JP2005504059A - 疾患を処置するための置換アリール７−アザ［２．２．１］ビシクロヘプタン - Google Patents

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Publication number

JP2005504059A

JP2005504059A JP2003523246A JP2003523246A JP2005504059A JP 2005504059 A JP2005504059 A JP 2005504059A JP 2003523246 A JP2003523246 A JP 2003523246A JP 2003523246 A JP2003523246 A JP 2003523246A JP 2005504059 A JP2005504059 A JP 2005504059A

Authority

JP

Japan

Prior art keywords

azabicyclo

hept

benzamide

yloxy

ylsulfanyl

Prior art date

2001-08-24

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.)

Withdrawn

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 84
• 201000010099 disease Diseases 0.000 title claims abstract description 62
• 125000003107 substituted aryl group Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 165
• 239000003814 drug Substances 0.000 claims abstract description 106
• 239000000203 mixture Substances 0.000 claims abstract description 49
• 150000003839 salts Chemical class 0.000 claims abstract description 43
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
• SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical group C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims abstract description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 145
• 125000001424 substituent group Chemical group 0.000 claims description 145
• -1 (2-cyanophenoxy) benzamide Chemical compound 0.000 claims description 108
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 90
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 87
• 229910052794 bromium Inorganic materials 0.000 claims description 84
• 229910052801 chlorine Inorganic materials 0.000 claims description 84
• 229910052740 iodine Inorganic materials 0.000 claims description 84
• 229910052731 fluorine Inorganic materials 0.000 claims description 83
• 229940079593 drug Drugs 0.000 claims description 82
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 80
• 208000024891 symptom Diseases 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 46
• 208000024827 Alzheimer disease Diseases 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims description 35
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 33
• 206010012289 Dementia Diseases 0.000 claims description 31
• 201000000980 schizophrenia Diseases 0.000 claims description 31
• 241000124008 Mammalia Species 0.000 claims description 26
• 125000001624 naphthyl group Chemical group 0.000 claims description 26
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 24
• 239000000164 antipsychotic agent Substances 0.000 claims description 24
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
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• 230000006735 deficit Effects 0.000 claims description 20
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• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 18
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 18
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 18
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 18
• 230000000561 anti-psychotic effect Effects 0.000 claims description 17
• 230000036506 anxiety Effects 0.000 claims description 17
• 230000001149 cognitive effect Effects 0.000 claims description 17
• 208000010877 cognitive disease Diseases 0.000 claims description 16
• 208000002193 Pain Diseases 0.000 claims description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 14
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• 208000019022 Mood disease Diseases 0.000 claims description 13
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 13
• 208000002780 macular degeneration Diseases 0.000 claims description 13
• 208000030507 AIDS Diseases 0.000 claims description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
• 201000010374 Down Syndrome Diseases 0.000 claims description 12
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 12
• 208000023105 Huntington disease Diseases 0.000 claims description 12
• 206010039966 Senile dementia Diseases 0.000 claims description 12
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 12
• 150000001350 alkyl halides Chemical class 0.000 claims description 12
• 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims description 12
• 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims description 12
• 231100000870 cognitive problem Toxicity 0.000 claims description 12
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 12
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 11
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 11
• 150000001721 carbon Chemical group 0.000 claims description 11
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 11
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 10
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 10
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 10
