JP2012515209A5 - - Google Patents
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- Publication number
- JP2012515209A5 JP2012515209A5 JP2011546319A JP2011546319A JP2012515209A5 JP 2012515209 A5 JP2012515209 A5 JP 2012515209A5 JP 2011546319 A JP2011546319 A JP 2011546319A JP 2011546319 A JP2011546319 A JP 2011546319A JP 2012515209 A5 JP2012515209 A5 JP 2012515209A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazin
- hexahydropyrrolo
- ylcarbonyl
- benzenesulfonamide
- formula
- Prior art date
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 26
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- -1 2,3-difluorophenyl Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 4
- AGPIHNZOZNKRGT-CYBMUJFWSA-N 5-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-4-chloro-2-fluoro-n-(2-fluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC(C(=O)N2C[C@H]3CCCN3CC2)=C(Cl)C=C1F AGPIHNZOZNKRGT-CYBMUJFWSA-N 0.000 claims 4
- 125000003725 azepanyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000000651 prodrug Chemical class 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- NTGHBMWKKZCQJX-UHFFFAOYSA-N 3-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine-2-carbonyl)-n-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(=O)N2CC3CCCCN3CC2)=C1 NTGHBMWKKZCQJX-UHFFFAOYSA-N 0.000 claims 1
- YKRLUOZLOMRDJR-UHFFFAOYSA-N 3-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine-2-carbonyl)-n-[4-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)N2CC3CCCCN3CC2)=C1 YKRLUOZLOMRDJR-UHFFFAOYSA-N 0.000 claims 1
- CQXJKNXBJWCGEY-OAHLLOKOSA-N 3-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-(2,6-difluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC(F)=C1NS(=O)(=O)C1=CC=CC(C(=O)N2C[C@H]3CCCN3CC2)=C1 CQXJKNXBJWCGEY-OAHLLOKOSA-N 0.000 claims 1
- KHIZNEYVKZPOBP-MRXNPFEDSA-N 3-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-(2-fluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)N2C[C@H]3CCCN3CC2)=C1 KHIZNEYVKZPOBP-MRXNPFEDSA-N 0.000 claims 1
- PLLFHYFNEYOOHX-TZIWHRDSSA-N 3-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-[(1s)-2-hydroxy-1-phenylethyl]benzenesulfonamide Chemical compound C1([C@H](NS(=O)(=O)C=2C=C(C=CC=2)C(=O)N2C[C@H]3CCCN3CC2)CO)=CC=CC=C1 PLLFHYFNEYOOHX-TZIWHRDSSA-N 0.000 claims 1
- RYXLBQVNMNCNOZ-GOSISDBHSA-N 3-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-[4-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)N2C[C@H]3CCCN3CC2)=C1 RYXLBQVNMNCNOZ-GOSISDBHSA-N 0.000 claims 1
- CQXJKNXBJWCGEY-HNNXBMFYSA-N 3-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-(2,6-difluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC(F)=C1NS(=O)(=O)C1=CC=CC(C(=O)N2C[C@@H]3CCCN3CC2)=C1 CQXJKNXBJWCGEY-HNNXBMFYSA-N 0.000 claims 1
- KHIZNEYVKZPOBP-INIZCTEOSA-N 3-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-(2-fluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)N2C[C@@H]3CCCN3CC2)=C1 KHIZNEYVKZPOBP-INIZCTEOSA-N 0.000 claims 1
- YBOWDQUKLNJSSM-SFHVURJKSA-N 3-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-(3-fluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(=O)N2C[C@@H]3CCCN3CC2)=C1 YBOWDQUKLNJSSM-SFHVURJKSA-N 0.000 claims 1
- KHNAPMIJMHYYJN-TZIWHRDSSA-N 4-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-n-[(1s)-2-hydroxy-1-phenylethyl]benzenesulfonamide Chemical compound C1([C@H](NS(=O)(=O)C=2C=CC(=CC=2)C(=O)N2C[C@H]3CCCN3CC2)CO)=CC=CC=C1 KHNAPMIJMHYYJN-TZIWHRDSSA-N 0.000 claims 1
- IDIMHHNGWGAZGB-CYBMUJFWSA-N 5-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2,4-dichloro-n-(2-fluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC(C(=O)N2C[C@H]3CCCN3CC2)=C(Cl)C=C1Cl IDIMHHNGWGAZGB-CYBMUJFWSA-N 0.000 claims 1
