CA2682849C

CA2682849C - Sulfonamides and pharmaceutical compositions thereof

Sulfonamides and pharmaceutical compositions thereof Download PDF

Info

Publication number: CA2682849C
Authority: CA; Canada
Prior art keywords: alkyl; biphenyl; propane; trans; amide
Prior art date: 2007-04-03
Legal status : Expired - Fee Related

Application number

CA2682849A

Other languages

English (en)

French (fr)

Other versions

CA2682849A1 (en

Inventor

Kimberly Gail Estep

Anton Franz Josef Fliri

Christopher John O'donnell

Current Assignee

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

Priority date

2007-04-03

Filing date

2008-03-26

Publication date

2012-05-29

2008-03-26 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

2008-10-09 Publication of CA2682849A1 publication Critical patent/CA2682849A1/en

2012-05-29 Application granted granted Critical

2012-05-29 Publication of CA2682849C publication Critical patent/CA2682849C/en

Status Expired - Fee Related legal-status Critical Current

2028-03-26 Anticipated expiration legal-status Critical

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 13
229940124530 sulfonamide Drugs 0.000 title description 10
150000003456 sulfonamides Chemical class 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 219
150000003839 salts Chemical class 0.000 claims abstract description 48
125000000217 alkyl group Chemical group 0.000 claims description 136
-1 cyano, nitro, amino Chemical group 0.000 claims description 122
125000003118 aryl group Chemical group 0.000 claims description 94
125000001424 substituent group Chemical group 0.000 claims description 92
125000000753 cycloalkyl group Chemical group 0.000 claims description 88
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 86
125000001072 heteroaryl group Chemical group 0.000 claims description 84
229910052736 halogen Inorganic materials 0.000 claims description 82
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 78
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
125000003545 alkoxy group Chemical group 0.000 claims description 53
229910052757 nitrogen Inorganic materials 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 47
150000002367 halogens Chemical group 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 36
125000005842 heteroatom Chemical group 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
125000004093 cyano group Chemical group *C#N 0.000 claims description 30
125000003342 alkenyl group Chemical group 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
239000003814 drug Substances 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
208000002193 Pain Diseases 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
229910052760 oxygen Chemical group 0.000 claims description 19
239000011593 sulfur Chemical group 0.000 claims description 19
239000001301 oxygen Chemical group 0.000 claims description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
125000003282 alkyl amino group Chemical group 0.000 claims description 16
125000004663 dialkyl amino group Chemical group 0.000 claims description 16
230000002265 prevention Effects 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 15
101100495912 Arabidopsis thaliana CHR12 gene Proteins 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 14
201000000980 schizophrenia Diseases 0.000 claims description 14
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 13
208000012902 Nervous system disease Diseases 0.000 claims description 13
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 13
125000002837 carbocyclic group Chemical group 0.000 claims description 13
208000019695 Migraine disease Diseases 0.000 claims description 12
125000004104 aryloxy group Chemical group 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
229940079593 drug Drugs 0.000 claims description 12
206010027599 migraine Diseases 0.000 claims description 12
125000004385 trihaloalkyl group Chemical group 0.000 claims description 12
208000019901 Anxiety disease Diseases 0.000 claims description 11
206010012289 Dementia Diseases 0.000 claims description 11
