JP2013534208A5 - - Google Patents
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- Publication number
- JP2013534208A5 JP2013534208A5 JP2013519642A JP2013519642A JP2013534208A5 JP 2013534208 A5 JP2013534208 A5 JP 2013534208A5 JP 2013519642 A JP2013519642 A JP 2013519642A JP 2013519642 A JP2013519642 A JP 2013519642A JP 2013534208 A5 JP2013534208 A5 JP 2013534208A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- hydroxy
- methyl
- alkyl
- 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
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 215
- 239000001257 hydrogen Substances 0.000 claims description 215
- 150000002431 hydrogen Chemical group 0.000 claims description 145
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 133
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 101
- -1 hydroxyalkylamines Chemical group 0.000 claims description 96
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000004423 acyloxy group Chemical group 0.000 claims description 66
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 57
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 42
- 125000002252 acyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000001475 halogen functional group Chemical group 0.000 claims description 27
- 229930194542 Keto Natural products 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 26
- 125000000468 ketone group Chemical group 0.000 claims description 26
- 125000005354 acylalkyl group Chemical group 0.000 claims description 23
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 23
- 208000002193 Pain Diseases 0.000 claims description 21
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000003944 tolyl group Chemical group 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen 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
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 230000000472 traumatic effect Effects 0.000 claims description 4
- JNWRCNXXCLSNJN-UHFFFAOYSA-N 1-(dimethylamino)cyclohexan-1-ol Chemical compound CN(C)C1(O)CCCCC1 JNWRCNXXCLSNJN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 39
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical compound C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 description 18
- 0 *c1cc(CCN(*)[C@@]2CC3=CC=C(*)I(*)=C3)c2cc1 Chemical compound *c1cc(CCN(*)[C@@]2CC3=CC=C(*)I(*)=C3)c2cc1 0.000 description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000012848 Dextrorphan Substances 0.000 description 1
- JAQUASYNZVUNQP-PVAVHDDUSA-N dextrorphan Chemical compound C1C2=CC=C(O)C=C2[C@@]23CCN(C)[C@@H]1[C@H]2CCCC3 JAQUASYNZVUNQP-PVAVHDDUSA-N 0.000 description 1
- 229950006878 dextrorphan Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/837,545 US20110015219A1 (en) | 2009-07-16 | 2010-07-16 | (+)-Morphinans as Antagonists of Toll-Like Receptor 9 and Therapeutic Uses Thereof |
| US12/837,545 | 2010-07-16 | ||
| US12/975,407 US9562014B2 (en) | 2009-07-16 | 2010-12-22 | (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof |
| US12/975,407 | 2010-12-22 | ||
| PCT/US2010/061699 WO2012008984A1 (en) | 2010-07-16 | 2010-12-22 | (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013534208A JP2013534208A (ja) | 2013-09-02 |
| JP2013534208A5 true JP2013534208A5 (enExample) | 2014-01-30 |
| JP5911484B2 JP5911484B2 (ja) | 2016-04-27 |
Family
ID=43754707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013519642A Expired - Fee Related JP5911484B2 (ja) | 2010-07-16 | 2010-12-22 | トール様受容体９のアンタゴニストとしての（＋）−モルフィナンおよびその治療的使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US9562014B2 (enExample) |
| EP (1) | EP2593095B1 (enExample) |
| JP (1) | JP5911484B2 (enExample) |
| AU (1) | AU2010357625B2 (enExample) |
| CA (1) | CA2768199C (enExample) |
| ES (1) | ES2728701T3 (enExample) |
| PL (1) | PL2593095T3 (enExample) |