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• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 230000005586 smoking cessation Effects 0.000 claims description 10
• 230000009529 traumatic brain injury Effects 0.000 claims description 10
• 208000027534 Emotional disease Diseases 0.000 claims description 9
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 9
• 206010036631 Presenile dementia Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
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• 208000012661 Dyskinesia Diseases 0.000 claims description 8
• 230000006399 behavior Effects 0.000 claims description 8
• 230000037396 body weight Effects 0.000 claims description 8
• 230000008482 dysregulation Effects 0.000 claims description 8
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
• 229940122578 Acetylcholine receptor agonist Drugs 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 230000036651 mood Effects 0.000 claims description 5
• VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 4
• LJSXLBOWXISZSL-DVVUODLYSA-N 3-amino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-4-hydroxybenzamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C1=CC=C(O)C(N)=C1 LJSXLBOWXISZSL-DVVUODLYSA-N 0.000 claims description 4
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• JRMUJBVACCSWQJ-FHLIZLRMSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-4-phenoxybenzamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 JRMUJBVACCSWQJ-FHLIZLRMSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• QEESGIQNGYFBNV-HYVNUMGLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-7-methoxynaphthalene-2-carboxamide Chemical compound C1=CC(OC)=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 QEESGIQNGYFBNV-HYVNUMGLSA-N 0.000 claims description 3
• WIGQZHZLVXRJIU-OWCLPIDISA-N 2-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2,7-dicarboxamide Chemical compound C1=CC(C(N)=O)=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 WIGQZHZLVXRJIU-OWCLPIDISA-N 0.000 claims description 2
• SLCLHMXVUAIHCN-FHLIZLRMSA-N 5-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2-carboxamide Chemical compound CC(=O)NC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 SLCLHMXVUAIHCN-FHLIZLRMSA-N 0.000 claims description 2
• ABBIGPDJXMZYPC-UHOFOFEASA-N 5-amino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2-carboxamide Chemical compound NC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 ABBIGPDJXMZYPC-UHOFOFEASA-N 0.000 claims description 2
• AEJKBGZIDJPZIF-UHOFOFEASA-N 6-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-1,6-dicarboxamide Chemical compound NC(=O)C1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 AEJKBGZIDJPZIF-UHOFOFEASA-N 0.000 claims description 2
• RKRZHFKRQBPXFQ-FGTMMUONSA-N 7-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2-carboxamide Chemical compound C1=CC(NC(C)=O)=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 RKRZHFKRQBPXFQ-FGTMMUONSA-N 0.000 claims description 2
• LQJQMGNNGZFRIP-OWCLPIDISA-N 7-amino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2-carboxamide Chemical compound C1=CC(N)=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 LQJQMGNNGZFRIP-OWCLPIDISA-N 0.000 claims description 2
• OSLRJPDDERTNKG-UHOFOFEASA-N 7-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-1,7-dicarboxamide Chemical compound C1=CC=C(C(N)=O)C2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 OSLRJPDDERTNKG-UHOFOFEASA-N 0.000 claims description 2
• RNZRYEXTDPECAV-FHLIZLRMSA-N 8-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2-carboxamide Chemical compound C1=CC=C(NC(C)=O)C2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 RNZRYEXTDPECAV-FHLIZLRMSA-N 0.000 claims description 2
• BVRCQGFIIFZGQK-UHOFOFEASA-N 8-amino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]naphthalene-2-carboxamide Chemical compound C1=CC=C(N)C2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 BVRCQGFIIFZGQK-UHOFOFEASA-N 0.000 claims description 2
• LVWGXHXKWNNKCQ-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2,3-dihydro-1h-indene-5-carboxamide Chemical compound C1=C2CCCC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 LVWGXHXKWNNKCQ-QLFBSQMISA-N 0.000 claims description 2
• GZMQUPVQBFDBJG-FHLIZLRMSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-phenoxybenzamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 GZMQUPVQBFDBJG-FHLIZLRMSA-N 0.000 claims description 2
• FOCKAELGYXOAMO-FGTMMUONSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-4-benzoylbenzamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 FOCKAELGYXOAMO-FGTMMUONSA-N 0.000 claims description 2
• XBRFIBBDOKZJQX-CEXWTWQISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-4-benzylbenzamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 XBRFIBBDOKZJQX-CEXWTWQISA-N 0.000 claims description 2