230000001154 acute effect Effects 0.000 claims description 11
230000000926 neurological effect Effects 0.000 claims description 11
208000020016 psychiatric disease Diseases 0.000 claims description 11
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 9
206010015037 epilepsy Diseases 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
208000019116 sleep disease Diseases 0.000 claims description 9
208000024827 Alzheimer disease Diseases 0.000 claims description 8
201000006474 Brain Ischemia Diseases 0.000 claims description 8
206010048962 Brain oedema Diseases 0.000 claims description 8
206010008120 Cerebral ischaemia Diseases 0.000 claims description 8
208000027691 Conduct disease Diseases 0.000 claims description 8
206010010904 Convulsion Diseases 0.000 claims description 8
206010011878 Deafness Diseases 0.000 claims description 8
206010019196 Head injury Diseases 0.000 claims description 8
208000010496 Heart Arrest Diseases 0.000 claims description 8
208000023105 Huntington disease Diseases 0.000 claims description 8
208000019022 Mood disease Diseases 0.000 claims description 8
208000008238 Muscle Spasticity Diseases 0.000 claims description 8
208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 claims description 8
208000018737 Parkinson disease Diseases 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 8
208000017442 Retinal disease Diseases 0.000 claims description 8
206010038923 Retinopathy Diseases 0.000 claims description 8
208000005392 Spasm Diseases 0.000 claims description 8
208000006011 Stroke Diseases 0.000 claims description 8
208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 8
206010043118 Tardive Dyskinesia Diseases 0.000 claims description 8
208000009205 Tinnitus Diseases 0.000 claims description 8
206010044565 Tremor Diseases 0.000 claims description 8
206010046543 Urinary incontinence Diseases 0.000 claims description 8
206010047700 Vomiting Diseases 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
230000036506 anxiety Effects 0.000 claims description 8
208000006752 brain edema Diseases 0.000 claims description 8
206010008118 cerebral infarction Diseases 0.000 claims description 8
208000010877 cognitive disease Diseases 0.000 claims description 8
230000036461 convulsion Effects 0.000 claims description 8
230000006378 damage Effects 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 8
230000010370 hearing loss Effects 0.000 claims description 8
231100000888 hearing loss Toxicity 0.000 claims description 8
208000016354 hearing loss disease Diseases 0.000 claims description 8
230000002218 hypoglycaemic effect Effects 0.000 claims description 8
208000014674 injury Diseases 0.000 claims description 8
208000002780 macular degeneration Diseases 0.000 claims description 8
230000003387 muscular Effects 0.000 claims description 8
230000003961 neuronal insult Effects 0.000 claims description 8
208000033300 perinatal asphyxia Diseases 0.000 claims description 8
208000018198 spasticity Diseases 0.000 claims description 8
210000000278 spinal cord Anatomy 0.000 claims description 8
231100000886 tinnitus Toxicity 0.000 claims description 8
230000008733 trauma Effects 0.000 claims description 8
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
UQIYZJCPYGLLNO-PMACEKPBSA-N n-[(3s,4s)-4-hydroxy-4-(4-phenylphenyl)oxan-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@H]1COCC[C@]1(O)C1=CC=C(C=2C=CC=CC=2)C=C1 UQIYZJCPYGLLNO-PMACEKPBSA-N 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
206010044652 trigeminal neuralgia Diseases 0.000 claims description 7
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
208000020685 sleep-wake disease Diseases 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
AJUOAQLCQZVPLR-VQTJNVASSA-N n-[(3s,4s)-4-(4-phenylphenyl)piperidin-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CNCC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 AJUOAQLCQZVPLR-VQTJNVASSA-N 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
OHVCFKGVAPQNMI-LEWJYISDSA-N n-[(3s,4s)-1-methyl-4-(4-phenylphenyl)piperidin-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CN(C)CC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 OHVCFKGVAPQNMI-LEWJYISDSA-N 0.000 claims description 4