| WO (1) | WO2012008984A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10363251B2 (en) | 2009-07-16 | 2019-07-30 | Mallinckrodt Llc | (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof |
| US8829020B2 (en) | 2009-07-16 | 2014-09-09 | Mallinckrodt Llc | Compounds and compositions for use in phototherapy and in treatment of ocular neovascular disease and cancers |
| PL2453895T3 (pl) * | 2009-07-16 | 2018-10-31 | Mallinckrodt Llc | (+)-morfinany jako antagonisty receptora toll-like 9 i ich zastosowania terapeutyczne |
| WO2012008984A1 (en) | 2010-07-16 | 2012-01-19 | Mallinckrodt Llc | (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof |
| IN2014DN03009A (enExample) | 2011-10-26 | 2015-05-08 | Kempharm Inc | |
| CN102579444A (zh) * | 2012-01-21 | 2012-07-18 | 张有成 | 青藤碱在制备抑制肿瘤侵袭转移的药物中的应用 |
| GB201308440D0 (en) | 2013-05-10 | 2013-06-19 | Dalgleish Angus | Therapeutic |
| WO2015082932A1 (en) | 2013-12-05 | 2015-06-11 | The University Of Bath | Novel opioid compounds and their uses |
| CA2969221C (en) | 2014-12-02 | 2021-01-12 | Travis Mickle | Benzoic acid, benzoic acid derivatives and heteroaryl carboxylic acid conjugates of oxymorphone, prodrugs, methods of making and use thereof |
| JP6702184B2 (ja) * | 2015-03-24 | 2020-05-27 | 東レ株式会社 | 低アルブミン血症の改善剤 |
| US9757372B2 (en) * | 2015-03-25 | 2017-09-12 | Taiwanj Pharmaceuticals Co., Ltd. | Toll-like receptor 4 antagonists and use in autoimmune liver diseases |
| US10653687B2 (en) | 2015-11-18 | 2020-05-19 | INSERM (Institut National de la Santé et de la Recherche Médicale | Methods and pharmaceutical compostions for treating rhabdomyolysis |
| CN110290792A (zh) * | 2017-01-05 | 2019-09-27 | 景凯生物科技股份有限公司 | 吗啡喃衍生物和其用于治疗自体免疫、发炎或感染相关的障碍的组合物 |
| WO2019018354A1 (en) * | 2017-07-18 | 2019-01-24 | Merck Patent Gmbh | ANTAGONISTS OF TLR7 / 8 AND USES THEREOF |
| CA3091826A1 (en) * | 2018-02-23 | 2019-08-29 | Rhodes Technologies | Novel opioid compounds and uses thereof |
| CN109288840A (zh) * | 2018-11-23 | 2019-02-01 | 中国科学院长春应用化学研究所 | 二元纳曲酮衍生物的应用 |
| US12637411B2 (en) | 2019-01-30 | 2026-05-26 | Mggm Llc | Structurally modified opioids for prevention and treatment of diseases and conditions |
| EP4125990A4 (en) * | 2020-03-24 | 2024-07-03 | University of Padova | MORPHINE ISOMERS AND THEIR STRUCTURAL MODIFICATIONS AS NMDAR ANTAGONISTS AND NEUROPLASTIGENS |
| CN115260098B (zh) * | 2022-06-09 | 2024-06-04 | 澳门科技大学 | Abcb5抑制剂在制备多耐药性类风湿性关节炎治疗药物中的应用 |
| JP2026086955A (ja) * | 2023-03-29 | 2026-05-27 | 日本ケミファ株式会社 | スピロ環状モルヒナン誘導体 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55133360A (en) * | 1979-04-03 | 1980-10-17 | Tatsuya Shono | Preparation of cyclic amine |
| US4521601A (en) | 1981-05-20 | 1985-06-04 | The United States Of America As Represented By The Department Of Health & Human Services | Practical total synthesis unnatural enantiomers of opium-derived morphinans |
| HU197750B (en) * | 1984-07-17 | 1989-05-29 | Alkaloida Vegyeszeti Gyar | Process for n-demethylation of morphine alkaloids |
| US5668285A (en) | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
| PT95069B (pt) | 1989-08-24 | 1997-10-31 | Searle & Co | Processo para a preparacao de (+)-isomeros de derivados de endoetano/endoetanoepoximofinano, uteis como agentes anti-tussicos |
| JPH04273880A (ja) * | 1991-02-28 | 1992-09-30 | Ono Pharmaceut Co Ltd | ジヒドロモルヒネ誘導体 |
| JP2525552B2 (ja) * | 1992-01-23 | 1996-08-21 | 東レ株式会社 | モルヒナン誘導体および医薬用途 |
| NZ268969A (en) * | 1993-07-23 | 1997-06-24 | Toray Industries | Morphinan derivatives and pharmaceutical compositions |
| US5919826A (en) * | 1996-10-24 | 1999-07-06 | Algos Pharmaceutical Corporation | Method of alleviating pain |
| ATE292625T1 (de) | 2000-10-31 | 2005-04-15 | Rensselaer Polytech Inst | 8-substituierte 2,6-methano-3-benzazocine und 3- substituierte morphinane als opioidrezeptorbindende agenzien |
