CN1N=CC=C1C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N OZHVYCLOYQETBT-UHFFFAOYSA-N 0.000 claims 1
- FEGQVSBVTHPTQK-UHFFFAOYSA-N CN1N=CC=C1C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound CN1N=CC=C1C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N FEGQVSBVTHPTQK-UHFFFAOYSA-N 0.000 claims 1
- LXBSTCDUYMGEOO-UHFFFAOYSA-N COC1=CC=C(C(=N1)C)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound COC1=CC=C(C(=N1)C)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 LXBSTCDUYMGEOO-UHFFFAOYSA-N 0.000 claims 1
- LXBSTCDUYMGEOO-SFHVURJKSA-N COC1=CC=C(C(=N1)C)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound COC1=CC=C(C(=N1)C)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 LXBSTCDUYMGEOO-SFHVURJKSA-N 0.000 claims 1
- LXBSTCDUYMGEOO-GOSISDBHSA-N COC1=CC=C(C(C)=N1)C1=CC2=C(O[C@@]3(CCN(C3)C#N)C(=O)N2)N=C1 Chemical compound COC1=CC=C(C(C)=N1)C1=CC2=C(O[C@@]3(CCN(C3)C#N)C(=O)N2)N=C1 LXBSTCDUYMGEOO-GOSISDBHSA-N 0.000 claims 1
- SBPLLHNOXZWXLE-UHFFFAOYSA-N COC1=CC=C(C=N1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound COC1=CC=C(C=N1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N SBPLLHNOXZWXLE-UHFFFAOYSA-N 0.000 claims 1
- PIFQPBIFXJOKCW-UHFFFAOYSA-N COC1=CC=C(C=N1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound COC1=CC=C(C=N1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N PIFQPBIFXJOKCW-UHFFFAOYSA-N 0.000 claims 1
- IKSFNMDFWYUAPZ-UHFFFAOYSA-N COC1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound COC1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N IKSFNMDFWYUAPZ-UHFFFAOYSA-N 0.000 claims 1
- PUABPVHTYFADID-UHFFFAOYSA-N COCCN1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound COCCN1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 PUABPVHTYFADID-UHFFFAOYSA-N 0.000 claims 1
- PUABPVHTYFADID-NRFANRHFSA-N COCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound COCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 PUABPVHTYFADID-NRFANRHFSA-N 0.000 claims 1
- PUABPVHTYFADID-OAQYLSRUSA-N COCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound COCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@]3(CN(CC3)C#N)C(N2)=O)N=C1 PUABPVHTYFADID-OAQYLSRUSA-N 0.000 claims 1
- XNJLFQMZCFESGX-VJSCVCEBSA-N C[C@@H]1C(NC2(CCN(C2)C#N)C(N1)=O)=O Chemical compound C[C@@H]1C(NC2(CCN(C2)C#N)C(N1)=O)=O XNJLFQMZCFESGX-VJSCVCEBSA-N 0.000 claims 1
- XNJLFQMZCFESGX-AADKRJSRSA-N C[C@H]1C(NC2(CCN(C2)C#N)C(N1)=O)=O Chemical compound C[C@H]1C(NC2(CCN(C2)C#N)C(N1)=O)=O XNJLFQMZCFESGX-AADKRJSRSA-N 0.000 claims 1
- 102100032539 Calpain-3 Human genes 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- HORIVRDTRLQLHV-UHFFFAOYSA-N ClC1=C(C=C(C=C1)OC(F)(F)F)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound ClC1=C(C=C(C=C1)OC(F)(F)F)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N HORIVRDTRLQLHV-UHFFFAOYSA-N 0.000 claims 1
- XOVJWWGPMBQSLT-UHFFFAOYSA-N ClC1=C(C=C(C=C1)OC(F)(F)F)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound ClC1=C(C=C(C=C1)OC(F)(F)F)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N XOVJWWGPMBQSLT-UHFFFAOYSA-N 0.000 claims 1
- ALSNTBAFYRVIGH-UHFFFAOYSA-N ClC1=C(COC=2C=C(C=CC=2)C2=CC=C3CC4(C(NC3=C2)=O)CN(CC4)C#N)C=CC=C1 Chemical compound ClC1=C(COC=2C=C(C=CC=2)C2=CC=C3CC4(C(NC3=C2)=O)CN(CC4)C#N)C=CC=C1 ALSNTBAFYRVIGH-UHFFFAOYSA-N 0.000 claims 1
- RXOGTPMEVGKQAS-UHFFFAOYSA-N ClC1=C(COC=2C=C(C=CC=2)C=2C=C3CC4(C(NC3=CC=2)=O)CN(CC4)C#N)C=CC=C1 Chemical compound ClC1=C(COC=2C=C(C=CC=2)C=2C=C3CC4(C(NC3=CC=2)=O)CN(CC4)C#N)C=CC=C1 RXOGTPMEVGKQAS-UHFFFAOYSA-N 0.000 claims 1
