KR20180110132A - 무스카린성 아세틸콜린 수용체 m1의 양성 알로스테릭 조절제 - Google Patents
무스카린성 아세틸콜린 수용체 m1의 양성 알로스테릭 조절제 Download PDFInfo
- Publication number
- KR20180110132A KR20180110132A KR1020187026643A KR20187026643A KR20180110132A KR 20180110132 A KR20180110132 A KR 20180110132A KR 1020187026643 A KR1020187026643 A KR 1020187026643A KR 20187026643 A KR20187026643 A KR 20187026643A KR 20180110132 A KR20180110132 A KR 20180110132A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- carboxamide
- pyridine
- thieno
- pyrazol
- 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.)
- Withdrawn
Links
- 230000003281 allosteric effect Effects 0.000 title abstract description 20
- 102000018154 Muscarinic acetylcholine receptor M1 Human genes 0.000 title 1
- 108050007299 Muscarinic acetylcholine receptor M1 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 242
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims abstract description 157
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims abstract description 157
- 238000000034 method Methods 0.000 claims abstract description 77
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 552
- -1 1-methyl-pyrazol-4-yl Chemical group 0.000 claims description 537
- 229910052739 hydrogen Inorganic materials 0.000 claims description 243
- 239000001257 hydrogen Substances 0.000 claims description 242
- 125000000217 alkyl group Chemical group 0.000 claims description 202
- 125000001072 heteroaryl group Chemical group 0.000 claims description 200
- 125000000623 heterocyclic group Chemical group 0.000 claims description 188
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 167
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 161
- DSARAHGYZHXMQZ-UHFFFAOYSA-N thieno[3,2-b]pyridine-5-carboxamide Chemical compound NC(=O)C1=CC=C2SC=CC2=N1 DSARAHGYZHXMQZ-UHFFFAOYSA-N 0.000 claims description 159
- 125000003118 aryl group Chemical group 0.000 claims description 155
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 131
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 102
- 125000003545 alkoxy group Chemical group 0.000 claims description 93
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 150000002367 halogens Chemical class 0.000 claims description 85
- 125000001188 haloalkyl group Chemical group 0.000 claims description 84
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 78
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 70
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 208000035475 disorder Diseases 0.000 claims description 47
- MRQVGIPVJXWABP-UHFFFAOYSA-N N1C(C(=O)N)=CC=C2N=CC=C21 Chemical compound N1C(C(=O)N)=CC=C2N=CC=C21 MRQVGIPVJXWABP-UHFFFAOYSA-N 0.000 claims description 46
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 39
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 29
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims description 28
- 201000000980 schizophrenia Diseases 0.000 claims description 26
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- XWEMRIPNLSTWIU-UHFFFAOYSA-N N1C(C(=O)N)=CC=C2N=NC=C21 Chemical compound N1C(C(=O)N)=CC=C2N=NC=C21 XWEMRIPNLSTWIU-UHFFFAOYSA-N 0.000 claims description 22
- 208000028017 Psychotic disease Diseases 0.000 claims description 22
- 229940079593 drug Drugs 0.000 claims description 22
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- 125000001544 thienyl group Chemical group 0.000 claims description 19
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- 125000004429 atom Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- CUGUZHHUEHTIIK-UHFFFAOYSA-N thieno[3,2-b]pyridine-5-carbaldehyde Chemical compound O=CC1=CC=C2SC=CC2=N1 CUGUZHHUEHTIIK-UHFFFAOYSA-N 0.000 claims description 16
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 15
- 208000002193 Pain Diseases 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
- 208000010877 cognitive disease Diseases 0.000 claims description 13
- LLPLGMQOBARRLK-UHFFFAOYSA-N ethyl thieno[3,2-b]pyridine-5-carboxylate Chemical compound CCOC(=O)c1ccc2sccc2n1 LLPLGMQOBARRLK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 11
- 206010012289 Dementia Diseases 0.000 claims description 10
