CA2656083A1

CA2656083A1 - Substituted aminomethyl benzamide compounds

Substituted aminomethyl benzamide compounds Download PDF

Info

Publication number: CA2656083A1
Authority: CA; Canada
Prior art keywords: 4alkyl; phenyl; methanone; diazepan; cyclopropyl
Prior art date: 2006-06-29
Legal status : Abandoned

Application number

CA002656083A

Other languages

English (en)

French (fr)

Inventor

Brett Allison

Nicholas I. Carruthers

Michael P. Curtis

John M. Keith

Michael A. Letavic

Emily M. Stocking

Current Assignee

Janssen Pharmaceutica NV

Original Assignee

Individual

Priority date

2006-06-29

Filing date

2007-06-21

Publication date

2008-01-03

2007-06-21 Application filed by Individual filed Critical Individual

2008-01-03 Publication of CA2656083A1 publication Critical patent/CA2656083A1/en

Status Abandoned legal-status Critical Current

Links

OMDXVUUWBNVTTO-UHFFFAOYSA-N n-(aminomethyl)benzamide Chemical class NCNC(=O)C1=CC=CC=C1 OMDXVUUWBNVTTO-UHFFFAOYSA-N 0.000 title abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims abstract description 28
108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims abstract description 28
102000004384 Histamine H3 receptors Human genes 0.000 claims abstract description 26
108090000981 Histamine H3 receptors Proteins 0.000 claims abstract description 26
201000010099 disease Diseases 0.000 claims abstract description 26
238000011282 treatment Methods 0.000 claims abstract description 22
230000001404 mediated effect Effects 0.000 claims abstract description 10
-1 2-hydroxy-2-methylpropyl Chemical group 0.000 claims description 179
150000001875 compounds Chemical class 0.000 claims description 115
201000006417 multiple sclerosis Diseases 0.000 claims description 62
208000035475 disorder Diseases 0.000 claims description 39
238000000034 method Methods 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 31
229940002612 prodrug Drugs 0.000 claims description 30
239000000651 prodrug Substances 0.000 claims description 30
125000005843 halogen group Chemical group 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
230000000694 effects Effects 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
239000002207 metabolite Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000002950 monocyclic group Chemical group 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
208000010877 cognitive disease Diseases 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 9
206010041349 Somnolence Diseases 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
206010016256 fatigue Diseases 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
230000013016 learning Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
208000019116 sleep disease Diseases 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
208000026139 Memory disease Diseases 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
230000006735 deficit Effects 0.000 claims description 6
239000003112 inhibitor Substances 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 5
206010024264 Lethargy Diseases 0.000 claims description 5
208000012886 Vertigo Diseases 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
206010027175 memory impairment Diseases 0.000 claims description 5
125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 5
208000020016 psychiatric disease Diseases 0.000 claims description 5
229940044551 receptor antagonist Drugs 0.000 claims description 5
239000002464 receptor antagonist Substances 0.000 claims description 5
231100000889 vertigo Toxicity 0.000 claims description 5
YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
208000000044 Amnesia Diseases 0.000 claims description 4
208000020925 Bipolar disease Diseases 0.000 claims description 4
208000001573 Cataplexy Diseases 0.000 claims description 4
206010012289 Dementia Diseases 0.000 claims description 4
208000030814 Eating disease Diseases 0.000 claims description 4
208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
235000014632 disordered eating Nutrition 0.000 claims description 4
230000006984 memory degeneration Effects 0.000 claims description 4
208000023060 memory loss Diseases 0.000 claims description 4
229960001165 modafinil Drugs 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
201000003631 narcolepsy Diseases 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 3
208000028698 Cognitive impairment Diseases 0.000 claims description 3
208000001456 Jet Lag Syndrome Diseases 0.000 claims description 3
208000020358 Learning disease Diseases 0.000 claims description 3
208000032140 Sleepiness Diseases 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 3
201000003723 learning disability Diseases 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 3
239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 3
201000009032 substance abuse Diseases 0.000 claims description 3
231100000736 substance abuse Toxicity 0.000 claims description 3
208000011117 substance-related disease Diseases 0.000 claims description 3
GNTOQRRKRNHLBL-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CCC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GNTOQRRKRNHLBL-UHFFFAOYSA-N 0.000 claims description 2
AJJXEACVSPXKMS-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(3,4-dichlorophenoxy)-4-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC=C(C(=O)N2CCN(CCC2)C2CC2)C=C1OC1=CC=C(Cl)C(Cl)=C1 AJJXEACVSPXKMS-UHFFFAOYSA-N 0.000 claims description 2
HASNZFFRDSPBMJ-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(SC)C(C)=C1 HASNZFFRDSPBMJ-UHFFFAOYSA-N 0.000 claims description 2
IRQHEXHOAZGQDN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-(6-methylpyridin-3-yl)oxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(C)N=C1 IRQHEXHOAZGQDN-UHFFFAOYSA-N 0.000 claims description 2