| WO2002080918A1 (en) | 2001-04-02 | 2002-10-17 | Toray Industries, Inc. | Remedial or prophylactic agent for frequent urination or urinary incontinence |
| US20040033253A1 (en) * | 2002-02-19 | 2004-02-19 | Ihor Shevchuk | Acyl opioid antagonists |
| GB2392670A (en) | 2002-09-03 | 2004-03-10 | Stylacats Ltd | (+)-Morphine production |
| US7238791B1 (en) * | 2005-12-16 | 2007-07-03 | Roche Diagnostics Operations, Inc. | 6-monoacetylmorphine derivatives useful in immunoassay |
| EP2012772A1 (en) | 2006-04-26 | 2009-01-14 | The Uab Research Foundation | Reducing cancer cell invasion using an inhibitor of toll like receptor signaling |
| CN101066948B (zh) | 2007-05-30 | 2012-01-04 | 广东工业大学 | 青藤碱催化氢化还原制备氢化青藤碱的方法 |
| JP2010533719A (ja) | 2007-07-17 | 2010-10-28 | マリンクロッド・インコーポレイテッド | 還元的アミノ化によるｎ−アルキル化オピエートの調製 |
| JP2010536787A (ja) | 2007-08-15 | 2010-12-02 | イデラ ファーマシューティカルズ インコーポレイテッド | Ｔｏｌｌ様受容体モジュレータ |
| CA2702680A1 (en) * | 2007-10-18 | 2009-04-23 | Aiko Biotechnology | Combination analgesic employing opioid and neutral antagonist |
| US20110251229A1 (en) * | 2007-10-30 | 2011-10-13 | The Regents Of The University Of Colorado | (+)-opioids and methods of use |
| JP5688974B2 (ja) | 2007-12-17 | 2015-03-25 | マリンクロッド エルエルシー | （＋）−オピエートの生成のためのプロセスおよび化合物 |
| WO2009078986A1 (en) | 2007-12-17 | 2009-06-25 | Mallinckrodt Inc. | Process for the preparation of buprenorphine and derivatives of buprenorphine |
| CN101265266B (zh) | 2008-04-23 | 2011-12-14 | 南京大学 | 青藤碱衍生物及其制备方法和应用 |
| NZ589963A (en) | 2008-06-17 | 2011-08-26 | Mallinckrodt Inc | Processes for the preparation of 6- beta-hydroxy morphinan compounds |
| EP2313400A4 (en) | 2008-07-10 | 2011-12-28 | Human Biomolecular Res Inst | SYNTHESIS OF METABOLIC STRENGTHS FOR ALCOHOL AND DRUG ABUSE |
| NZ591756A (en) | 2008-09-16 | 2013-04-26 | Mallinckrodt Llc | Processes for the synthesis of five and six membered heterocyclic rings |
| CN102227433B (zh) | 2008-09-30 | 2015-01-07 | 马林克罗特有限公司 | 烷基化吗啡喃衍生物的仲胺基团的方法 |
| SI2352494T1 (sl) * | 2008-10-30 | 2019-12-31 | Gruenenthal Gmbh | Nove in potentne dozirne oblike tapentadola |
| KR20100090155A (ko) * | 2009-02-05 | 2010-08-13 | 엘지전자 주식회사 | 이동 단말기 및 그의 프레즌스 정보 처리방법 |
| US8946419B2 (en) | 2009-02-23 | 2015-02-03 | Mallinckrodt Llc | (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives |
| US8563724B2 (en) * | 2009-02-23 | 2013-10-22 | Mallinckrodt Llc | (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives |
| CN102325777B (zh) | 2009-02-23 | 2015-08-12 | 马林克罗特公司 | (+)-吗啡喃*n-氧化物及其制备方法 |
| CA2764915C (en) * | 2009-06-11 | 2017-07-11 | Mallinckrodt Llc | Preparation of 6-alpha-amino n-substituted morphinans by catalytic hydrogen transfer |
| PL2453895T3 (pl) * | 2009-07-16 | 2018-10-31 | Mallinckrodt Llc | (+)-morfinany jako antagonisty receptora toll-like 9 i ich zastosowania terapeutyczne |
| WO2012008984A1 (en) | 2010-07-16 | 2012-01-19 | Mallinckrodt Llc | (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof |
-
2010
- 2010-12-22 WO PCT/US2010/061699 patent/WO2012008984A1/en not_active Ceased
- 2010-12-22 JP JP2013519642A patent/JP5911484B2/ja not_active Expired - Fee Related
- 2010-12-22 CA CA2768199A patent/CA2768199C/en active Active
- 2010-12-22 AU AU2010357625A patent/AU2010357625B2/en active Active
- 2010-12-22 ES ES10805351T patent/ES2728701T3/es active Active
- 2010-12-22 PL PL10805351T patent/PL2593095T3/pl unknown
- 2010-12-22 US US12/975,407 patent/US9562014B2/en active Active
- 2010-12-22 EP EP10805351.3A patent/EP2593095B1/en active Active
-
2016
- 2016-09-02 US US15/255,979 patent/US10604488B2/en active Active
-
2020
- 2020-02-03 US US16/779,796 patent/US11142502B2/en active Active
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