JP7428647B2 - バソプレシンＶ１ａ受容体拮抗薬としてのトリアゾロベンズアゼピン - Google Patents

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Publication number

JP7428647B2

JP7428647B2 JP2020532928A JP2020532928A JP7428647B2 JP 7428647 B2 JP7428647 B2 JP 7428647B2 JP 2020532928 A JP2020532928 A JP 2020532928A JP 2020532928 A JP2020532928 A JP 2020532928A JP 7428647 B2 JP7428647 B2 JP 7428647B2

Authority

JP

Japan

Prior art keywords

triazolo

chloro

trans

dihydro

cyclohexyl

Prior art date

2017-12-15

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.)

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• 229940044551 receptor antagonist Drugs 0.000 title description 8
• 239000002464 receptor antagonist Substances 0.000 title description 8
• 102000004136 Vasopressin Receptors Human genes 0.000 title description 7
• 108090000643 Vasopressin Receptors Proteins 0.000 title description 7
• QDEVEJYEXBFIJD-UHFFFAOYSA-N triazolo[4,5-i][1]benzazepine Chemical compound C1=CC2=CC=CC=NC2=C2C1=NN=N2 QDEVEJYEXBFIJD-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 403
• 229910052739 hydrogen Inorganic materials 0.000 claims description 183
• 239000001257 hydrogen Substances 0.000 claims description 183
• 238000000034 method Methods 0.000 claims description 155
• -1 tert-Butyl[1-(1,4'-bipiperidin-1'-yl)-8-chloro-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1] benzazepin-5-yl] carbamate Chemical compound 0.000 claims description 147
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 118
• 150000002431 hydrogen Chemical class 0.000 claims description 111
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 239000000203 mixture Substances 0.000 claims description 97
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 75
• 125000000623 heterocyclic group Chemical group 0.000 claims description 74
• DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 68
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims description 35
• 208000035475 disorder Diseases 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
• 239000003814 drug Substances 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 32
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 108010004977 Vasopressins Proteins 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 229940079593 drug Drugs 0.000 claims description 28
• 229960003726 vasopressin Drugs 0.000 claims description 28
• GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims description 27
• 102000002852 Vasopressins Human genes 0.000 claims description 27
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 25
• 208000029560 autism spectrum disease Diseases 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 239000012453 solvate Substances 0.000 claims description 24
• 230000016571 aggressive behavior Effects 0.000 claims description 22
• 208000019901 Anxiety disease Diseases 0.000 claims description 19
• 230000036506 anxiety Effects 0.000 claims description 19
• 150000004677 hydrates Chemical class 0.000 claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 125000003107 substituted aryl group Chemical group 0.000 claims description 17