- SAYOSPYPKYVLRO-UHFFFAOYSA-N ClC1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound ClC1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N SAYOSPYPKYVLRO-UHFFFAOYSA-N 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 1
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims 1
- 102000015782 Electron Transport Complex III Human genes 0.000 claims 1
- 108010024882 Electron Transport Complex III Proteins 0.000 claims 1
- WDCRZMDNYAREFO-UHFFFAOYSA-N FC1=C(C=C(C=C1)C)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound FC1=C(C=C(C=C1)C)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N WDCRZMDNYAREFO-UHFFFAOYSA-N 0.000 claims 1
- QVJXHQGNIZZKKN-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC1=CC=C(C=C1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 QVJXHQGNIZZKKN-UHFFFAOYSA-N 0.000 claims 1
- QVJXHQGNIZZKKN-KRWDZBQOSA-N FC1=CC=C(C=C1)C1=CC2=C(N[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC1=CC=C(C=C1)C1=CC2=C(N[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 QVJXHQGNIZZKKN-KRWDZBQOSA-N 0.000 claims 1
- HLYCKDSIIMKHFL-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC1=CC=C(C=C1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 HLYCKDSIIMKHFL-UHFFFAOYSA-N 0.000 claims 1
- TWRBYEBVRGHILJ-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound FC1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N TWRBYEBVRGHILJ-UHFFFAOYSA-N 0.000 claims 1
- OTEYMIAIGRFCQL-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC=1C=C(C=CC=1)C1=CC2=C(NC3(CN(CC3)C#N)C(N2)=O)N=C1 OTEYMIAIGRFCQL-UHFFFAOYSA-N 0.000 claims 1
- OTEYMIAIGRFCQL-KRWDZBQOSA-N FC=1C=C(C=CC=1)C1=CC2=C(N[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC=1C=C(C=CC=1)C1=CC2=C(N[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 OTEYMIAIGRFCQL-KRWDZBQOSA-N 0.000 claims 1
- WWIKEUVTLWVECX-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC=1C=C(C=CC=1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 WWIKEUVTLWVECX-UHFFFAOYSA-N 0.000 claims 1
- WWIKEUVTLWVECX-KRWDZBQOSA-N FC=1C=C(C=CC=1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound FC=1C=C(C=CC=1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 WWIKEUVTLWVECX-KRWDZBQOSA-N 0.000 claims 1
- ACLVQLXJKJDMIR-UHFFFAOYSA-N FC=1C=C(C=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound FC=1C=C(C=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N ACLVQLXJKJDMIR-UHFFFAOYSA-N 0.000 claims 1
- RUOOVPGBINYOFX-UHFFFAOYSA-N FC=1C=CC(=C(C=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)OC(C)C Chemical compound FC=1C=CC(=C(C=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N)OC(C)C RUOOVPGBINYOFX-UHFFFAOYSA-N 0.000 claims 1
- CPSNRECYRWTWFK-UHFFFAOYSA-N FC=1C=CC(=C(C=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)OC(C)C Chemical compound FC=1C=CC(=C(C=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N)OC(C)C CPSNRECYRWTWFK-UHFFFAOYSA-N 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 201000008892 GM1 Gangliosidosis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101001083553 Homo sapiens Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000010428 Muscle Weakness Diseases 0.000 claims 1
- 206010028372 Muscular weakness Diseases 0.000 claims 1
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims 1
- DLTIJIMEGPKPNQ-UHFFFAOYSA-N N1(CCOCC1)C(=O)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound N1(CCOCC1)C(=O)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N DLTIJIMEGPKPNQ-UHFFFAOYSA-N 0.000 claims 1