- TZICEEXQXMJPEC-UHFFFAOYSA-N ethyl thieno[3,2-b]pyridine-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OCC)=CC2=N1 TZICEEXQXMJPEC-UHFFFAOYSA-N 0.000 claims description 10
- 238000007429 general method Methods 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 208000004454 Hyperalgesia Diseases 0.000 claims description 8
- 208000019022 Mood disease Diseases 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 7
- 229960002428 fentanyl Drugs 0.000 claims description 7
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 6
- 208000027520 Somatoform disease Diseases 0.000 claims description 6
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 6
- 239000010977 jade Substances 0.000 claims description 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 6
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- 230000003542 behavioural effect Effects 0.000 claims description 5
- CWBYTSQAVGCXFW-UHFFFAOYSA-N thieno[3,2-b]pyridine-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=CC2=N1 CWBYTSQAVGCXFW-UHFFFAOYSA-N 0.000 claims description 5
- 208000020706 Autistic disease Diseases 0.000 claims description 4
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- 206010053552 allodynia Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 208000024714 major depressive disease Diseases 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims description 4
- 208000006820 Arthralgia Diseases 0.000 claims description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- 206010003805 Autism Diseases 0.000 claims description 3
- 206010006002 Bone pain Diseases 0.000 claims description 3
- 206010058019 Cancer Pain Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 206010019233 Headaches Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
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- 231100000869 headache Toxicity 0.000 claims description 3
- 208000004371 toothache Diseases 0.000 claims description 3
- MTMYABMPAAPRBV-UHFFFAOYSA-N 1-methyl-7-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=NC(=CC(=C21)CC1=CC=C(C=C1)C1=NN(C=C1)C)C(=O)NC1CC2(COC2)C1 MTMYABMPAAPRBV-UHFFFAOYSA-N 0.000 claims description 2
- DIOGQVZLZFMKSY-UHFFFAOYSA-N 1-methyl-7-[[6-(1-methylpyrazol-3-yl)pyridin-3-yl]methyl]-N-(oxan-4-yl)pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=NC(=CC(=C21)CC=1C=NC(=CC=1)C1=NN(C=C1)C)C(=O)NC1CCOCC1 DIOGQVZLZFMKSY-UHFFFAOYSA-N 0.000 claims description 2
- PPXAMGLSBKCGNR-UHFFFAOYSA-N 1-methyl-N-(oxan-4-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=NC(=CC(=C21)CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CCOCC1 PPXAMGLSBKCGNR-UHFFFAOYSA-N 0.000 claims description 2
- DOFBCUVYMARYHU-UHFFFAOYSA-N 1-methyl-N-(oxetan-2-ylmethyl)-7-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[4,3-b]pyridine-5-carboxamide Chemical compound CN1N=CC2=NC(=CC(=C21)CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NCC1OCC1 DOFBCUVYMARYHU-UHFFFAOYSA-N 0.000 claims description 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 2
- ANANTWMZDKOVED-UHFFFAOYSA-N 2-methyl-N-(oxan-4-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CC2=NC(=CC(=C2S1)CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CCOCC1 ANANTWMZDKOVED-UHFFFAOYSA-N 0.000 claims description 2
- ZKRJFLGSAYBHEQ-UHFFFAOYSA-N 3-methyl-7-[(6-methylpyridin-3-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC=1C=NC(=CC=1)C)C(=O)NC1CCOCC1 ZKRJFLGSAYBHEQ-UHFFFAOYSA-N 0.000 claims description 2
- OPGYNLZVQZZBGQ-UHFFFAOYSA-N 3-methyl-7-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(2-oxaspiro[3.3]heptan-6-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)C1=NN(C=C1)C)C(=O)NC1CC2(COC2)C1 OPGYNLZVQZZBGQ-UHFFFAOYSA-N 0.000 claims description 2
- ZZXDNTZMFZPPIG-UHFFFAOYSA-N 3-methyl-N-(oxan-4-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CCOCC1 ZZXDNTZMFZPPIG-UHFFFAOYSA-N 0.000 claims description 2
- XRSRCSXADBOHMA-UHFFFAOYSA-N 3-methyl-N-(oxetan-2-ylmethyl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NCC1OCC1 XRSRCSXADBOHMA-UHFFFAOYSA-N 0.000 claims description 2
- YMDUHFWIMMAOQH-UHFFFAOYSA-N 3-methyl-N-(oxetan-3-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1COC1 YMDUHFWIMMAOQH-UHFFFAOYSA-N 0.000 claims description 2