• IJKOXDNWLFKIGJ-UHFFFAOYSA-N 1h-1-benzazepin-5-amine Chemical compound NC1=CC=CNC2=CC=CC=C12 IJKOXDNWLFKIGJ-UHFFFAOYSA-N 0.000 claims description 16
• 239000013543 active substance Substances 0.000 claims description 16
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 15
• WAYZQLIRXHPOCN-UHFFFAOYSA-N 5,6-dihydro-4h-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound C1CCC2=NN=CN2C2=CC=CC=C21 WAYZQLIRXHPOCN-UHFFFAOYSA-N 0.000 claims description 14
• 230000003542 behavioural effect Effects 0.000 claims description 13
• 208000010877 cognitive disease Diseases 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 230000001575 pathological effect Effects 0.000 claims description 12
• 208000024891 symptom Diseases 0.000 claims description 12
• 208000011580 syndromic disease Diseases 0.000 claims description 12
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 239000000460 chlorine Chemical group 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 11
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
• 206010001488 Aggression Diseases 0.000 claims description 10
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 10
• 210000003169 central nervous system Anatomy 0.000 claims description 10
• 230000002093 peripheral effect Effects 0.000 claims description 10
• 208000012761 aggressive behavior Diseases 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 230000028327 secretion Effects 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
• 201000010374 Down Syndrome Diseases 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 230000008485 antagonism Effects 0.000 claims description 8
• 239000001961 anticonvulsive agent Substances 0.000 claims description 8
• 230000036772 blood pressure Effects 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 239000011737 fluorine Chemical group 0.000 claims description 8
• 208000013403 hyperactivity Diseases 0.000 claims description 8
• 206010022998 Irritability Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 230000007774 longterm Effects 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 210000005002 female reproductive tract Anatomy 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 239000002220 antihypertensive agent Substances 0.000 claims description 5
• 229940127088 antihypertensive drug Drugs 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• DJAFDCOYZMFSOL-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC(N2)=S)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC(N2)=S)OC)C=1 DJAFDCOYZMFSOL-UHFFFAOYSA-N 0.000 claims description 4
• QQCDWCOXUBUYDI-HTICZQJRSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 QQCDWCOXUBUYDI-HTICZQJRSA-N 0.000 claims description 4
• UMBUQXQLBUDEPT-UHFFFAOYSA-N ClC=1C=CC2=C(CC3(OCCO3)CC(N2)=O)C=1 Chemical compound ClC=1C=CC2=C(CC3(OCCO3)CC(N2)=O)C=1 UMBUQXQLBUDEPT-UHFFFAOYSA-N 0.000 claims description 4
• QQCDWCOXUBUYDI-WBAXXEDZSA-N ClC=1C=CC2=C(C[C@@H](CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 Chemical compound ClC=1C=CC2=C(C[C@@H](CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 QQCDWCOXUBUYDI-WBAXXEDZSA-N 0.000 claims description 4
• QQCDWCOXUBUYDI-ZTFGCOKTSA-N ClC=1C=CC2=C(C[C@H](CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 Chemical compound ClC=1C=CC2=C(C[C@H](CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 QQCDWCOXUBUYDI-ZTFGCOKTSA-N 0.000 claims description 4