- OJPIRCLHWDRREC-UHFFFAOYSA-N N1(CCOCC1)C(=O)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound N1(CCOCC1)C(=O)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N OJPIRCLHWDRREC-UHFFFAOYSA-N 0.000 claims 1
- BQQJOPMEEYFNJZ-UHFFFAOYSA-N N1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound N1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 BQQJOPMEEYFNJZ-UHFFFAOYSA-N 0.000 claims 1
- BQQJOPMEEYFNJZ-SFHVURJKSA-N N1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound N1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 BQQJOPMEEYFNJZ-SFHVURJKSA-N 0.000 claims 1
- SNEYCKLYNHQRKM-UHFFFAOYSA-N N1N=CC2=C(C=CC=C12)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound N1N=CC2=C(C=CC=C12)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N SNEYCKLYNHQRKM-UHFFFAOYSA-N 0.000 claims 1
- SNEYCKLYNHQRKM-HXUWFJFHSA-N N1N=CC2=C(C=CC=C12)C1=CC=C2C[C@@]3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound N1N=CC2=C(C=CC=C12)C1=CC=C2C[C@@]3(C(NC2=C1)=O)CN(CC3)C#N SNEYCKLYNHQRKM-HXUWFJFHSA-N 0.000 claims 1
- SNEYCKLYNHQRKM-FQEVSTJZSA-N N1N=CC2=C(C=CC=C12)C1=CC=C2C[C@]3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound N1N=CC2=C(C=CC=C12)C1=CC=C2C[C@]3(C(NC2=C1)=O)CN(CC3)C#N SNEYCKLYNHQRKM-FQEVSTJZSA-N 0.000 claims 1
- YDVWMYPUVSXYTM-UHFFFAOYSA-N N1N=CC2=C(C=CC=C12)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound N1N=CC2=C(C=CC=C12)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N YDVWMYPUVSXYTM-UHFFFAOYSA-N 0.000 claims 1
- YDVWMYPUVSXYTM-FQEVSTJZSA-N N1N=CC2=C(C=CC=C12)C=1C=C2C[C@]3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound N1N=CC2=C(C=CC=C12)C=1C=C2C[C@]3(C(NC2=CC=1)=O)CN(CC3)C#N YDVWMYPUVSXYTM-FQEVSTJZSA-N 0.000 claims 1
- VMYCCQKEESXWBV-UHFFFAOYSA-N N1N=CC2=C(C=CC=C12)C=1C=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=1 Chemical compound N1N=CC2=C(C=CC=C12)C=1C=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=1 VMYCCQKEESXWBV-UHFFFAOYSA-N 0.000 claims 1
- VMYCCQKEESXWBV-SFHVURJKSA-N N1N=CC2=C(C=CC=C12)C=1C=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=1 Chemical compound N1N=CC2=C(C=CC=C12)C=1C=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=1 VMYCCQKEESXWBV-SFHVURJKSA-N 0.000 claims 1
- ZXHCRZMGHWGSKM-UHFFFAOYSA-N O1CCN(CC1)CC1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound O1CCN(CC1)CC1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N ZXHCRZMGHWGSKM-UHFFFAOYSA-N 0.000 claims 1
- UIMBORCBJIEWFU-UHFFFAOYSA-N O1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound O1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N UIMBORCBJIEWFU-UHFFFAOYSA-N 0.000 claims 1
- WILBBQABUGZBOR-UHFFFAOYSA-N O1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound O1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N WILBBQABUGZBOR-UHFFFAOYSA-N 0.000 claims 1
- MMGDEKVOXDXWEK-UHFFFAOYSA-N O1CCN(CC1)S(=O)(=O)C=1C=C(C=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N Chemical compound O1CCN(CC1)S(=O)(=O)C=1C=C(C=CC=1)C1=CC=C2CC3(C(NC2=C1)=O)CN(CC3)C#N MMGDEKVOXDXWEK-UHFFFAOYSA-N 0.000 claims 1
- UUHPZBKRZQBSHZ-UHFFFAOYSA-N O1CCN(CC1)S(=O)(=O)C=1C=C(C=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N Chemical compound O1CCN(CC1)S(=O)(=O)C=1C=C(C=CC=1)C=1C=C2CC3(C(NC2=CC=1)=O)CN(CC3)C#N UUHPZBKRZQBSHZ-UHFFFAOYSA-N 0.000 claims 1
- QEPOMPAAPNDUNU-UHFFFAOYSA-N O=C1C2(CCN(C2)C#N)CCN1 Chemical compound O=C1C2(CCN(C2)C#N)CCN1 QEPOMPAAPNDUNU-UHFFFAOYSA-N 0.000 claims 1
- YNUMKYHDIYQTPH-UHFFFAOYSA-N O=C1NC2(CCN(C2)C#N)C(NC1)=O Chemical compound O=C1NC2(CCN(C2)C#N)C(NC1)=O YNUMKYHDIYQTPH-UHFFFAOYSA-N 0.000 claims 1
