JP2012530084A - ジアザホモアダマンタン誘導体およびこの使用方法 - Google Patents
ジアザホモアダマンタン誘導体およびこの使用方法 Download PDFInfo
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- JP2012530084A JP2012530084A JP2012515322A JP2012515322A JP2012530084A JP 2012530084 A JP2012530084 A JP 2012530084A JP 2012515322 A JP2012515322 A JP 2012515322A JP 2012515322 A JP2012515322 A JP 2012515322A JP 2012530084 A JP2012530084 A JP 2012530084A
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- Prior art keywords
- diazatricyclo
- undecane
- pyridin
- alkyl
- haloalkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 170
- 150000001875 compounds Chemical class 0.000 claims abstract description 335
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 101
- -1 1,3-thiazolyl Chemical group 0.000 claims description 86
- 208000002193 Pain Diseases 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 68
- 230000036407 pain Effects 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 150000002431 hydrogen Chemical group 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 27
- RDJCJGGWKBHSFT-UHFFFAOYSA-N 4-[5-(3-fluoro-4-methoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.13,8]undecane Chemical compound C1=C(F)C(OC)=CC=C1C1=CN=CC(N2C3CC4CC(CN(C4)C3)C2)=C1 RDJCJGGWKBHSFT-UHFFFAOYSA-N 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 22
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- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims description 18
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- PUKDMCGPIQUYKV-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.13,8]undecane Chemical compound C1=CC(OC)=CC=C1C1=CN=C(N2C3CC4CC(CN(C4)C3)C2)S1 PUKDMCGPIQUYKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
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- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- QSJXHKFTZFDXSD-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-5-one Chemical compound O=C1NC(C2)CN3CC1CC2C3 QSJXHKFTZFDXSD-UHFFFAOYSA-N 0.000 claims description 8
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- 208000004550 Postoperative Pain Diseases 0.000 claims description 7
- 231100000869 headache Toxicity 0.000 claims description 7
- 210000004558 lewy body Anatomy 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
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- KSQMYSXLVHHAPH-UHFFFAOYSA-N C1C2CN(C3)CC1CC3CN2C1=CC=C(C=2C=C3C=CSC3=CC=2)N=N1 Chemical compound C1C2CN(C3)CC1CC3CN2C1=CC=C(C=2C=C3C=CSC3=CC=2)N=N1 KSQMYSXLVHHAPH-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001624 naphthyl group Chemical group 0.000 claims description 6
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- QZFQDVLIAQNSLM-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(thieno[2,3-c]pyridin-5-yl)methanone Chemical compound C=1C=2C=CSC=2C=NC=1C(=O)N1CC(C2)CN3CC1CC2C3 QZFQDVLIAQNSLM-UHFFFAOYSA-N 0.000 claims description 5
- HTIKEGIKZQYHTO-UHFFFAOYSA-N 2-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-5-phenyl-1,3,4-oxadiazole Chemical compound C1C(C2)CC3CN2CC1CN3C(O1)=NN=C1C1=CC=CC=C1 HTIKEGIKZQYHTO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- RVITZLSAWXNUEF-UHFFFAOYSA-N 4-(6-phenylpyridazin-3-yl)-1,4-diazatricyclo[4.3.1.13,8]undecane Chemical compound C1C(C2)CC3CN2CC1CN3C(N=N1)=CC=C1C1=CC=CC=C1 RVITZLSAWXNUEF-UHFFFAOYSA-N 0.000 claims description 5
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 5
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- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
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- 208000000450 Pelvic Pain Diseases 0.000 claims description 5
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- 208000008765 Sciatica Diseases 0.000 claims description 5
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 206010053552 allodynia Diseases 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000009610 hypersensitivity Effects 0.000 claims description 5
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- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 4
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 4
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- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- UFEPSYPWWUXPPQ-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound C1=C(Cl)C(F)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 UFEPSYPWWUXPPQ-UHFFFAOYSA-N 0.000 claims description 3
- APMHSXJCMXBHJY-UHFFFAOYSA-N (3-chlorophenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound ClC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 APMHSXJCMXBHJY-UHFFFAOYSA-N 0.000 claims description 3