• 229940125681 anticonvulsant agent Drugs 0.000 claims description 4
• 230000006806 disease prevention Effects 0.000 claims description 4
• 229940001470 psychoactive drug Drugs 0.000 claims description 4
• 239000004089 psychotropic agent Substances 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• VJNXFBGJUZSILI-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]oxy-7-chloro-1,3,4,5-tetrahydro-1-benzazepin-2-one Chemical compound [Si](C)(C)(C(C)(C)C)OC1CC(NC2=C(C1)C=C(C=C2)Cl)=O VJNXFBGJUZSILI-UHFFFAOYSA-N 0.000 claims description 3
• HMARJCDNPAINMZ-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]oxy-7-chloro-1,3,4,5-tetrahydro-1-benzazepine-2-thione Chemical compound [Si](C)(C)(C(C)(C)C)OC1CC(NC2=C(C1)C=C(C=C2)Cl)=S HMARJCDNPAINMZ-UHFFFAOYSA-N 0.000 claims description 3
• ZNRPDDBXHZYOJD-UHFFFAOYSA-N BrC=1C=CC2=C(CC3(OCCO3)CC(N2)=O)C=1 Chemical compound BrC=1C=CC2=C(CC3(OCCO3)CC(N2)=O)C=1 ZNRPDDBXHZYOJD-UHFFFAOYSA-N 0.000 claims description 3
• WLFNHMWINPOHPP-WQUIYQLNSA-N C(C)(C)(C)OC(NC1CC=2N(C3=C(C1)C=C(C=C3)C(F)(F)F)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2)=O Chemical compound C(C)(C)(C)OC(NC1CC=2N(C3=C(C1)C=C(C=C3)C(F)(F)F)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2)=O WLFNHMWINPOHPP-WQUIYQLNSA-N 0.000 claims description 3
• DHYXYWFGIXCEBM-UHFFFAOYSA-N CSC1=Nc2ccc(Cl)cc2CC(C1)NC(=O)OC(C)(C)C Chemical compound CSC1=Nc2ccc(Cl)cc2CC(C1)NC(=O)OC(C)(C)C DHYXYWFGIXCEBM-UHFFFAOYSA-N 0.000 claims description 3
• OVQBNSTZHOMVGU-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC(N2)=O)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC(N2)=O)OC)C=1 OVQBNSTZHOMVGU-UHFFFAOYSA-N 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 210000000056 organ Anatomy 0.000 claims description 3
• TTXSMEQCMXDAID-UHFFFAOYSA-N tert-butyl N-(7-bromo-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-4-yl)carbamate Chemical compound C(C)(C)(C)OC(NC1CC(NC2=C(C1)C=C(C=C2)Br)=O)=O TTXSMEQCMXDAID-UHFFFAOYSA-N 0.000 claims description 3
• ZYASSRYHQHYBBJ-UHFFFAOYSA-N tert-butyl N-(7-bromo-2-sulfanylidene-1,3,4,5-tetrahydro-1-benzazepin-4-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CC2=C(NC(=S)C1)C=CC(Br)=C2 ZYASSRYHQHYBBJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• UDWXJDDCPSNETR-NYRJJRHWSA-N 8-chloro-5-methoxy-1-[(3R)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@H]3CN(CC3)CC3=NC=CC=C3)OC)C1 UDWXJDDCPSNETR-NYRJJRHWSA-N 0.000 claims description 2
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• UDWXJDDCPSNETR-UHFFFAOYSA-N 8-chloro-5-methoxy-1-[1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CN(CC3)CC3=NC=CC=C3)OC)C1 UDWXJDDCPSNETR-UHFFFAOYSA-N 0.000 claims description 2
• FOCZDJFENGYPGL-DBTMUERSSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(=O)N3CCCCC3)O)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(=O)N3CCCCC3)O)C1 FOCZDJFENGYPGL-DBTMUERSSA-N 0.000 claims description 2
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• ZLOQMNNGNPKUTE-NSISKUIASA-N C(C)(=O)N[C@H]1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 Chemical compound C(C)(=O)N[C@H]1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 ZLOQMNNGNPKUTE-NSISKUIASA-N 0.000 claims description 2