- AGPIHNZOZNKRGT-ZDUSSCGKSA-N 5-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-4-chloro-2-fluoro-n-(2-fluorophenyl)benzenesulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC(C(=O)N2C[C@@H]3CCCN3CC2)=C(Cl)C=C1F AGPIHNZOZNKRGT-ZDUSSCGKSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010012434 Dermatitis allergic Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000004454 Hyperalgesia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010020853 Hypertonic bladder Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 1
- 208000008930 Low Back Pain Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000008765 Sciatica Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 208000026723 Urinary tract disease Diseases 0.000 claims 1
- FZLDXPOFLGONMF-LJQANCHMSA-N [(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[2-chloro-4-fluoro-5-[4-(4-fluorophenyl)piperazin-1-yl]sulfonylphenyl]methanone Chemical compound C1=CC(F)=CC=C1N1CCN(S(=O)(=O)C=2C(=CC(Cl)=C(C(=O)N3C[C@H]4CCCN4CC3)C=2)F)CC1 FZLDXPOFLGONMF-LJQANCHMSA-N 0.000 claims 1
- GAGSUTMMGKVUCP-MRXNPFEDSA-N [(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[2-chloro-5-(2,3-dihydroindol-1-ylsulfonyl)-4-fluorophenyl]methanone Chemical compound C1CN2CCC[C@@H]2CN1C(=O)C1=C(Cl)C=C(F)C(S(=O)(=O)N2C3=CC=CC=C3CC2)=C1 GAGSUTMMGKVUCP-MRXNPFEDSA-N 0.000 claims 1
- HRCAYCQDIMSMJS-MUUNZHRXSA-N [(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[3-(4-benzhydrylpiperazin-1-yl)sulfonylphenyl]methanone Chemical compound C([C@H]1CCCN1CC1)N1C(=O)C(C=1)=CC=CC=1S(=O)(=O)N(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HRCAYCQDIMSMJS-MUUNZHRXSA-N 0.000 claims 1
- ZDPSZHMSLVWWKX-MUUNZHRXSA-N [(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[3-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylphenyl]methanone Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2C[C@H]3CCCN3CC2)CC1 ZDPSZHMSLVWWKX-MUUNZHRXSA-N 0.000 claims 1
- HRCAYCQDIMSMJS-NDEPHWFRSA-N [(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[3-(4-benzhydrylpiperazin-1-yl)sulfonylphenyl]methanone Chemical compound C([C@@H]1CCCN1CC1)N1C(=O)C(C=1)=CC=CC=1S(=O)(=O)N(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HRCAYCQDIMSMJS-NDEPHWFRSA-N 0.000 claims 1
- GQMHURPKRZFOJV-QFIPXVFZSA-N [(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[3-[4-(4-fluorophenyl)piperazin-1-yl]sulfonylphenyl]methanone Chemical compound C1=CC(F)=CC=C1N1CCN(S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2C[C@@H]3CCCN3CC2)CC1 GQMHURPKRZFOJV-QFIPXVFZSA-N 0.000 claims 1
- ZDPSZHMSLVWWKX-NDEPHWFRSA-N [(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-[3-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylphenyl]methanone Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(S(=O)(=O)C=2C=C(C=CC=2)C(=O)N2C[C@@H]3CCCN3CC2)CC1 ZDPSZHMSLVWWKX-NDEPHWFRSA-N 0.000 claims 1
- FMJDPDFOYAFJHW-MUUNZHRXSA-N [3-[[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]sulfonyl]phenyl]-(4-benzhydrylpiperazin-1-yl)methanone Chemical compound C=1C=CC(S(=O)(=O)N2C[C@H]3CCCN3CC2)=CC=1C(=O)N(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 FMJDPDFOYAFJHW-MUUNZHRXSA-N 0.000 claims 1
- OUYFGDJNIFQCCM-MUUNZHRXSA-N [3-[[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]sulfonyl]phenyl]-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C(=O)C=2C=C(C=CC=2)S(=O)(=O)N2C[C@H]3CCCN3CC2)CC1 OUYFGDJNIFQCCM-MUUNZHRXSA-N 0.000 claims 1
- FMJDPDFOYAFJHW-NDEPHWFRSA-N [3-[[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]sulfonyl]phenyl]-(4-benzhydrylpiperazin-1-yl)methanone Chemical compound C=1C=CC(S(=O)(=O)N2C[C@@H]3CCCN3CC2)=CC=1C(=O)N(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 FMJDPDFOYAFJHW-NDEPHWFRSA-N 0.000 claims 1
