EA009860B1 - Пиперазинил- и диазапанилбензамиды и бензтиоамиды - Google Patents

Info

Publication number

EA009860B1

EA009860B1 EA200500528A EA200500528A EA009860B1 EA 009860 B1 EA009860 B1 EA 009860B1 EA 200500528 A EA200500528 A EA 200500528A EA 200500528 A EA200500528 A EA 200500528A EA 009860 B1 EA009860 B1 EA 009860B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methanone

phenyl

isopropylpiperazin

ylmethylphenyl

dihydrochloride

Prior art date

2002-10-23

Links

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• Global Dossier
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• 125000004193 piperazinyl group Chemical group 0.000 title claims abstract description 10
• QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical class NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 title abstract description 4
• 229940054066 benzamide antipsychotics Drugs 0.000 title abstract description 4
• 150000003936 benzamides Chemical class 0.000 title abstract description 4
• 238000000034 method Methods 0.000 claims abstract description 51
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 49
• 229960001340 histamine Drugs 0.000 claims abstract description 25
• 239000000203 mixture Substances 0.000 claims abstract description 25
• 230000001404 mediated effect Effects 0.000 claims abstract description 8
• -1 cyano, hydroxy Chemical group 0.000 claims description 247
• 150000001875 compounds Chemical class 0.000 claims description 167
• 125000000623 heterocyclic group Chemical group 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 26
• 208000035475 disorder Diseases 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 20
• 102000005962 receptors Human genes 0.000 claims description 18
• 108020003175 receptors Proteins 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 150000001408 amides Chemical class 0.000 claims description 16
• 229940079593 drug Drugs 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000002883 imidazolyl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 230000015572 biosynthetic process Effects 0.000 claims description 13
• 150000002148 esters Chemical class 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 208000020925 Bipolar disease Diseases 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 206010020751 Hypersensitivity Diseases 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 8
• 208000010877 cognitive disease Diseases 0.000 claims description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• 102000000543 Histamine Receptors Human genes 0.000 claims description 7
• 108010002059 Histamine Receptors Proteins 0.000 claims description 7
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 7
• 208000030961 allergic reaction Diseases 0.000 claims description 7
• 210000002345 respiratory system Anatomy 0.000 claims description 7
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
• 201000010105 allergic rhinitis Diseases 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 238000003786 synthesis reaction Methods 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 206010012289 Dementia Diseases 0.000 claims description 5
• 241001465754 Metazoa Species 0.000 claims description 5
• 208000003251 Pruritus Diseases 0.000 claims description 5
• 230000009471 action Effects 0.000 claims description 5
• 239000005557 antagonist Substances 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 230000027455 binding Effects 0.000 claims description 5
• 150000003857 carboxamides Chemical group 0.000 claims description 5
• 238000002648 combination therapy Methods 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 208000013403 hyperactivity Diseases 0.000 claims description 5
• 206010022437 insomnia Diseases 0.000 claims description 5
• 239000003446 ligand Substances 0.000 claims description 5
• 201000003631 narcolepsy Diseases 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000028698 Cognitive impairment Diseases 0.000 claims description 4
• 208000019695 Migraine disease Diseases 0.000 claims description 4
• 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 4
• 230000008901 benefit Effects 0.000 claims description 4
• 230000006735 deficit Effects 0.000 claims description 4
• 206010015037 epilepsy Diseases 0.000 claims description 4
• 239000000938 histamine H1 antagonist Substances 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 230000005764 inhibitory process Effects 0.000 claims description 4
• 230000007803 itching Effects 0.000 claims description 4