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• GGQPIICXXDCPPQ-UHFFFAOYSA-N tert-butyl N-(7-chloro-2-sulfanylidene-1,3,4,5-tetrahydro-1-benzazepin-4-yl)carbamate Chemical compound C(C)(C)(C)OC(NC1CC(NC2=C(C1)C=C(C=C2)Cl)=S)=O GGQPIICXXDCPPQ-UHFFFAOYSA-N 0.000 claims description 2
• SLGBWCXMNHBTQJ-UHFFFAOYSA-N tert-butyl N-[8-chloro-1-(1-pyridin-2-ylpiperidin-4-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)C2CCN(CC2)C2=NC=CC=C2)=O SLGBWCXMNHBTQJ-UHFFFAOYSA-N 0.000 claims description 2
• BKANAFXTPKJRDD-UHFFFAOYSA-N tert-butyl N-[8-chloro-1-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)N2CCN(CC2)C2=NC=CC=C2Cl)=O BKANAFXTPKJRDD-UHFFFAOYSA-N 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• JSEYAPGSGXYHIJ-UHFFFAOYSA-N 1'-(8-chloro-5-methoxy-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-1-yl)spiro[1H-2-benzofuran-3,4'-piperidine] Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)OC)C1 JSEYAPGSGXYHIJ-UHFFFAOYSA-N 0.000 claims 1
• KIFRZXVXNQREGA-UHFFFAOYSA-N 8'-chloro-1'-(1-pyrimidin-2-ylazetidin-3-yl)spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CN(C4)C4=NC=CC=N4)OCCO3)C1 KIFRZXVXNQREGA-UHFFFAOYSA-N 0.000 claims 1
• WCUZKFFWOPTWGC-UHFFFAOYSA-N 8'-chloro-1'-(4-piperidin-1-ylpiperidin-1-yl)spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound N1(CCCCC1)C1CCN(CC1)C1=NN=C2N1C1=C(CC3(C2)OCCO3)C=C(C=C1)Cl WCUZKFFWOPTWGC-UHFFFAOYSA-N 0.000 claims 1
• HRFBIIIFVXUOAQ-UHFFFAOYSA-N 8'-chloro-1'-(4-pyridin-2-yloxypiperidin-1-yl)spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)N4CCC(CC4)OC4=NC=CC=C4)OCCO3)C1 HRFBIIIFVXUOAQ-UHFFFAOYSA-N 0.000 claims 1
• BEMGGBQAFLIMHD-MRXNPFEDSA-N 8'-chloro-1'-[(3R)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@H]4CN(CC4)CC4=NC=CC=C4)OCCO3)C1 BEMGGBQAFLIMHD-MRXNPFEDSA-N 0.000 claims 1
• HHUJZNAZACMNKH-QGZVFWFLSA-N 8'-chloro-1'-[(3R)-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@H]4CN(CC4)CC=4C=NC=CC4)OCCO3)C1 HHUJZNAZACMNKH-QGZVFWFLSA-N 0.000 claims 1
• BEMGGBQAFLIMHD-INIZCTEOSA-N 8'-chloro-1'-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CN(CC4)CC4=NC=CC=C4)OCCO3)C1 BEMGGBQAFLIMHD-INIZCTEOSA-N 0.000 claims 1
• HHUJZNAZACMNKH-KRWDZBQOSA-N 8'-chloro-1'-[(3S)-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CN(CC4)CC=4C=NC=CC4)OCCO3)C1 HHUJZNAZACMNKH-KRWDZBQOSA-N 0.000 claims 1
• BEMGGBQAFLIMHD-UHFFFAOYSA-N 8'-chloro-1'-[1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CN(CC4)CC4=NC=CC=C4)OCCO3)C1 BEMGGBQAFLIMHD-UHFFFAOYSA-N 0.000 claims 1
• HHUJZNAZACMNKH-UHFFFAOYSA-N 8'-chloro-1'-[1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CN(CC4)CC=4C=NC=CC4)OCCO3)C1 HHUJZNAZACMNKH-UHFFFAOYSA-N 0.000 claims 1
• ZSQKKXPLKFWEOD-GOSISDBHSA-N 8'-chloro-1'-[1-[(3R)-oxolan-3-yl]piperidin-4-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CCN(CC4)[C@H]4COCC4)OCCO3)C1 ZSQKKXPLKFWEOD-GOSISDBHSA-N 0.000 claims 1
• OYPUURFAOBBZMP-UHFFFAOYSA-N 8'-chloro-1'-[4-(3-chloropyridin-2-yl)piperazin-1-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)N4CCN(CC4)C4=NC=CC=C4Cl)OCCO3)C1 OYPUURFAOBBZMP-UHFFFAOYSA-N 0.000 claims 1