- OUYFGDJNIFQCCM-NDEPHWFRSA-N [3-[[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]sulfonyl]phenyl]-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C(=O)C=2C=C(C=CC=2)S(=O)(=O)N2C[C@@H]3CCCN3CC2)CC1 OUYFGDJNIFQCCM-NDEPHWFRSA-N 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 206010053552 allodynia Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
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- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
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- 230000004054 inflammatory process Effects 0.000 claims 1
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- 238000000034 method Methods 0.000 claims 1
- PGTKRXNTBSUGKM-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(4-piperidin-1-ylpiperidine-1-carbonyl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)N2CCC(CC2)N2CCCCC2)=C1 PGTKRXNTBSUGKM-UHFFFAOYSA-N 0.000 claims 1
- TYCVFQIHNMKHJV-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(4-pyrrolidin-1-ylpiperidine-1-carbonyl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)N2CCC(CC2)N2CCCC2)=C1 TYCVFQIHNMKHJV-UHFFFAOYSA-N 0.000 claims 1
- FMHFQMSHZHILDG-OAQYLSRUSA-N n-[3-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]phenyl]-n-propan-2-yl-3-(trifluoromethyl)benzenesulfonamide Chemical compound C=1C=CC(C(=O)N2C[C@H]3CCCN3CC2)=CC=1N(C(C)C)S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 FMHFQMSHZHILDG-OAQYLSRUSA-N 0.000 claims 1
- WYKKYPQOAAYHTB-HSZRJFAPSA-N n-[4-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-chlorophenyl]-2,2-diphenylacetamide Chemical compound ClC1=CC(C(=O)N2C[C@H]3CCCN3CC2)=CC=C1NC(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 WYKKYPQOAAYHTB-HSZRJFAPSA-N 0.000 claims 1
- BBRCLJMUOZNGJS-QGZVFWFLSA-N n-[4-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-chlorophenyl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC=C(C(=O)N2C[C@H]3CCCN3CC2)C=C1Cl BBRCLJMUOZNGJS-QGZVFWFLSA-N 0.000 claims 1
- MHCUFMBGRRJYKY-OAQYLSRUSA-N n-[4-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-chlorophenyl]naphthalene-2-carboxamide Chemical compound C1CN2CCC[C@@H]2CN1C(=O)C1=CC=C(NC(=O)C=2C=C3C=CC=CC3=CC=2)C(Cl)=C1 MHCUFMBGRRJYKY-OAQYLSRUSA-N 0.000 claims 1
- CZWGPXLJPYDHGK-HSZRJFAPSA-N n-[4-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-methylphenyl]naphthalene-2-carboxamide Chemical compound C1CN2CCC[C@@H]2CN1C(=O)C1=CC=C(NC(=O)C=2C=C3C=CC=CC3=CC=2)C(C)=C1 CZWGPXLJPYDHGK-HSZRJFAPSA-N 0.000 claims 1
- RAGZMQXBGQELKC-HSZRJFAPSA-N n-[5-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-chlorophenyl]-2,2-diphenylacetamide Chemical compound ClC1=CC=C(C(=O)N2C[C@H]3CCCN3CC2)C=C1NC(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 RAGZMQXBGQELKC-HSZRJFAPSA-N 0.000 claims 1
- BLPCUCQQGPCUAP-QGZVFWFLSA-N n-[5-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-chlorophenyl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(C(=O)N2C[C@H]3CCCN3CC2)=CC=C1Cl BLPCUCQQGPCUAP-QGZVFWFLSA-N 0.000 claims 1
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| ES2527589T3 (es) | 2008-04-24 | 2015-01-27 | Msd K.K. | Inhibidor de la enzima de elongación de ácidos grasos de cadena larga que comprende un derivado de arilsulfonilo como principio activo |
| TW201028421A (en) * | 2009-01-15 | 2010-08-01 | Abbott Lab | Novel benzenesulfonamides as calcium channel blockers |
| US9296692B2 (en) * | 2011-09-15 | 2016-03-29 | Taipei Medical University | Use of indolyl and indolinyl hydroxamates for treating heart failure of neuronal injury |
| WO2013049164A1 (en) | 2011-09-29 | 2013-04-04 | Abbvie Inc. | SUBSTITUTED OCTAHYDROPYRROLO[1,2-a]PYRAZINES AS CALCIUM CHANNEL BLOCKERS |
| UY34349A (es) | 2011-09-29 | 2013-04-05 | Abb Vie Inc | OCTAHIDROPIRROLO[1,2-a]PIRAZINA SULFONAMIDAS SUSTITUIDAS COMO BLOQUEADORES DE CANALES DE CALCIO |