- UVVVHZPFZFAFJG-UHFFFAOYSA-N O=C1NC2(CCN(C2)C#N)C(NC1C1=CC=CC=C1)=O Chemical compound O=C1NC2(CCN(C2)C#N)C(NC1C1=CC=CC=C1)=O UVVVHZPFZFAFJG-UHFFFAOYSA-N 0.000 claims 1
- JAPNDZYJAAJNDF-UHFFFAOYSA-N O=C1NC2=C(COC11CN(CC1)C#N)C=CC=C2 Chemical compound O=C1NC2=C(COC11CN(CC1)C#N)C=CC=C2 JAPNDZYJAAJNDF-UHFFFAOYSA-N 0.000 claims 1
- VVVGWQJGHKIEJS-UHFFFAOYSA-N O=C1NC2=C(NC11CN(CC1)C#N)C=CC=N2 Chemical compound O=C1NC2=C(NC11CN(CC1)C#N)C=CC=N2 VVVGWQJGHKIEJS-UHFFFAOYSA-N 0.000 claims 1
- ZWXNQXPVMSIGMU-UHFFFAOYSA-N O=C1NC2=C(NC11CN(CC1)C#N)N=C(C=C2)C(F)(F)F Chemical compound O=C1NC2=C(NC11CN(CC1)C#N)N=C(C=C2)C(F)(F)F ZWXNQXPVMSIGMU-UHFFFAOYSA-N 0.000 claims 1
- TYZJHOTUKGSKAO-UHFFFAOYSA-N O=C1NC2=C(NC11CN(CC1)C#N)N=C(C=C2)C1=CC=CC=C1 Chemical compound O=C1NC2=C(NC11CN(CC1)C#N)N=C(C=C2)C1=CC=CC=C1 TYZJHOTUKGSKAO-UHFFFAOYSA-N 0.000 claims 1
- GTBXEQCNEFSZRE-UHFFFAOYSA-N O=C1NC2=C(NC11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 Chemical compound O=C1NC2=C(NC11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 GTBXEQCNEFSZRE-UHFFFAOYSA-N 0.000 claims 1
- QSVNEFGIDRZGEW-UHFFFAOYSA-N O=C1NC2=C(NC11CN(CC1)C#N)N=CC=C2 Chemical compound O=C1NC2=C(NC11CN(CC1)C#N)N=CC=C2 QSVNEFGIDRZGEW-UHFFFAOYSA-N 0.000 claims 1
- FYLPWNSSPLONCB-UHFFFAOYSA-N O=C1NC2=C(NCC11CN(CC1)C#N)N=CC=C2 Chemical compound O=C1NC2=C(NCC11CN(CC1)C#N)N=CC=C2 FYLPWNSSPLONCB-UHFFFAOYSA-N 0.000 claims 1
- GTBXEQCNEFSZRE-KRWDZBQOSA-N O=C1NC2=C(N[C@@]11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 Chemical compound O=C1NC2=C(N[C@@]11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 GTBXEQCNEFSZRE-KRWDZBQOSA-N 0.000 claims 1
- VNNWQCNZXZGJPE-UHFFFAOYSA-N O=C1NC2=C(OC11CCN(C1)C#N)N=CC=C2 Chemical compound O=C1NC2=C(OC11CCN(C1)C#N)N=CC=C2 VNNWQCNZXZGJPE-UHFFFAOYSA-N 0.000 claims 1
- KOVBFCNYAQNHLI-UHFFFAOYSA-N O=C1NC2=C(OC11CN(CC1)C#N)N=C(C=C2)C(=O)N1CCCCC1 Chemical compound O=C1NC2=C(OC11CN(CC1)C#N)N=C(C=C2)C(=O)N1CCCCC1 KOVBFCNYAQNHLI-UHFFFAOYSA-N 0.000 claims 1
- ADBCOBFTXNWWHQ-UHFFFAOYSA-N O=C1NC2=C(OC11CN(CC1)C#N)N=C(C=C2)C1=CC=CC=C1 Chemical compound O=C1NC2=C(OC11CN(CC1)C#N)N=C(C=C2)C1=CC=CC=C1 ADBCOBFTXNWWHQ-UHFFFAOYSA-N 0.000 claims 1
- MKBZOPTVVUKRGE-UHFFFAOYSA-N O=C1NC2=C(OC11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 Chemical compound O=C1NC2=C(OC11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 MKBZOPTVVUKRGE-UHFFFAOYSA-N 0.000 claims 1
- MKBZOPTVVUKRGE-KRWDZBQOSA-N O=C1NC2=C(O[C@@]11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 Chemical compound O=C1NC2=C(O[C@@]11CN(CC1)C#N)N=CC(=C2)C1=CC=CC=C1 MKBZOPTVVUKRGE-KRWDZBQOSA-N 0.000 claims 1
- VNNWQCNZXZGJPE-NSHDSACASA-N O=C1NC2=C(O[C@@]11CN(CC1)C#N)N=CC=C2 Chemical compound O=C1NC2=C(O[C@@]11CN(CC1)C#N)N=CC=C2 VNNWQCNZXZGJPE-NSHDSACASA-N 0.000 claims 1
- XLSOPVXQIKWFHM-UHFFFAOYSA-N O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)N1CCCCC1 Chemical compound O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)N1CCCCC1 XLSOPVXQIKWFHM-UHFFFAOYSA-N 0.000 claims 1
- YBJLBBAQJULGQF-UHFFFAOYSA-N O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)OC(F)(F)F Chemical compound O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)OC(F)(F)F YBJLBBAQJULGQF-UHFFFAOYSA-N 0.000 claims 1
- JGVSDCTUYFHCOD-UHFFFAOYSA-N O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C1=CC=C(C=C1)OC1=CC=CC=C1 Chemical compound O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C1=CC=C(C=C1)OC1=CC=CC=C1 JGVSDCTUYFHCOD-UHFFFAOYSA-N 0.000 claims 1