WRACQGSYQITGPK-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[2-(trifluoromethoxy)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1OC(F)(F)F WRACQGSYQITGPK-UHFFFAOYSA-N 0.000 claims description 2
BPYJWNTUBNVSJN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[2-(trifluoromethyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1C(F)(F)F BPYJWNTUBNVSJN-UHFFFAOYSA-N 0.000 claims description 2
DMKNBJGZUPGVEW-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 DMKNBJGZUPGVEW-UHFFFAOYSA-N 0.000 claims description 2
JTTOIYGKVCKBNW-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethyl)pyridin-2-yl]sulfanylphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1SC1=CC(C(F)(F)F)=CC=N1 JTTOIYGKVCKBNW-UHFFFAOYSA-N 0.000 claims description 2
PUCXAAZLYORUSG-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(SC(F)(F)F)C=C1 PUCXAAZLYORUSG-UHFFFAOYSA-N 0.000 claims description 2
ZRHGDWMRFCDZHY-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-phenoxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1 ZRHGDWMRFCDZHY-UHFFFAOYSA-N 0.000 claims description 2
NTCDZWFHVBSFMK-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-pyridin-2-yloxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=N1 NTCDZWFHVBSFMK-UHFFFAOYSA-N 0.000 claims description 2
MJSYNNLNHBQPKS-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-pyridin-2-ylsulfanylphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1SC1=CC=CC=N1 MJSYNNLNHBQPKS-UHFFFAOYSA-N 0.000 claims description 2
SZLNZRZZYLIKDT-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-pyridin-3-yloxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CN=C1 SZLNZRZZYLIKDT-UHFFFAOYSA-N 0.000 claims description 2
RWTPCDGKWMQRGA-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(2,3-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(Cl)=C1Cl RWTPCDGKWMQRGA-UHFFFAOYSA-N 0.000 claims description 2
LNWOQXOSMRBZBN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(2,3-difluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(F)=C1F LNWOQXOSMRBZBN-UHFFFAOYSA-N 0.000 claims description 2
ORIYQOUBEPERFH-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(2-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1F ORIYQOUBEPERFH-UHFFFAOYSA-N 0.000 claims description 2
ANDYBNKRXGVQGP-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ANDYBNKRXGVQGP-UHFFFAOYSA-N 0.000 claims description 2
PIVRFBAMCBQCDZ-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(3-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(F)=C1 PIVRFBAMCBQCDZ-UHFFFAOYSA-N 0.000 claims description 2
DIKWOUATAGYMJW-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(3-methoxyphenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(OC)=C1 DIKWOUATAGYMJW-UHFFFAOYSA-N 0.000 claims description 2
LOMPCAVUANIGGY-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(4-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(F)C=C1 LOMPCAVUANIGGY-UHFFFAOYSA-N 0.000 claims description 2
OWBACNIWWBKBHC-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(morpholin-4-ylmethyl)-3-pyridin-3-yloxyphenyl]methanone Chemical compound C=1C=C(CN2CCOCC2)C(OC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CC1 OWBACNIWWBKBHC-UHFFFAOYSA-N 0.000 claims description 2
KMHZJBNYIWFWAY-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(piperidin-1-ylmethyl)-3-pyridin-3-yloxyphenyl]methanone Chemical compound C=1C=C(CN2CCCCC2)C(OC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CC1 KMHZJBNYIWFWAY-UHFFFAOYSA-N 0.000 claims description 2
NURMXNUIQVJHSR-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-[(3,4-dichlorophenyl)methoxy]-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OCC1=CC=C(Cl)C(Cl)=C1 NURMXNUIQVJHSR-UHFFFAOYSA-N 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
208000017164 Chronobiology disease Diseases 0.000 claims description 2
208000019695 Migraine disease Diseases 0.000 claims description 2
208000016285 Movement disease Diseases 0.000 claims description 2
208000007920 Neurogenic Inflammation Diseases 0.000 claims description 2
208000008589 Obesity Diseases 0.000 claims description 2
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
208000018737 Parkinson disease Diseases 0.000 claims description 2
208000005793 Restless legs syndrome Diseases 0.000 claims description 2
206010038910 Retinitis Diseases 0.000 claims description 2
229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 claims description 2
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 2
KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims description 2
FSAUBGQRVAOUAE-UHFFFAOYSA-N [3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(SC)C=C1 FSAUBGQRVAOUAE-UHFFFAOYSA-N 0.000 claims description 2
BUDXPODSGXONSZ-UHFFFAOYSA-N [3-(methylaminomethyl)-4-[4-(trifluoromethyl)phenoxy]phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 BUDXPODSGXONSZ-UHFFFAOYSA-N 0.000 claims description 2
GTKIXXYJXPDXOP-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-(3,4-dichlorophenoxy)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1=CC=C(C(=O)N2CCN(CCC2)C2CC2)C=C1CNC1CC1 GTKIXXYJXPDXOP-UHFFFAOYSA-N 0.000 claims description 2
FUZGNJYLLVRAMT-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-(3,4-dichlorophenoxy)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1CNC2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FUZGNJYLLVRAMT-UHFFFAOYSA-N 0.000 claims description 2
NQRPBAJKYSQQRJ-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-pyridin-3-yloxyphenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C=1C=C(OC=2C=NC=CC=2)C(CNC2CC2)=CC=1C(=O)N(CC1)CCCN1C1CC1 NQRPBAJKYSQQRJ-UHFFFAOYSA-N 0.000 claims description 2
QYNGZGASLPHHCL-UHFFFAOYSA-N [3-phenylmethoxy-4-(piperidin-1-ylmethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1OCC=2C=CC=CC=2)=CC=C1CN1CCCCC1 QYNGZGASLPHHCL-UHFFFAOYSA-N 0.000 claims description 2
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