• MQXLYIKREIXAEQ-UHFFFAOYSA-N 8'-chloro-1'-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylspiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)N4CCC2(CC4)OCC4=C2C=CC=C4)OCCO3)C1 MQXLYIKREIXAEQ-UHFFFAOYSA-N 0.000 claims 1
• MJAZJWNDROEKLZ-UHFFFAOYSA-N 8-chloro-1-(3,3-difluorocyclobutyl)-N-propan-2-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CC(C3)(F)F)NC(C)C)C1 MJAZJWNDROEKLZ-UHFFFAOYSA-N 0.000 claims 1
• PMWABJQCQUQUHR-UHFFFAOYSA-N 8-chloro-1-(4,4-difluorocyclohexyl)-N-propan-2-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CCC(CC3)(F)F)NC(C)C)C1 PMWABJQCQUQUHR-UHFFFAOYSA-N 0.000 claims 1
• BNQBQRFMXOGMSI-UHFFFAOYSA-N 8-chloro-1-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-yl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepin-5-one Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)=O)C1 BNQBQRFMXOGMSI-UHFFFAOYSA-N 0.000 claims 1
• GRVPIDSKKZPVAA-UHFFFAOYSA-N 8-chloro-1-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-ol Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)O)C1 GRVPIDSKKZPVAA-UHFFFAOYSA-N 0.000 claims 1
• WIRPYLVADCJHBL-QNSVNVJESA-N 8-chloro-5-methoxy-1-[1-[(3R)-oxolan-3-yl]piperidin-4-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CCN(CC3)[C@H]3COCC3)OC)C1 WIRPYLVADCJHBL-QNSVNVJESA-N 0.000 claims 1
• QVRBVDNHXKKVJZ-UHFFFAOYSA-N 8-chloro-N-propan-2-yl-1-(1-pyridin-2-ylpiperidin-4-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CCN(CC3)C3=NC=CC=C3)NC(C)C)C1 QVRBVDNHXKKVJZ-UHFFFAOYSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
• OBVBLDJLCMXBQA-WKILWMFISA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(=O)N3CCCCC3)=O)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(=O)N3CCCCC3)=O)C1 OBVBLDJLCMXBQA-WKILWMFISA-N 0.000 claims 1
• DIVLJYQGCNIMNE-UMSPYCQHSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)=O)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)=O)C1 DIVLJYQGCNIMNE-UMSPYCQHSA-N 0.000 claims 1
• ZFSHSSDVSJMTOL-LWOYVPTGSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)N)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)N)C1 ZFSHSSDVSJMTOL-LWOYVPTGSA-N 0.000 claims 1
• UWHLUYKSBBMFHF-HYUCUAJZSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)NC(C)C)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)NC(C)C)C1 UWHLUYKSBBMFHF-HYUCUAJZSA-N 0.000 claims 1
• KUXZNNBJYQOKDZ-LWOYVPTGSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)O)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)O)C1 KUXZNNBJYQOKDZ-LWOYVPTGSA-N 0.000 claims 1
• UGMZYQMKFNVTDY-PPUGGXLSSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)=O)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)=O)C1 UGMZYQMKFNVTDY-PPUGGXLSSA-N 0.000 claims 1
• XBEBZNYESOZRCX-HTICZQJRSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 XBEBZNYESOZRCX-HTICZQJRSA-N 0.000 claims 1
• KOSDJOMPHPTUCN-WQUIYQLNSA-N BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)NC(C)C)C1 Chemical compound BrC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)NC(C)C)C1 KOSDJOMPHPTUCN-WQUIYQLNSA-N 0.000 claims 1
• VXHOMFSMKRQHAJ-MQMHXKEQSA-N BrC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CC[C@H](CC4)C(F)(F)F)OCCO3)C1 Chemical compound BrC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CC[C@H](CC4)C(F)(F)F)OCCO3)C1 VXHOMFSMKRQHAJ-MQMHXKEQSA-N 0.000 claims 1