- JHIOEZVCYAPVFW-UHFFFAOYSA-N O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C=1C=NC=NC=1 Chemical compound O=C1NC2=CC(=CC=C2CC11CN(CC1)C#N)C=1C=NC=NC=1 JHIOEZVCYAPVFW-UHFFFAOYSA-N 0.000 claims 1
- HDLMPSNMBBGCFY-UHFFFAOYSA-N O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)N1CCCCC1 Chemical compound O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)N1CCCCC1 HDLMPSNMBBGCFY-UHFFFAOYSA-N 0.000 claims 1
- HBYKBRFTTORKEJ-UHFFFAOYSA-N O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)OC(F)(F)F Chemical compound O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC(=CC=C1)OC(F)(F)F HBYKBRFTTORKEJ-UHFFFAOYSA-N 0.000 claims 1
- KODIVRRACQHANN-UHFFFAOYSA-N O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC=C(C=C1)OC1=CC=CC=C1 Chemical compound O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC=C(C=C1)OC1=CC=CC=C1 KODIVRRACQHANN-UHFFFAOYSA-N 0.000 claims 1
- JJRODOFXOSSRAM-UHFFFAOYSA-N O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC=CC=C1 Chemical compound O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C1=CC=CC=C1 JJRODOFXOSSRAM-UHFFFAOYSA-N 0.000 claims 1
- IGUWCEQSRYMPRU-UHFFFAOYSA-N O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C=1C=NC=NC=1 Chemical compound O=C1NC2=CC=C(C=C2CC11CN(CC1)C#N)C=1C=NC=NC=1 IGUWCEQSRYMPRU-UHFFFAOYSA-N 0.000 claims 1
- JJRODOFXOSSRAM-IBGZPJMESA-N O=C1NC2=CC=C(C=C2C[C@@]11CN(CC1)C#N)C1=CC=CC=C1 Chemical compound O=C1NC2=CC=C(C=C2C[C@@]11CN(CC1)C#N)C1=CC=CC=C1 JJRODOFXOSSRAM-IBGZPJMESA-N 0.000 claims 1
- KZOIOGWZQUKLLJ-UHFFFAOYSA-N O=C1NC2=CC=CC=C2CC11CN(CC1)C#N Chemical compound O=C1NC2=CC=CC=C2CC11CN(CC1)C#N KZOIOGWZQUKLLJ-UHFFFAOYSA-N 0.000 claims 1
- QEPOMPAAPNDUNU-MRVPVSSYSA-N O=C1[C@@]2(CCN(C2)C#N)CCN1 Chemical compound O=C1[C@@]2(CCN(C2)C#N)CCN1 QEPOMPAAPNDUNU-MRVPVSSYSA-N 0.000 claims 1
- VOUXMXJHMPKVEG-UHFFFAOYSA-N OCCN1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound OCCN1N=CC2=C(C=CC=C12)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 VOUXMXJHMPKVEG-UHFFFAOYSA-N 0.000 claims 1
- VOUXMXJHMPKVEG-FQEVSTJZSA-N OCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound OCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 VOUXMXJHMPKVEG-FQEVSTJZSA-N 0.000 claims 1
- VOUXMXJHMPKVEG-HXUWFJFHSA-N OCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound OCCN1N=CC2=C(C=CC=C12)C1=CC2=C(O[C@]3(CN(CC3)C#N)C(N2)=O)N=C1 VOUXMXJHMPKVEG-HXUWFJFHSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 102000004316 Oxidoreductases Human genes 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000013234 Pearson syndrome Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 210000000601 blood cell Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- DTPSXFMGMQOVTG-UHFFFAOYSA-N n-[4-[3-(2-aminocyclopropyl)phenoxy]-1-(benzylamino)-1-oxobutan-2-yl]benzamide Chemical compound NC1CC1C1=CC=CC(OCCC(NC(=O)C=2C=CC=CC=2)C(=O)NCC=2C=CC=CC=2)=C1 DTPSXFMGMQOVTG-UHFFFAOYSA-N 0.000 claims 1
- 101150022123 ncl-1 gene Proteins 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- NUPLDGNLPVWCFT-UHFFFAOYSA-N pyrido[2,3-b][1,4]diazepin-4-one Chemical compound O=C1C=CN=C2C=CC=NC2=N1 NUPLDGNLPVWCFT-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 150000003573 thiols Chemical group 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021158986A JP7280928B2 (ja) | 2016-03-04 | 2021-09-29 | 脱ユビキチン化酵素（ｄｕｂ）阻害剤としてのスピロ縮合ピロリジン誘導体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1603779.8A GB201603779D0 (en) | 2016-03-04 | 2016-03-04 | Novel compounds |
| GB1603779.8 | 2016-03-04 | ||