BPARXNSVUVHFPR-LEWJYISDSA-N N-[(3R,4R)-3-[4-(4-cyanophenyl)phenyl]piperidin-4-yl]propane-2-sulfonamide Chemical compound C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CNCC[C@H]1NS(=O)(=O)C(C)C BPARXNSVUVHFPR-LEWJYISDSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
UQYVMJZPZUSCGJ-FCHUYYIVSA-N n-[(3r,4r)-1-acetyl-3-(4-phenylphenyl)piperidin-4-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CCN(C(C)=O)C[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 UQYVMJZPZUSCGJ-FCHUYYIVSA-N 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
UEBAPWPNHBAQPN-LEWJYISDSA-N C1(=CC=C(C=C1)[C@H]1[C@@H](CN(CC1)S(=O)(=O)C)NS(=O)(=O)C(C)C)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)[C@H]1[C@@H](CN(CC1)S(=O)(=O)C)NS(=O)(=O)C(C)C)C1=CC=CC=C1 UEBAPWPNHBAQPN-LEWJYISDSA-N 0.000 claims description 2
AIEFMARVOUBDMK-VQTJNVASSA-N CCCS(=O)(=O)N[C@@H]1CNCC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 Chemical compound CCCS(=O)(=O)N[C@@H]1CNCC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 AIEFMARVOUBDMK-VQTJNVASSA-N 0.000 claims description 2
WWJUAKCORLBGOO-RBUKOAKNSA-N CCS(=O)(=O)N[C@@H]1CNCC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 Chemical compound CCS(=O)(=O)N[C@@H]1CNCC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 WWJUAKCORLBGOO-RBUKOAKNSA-N 0.000 claims description 2
HDBIOHMGTWCIQG-VQTJNVASSA-N N-[(3R,4R)-3-(4-phenylphenyl)piperidin-4-yl]propane-2-sulfonamide Chemical compound C1(=CC=C(C=C1)[C@@H]1CNCC[C@H]1NS(=O)(=O)C(C)C)C1=CC=CC=C1 HDBIOHMGTWCIQG-VQTJNVASSA-N 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
UQIYZJCPYGLLNO-UXHICEINSA-N n-[(3r,4s)-4-hydroxy-4-(4-phenylphenyl)oxan-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1COCC[C@]1(O)C1=CC=C(C=2C=CC=CC=2)C=C1 UQIYZJCPYGLLNO-UXHICEINSA-N 0.000 claims description 2
OHVCFKGVAPQNMI-NHCUHLMSSA-N n-[(3s,4r)-1-methyl-4-(4-phenylphenyl)piperidin-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CN(C)CC[C@@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 OHVCFKGVAPQNMI-NHCUHLMSSA-N 0.000 claims description 2
OBPPZUVOBBSMCI-LEWJYISDSA-N n-methyl-4-[4-[(3s,4s)-3-(propan-2-ylsulfonylamino)oxan-4-yl]phenyl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C([C@H]2[C@@H](COCC2)NS(=O)(=O)C(C)C)C=C1 OBPPZUVOBBSMCI-LEWJYISDSA-N 0.000 claims description 2
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 5
208000007101 Muscle Cramp Diseases 0.000 claims 5
208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 5
238000004519 manufacturing process Methods 0.000 claims 2
SBNCHFAHKQJMQH-VQTJNVASSA-N 2-[4-[(3r,4r)-4-(propan-2-ylsulfonylamino)piperidin-3-yl]phenyl]benzamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CCNC[C@H]1C1=CC=C(C=2C(=CC=CC=2)C(N)=O)C=C1 SBNCHFAHKQJMQH-VQTJNVASSA-N 0.000 claims 1
QZFBJPZPYHUGAA-LEWJYISDSA-N 3,5-difluoro-n-[4-[(3r,4r)-1-methyl-4-(propan-2-ylsulfonylamino)piperidin-3-yl]phenyl]benzamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CCN(C)C[C@H]1C(C=C1)=CC=C1NC(=O)C1=CC(F)=CC(F)=C1 QZFBJPZPYHUGAA-LEWJYISDSA-N 0.000 claims 1
FIGDQGWUBUWIHS-LEWJYISDSA-N C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)[C@@H]1CNCC[C@H]1NS(=O)(=O)C(C)C Chemical compound C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)[C@@H]1CNCC[C@H]1NS(=O)(=O)C(C)C FIGDQGWUBUWIHS-LEWJYISDSA-N 0.000 claims 1
OXOFFXGUEGRPGR-LEWJYISDSA-N C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C Chemical compound C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C OXOFFXGUEGRPGR-LEWJYISDSA-N 0.000 claims 1
PVGDTNAGQLDZBQ-FCHUYYIVSA-N C(C)(=O)N1C[C@H]([C@@H](CC1)C1=CC=C(C=C1)C1=CC=CC=C1)NS(=O)(=O)C(C)C Chemical compound C(C)(=O)N1C[C@H]([C@@H](CC1)C1=CC=C(C=C1)C1=CC=CC=C1)NS(=O)(=O)C(C)C PVGDTNAGQLDZBQ-FCHUYYIVSA-N 0.000 claims 1
ZNUAEBNWRRRIFD-XZOQPEGZSA-N C(C)(=O)N1C[C@H]([C@@H](CC1)NS(=O)(=O)C(C)C)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N Chemical compound C(C)(=O)N1C[C@H]([C@@H](CC1)NS(=O)(=O)C(C)C)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N ZNUAEBNWRRRIFD-XZOQPEGZSA-N 0.000 claims 1
