JP4416198B2 - アニリド誘導体、その製造法および用途 - Google Patents

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Publication number

JP4416198B2

JP4416198B2 JP36078098A JP36078098A JP4416198B2 JP 4416198 B2 JP4416198 B2 JP 4416198B2 JP 36078098 A JP36078098 A JP 36078098A JP 36078098 A JP36078098 A JP 36078098A JP 4416198 B2 JP4416198 B2 JP 4416198B2

Authority

JP

Japan

Prior art keywords

group

optionally substituted

compound

added

atom

Prior art date

1997-12-19

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.)

Expired - Fee Related

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• 238000004519 manufacturing process Methods 0.000 title description 75
• 150000003931 anilides Chemical class 0.000 title description 5
• 239000000203 mixture Substances 0.000 claims description 179
• 150000001875 compounds Chemical class 0.000 claims description 143
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 110
• 125000001424 substituent group Chemical group 0.000 claims description 102
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 62
• 125000003277 amino group Chemical group 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 53
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 44
• 125000004432 carbon atom Chemical group C* 0.000 claims description 42
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 35
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 33
• 229910052717 sulfur Inorganic materials 0.000 claims description 32
• 150000001450 anions Chemical class 0.000 claims description 31
• 125000004434 sulfur atom Chemical group 0.000 claims description 30
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 24
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
• 125000004437 phosphorous atom Chemical group 0.000 claims description 23
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 20
• 229910052698 phosphorus Inorganic materials 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000004429 atom Chemical group 0.000 claims description 17
• 125000004122 cyclic group Chemical group 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
• 125000001453 quaternary ammonium group Chemical group 0.000 claims description 17
• 102000004497 CCR2 Receptors Human genes 0.000 claims description 16
• 108010017312 CCR2 Receptors Proteins 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 150000002430 hydrocarbons Chemical group 0.000 claims description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical class C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 12
• 229930192474 thiophene Chemical class 0.000 claims description 12
• 150000004714 phosphonium salts Chemical class 0.000 claims description 10
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical class C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical class C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 9
• 238000006722 reduction reaction Methods 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 208000009525 Myocarditis Diseases 0.000 claims description 7
• 239000000470 constituent Substances 0.000 claims description 7
• 208000010125 myocardial infarction Diseases 0.000 claims description 7
• 238000006482 condensation reaction Methods 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 239000002464 receptor antagonist Substances 0.000 claims description 5
• 229940044551 receptor antagonist Drugs 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Chemical class C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
• KIMSFLVXAKXGOD-UHFFFAOYSA-N 3-(4-methylphenyl)-8,9-dihydro-7h-benzo[7]annulene-6-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(CCCC(=C2)C(O)=O)C2=C1 KIMSFLVXAKXGOD-UHFFFAOYSA-N 0.000 claims description 3
• AFVSNJKADUDUSL-UHFFFAOYSA-N 7-(4-ethoxyphenyl)-n-[4-[[methyl(oxan-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoxepine-4-carboxamide Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(OCCC(=C2)C(=O)NC=3C=CC(CN(C)C4CCOCC4)=CC=3)C2=C1 AFVSNJKADUDUSL-UHFFFAOYSA-N 0.000 claims description 3
• 230000008485 antagonism Effects 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• SIVMATYKQPCGGC-UHFFFAOYSA-N n-[4-[[methyl(oxan-4-yl)amino]methyl]phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide Chemical compound C1COCCC1N(C)CC(C=C1)=CC=C1NC(=O)C(CCOC1=CC=2)=CC1=CC=2C1=CC=C(C)C=C1 SIVMATYKQPCGGC-UHFFFAOYSA-N 0.000 claims description 3
• SJZNSLXNGDTPRV-UHFFFAOYSA-N n-[4-[[methyl(oxan-4-yl)amino]methyl]phenyl]-7-(4-morpholin-4-ylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide Chemical compound C1COCCC1N(C)CC(C=C1)=CC=C1NC(=O)C(CCOC1=CC=2)=CC1=CC=2C(C=C1)=CC=C1N1CCOCC1 SJZNSLXNGDTPRV-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 3
• YCLWOGPIRAHCJA-UHFFFAOYSA-O 7-(4-methylphenyl)-n-[4-[(1-methylpiperidin-1-ium-1-yl)methyl]phenyl]-2,3-dihydro-1-benzoxepine-4-carboxamide Chemical class C1=CC(C)=CC=C1C1=CC=C(OCCC(=C2)C(=O)NC=3C=CC(C[N+]4(C)CCCCC4)=CC=3)C2=C1 YCLWOGPIRAHCJA-UHFFFAOYSA-O 0.000 claims description 2
• BSMLTNRLIDFWEA-UHFFFAOYSA-O 7-(4-methylphenyl)-n-[4-[(1-methylpiperidin-1-ium-1-yl)methyl]phenyl]-3,4-dihydronaphthalene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=C(CCC(=C2)C(=O)NC=3C=CC(C[N+]4(C)CCCCC4)=CC=3)C2=C1 BSMLTNRLIDFWEA-UHFFFAOYSA-O 0.000 claims description 2
• 238000010511 deprotection reaction Methods 0.000 claims description 2
• 230000003647 oxidation Effects 0.000 claims description 2
• 238000007254 oxidation reaction Methods 0.000 claims description 2
• 238000005956 quaternization reaction Methods 0.000 claims description 2
• 150000001555 benzenes Chemical class 0.000 claims 2