• 201000003152 motion sickness Diseases 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 102000004384 Histamine H3 receptors Human genes 0.000 claims description 3
• 108090000981 Histamine H3 receptors Proteins 0.000 claims description 3
• 206010028748 Nasal obstruction Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 230000037007 arousal Effects 0.000 claims description 3
• 208000028683 bipolar I disease Diseases 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 238000011161 development Methods 0.000 claims description 3
• 208000002173 dizziness Diseases 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 206010027599 migraine Diseases 0.000 claims description 3
• 210000003928 nasal cavity Anatomy 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 208000024891 symptom Diseases 0.000 claims description 3
• 208000027559 Appetite disease Diseases 0.000 claims description 2
• 208000012902 Nervous system disease Diseases 0.000 claims description 2
• 208000025966 Neurological disease Diseases 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 230000027288 circadian rhythm Effects 0.000 claims description 2
• 238000002474 experimental method Methods 0.000 claims description 2
• 239000012528 membrane Substances 0.000 claims description 2
• 230000008569 process Effects 0.000 claims description 2
• 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 2
• 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 2
• 201000009032 substance abuse Diseases 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 239000000047 product Substances 0.000 claims 74
• 235000002639 sodium chloride Nutrition 0.000 claims 22
• 102100030817 Liver carboxylesterase 1 Human genes 0.000 claims 19
• 101710169844 Sesquipedalian-1 Proteins 0.000 claims 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 17
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 14
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 14
• 210000004027 cell Anatomy 0.000 claims 14
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 14
• 125000003386 piperidinyl group Chemical group 0.000 claims 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
• 125000006239 protecting group Chemical group 0.000 claims 13
• GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
• AQNQFXMDJLAVOU-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 AQNQFXMDJLAVOU-UHFFFAOYSA-N 0.000 claims 11
• DSNALXIKDKGHLJ-UHFFFAOYSA-N [4-(piperidin-1-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 DSNALXIKDKGHLJ-UHFFFAOYSA-N 0.000 claims 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
• 150000004657 carbamic acid derivatives Chemical class 0.000 claims 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 11
• YDVOHRKXZGOHEG-UHFFFAOYSA-N [4-(azepan-1-ylmethyl)phenyl]-(4-butan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCCC1 YDVOHRKXZGOHEG-UHFFFAOYSA-N 0.000 claims 10
• YLVOZJYPBJFSFJ-UHFFFAOYSA-N [4-(morpholin-4-ylmethyl)phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 YLVOZJYPBJFSFJ-UHFFFAOYSA-N 0.000 claims 10
• 125000002757 morpholinyl group Chemical group 0.000 claims 10
• FXUFLERGGYYBSJ-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-(morpholin-4-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 FXUFLERGGYYBSJ-UHFFFAOYSA-N 0.000 claims 9
• ZXUDWXNHQQHHOG-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCC1 ZXUDWXNHQQHHOG-UHFFFAOYSA-N 0.000 claims 9
• CVRHIQNRTHGXBL-UHFFFAOYSA-N (4-cyclohexylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone Chemical compound C=1C=C(CN2CCCCC2)C=CC=1C(=O)N(CC1)CCN1C1CCCCC1 CVRHIQNRTHGXBL-UHFFFAOYSA-N 0.000 claims 9
• WOBNBEKMLTZEQM-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCC1 WOBNBEKMLTZEQM-UHFFFAOYSA-N 0.000 claims 9
• GFVFMRCJTPWIGF-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CC(C(F)(F)F)CCC1 GFVFMRCJTPWIGF-UHFFFAOYSA-N 0.000 claims 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
• LMEVWMCUUXVYRX-UHFFFAOYSA-N [4-(azepan-1-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCCC1 LMEVWMCUUXVYRX-UHFFFAOYSA-N 0.000 claims 9
• JTBLLBRXTOEAIZ-UHFFFAOYSA-N [4-(morpholin-4-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 JTBLLBRXTOEAIZ-UHFFFAOYSA-N 0.000 claims 9
• BBXGPXOLUQTZAV-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-[(dimethylamino)methyl]phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 BBXGPXOLUQTZAV-UHFFFAOYSA-N 0.000 claims 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 8
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 8
• 239000002253 acid Substances 0.000 claims 8
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 8
• 125000004432 carbon atom Chemical group C* 0.000 claims 8