DGKXTAVYDLXQCE-XZOQPEGZSA-N C(C)(=O)N1C[C@H]([C@@H](CC1)NS(=O)(=O)C(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N Chemical compound C(C)(=O)N1C[C@H]([C@@H](CC1)NS(=O)(=O)C(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N DGKXTAVYDLXQCE-XZOQPEGZSA-N 0.000 claims 1
BHSHPWYKOZJAQM-LEWJYISDSA-N C1(=CC=C(C=C1)[C@@H]1CN(CC[C@H]1NS(=O)(=O)C(C)C)C)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)[C@@H]1CN(CC[C@H]1NS(=O)(=O)C(C)C)C)C1=CC=CC=C1 BHSHPWYKOZJAQM-LEWJYISDSA-N 0.000 claims 1
AIEFMARVOUBDMK-WOJBJXKFSA-N C1(=CC=C(C=C1)[C@@H]1[C@@H](CNCC1)NS(=O)(=O)CCC)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)[C@@H]1[C@@H](CNCC1)NS(=O)(=O)CCC)C1=CC=CC=C1 AIEFMARVOUBDMK-WOJBJXKFSA-N 0.000 claims 1
DDCRNXOLUCWOLF-VQTJNVASSA-N C1(=CC=C(C=C1)[C@H]1[C@@H](CNCC1)NS(=O)(=O)C1CC1)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)[C@H]1[C@@H](CNCC1)NS(=O)(=O)C1CC1)C1=CC=CC=C1 DDCRNXOLUCWOLF-VQTJNVASSA-N 0.000 claims 1
CTIHQDLQUKKQSU-ZWKOTPCHSA-N C1(=CC=C(C=C1)[C@H]1[C@@H](CNCC1)NS(=O)(=O)CC(F)(F)F)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)[C@H]1[C@@H](CNCC1)NS(=O)(=O)CC(F)(F)F)C1=CC=CC=C1 CTIHQDLQUKKQSU-ZWKOTPCHSA-N 0.000 claims 1
KFUPNKOHSVGUCV-LEWJYISDSA-N CS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C Chemical compound CS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C KFUPNKOHSVGUCV-LEWJYISDSA-N 0.000 claims 1
MXPCMUMSLMXNRG-AZUAARDMSA-N ClC1=C(C=C(C=C1)Cl)C1=CC=C(C=C1)[C@@H]1CNCC[C@H]1NS(=O)(=O)C(C)C Chemical compound ClC1=C(C=C(C=C1)Cl)C1=CC=C(C=C1)[C@@H]1CNCC[C@H]1NS(=O)(=O)C(C)C MXPCMUMSLMXNRG-AZUAARDMSA-N 0.000 claims 1
JHBFJLQBKJDAHB-AZUAARDMSA-N ClC1=C(C=CC=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C Chemical compound ClC1=C(C=CC=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C JHBFJLQBKJDAHB-AZUAARDMSA-N 0.000 claims 1
HDFQQTFNJSGKLY-VQTJNVASSA-N FC1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C Chemical compound FC1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@@H](COCC1)NS(=O)(=O)C(C)C HDFQQTFNJSGKLY-VQTJNVASSA-N 0.000 claims 1
DAAVTRWSLANBKI-LEWJYISDSA-N N-[(3R,4R)-1-methylsulfonyl-3-(4-phenylphenyl)piperidin-4-yl]propane-2-sulfonamide Chemical compound C1(=CC=C(C=C1)[C@@H]1CN(CC[C@H]1NS(=O)(=O)C(C)C)S(=O)(=O)C)C1=CC=CC=C1 DAAVTRWSLANBKI-LEWJYISDSA-N 0.000 claims 1
CRIVUJZGJKUCHW-RBUKOAKNSA-N N-[(3S,4R)-3-(4-phenylphenyl)oxan-4-yl]ethanesulfonamide Chemical compound C1(=CC=C(C=C1)[C@@H]1COCC[C@H]1NS(=O)(=O)CC)C1=CC=CC=C1 CRIVUJZGJKUCHW-RBUKOAKNSA-N 0.000 claims 1
KGCDTOVRNIRCDU-YADHBBJMSA-N n-[(3r,4r)-1-ethyl-4-(4-phenylphenyl)piperidin-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@H]1CN(CC)CC[C@@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 KGCDTOVRNIRCDU-YADHBBJMSA-N 0.000 claims 1
OHVCFKGVAPQNMI-RTWAWAEBSA-N n-[(3r,4r)-1-methyl-4-(4-phenylphenyl)piperidin-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@H]1CN(C)CC[C@@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 OHVCFKGVAPQNMI-RTWAWAEBSA-N 0.000 claims 1
XFEDFOXMYWNKFP-AZUAARDMSA-N n-[(3r,4r)-3-[4-(2-chlorophenyl)phenyl]piperidin-4-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CCNC[C@H]1C1=CC=C(C=2C(=CC=CC=2)Cl)C=C1 XFEDFOXMYWNKFP-AZUAARDMSA-N 0.000 claims 1
ISOXAQDJAMYCHH-FCHUYYIVSA-N n-[(3r,4r)-3-[4-(4-cyanophenyl)phenyl]-1-methylpiperidin-4-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CCN(C)C[C@H]1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 ISOXAQDJAMYCHH-FCHUYYIVSA-N 0.000 claims 1
ZHTWZDGBHZMKRE-VQTJNVASSA-N n-[(3s,4r)-3-(4-phenylphenyl)oxan-4-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1CCOC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 ZHTWZDGBHZMKRE-VQTJNVASSA-N 0.000 claims 1
YRTDLVQUWRIFAT-WOJBJXKFSA-N n-[(3s,4r)-4-(4-phenylphenyl)oxan-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@@H]1COCC[C@@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 YRTDLVQUWRIFAT-WOJBJXKFSA-N 0.000 claims 1
ZHTWZDGBHZMKRE-PMACEKPBSA-N n-[(3s,4s)-3-(4-phenylphenyl)oxan-4-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@H]1CCOC[C@H]1C1=CC=C(C=2C=CC=CC=2)C=C1 ZHTWZDGBHZMKRE-PMACEKPBSA-N 0.000 claims 1
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