• JFCWKHWJTILAHF-RUCARUNLSA-N BrC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CC[C@H](CC4)OC4=NC=CC=C4)OCCO3)C1 Chemical compound BrC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CC[C@H](CC4)OC4=NC=CC=C4)OCCO3)C1 JFCWKHWJTILAHF-RUCARUNLSA-N 0.000 claims 1
• GVRGESABYKHKKV-QHARRCRTSA-N C(C)(=O)OC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 Chemical compound C(C)(=O)OC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 GVRGESABYKHKKV-QHARRCRTSA-N 0.000 claims 1
• MDQWUBHUEBYQMU-NGZATLCBSA-N C1(CC1)COC1CC=2N(C3=C(C1)C=C(C=C3)C(F)(F)F)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 Chemical compound C1(CC1)COC1CC=2N(C3=C(C1)C=C(C=C3)C(F)(F)F)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 MDQWUBHUEBYQMU-NGZATLCBSA-N 0.000 claims 1
• LABSAXNUXJEWLA-NGZATLCBSA-N C1(CC1)COC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 Chemical compound C1(CC1)COC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 LABSAXNUXJEWLA-NGZATLCBSA-N 0.000 claims 1
• ZHZHBBGIGQRSGS-KKLGJNPISA-N CC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 Chemical compound CC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 ZHZHBBGIGQRSGS-KKLGJNPISA-N 0.000 claims 1
• ZZSCZFHGIMBWEO-CTTUZFCVSA-N CC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)NC(C)C)C1 Chemical compound CC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)NC(C)C)C1 ZZSCZFHGIMBWEO-CTTUZFCVSA-N 0.000 claims 1
• KEDUSLZYNWUVKL-MYPZOXIJSA-N CN(CC(=O)OC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN=2)[C@@H]1CC[C@H](CC1)OC1=NC=CC=C1)C Chemical compound CN(CC(=O)OC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN=2)[C@@H]1CC[C@H](CC1)OC1=NC=CC=C1)C KEDUSLZYNWUVKL-MYPZOXIJSA-N 0.000 claims 1
• HHQNFEZHCJDCMD-UHFFFAOYSA-N COC1(C)CCC(CC1)c1nnc2CC(Cc3cc(Cl)ccc3-n12)NC(C)C Chemical compound COC1(C)CCC(CC1)c1nnc2CC(Cc3cc(Cl)ccc3-n12)NC(C)C HHQNFEZHCJDCMD-UHFFFAOYSA-N 0.000 claims 1
• XQPQPFJAKYSONQ-DUWYVTJWSA-N COC1CC=2N(C3=C(C1)C=C(C=C3)C(F)(F)F)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 Chemical compound COC1CC=2N(C3=C(C1)C=C(C=C3)C(F)(F)F)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 XQPQPFJAKYSONQ-DUWYVTJWSA-N 0.000 claims 1
• ILLBGVTVRMGAKN-NTPOMRHGSA-N COC1CC=2N(C3=C(C1)C=CC=C3)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 Chemical compound COC1CC=2N(C3=C(C1)C=CC=C3)C(=NN2)[C@@H]2CC[C@H](CC2)OC2=NC=CC=C2 ILLBGVTVRMGAKN-NTPOMRHGSA-N 0.000 claims 1
• CUJXTRXYZUGRGH-UHFFFAOYSA-N COC1Cc2nnc(C3CCN(CC3)C3CCOCC3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(C3CCN(CC3)C3CCOCC3)n2-c2ccc(Cl)cc2C1 CUJXTRXYZUGRGH-UHFFFAOYSA-N 0.000 claims 1
• WIRPYLVADCJHBL-ZENAZSQFSA-N COC1Cc2nnc(C3CCN(CC3)[C@H]3CCOC3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(C3CCN(CC3)[C@H]3CCOC3)n2-c2ccc(Cl)cc2C1 WIRPYLVADCJHBL-ZENAZSQFSA-N 0.000 claims 1
• UYSQEAPPBIMHCL-UHFFFAOYSA-N COC1Cc2nnc(N3CCN(CC3)c3ccccn3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(N3CCN(CC3)c3ccccn3)n2-c2ccc(Cl)cc2C1 UYSQEAPPBIMHCL-UHFFFAOYSA-N 0.000 claims 1
• UDWXJDDCPSNETR-FUKCDUGKSA-N COC1Cc2nnc([C@H]3CCN(Cc4ccccn4)C3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc([C@H]3CCN(Cc4ccccn4)C3)n2-c2ccc(Cl)cc2C1 UDWXJDDCPSNETR-FUKCDUGKSA-N 0.000 claims 1