- ADEKJVNFIQUGRR-UHFFFAOYSA-N 4h-pyridin-3-one Chemical compound O=C1CC=CN=C1 ADEKJVNFIQUGRR-UHFFFAOYSA-N 0.000 claims description 2
- VFWXBDIAFDIYOI-UHFFFAOYSA-N 7-(6-methylpyridin-3-yl)oxy-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CC=C(C=N1)OC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 VFWXBDIAFDIYOI-UHFFFAOYSA-N 0.000 claims description 2
- QAUPZZCGMAQJHC-UHFFFAOYSA-N 7-[(2-methyl-1,3-thiazol-5-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC=1SC(=CN=1)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 QAUPZZCGMAQJHC-UHFFFAOYSA-N 0.000 claims description 2
- JLVMAJPIMCABSS-UHFFFAOYSA-N 7-[(2-methylpyrimidin-5-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=NC=C(C=N1)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 JLVMAJPIMCABSS-UHFFFAOYSA-N 0.000 claims description 2
- WQYKQQSIHUURPZ-UHFFFAOYSA-N 7-[(6-methylpyridin-3-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CC=C(C=N1)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 WQYKQQSIHUURPZ-UHFFFAOYSA-N 0.000 claims description 2
- AUYIWKJWXUGEEP-UHFFFAOYSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)NC2CCOCC2)C=CS3)C=CC(=C1)C=1C=NN(C=1)C AUYIWKJWXUGEEP-UHFFFAOYSA-N 0.000 claims description 2
- JXFVGYPQMOFXHS-RXVVDRJESA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycycloheptyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCCC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C JXFVGYPQMOFXHS-RXVVDRJESA-N 0.000 claims description 2
- GWCHKGFZEWYELB-PXNSSMCTSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C GWCHKGFZEWYELB-PXNSSMCTSA-N 0.000 claims description 2
- LRJODMPWAHMKAD-LPHOPBHVSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclopentyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C LRJODMPWAHMKAD-LPHOPBHVSA-N 0.000 claims description 2
- CTPRLUZDNKPGGJ-AVRDEDQJSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-methoxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCC2)OC)C=CS3)C=CC(=C1)C=1C=NN(C=1)C CTPRLUZDNKPGGJ-AVRDEDQJSA-N 0.000 claims description 2
- RHKDYFYFZCKMNN-KPMSDPLLSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(2R)-2-hydroxycyclobutyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)NC2[C@@H](CC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C RHKDYFYFZCKMNN-KPMSDPLLSA-N 0.000 claims description 2
- MGVWLFWVJROTFO-DENIHFKCSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1R,2R)-2-hydroxycyclobutyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@H]2[C@@H](CC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C MGVWLFWVJROTFO-DENIHFKCSA-N 0.000 claims description 2
- AYCMUDSXHDFAKP-DHLKQENFSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycycloheptyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCCC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C AYCMUDSXHDFAKP-DHLKQENFSA-N 0.000 claims description 2
- AKFJNWKCQBHMLB-URXFXBBRSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C AKFJNWKCQBHMLB-URXFXBBRSA-N 0.000 claims description 2
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- QZYHLNIINMOPSX-URXFXBBRSA-N 7-[[2-fluoro-4-(1-methylpyrazol-4-yl)phenyl]methyl]-N-[(1S,2S)-2-hydroxycycloheptyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)C=1C=NN(C=1)C)CC1=C2C(=NC(=C1)C(=O)N[C@@H]1[C@H](CCCCC1)O)C=CS2 QZYHLNIINMOPSX-URXFXBBRSA-N 0.000 claims description 2
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Classifications
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- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
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| US62/402,438 | 2016-09-30 | ||
| PCT/US2017/018140 WO2017143041A1 (en) | 2016-02-16 | 2017-02-16 | Positive allosteric modulators of the muscarinic acetylcholine receptor m1 |
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| KR20180110132A true KR20180110132A (ko) | 2018-10-08 |
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| ES2824495T3 (es) * | 2016-09-02 | 2021-05-12 | Suven Life Sciences Ltd | Moduladores alostéricos positivos del receptor muscarínico M1 |
| EA035599B1 (ru) * | 2017-04-13 | 2020-07-14 | Сувен Лайф Сайенсиз Лимитед | Позитивные аллостерические модуляторы мускариновых m1-рецепторов |