| PCT/GB2017/050565 WO2017149313A1 (en) | 2016-03-04 | 2017-03-02 | Spiro-condensed pyrrolidine derivatives as deubiquitylating enzymes (dub) inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021158986A Division JP7280928B2 (ja) | 2016-03-04 | 2021-09-29 | 脱ユビキチン化酵素（ｄｕｂ）阻害剤としてのスピロ縮合ピロリジン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019507177A JP2019507177A (ja) | 2019-03-14 |
| JP2019507177A5 true JP2019507177A5 (https=) | 2020-02-27 |
| JP6959247B2 JP6959247B2 (ja) | 2021-11-02 |
Family
ID=55859019
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018546518A Active JP6959247B2 (ja) | 2016-03-04 | 2017-03-02 | 脱ユビキチン化酵素（ｄｕｂ）阻害剤としてのスピロ縮合ピロリジン誘導体 |
| JP2021158986A Active JP7280928B2 (ja) | 2016-03-04 | 2021-09-29 | 脱ユビキチン化酵素（ｄｕｂ）阻害剤としてのスピロ縮合ピロリジン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021158986A Active JP7280928B2 (ja) | 2016-03-04 | 2021-09-29 | 脱ユビキチン化酵素（ｄｕｂ）阻害剤としてのスピロ縮合ピロリジン誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US10654853B2 (https=) |
| EP (2) | EP4067355A1 (https=) |
| JP (2) | JP6959247B2 (https=) |
| KR (1) | KR102384139B1 (https=) |
| CN (1) | CN108602823B (https=) |
| AU (1) | AU2017225371B2 (https=) |
| BR (1) | BR112018017086B1 (https=) |
| CA (1) | CA3016370C (https=) |
| CO (1) | CO2018009275A2 (https=) |
| ES (1) | ES2919549T3 (https=) |
| GB (1) | GB201603779D0 (https=) |
| IL (1) | IL261552B (https=) |
| MA (1) | MA43701A (https=) |
| MX (1) | MX382562B (https=) |
| MY (1) | MY196836A (https=) |
| RU (1) | RU2730552C2 (https=) |
| SG (1) | SG11201807301SA (https=) |
| WO (1) | WO2017149313A1 (https=) |
| ZA (1) | ZA201803910B (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX373656B (es) | 2015-03-30 | 2020-04-02 | Mission Therapeutics Ltd | Compuestos de 1-ciano-pirrolidina como inhibidores de las enzimas desubiquitinantes, como la hidrolasa 30 de la c-terminal de la ubiquitina (usp30), y el uso de los mismos en el tratamiento de condiciones de disfunción mitocondrial y tratamiento de cancér. |
| US10669234B2 (en) | 2015-07-14 | 2020-06-02 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
| GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
| GB201522267D0 (en) | 2015-12-17 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201522768D0 (en) | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201602854D0 (en) | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
| GB201603779D0 (en) * | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| JP6959252B2 (ja) | 2016-03-24 | 2021-11-02 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
| ES2850349T3 (es) | 2016-09-27 | 2021-08-27 | Mission Therapeutics Ltd | Derivados de cianopirrolidina con actividad como inhibidores de USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| JP7208931B2 (ja) | 2017-06-20 | 2023-01-19 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての活性をもつ置換シアノピロリジン類 |
| BR112020003725A2 (pt) | 2017-10-06 | 2020-11-03 | Forma Therapeutics, Inc. | inibição da peptidase 30 específica de ubiquitina |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的ペプチダーゼ３０（ｕｓｐ３０）阻害剤として有用な縮合二環化合物 |
| JP7434285B2 (ja) | 2018-08-14 | 2024-02-20 | アムジエン・インコーポレーテツド | Ｎ－シアノ－７－アザノルボルナン誘導体及びその使用 |
| LT3860989T (lt) | 2018-10-05 | 2023-06-12 | Forma Therapeutics, Inc. | Sulieti pirolinai, kurie veikia kaip ubikvitinui specifinės proteazės 30 (ups30) inhibitoriai |
| GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