• GYARJNRKOJFJCW-UCFFOFKASA-N COC1Cc2nnc([C@H]3CCN(Cc4cccnc4)C3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc([C@H]3CCN(Cc4cccnc4)C3)n2-c2ccc(Cl)cc2C1 GYARJNRKOJFJCW-UCFFOFKASA-N 0.000 claims 1
• OVUNSNSDJHVNQZ-UVXAETBJSA-N COC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)NC(C)C)C1 Chemical compound COC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)NC(C)C)C1 OVUNSNSDJHVNQZ-UVXAETBJSA-N 0.000 claims 1
• MUXMESUXGXTQQX-MXEVPWJHSA-N Cl.COC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 Chemical compound Cl.COC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)OC3=NC=CC=C3)N)C1 MUXMESUXGXTQQX-MXEVPWJHSA-N 0.000 claims 1
• DXHOUADQSKQZTI-KVNJHPKUSA-N Cl.N1=C(C=CC=C1)O[C@@H]1CC[C@H](CC1)C1=NN=C2N1C1=C(CC(C2)N)C=C(C=C1)C(F)(F)F Chemical compound Cl.N1=C(C=CC=C1)O[C@@H]1CC[C@H](CC1)C1=NN=C2N1C1=C(CC(C2)N)C=C(C=C1)C(F)(F)F DXHOUADQSKQZTI-KVNJHPKUSA-N 0.000 claims 1
• ZXTVORRSLJVURS-UMSPYCQHSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)=O)C1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)=O)C1 ZXTVORRSLJVURS-UMSPYCQHSA-N 0.000 claims 1
• RBCCZHJOYCCOQG-LWOYVPTGSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)N)C1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)N)C1 RBCCZHJOYCCOQG-LWOYVPTGSA-N 0.000 claims 1
• DWMPCSFXTHUDNL-HYUCUAJZSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)NC(C)C)C1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@@H]3CC[C@H](CC3)C(F)(F)F)NC(C)C)C1 DWMPCSFXTHUDNL-HYUCUAJZSA-N 0.000 claims 1
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• ZPWUGEWZHYCHEK-UHFFFAOYSA-N methyl 2-[2-[(2-amino-5-chlorophenyl)methyl]-1,3-dioxolan-2-yl]acetate Chemical compound COC(CC1(OCCO1)CC1=C(C=CC(=C1)Cl)N)=O ZPWUGEWZHYCHEK-UHFFFAOYSA-N 0.000 description 2
• PLBOBPORZSFFHB-UHFFFAOYSA-N methyl 2-[2-[(2-amino-5-fluorophenyl)methyl]-1,3-dioxolan-2-yl]acetate Chemical compound COC(=O)CC1(OCCO1)CC2=C(C=CC(=C2)F)N PLBOBPORZSFFHB-UHFFFAOYSA-N 0.000 description 2
• NQVJEZKKZQMFHY-UHFFFAOYSA-N methyl 2-[2-[(5-bromo-2-nitrophenyl)methyl]-1,3-dioxolan-2-yl]acetate Chemical compound COC(CC1(OCCO1)CC1=C(C=CC(=C1)Br)[N+](=O)[O-])=O NQVJEZKKZQMFHY-UHFFFAOYSA-N 0.000 description 2
• KPWOUZTWNUSROD-UHFFFAOYSA-N methyl 2-[2-[(5-chloro-2-nitrophenyl)methyl]-1,3-dioxan-2-yl]acetate Chemical compound ClC=1C=CC(=C(CC2(OCCCO2)CC(=O)OC)C=1)[N+](=O)[O-] KPWOUZTWNUSROD-UHFFFAOYSA-N 0.000 description 2
• VXPFHGLZFGPPGC-UHFFFAOYSA-N methyl 2-[2-[(5-chloro-2-nitrophenyl)methyl]-1,3-dioxepan-2-yl]acetate Chemical compound COC(=O)CC1(OCCCCO1)CC2=C(C=CC(=C2)Cl)[N+](=O)[O-] VXPFHGLZFGPPGC-UHFFFAOYSA-N 0.000 description 2
• DUXMIMSPTUCABT-UHFFFAOYSA-N methyl 2-[2-[(5-chloro-2-nitrophenyl)methyl]-1,3-dioxolan-2-yl]acetate Chemical compound COC(=O)CC1(CC2=C(C=CC(Cl)=C2)[N+]([O-])=O)OCCO1 DUXMIMSPTUCABT-UHFFFAOYSA-N 0.000 description 2
• OOHMHBGAXJJSAN-UHFFFAOYSA-N methyl 3-[tert-butyl(dimethyl)silyl]oxy-4-(5-chloro-2-nitrophenyl)butanoate Chemical compound CC(C)(C)[Si](C)(C)OC(CC1=C(C=CC(=C1)Cl)[N+](=O)[O-])CC(=O)OC OOHMHBGAXJJSAN-UHFFFAOYSA-N 0.000 description 2
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