- GVOXZLAEIZBSPH-UHFFFAOYSA-N (5-chloro-2-fluorophenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound FC1=CC=C(Cl)C=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 GVOXZLAEIZBSPH-UHFFFAOYSA-N 0.000 claims description 3
- ZAJVRLDMHXFICV-UHFFFAOYSA-N (5-chloro-2-methoxyphenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound COC1=CC=C(Cl)C=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 ZAJVRLDMHXFICV-UHFFFAOYSA-N 0.000 claims description 3
- XRRUCMXUIAATKQ-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1,2,3,4-tetrahydronaphthalen-2-yl)methanone Chemical compound C1CC2=CC=CC=C2CC1C(=O)N1CC(C2)CN3CC1CC2C3 XRRUCMXUIAATKQ-UHFFFAOYSA-N 0.000 claims description 3
- YNRCDWSRGVZPCH-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1H-indazol-3-yl)methanone Chemical compound N=1NC2=CC=CC=C2C=1C(=O)N1CC(C2)CN3CC1CC2C3 YNRCDWSRGVZPCH-UHFFFAOYSA-N 0.000 claims description 3
- PCPNXIMJIARXAV-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1H-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)N1CC(C2)CN3CC1CC2C3 PCPNXIMJIARXAV-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21847909P | 2009-06-19 | 2009-06-19 | |
| US61/218,479 | 2009-06-19 | ||
| PCT/CN2010/000889 WO2010145208A1 (en) | 2009-06-19 | 2010-06-18 | Diazahomoadamantane derivatives and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012530084A true JP2012530084A (ja) | 2012-11-29 |
| JP2012530084A5 JP2012530084A5 (enExample) | 2013-08-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012515322A Ceased JP2012530084A (ja) | 2009-06-19 | 2010-06-18 | ジアザホモアダマンタン誘導体およびこの使用方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8846661B2 (enExample) |
| EP (1) | EP2443122B1 (enExample) |
| JP (1) | JP2012530084A (enExample) |
| KR (1) | KR20120044978A (enExample) |
| CN (1) | CN102459268A (enExample) |
| AU (1) | AU2010262643B2 (enExample) |
| BR (1) | BRPI1015043A2 (enExample) |
| CA (1) | CA2765466A1 (enExample) |
| IL (2) | IL216883A (enExample) |
| MX (1) | MX2011014019A (enExample) |
| NZ (1) | NZ597511A (enExample) |
| PE (1) | PE20121066A1 (enExample) |
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| WO2016100184A1 (en) | 2014-12-16 | 2016-06-23 | Forum Pharmaceuticals, Inc. | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| JP2018516973A (ja) | 2015-06-10 | 2018-06-28 | フォーラム・ファーマシューティカルズ・インコーポレイテッドＦｏｒｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | α７−ニコチン性アセチルコリン受容体のアゴニストとしてのアミノベンゾイソオキサゾール化合物 |
| EP3334740A4 (en) | 2015-08-12 | 2019-02-06 | Axovant Sciences GmbH | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF ALPHA 7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| AU2018282154B2 (en) | 2017-06-05 | 2022-04-07 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| WO2019005993A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| AU2019219678A1 (en) * | 2018-02-08 | 2020-08-27 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Heteroaryl compounds, pharmaceutical compositions thereof, and their therapeutic use |
| BR112020019373A2 (pt) | 2018-03-27 | 2020-12-29 | Ptc Therapeutics, Inc. | Compostos para o tratamento da doença de hutington |
| WO2020005877A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| IL279688B2 (en) | 2018-06-27 | 2025-01-01 | Ptc Therapeutics Inc | Heterocyclic and heteroaryl compounds for the treatment of Huntington's disease |
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| JP2019500352A (ja) * | 2015-12-10 | 2019-01-10 | ピーティーシー セラピューティクス， インコーポレイテッド | ハンチントン病の治療方法 |
| JP2021042211A (ja) * | 2015-12-10 | 2021-03-18 | ピーティーシー セラピューティクス， インコーポレイテッド | ハンチントン病の治療方法 |
| JP7025508B2 (ja) | 2015-12-10 | 2022-02-24 | ピーティーシー セラピューティクス， インコーポレイテッド | ハンチントン病の治療方法 |
Also Published As
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| KR20120044978A (ko) | 2012-05-08 |
| NZ597511A (en) | 2014-01-31 |
| IL216883A0 (en) | 2012-02-29 |
| AU2010262643A1 (en) | 2012-02-02 |
| CA2765466A1 (en) | 2010-12-23 |
| WO2010145208A1 (en) | 2010-12-23 |
| EP2443122B1 (en) | 2014-03-05 |
| RU2012101784A (ru) | 2013-07-27 |
| CN102459268A (zh) | 2012-05-16 |
| US20100324027A1 (en) | 2010-12-23 |
| MX2011014019A (es) | 2012-02-22 |
| RU2549551C2 (ru) | 2015-04-27 |
| US8846661B2 (en) | 2014-09-30 |
| EP2443122A1 (en) | 2012-04-25 |
| BRPI1015043A2 (pt) | 2019-07-09 |
| SG176921A1 (en) | 2012-01-30 |
| IL236830A0 (en) | 2015-03-31 |
| AU2010262643B2 (en) | 2015-02-19 |
| EP2443122A4 (en) | 2012-12-19 |
| RU2015110025A (ru) | 2015-08-20 |
| IL216883A (en) | 2015-02-26 |
| PE20121066A1 (es) | 2012-09-13 |
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