• PODLDCSLTYPEOD-UHFFFAOYSA-O 3-(4-methylphenyl)-n-[4-[(1-methylpiperidin-1-ium-1-yl)methyl]phenyl]-8,9-dihydro-7h-benzo[7]annulene-6-carboxamide Chemical class C1=CC(C)=CC=C1C1=CC=C(CCCC(=C2)C(=O)NC=3C=CC(C[N+]4(C)CCCCC4)=CC=3)C2=C1 PODLDCSLTYPEOD-UHFFFAOYSA-O 0.000 claims 1
• RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical class CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 claims 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
• 150000002240 furans Chemical class 0.000 claims 1
• 229910052760 oxygen Inorganic materials 0.000 claims 1
• 239000001301 oxygen Substances 0.000 claims 1
• 125000006413 ring segment Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 504
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 303
• -1 cyclohexanediene Chemical class 0.000 description 213
• 239000002904 solvent Substances 0.000 description 184
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 174
• 235000019439 ethyl acetate Nutrition 0.000 description 168
• 230000002829 reductive effect Effects 0.000 description 168
• 238000005160 1H NMR spectroscopy Methods 0.000 description 140
• 239000013078 crystal Substances 0.000 description 134
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 129
• 239000012044 organic layer Substances 0.000 description 107
• 238000000921 elemental analysis Methods 0.000 description 101
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 98
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 92
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 88
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
• 229910001868 water Inorganic materials 0.000 description 88
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 79
• 239000011541 reaction mixture Substances 0.000 description 75
• 239000000243 solution Substances 0.000 description 69
• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
• 238000006243 chemical reaction Methods 0.000 description 58
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
• 235000002639 sodium chloride Nutrition 0.000 description 47
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 238000000034 method Methods 0.000 description 45
• 238000004440 column chromatography Methods 0.000 description 44
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 44
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 41
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 39
• 238000010992 reflux Methods 0.000 description 36
• APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 35
• 229910052736 halogen Inorganic materials 0.000 description 32
• 150000002367 halogens Chemical class 0.000 description 32
• 239000000460 chlorine Substances 0.000 description 31
• 238000001914 filtration Methods 0.000 description 31
• 125000000217 alkyl group Chemical group 0.000 description 30
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 27
• 229910052801 chlorine Inorganic materials 0.000 description 27
• WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 27
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 26
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 26
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 26
• 229910052794 bromium Inorganic materials 0.000 description 26
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 26
• 238000002360 preparation method Methods 0.000 description 26
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 26
• UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 25
• 229910000027 potassium carbonate Inorganic materials 0.000 description 25
• 238000003756 stirring Methods 0.000 description 25
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 description 24
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 24
• 239000011737 fluorine Substances 0.000 description 24
• 229910052731 fluorine Inorganic materials 0.000 description 24
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 20
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
• 125000003396 thiol group Chemical group [H]S* 0.000 description 20
• 125000003342 alkenyl group Chemical group 0.000 description 19
• 125000000753 cycloalkyl group Chemical group 0.000 description 19
• KDPZXWBYKYRKMR-UHFFFAOYSA-N n-[4-(chloromethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=C(CCC(=C2)C(=O)NC=3C=CC(CCl)=CC=3)C2=C1 KDPZXWBYKYRKMR-UHFFFAOYSA-N 0.000 description 19
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 16
• 239000012300 argon atmosphere Substances 0.000 description 16
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 16
• 229910052739 hydrogen Inorganic materials 0.000 description 16
• 239000001257 hydrogen Substances 0.000 description 16
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
• 239000012298 atmosphere Substances 0.000 description 15
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
• 125000000547 substituted alkyl group Chemical group 0.000 description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
• 125000003710 aryl alkyl group Chemical group 0.000 description 14
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• 125000003107 substituted aryl group Chemical group 0.000 description 14
• DRYFDUUAYSVNSN-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCCCC1 DRYFDUUAYSVNSN-UHFFFAOYSA-N 0.000 description 13
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 13
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 13
• BLMOJJMSHQLJAR-UHFFFAOYSA-N n-[4-(chloromethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide Chemical compound C1=CC(CCl)=CC=C1NC(=O)C1=CC2=CC(C=3C=CC=CC=3)=CC=C2CC1 BLMOJJMSHQLJAR-UHFFFAOYSA-N 0.000 description 13
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 13
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
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