| WO2021204856A1 (en) | 2020-04-08 | 2021-10-14 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| IL298526A (en) | 2020-05-28 | 2023-01-01 | Mission Therapeutics Ltd | N-(1-cyano-pyrrolidin-3-yl)-5-(3-(trifluoromethyl)phenyl)oxazole-2-carboxamide derivatives and the corresponding oxadiazole derivatives as usp30 inhibitors for the treatment of mitochondrial dysfunction |
| BR112022019722A2 (pt) | 2020-06-04 | 2022-12-20 | Mission Therapeutics Ltd | N-cianopirrolidinas com atividade como inibidores de usp30 |
| DK4161929T3 (da) | 2020-06-08 | 2025-08-18 | Mission Therapeutics Ltd | 1-(5-(2-cyanopyridin-4-yl)oxazol-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyrrol-5(1h)-carbonitril som usp30-hæmmer til anvendelse i behandling af mitokondriedysfunktion, cancer og fibrose |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| CN116143782B (zh) * | 2021-11-22 | 2024-04-12 | 西南大学 | 一类螺[吡咯烷-2,3'-喹啉]-2'-酮类衍生物的设计合成与应用 |
| US20250034122A1 (en) | 2021-12-01 | 2025-01-30 | Mission Therapeutics Limited | Substituted n-cyanopyrrolidines with activity as usp30 inhibitors |
| MX2024007932A (es) * | 2021-12-23 | 2024-09-18 | Univ Leuven Kath | Spiros y analogos relacionados para inhibir yap/taz-tead. |
| WO2024151847A1 (en) * | 2023-01-13 | 2024-07-18 | The University Of North Carolina At Chapel Hill | Identification of otud7b inhibitor 7bi and its application in reducing growth of nsclc and leukemia cells |
| GB202408928D0 (en) | 2024-06-21 | 2024-08-07 | Mission Therapeutics Ltd | Novel compounds |
| GB202411060D0 (en) | 2024-07-29 | 2024-09-11 | Mission Therapeutics Ltd | Novel compounds |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001077073A1 (en) | 2000-04-06 | 2001-10-18 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| SG176463A1 (en) | 2005-02-22 | 2011-12-29 | Univ Michigan | Small molecule inhibitors of mdm2 and uses thereof |
| SG174107A1 (en) * | 2006-08-30 | 2011-09-29 | Univ Michigan | New small molecule inhibitors of mdm2 and the uses thereof |
| WO2008144507A2 (en) | 2007-05-16 | 2008-11-27 | President And Fellows Of Harvard College | Spirooxindole inhibitors of aurora kinase |
| PE20090606A1 (es) * | 2007-08-20 | 2009-06-17 | Glaxo Group Ltd | Nuevos inhibidores de catepsina c y uso |
| US8088815B2 (en) * | 2009-12-02 | 2012-01-03 | Hoffman-La Roche Inc. | Spiroindolinone pyrrolidines |
| GB0922589D0 (en) | 2009-12-23 | 2010-02-10 | Almac Discovery Ltd | Pharmaceutical compounds |
| AU2012226890B2 (en) | 2011-03-10 | 2016-10-06 | Daiichi Sankyo Company, Limited | Dispiropyrrolidine derivative |
| EP2752191A1 (en) | 2013-01-07 | 2014-07-09 | Sanofi | Compositions and methods using hdm2 antagonist and mek inhibitor |
| GB201416754D0 (en) * | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| MX373656B (es) | 2015-03-30 | 2020-04-02 | Mission Therapeutics Ltd | Compuestos de 1-ciano-pirrolidina como inhibidores de las enzimas desubiquitinantes, como la hidrolasa 30 de la c-terminal de la ubiquitina (usp30), y el uso de los mismos en el tratamiento de condiciones de disfunción mitocondrial y tratamiento de cancér. |
| US10669234B2 (en) * | 2015-07-14 | 2020-06-02 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
| GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
| GB201522267D0 (en) | 2015-12-17 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201522768D0 (en) | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201602854D0 (en) * | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
| GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| JP6959252B2 (ja) | 2016-03-24 | 2021-11-02 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