• 125000004076 pyridyl group Chemical group 0.000 claims 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims 8
• 150000003254 radicals Chemical class 0.000 claims 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims 8
• 125000001425 triazolyl group Chemical group 0.000 claims 8
• NTTSVWFRPRPGSL-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[4-(morpholin-4-ylmethyl)phenyl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 NTTSVWFRPRPGSL-UHFFFAOYSA-N 0.000 claims 7
• BRKXEPOVUAANEO-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-(thiomorpholin-4-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCSCC1 BRKXEPOVUAANEO-UHFFFAOYSA-N 0.000 claims 7
• OMZLNVHEKAYHQZ-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[(pyridin-2-ylamino)methyl]phenyl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=CC=N1 OMZLNVHEKAYHQZ-UHFFFAOYSA-N 0.000 claims 7
• OBVVMIGIVHXHAY-UHFFFAOYSA-N [4-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-ylmethyl)phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CC2CCCCC2CC1 OBVVMIGIVHXHAY-UHFFFAOYSA-N 0.000 claims 7
• UBXYHWUPXXOZHQ-UHFFFAOYSA-N [4-(diethylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1=CC(CN(CC)CC)=CC=C1C(=O)N1CCN(C(C)C)CC1 UBXYHWUPXXOZHQ-UHFFFAOYSA-N 0.000 claims 7
• JZEBFUFSOGWXOE-UHFFFAOYSA-N [4-[(1-methoxypropan-2-ylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CNC(C)COC)=CC=C1C(=O)N1CCN(C(C)C)CC1 JZEBFUFSOGWXOE-UHFFFAOYSA-N 0.000 claims 7
• HEMGCELGHZBNNP-UHFFFAOYSA-N [4-[(2-methoxyethylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CNCCOC)=CC=C1C(=O)N1CCN(C(C)C)CC1 HEMGCELGHZBNNP-UHFFFAOYSA-N 0.000 claims 7
• UWGFUAMLLPGZJU-UHFFFAOYSA-N [4-[(benzylamino)methyl]phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CNCC1=CC=CC=C1 UWGFUAMLLPGZJU-UHFFFAOYSA-N 0.000 claims 7
• QLIWADBXAORKRS-UHFFFAOYSA-N [4-[(benzylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNCC1=CC=CC=C1 QLIWADBXAORKRS-UHFFFAOYSA-N 0.000 claims 7
• POJSCBVLEPVECE-UHFFFAOYSA-N [4-[(dimethylamino)methyl]phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(CC)CC)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 POJSCBVLEPVECE-UHFFFAOYSA-N 0.000 claims 7
• KWTTXWTWWPKHOC-UHFFFAOYSA-N [4-[[2-methoxyethyl(propyl)amino]methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CN(CCOC)CCC)=CC=C1C(=O)N1CCN(C(C)C)CC1 KWTTXWTWWPKHOC-UHFFFAOYSA-N 0.000 claims 7
• QSNGIHWLYIXPHW-UHFFFAOYSA-N [4-[[ethyl(2-methoxyethyl)amino]methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CN(CCOC)CC)=CC=C1C(=O)N1CCN(C(C)C)CC1 QSNGIHWLYIXPHW-UHFFFAOYSA-N 0.000 claims 7
• 125000004122 cyclic group Chemical group 0.000 claims 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
• GTYXNHAYBSHWLL-UHFFFAOYSA-N [4-[(dimethylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 GTYXNHAYBSHWLL-UHFFFAOYSA-N 0.000 claims 6
• 150000001299 aldehydes Chemical class 0.000 claims 6
• 238000003776 cleavage reaction Methods 0.000 claims 6
• 239000002552 dosage form Substances 0.000 claims 6
• 239000011541 reaction mixture Substances 0.000 claims 6
• 230000007017 scission Effects 0.000 claims 6
• 239000007787 solid Substances 0.000 claims 6
• 239000000243 solution Substances 0.000 claims 6
• 239000003826 tablet Substances 0.000 claims 6
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 claims 6
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims 6
• YFTOGXGALVURKM-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CC(C(F)(F)F)CCC1 YFTOGXGALVURKM-UHFFFAOYSA-N 0.000 claims 5
• DYRDMOISOZFIHC-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[4-[(dimethylamino)methyl]phenyl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 DYRDMOISOZFIHC-UHFFFAOYSA-N 0.000 claims 5
• OZEFFBHWWRSIQI-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(morpholin-4-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 OZEFFBHWWRSIQI-UHFFFAOYSA-N 0.000 claims 5
• NIXYZZVUBZQMAO-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 NIXYZZVUBZQMAO-UHFFFAOYSA-N 0.000 claims 5
• CZSFUWHJOGCOQT-UHFFFAOYSA-N (4-pentan-3-ylpiperazin-1-yl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCC1 CZSFUWHJOGCOQT-UHFFFAOYSA-N 0.000 claims 5
• DNCYBIWEMYYNKN-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methanone Chemical compound C1CN(C(C)C)CCN1CC1=CC=C(C(=O)N2CCN(CC2)C(C)C)C=C1 DNCYBIWEMYYNKN-UHFFFAOYSA-N 0.000 claims 5
• VGRYSYGIGQYWPW-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[[5-(trifluoromethyl)pyridin-2-yl]amino]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=C(C(F)(F)F)C=N1 VGRYSYGIGQYWPW-UHFFFAOYSA-N 0.000 claims 5
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