• DPIKWMKYMYJBPZ-NZSAHSFTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(3-hydroxyprop-1-ynyl)naphthalene-2-carboxamide Chemical compound OCC#CC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 DPIKWMKYMYJBPZ-NZSAHSFTSA-N 0.000 claims description 2
• JPEPXZBJVVUVQC-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(methylamino)naphthalene-2-carboxamide Chemical compound CNC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 JPEPXZBJVVUVQC-XOKHGSTOSA-N 0.000 claims description 2
• QBMOZHKIXODANK-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(trifluoromethyl)naphthalene-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 QBMOZHKIXODANK-UHOFOFEASA-N 0.000 claims description 2
• BIOMOBDEHQDDGQ-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-bromonaphthalene-2-carboxamide Chemical compound BrC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 BIOMOBDEHQDDGQ-UHOFOFEASA-N 0.000 claims description 2
• IJDLWQABYIUSKX-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-chloronaphthalene-2-carboxamide Chemical compound ClC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 IJDLWQABYIUSKX-UHOFOFEASA-N 0.000 claims description 2
• BBHNFLKJPKLHEX-HYVNUMGLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-cyanonaphthalene-2-carboxamide Chemical compound N#CC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 BBHNFLKJPKLHEX-HYVNUMGLSA-N 0.000 claims description 2
• FWTNIBDPQFLWGK-BPQIPLTHSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-ethenylnaphthalene-2-carboxamide Chemical compound C=CC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 FWTNIBDPQFLWGK-BPQIPLTHSA-N 0.000 claims description 2
• KQNHIFLRBZWHIR-BPQIPLTHSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-ethynylnaphthalene-2-carboxamide Chemical compound C#CC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 KQNHIFLRBZWHIR-BPQIPLTHSA-N 0.000 claims description 2
• XZGSAFPYGRPSPH-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-fluoronaphthalene-2-carboxamide Chemical compound FC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 XZGSAFPYGRPSPH-UHOFOFEASA-N 0.000 claims description 2
• RCVPLFYGVUOJPY-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-formamidonaphthalene-2-carboxamide Chemical compound O=CNC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 RCVPLFYGVUOJPY-XOKHGSTOSA-N 0.000 claims description 2
• PHSSVACIAKWYEI-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-hydroxynaphthalene-2-carboxamide Chemical compound OC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 PHSSVACIAKWYEI-VHDGCEQUSA-N 0.000 claims description 2
• HWBUIUIOEGHUBQ-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-iodonaphthalene-2-carboxamide Chemical compound IC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 HWBUIUIOEGHUBQ-UHOFOFEASA-N 0.000 claims description 2
• VKJPSLHRUJQLQC-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-methoxynaphthalene-2-carboxamide Chemical compound COC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 VKJPSLHRUJQLQC-VNQPRFMTSA-N 0.000 claims description 2
• QRGIIVXXEUUWLN-HYVNUMGLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-methylnaphthalene-2-carboxamide Chemical compound CC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 QRGIIVXXEUUWLN-HYVNUMGLSA-N 0.000 claims description 2
• MHCHLKRCPXDJKV-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-methylsulfanylnaphthalene-2-carboxamide Chemical compound CSC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 MHCHLKRCPXDJKV-VNQPRFMTSA-N 0.000 claims description 2
• ZCKZJBVQPKXFOR-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-nitronaphthalene-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 ZCKZJBVQPKXFOR-VHDGCEQUSA-N 0.000 claims description 2
• MFGNTAYOMGUUFG-NZSAHSFTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-prop-1-ynylnaphthalene-2-carboxamide Chemical compound CC#CC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 MFGNTAYOMGUUFG-NZSAHSFTSA-N 0.000 claims description 2
• FPXKGPJYULFNND-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-sulfanylnaphthalene-2-carboxamide Chemical compound SC1=CC=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 FPXKGPJYULFNND-VHDGCEQUSA-N 0.000 claims description 2
• QMXJMUWVQIISCI-CEXWTWQISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-7-(3-hydroxyprop-1-ynyl)naphthalene-2-carboxamide Chemical compound C1=CC(C#CCO)=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 QMXJMUWVQIISCI-CEXWTWQISA-N 0.000 claims description 2
• RZLJERNNQQYUCU-IXDOHACOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-7-(methylamino)naphthalene-2-carboxamide Chemical compound C1=CC(NC)=CC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 RZLJERNNQQYUCU-IXDOHACOSA-N 0.000 claims description 2
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