| ES2850349T3 (es) | 2016-09-27 | 2021-08-27 | Mission Therapeutics Ltd | Derivados de cianopirrolidina con actividad como inhibidores de USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
-
2016
- 2016-03-04 GB GBGB1603779.8A patent/GB201603779D0/en not_active Ceased
-
2017
- 2017-03-02 WO PCT/GB2017/050565 patent/WO2017149313A1/en not_active Ceased
- 2017-03-02 BR BR112018017086-0A patent/BR112018017086B1/pt active IP Right Grant
- 2017-03-02 MA MA043701A patent/MA43701A/fr unknown
- 2017-03-02 CN CN201780010388.5A patent/CN108602823B/zh active Active
- 2017-03-02 MX MX2018008271A patent/MX382562B/es unknown
- 2017-03-02 EP EP22172828.0A patent/EP4067355A1/en not_active Withdrawn
- 2017-03-02 JP JP2018546518A patent/JP6959247B2/ja active Active
- 2017-03-02 RU RU2018133279A patent/RU2730552C2/ru active
- 2017-03-02 KR KR1020187028269A patent/KR102384139B1/ko active Active
- 2017-03-02 AU AU2017225371A patent/AU2017225371B2/en active Active
- 2017-03-02 CA CA3016370A patent/CA3016370C/en active Active
- 2017-03-02 US US16/078,518 patent/US10654853B2/en active Active
- 2017-03-02 ES ES17709766T patent/ES2919549T3/es active Active
- 2017-03-02 SG SG11201807301SA patent/SG11201807301SA/en unknown
- 2017-03-02 MY MYPI2018001499A patent/MY196836A/en unknown
- 2017-03-02 EP EP17709766.4A patent/EP3423454B1/en active Active
-
2018
- 2018-06-12 ZA ZA2018/03910A patent/ZA201803910B/en unknown
- 2018-09-02 IL IL261552A patent/IL261552B/en active IP Right Grant
- 2018-09-04 CO CONC2018/0009275A patent/CO2018009275A2/es unknown
-
2020
- 2020-04-08 US US16/843,408 patent/US11236092B2/en active Active
-
2021
- 2021-09-29 JP JP2021158986A patent/JP7280928B2/ja active Active
- 2021-12-14 US US17/550,071 patent/US20220106315A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019507177A5 (https=) | ||
| TWI766261B (zh) | 蛋白質酪胺酸磷酸酶抑制劑 | |
| US11185592B2 (en) | Spirocyclic degronimers for target protein degradation | |
| ES2870203T3 (es) | Compuesto derivado tricíclico, método para prepararlo y composición farmacéutica que comprende el mismo | |
| KR101877187B1 (ko) | 치환된 다이하이드로이소퀴놀린온 화합물 | |
| JP2024514338A (ja) | 複素環式誘導体阻害剤及びその調製方法及びその用途 | |
| US9926271B2 (en) | Octahydrocyclopentapyrroles, their preparation and use | |
| Da Silva et al. | Biological activity and synthetic metodologies for the preparation of fluoroquinolones, a class of potent antibacterial agents | |
| JP2019532945A5 (https=) | ||
| US10787453B2 (en) | Octahydropyrrolopyrroles their preparation and use | |
| CN105102442B (zh) | 作为抗癌药的喹啉衍生物 | |
| EP4204418A1 (en) | Rapidly accelerating fibrosarcoma protein degrading compounds and associated methods of use | |
| JP2019509274A5 (https=) | ||
| CN111484480A (zh) | 一种多环类衍生物抑制剂、其制备方法和应用 | |
| JP2018524367A5 (https=) | ||
| PT2794600T (pt) | Derivados de 2,3-di-hidro-benzo[1,4]oxazina e compostos relacionados como inibidores de fosfoinositídeo-3-cinase (pi3k) para o tratamento de, por exemplo, artrite reumatoide | |
| CN105518001A (zh) | Bet蛋白抑制性的改性的二氢喹喔啉酮类化合物和二氢吡啶并吡嗪酮类化合物 | |
| TWI818424B (zh) | 含氮多環稠環類化合物，其藥物組合物、製備方法和用途 | |
| TWI532740B (zh) | ２－胺基－３－（咪唑－２－基）－吡啶－４－酮衍生物、其製備方法及其治療用途 | |
| CN108699065A (zh) | 作为激酶抑制剂的三环类化合物和组合物 | |
| CN104447701A (zh) | 吡唑类衍生物及其用途 | |
| WO1997017970A1 (fr) | Inhibiteurs de la neurotoxicite de l'acide kainique et derives de la pyridothiazine | |
| TWI838644B (zh) | 芳甲醯取代的三環化合物及其製法和用途 | |
| CN117460731A (zh) | 杂环内酰胺类化合物，其制法与医药上的用途 | |
| US20230257371A1 (en) | Cyclic cyanoenone derivatives as modulators of keap1 |