| JP7123042B2 (ja) * | 2017-06-20 | 2022-08-22 | 武田薬品工業株式会社 | 複素環化合物 |
| HRP20231236T1 (hr) | 2017-06-20 | 2024-02-16 | Takeda Pharmaceutical Company Limited | Heterociklički spoj i njegova uporaba kao pozitivnog alosteričnog modulatora kolinergičkog muskarinskog m1 receptora |
| CA3079617A1 (en) | 2017-10-20 | 2019-04-25 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| MA50464A (fr) | 2017-10-27 | 2021-06-02 | Suven Life Sciences Ltd | Amides polycycliques utilisés en tant que modulateurs allostériques positifs du récepteur muscarinique m1 |
| WO2019089676A1 (en) | 2017-10-31 | 2019-05-09 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| IL276411B2 (en) | 2018-02-02 | 2024-04-01 | Univ Vanderbilt | M4 muscarinic acetylcholine receptor antagonists |
| US11851406B2 (en) * | 2018-06-13 | 2023-12-26 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M1 |
| WO2020067456A1 (ja) | 2018-09-28 | 2020-04-02 | 武田薬品工業株式会社 | 複素環化合物 |
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| WO2020086864A1 (en) | 2018-10-24 | 2020-04-30 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m1 |
| EP3643711A1 (en) * | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
| US12319701B2 (en) | 2019-10-04 | 2025-06-03 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
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| US4608079A (en) | 1983-08-02 | 1986-08-26 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| DE4129603A1 (de) * | 1991-09-06 | 1993-03-11 | Thomae Gmbh Dr K | Kondensierte 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US6239142B1 (en) | 1999-03-09 | 2001-05-29 | Pharmacia & Upjohn Company | 4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5carboxamides as antiviral agents |
| NZ521978A (en) * | 2000-04-28 | 2004-10-29 | Acadia Pharm Inc | Compounds that affect cholinergic receptors and are particularly muscarinic agonists |
| US6911543B2 (en) | 2001-10-02 | 2005-06-28 | Pfizer Inc. | Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease |
| EP2512243B1 (en) | 2009-12-17 | 2016-04-06 | Merck Sharp & Dohme Corp. | Quinoline amide m1 receptor positive allosteric modulators |
| US8815902B2 (en) | 2010-06-15 | 2014-08-26 | Merck Sharp & Dohme Corp. | Tetrahydroquinoline amide M1 receptor positive allosteric modulators |
| US8940765B2 (en) * | 2011-05-17 | 2015-01-27 | Merck Sharp & Dohme Corp. | N-linked quinolineamide M1 receptor positive allosteric modulators |
| US20160200733A1 (en) | 2013-08-23 | 2016-07-14 | Vanderbilt University | Substituted thieno[2,3-b]pyridine-2-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| TW201512197A (zh) | 2013-08-30 | 2015-04-01 | Hoffmann La Roche | 吡咯并吡啶或吡唑并吡啶衍生物 |
| GB201317363D0 (en) | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| MX2016008536A (es) | 2014-01-22 | 2016-09-26 | Hoffmann La Roche | Derivados de fluoro-naftilo. |
| JP6571077B2 (ja) | 2014-06-13 | 2019-09-04 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| WO2016009297A1 (en) | 2014-07-18 | 2016-01-21 | Pfizer Inc. | Pyridine derivatives as muscarinic m1 receptor positive allosteric modulators |
| WO2016029454A1 (en) | 2014-08-29 | 2016-03-03 | Merck Sharp & Dohme Corp. | TETRAHYDRONAPHTHYRIDINE DERIVATIVES AS mGluR2-NEGATIVE ALLOSTERIC MODULATORS, COMPOSITIONS, AND THEIR USE |
| ES2824495T3 (es) | 2016-09-02 | 2021-05-12 | Suven Life Sciences Ltd | Moduladores alostéricos positivos del receptor muscarínico M1 |
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| IL261058A (en) | 2018-10-31 |
| MX2018009952A (es) | 2018-11-29 |
| CN109069491A (zh) | 2018-12-21 |
| EP3416639B1 (en) | 2022-06-08 |
| WO2017143041A1 (en) | 2017-08-24 |
| US11111251B2 (en) | 2021-09-07 |
| MA44253A (fr) | 2018-12-26 |
| BR112018016689A2 (pt) | 2019-02-12 |
| EP3416639A4 (en) | 2019-07-03 |
| AU2017221404A1 (en) | 2018-08-23 |
| CA3014791A1 (en) | 2017-08-24 |
| CL2018002335A1 (es) | 2019-02-01 |
| EP3416639A1 (en) | 2018-12-26 |
| EA201891854A1 (ru) | 2019-01-31 |
| JP2019504901A (ja) | 2019-02-21 |
| US20210230180A1 (en) | 2021-07-29 |
| PH12018501731A1 (en) | 2019-06-17 |
| MX385975B (es) | 2025-03-18 |
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