| US20130178477A1 (en) * | 2012-01-05 | 2013-07-11 | Abbvie Inc. | Methods of treating diabetic neuropathy using benzenesulfonamides |
| JP2016503007A (ja) | 2012-12-12 | 2016-02-01 | アッヴィ・インコーポレイテッド | 疼痛治療におけるカルシウムチャネル遮断薬として有用なジアゼピン誘導体 |
| KR102300576B1 (ko) * | 2013-09-10 | 2021-09-08 | 보드 오브 리전츠 더 유니버시티 오브 텍사스 시스템 | 절단된 선종성 결장 폴립증 (ａｐｃ) 단백질을 타겟화하는 치료제 |
| US9700549B2 (en) | 2013-10-03 | 2017-07-11 | David Wise | Compositions and methods for treating pelvic pain and other conditions |
| US10082496B2 (en) | 2014-09-10 | 2018-09-25 | Board Of Regents Of The University Of Texas System | Targeting emopamil binding protein (EBP) with small molecules that induce an abnormal feedback response by lowering endogenous cholesterol biosynthesis |
| DK3364993T3 (da) | 2015-10-22 | 2023-01-09 | Cavion Inc | Fremgangsmåder til behandling af angelman syndrom |
| CN110545806A (zh) | 2017-02-15 | 2019-12-06 | 卡维昂公司 | 钙通道抑制剂 |
| CN110770221B (zh) | 2017-04-26 | 2023-09-08 | 卡维昂公司 | 用于改善记忆和认知以及用于治疗记忆和认知障碍的方法 |
| TW202406538A (zh) | 2018-01-10 | 2024-02-16 | 美商克拉治療有限責任公司 | 包含苯基磺醯胺之醫藥組合物及其治療應用 |
| WO2020038435A1 (en) | 2018-08-24 | 2020-02-27 | Sunshine Lake Pharma Co., Ltd. | Pyridinylmethylenepiperidine derivatives and uses thereof |
| TWI879741B (zh) | 2018-10-03 | 2025-04-11 | 美商卡凡恩公司 | 以(r)-2-(4-異丙基苯基)-n-(1-(5-(2,2,2-三氟乙氧基)吡啶-2-基)乙基)乙醯胺治療自發性震顫 |
| AR116898A1 (es) * | 2018-10-30 | 2021-06-23 | H Lundbeck As | DERIVADOS DE ARILSULFONILPIRROLCARBOXAMIDA COMO ACTIVADORES DE CANALES DE POTASIO Kv3 |
| EP3996746A4 (en) | 2019-07-11 | 2023-08-23 | Praxis Precision Medicines, Inc. | T-TYPE CALCIUM CHANNEL MODULATOR FORMULATIONS AND METHODS OF USE THEREOF |
| AU2020311404A1 (en) * | 2019-07-11 | 2022-03-03 | Cura Therapeutics, Llc | Sulfone compounds and pharmaceutical compositions thereof, and their therapeutic applications for the treatment of neurodegenerative diseases |
| CN117229257B (zh) * | 2022-06-06 | 2026-01-30 | 中国药科大学 | 间氨磺酰苯甲酰胺类化合物及制法、药物组合物和应用 |
| WO2025255502A1 (en) | 2024-06-07 | 2025-12-11 | Cavion, Inc. | PYRIDYL AMIDE Cav3 CHANNEL MODULATORS |
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| EP1165508B1 (en) | 1999-04-07 | 2004-06-23 | The University of Virginia Patent Foundation | Anticancer calcium channel blockers |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| US7223754B2 (en) | 2003-03-10 | 2007-05-29 | Dynogen Pharmaceuticals, Inc. | Thiazolidinone, oxazolidinone, and imidazolone derivatives for treating lower urinary tract and related disorders |
| ATE482747T1 (de) * | 2003-04-11 | 2010-10-15 | High Point Pharmaceuticals Llc | Neue amide derivate und deren pharmazeutische verwendungen |
| DE602004012083T2 (de) * | 2003-04-15 | 2009-04-23 | Astrazeneca Ab | Neue Verbindungen, die als Verstärker von Glutamatrezeptoren dienen |
| EP1866298A2 (en) * | 2005-03-31 | 2007-12-19 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
| WO2007052843A1 (ja) * | 2005-11-04 | 2007-05-10 | Takeda Pharmaceutical Company Limited | 複素環アミド化合物およびその用途 |
| WO2008043183A1 (en) * | 2006-10-13 | 2008-04-17 | Neuromed Pharmaceuticals Ltd. | Cyclopropyl-piperazine compounds as calcium channel blockers |
| KR20100033981A (ko) * | 2007-06-03 | 2010-03-31 | 벤더르빌트 유니버시티 | 벤즈아미드 대사성 글루타민산염 수용체5 양성 알로스테릭 조절자 및 이의 제조 및 사용방법 |
| ES2527589T3 (es) | 2008-04-24 | 2015-01-27 | Msd K.K. | Inhibidor de la enzima de elongación de ácidos grasos de cadena larga que comprende un derivado de arilsulfonilo como principio activo |
| TW201028421A (en) * | 2009-01-15 | 2010-08-01 | Abbott Lab | Novel benzenesulfonamides as calcium channel blockers |
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