JP2018510218A5 - - Google Patents
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- JP2018510218A5 JP2018510218A5 JP2018500267A JP2018500267A JP2018510218A5 JP 2018510218 A5 JP2018510218 A5 JP 2018510218A5 JP 2018500267 A JP2018500267 A JP 2018500267A JP 2018500267 A JP2018500267 A JP 2018500267A JP 2018510218 A5 JP2018510218 A5 JP 2018510218A5
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- 150000001875 compounds Chemical class 0.000 claims 26
- 238000006243 chemical reaction Methods 0.000 claims 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 11
- 239000011780 sodium chloride Substances 0.000 claims 11
- -1 alkyl ketone Chemical class 0.000 claims 7
- 239000000376 reactant Substances 0.000 claims 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000010452 phosphate Substances 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000011261 inert gas Substances 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N Beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- QJYKUYUDWYBTAI-UHFFFAOYSA-N C=1C=CC=CC=1OBOC1=CC=CC=C1 Chemical compound C=1C=CC=CC=1OBOC1=CC=CC=C1 QJYKUYUDWYBTAI-UHFFFAOYSA-N 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N Diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims 1
- PWXJULSLLONQHY-UHFFFAOYSA-M N-phenylcarbamate Chemical compound [O-]C(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-M 0.000 claims 1
- DQCKKXVULJGBQN-XFWGSAIBSA-N Naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 claims 1
- 229960003086 Naltrexone Drugs 0.000 claims 1
- APSUXPSYBJVPPS-YAUKWVCOSA-N Norbinaltorphimine Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CC=2C=3C[C@]4(O)[C@]67CCN(CC8CC8)[C@@H]4CC=4C7=C(C(=CC=4)O)O[C@H]6C=3NC=25)O)CC1)O)CC1CC1 APSUXPSYBJVPPS-YAUKWVCOSA-N 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N OBO Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N Phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 1
- IIMIOEBMYPRQGU-UHFFFAOYSA-L Picoplatin Chemical group N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 229910052786 argon Inorganic materials 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N benzenesulfinylbenzene Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 229940077388 benzenesulfonate Drugs 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- NHFDIUPJVYYTLG-UHFFFAOYSA-N carbononitridic isocyanide Chemical compound [C-]#[N+]C#N NHFDIUPJVYYTLG-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 1
- PNJNEOZSJYVACY-UHFFFAOYSA-N diphenoxyborinate Chemical compound C=1C=CC=CC=1OB([O-])OC1=CC=CC=C1 PNJNEOZSJYVACY-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- 239000001307 helium Substances 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium(0) Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 150000007524 organic acids Chemical group 0.000 claims 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-M phenyl carbonate Chemical compound [O-]C(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-M 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Claims (31)
- 前記式Iの化合物がノル−ビナルトルフィミン(norBNI)である、請求項1に記載の方法。
- 前記ヒドラジン試薬が式H2N−N(R)2の化合物であって各RがHまたは独立に選択される置換基である、請求項1に記載の方法。
- 前記方法が、極性溶媒中で式IIの化合物としてのナルトレキソンまたはその塩をヒドラジンと反応させることによってノル−ビナルトルフィミン(norBNI)またはその塩を生成する、請求項3に記載の方法。
- 前記反応がワンポット合成として行われる、請求項1〜4のいずれか1項に記載の方法。
- 前記反応が副生成物のクロマトグラフィーによる分離または化学抽出を含まない、請求項1〜5のいずれか1項に記載の方法。
- 前記反応の前記生成物が、少なくとも約80%の式Iの化合物もしくはその塩、または少なくとも約90%の式Iの化合物もしくはその塩、または少なくとも約95%の式Iの化合物もしくはその塩、または少なくとも約99%の式Iの化合物もしくはその塩である、請求項1〜6のいずれか1項に記載の方法。
- 前記反応生成物が生成物全体の約20%未満で対応するアジンを含む、請求項7に記載の方法。
- 前記反応が約6時間未満継続する、請求項1〜8のいずれか1項に記載の方法。
- 前記反応が1〜約5時間継続する、請求項9に記載の方法。
- 前記反応が少なくとも約1kgの式IIの化合物を用いて行われる、請求項1〜10のいずれか1項に記載の方法。
- 前記反応における前記式IIの化合物の濃度が約0.3M以上である、請求項1〜11のいずれか1項に記載の方法。
- 前記反応における前記式IIの化合物の濃度が約0.1M〜約1Mである、請求項1〜11のいずれか1項に記載の方法。
- 前記反応が式IIの化合物に対して約0.1〜約10モル当量のヒドラジン反応物を含む、請求項1〜13のいずれか1項に記載の方法。
- 前記反応が前記式IIの化合物に対して約0.2〜約5モル当量のヒドラジン反応物を含む、請求項14に記載の方法。
- 前記反応が式IIの化合物に対して約2モル当量未満のヒドラジン反応物を含む、請求項15に記載の方法。
- 前記反応が式IIの化合物に対して約0.5モル当量のヒドラジン反応物を含む、請求項16に記載の方法。
- 前記反応溶媒が極性である、請求項1〜17のいずれか1項に記載の方法。
- 前記溶媒がDMF(ジメチルホルムアミド)、水、メタノール、エタノール、またはこれらの混合物から選択される、請求項18に記載の方法。
- 前記反応混合物に不活性ガスを吹き込むことを更に含み、前記不活性ガスは任意選択的にはアルゴン、窒素、またはヘリウムである、請求項1〜19のいずれか1項に記載の方法。
- 前記反応が触媒の存在下で行われる、請求項1〜20のいずれか1項に記載の方法。
- 前記触媒が有機酸である、請求項21に記載の方法。
- 前記触媒がメタンスルホン酸(MeSO3H)及び/または硫酸である、請求項21に記載の方法。
- 前記反応中の前記酸触媒が、前記式IIの化合物に対して約0.5〜約5モル当量である、請求項23に記載の方法。
- 前記反応が前記式IIの化合物に対して1モル当量未満のヒドラジン反応物を有し、前記反応が前記式IIの化合物に対して約3〜約5モル当量のMeSO3Hを含む、請求項24に記載の方法。
- 前記反応が約95℃〜約105℃で維持される、請求項1〜25のいずれか1項に記載の方法。
- 前記方法が前記式Iの化合物のクロマトグラフィーによる分離または抽出を含まない、請求項1〜26のいずれか1項に記載の方法。
- 前記式Iの化合物の回収が、前記反応生成物の沈殿剤を集め、前記生成物を医薬的に許容可能な塩に変換することを含む、請求項1〜27のいずれか1項に記載の方法。
- 前記塩が二塩化物塩、酒石酸塩、クエン酸塩、二酢酸塩、硫酸塩、リン酸塩、または混合塩である、請求項28に記載の方法。
- 前記式Iの化合物が式I(B)または式I(C)の化合物であり、
- 前記化合物が式I(B)の化合物であり、Yが塩化物アニオンまたは硫酸アニオンを含む、請求項30に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562134758P | 2015-03-18 | 2015-03-18 | |
US62/134,758 | 2015-03-18 | ||
PCT/US2016/023107 WO2016149608A1 (en) | 2015-03-18 | 2016-03-18 | Methods for the chemical synthesis of pyrrole-linked bivalent compounds, and compositions thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018510218A JP2018510218A (ja) | 2018-04-12 |
JP2018510218A5 true JP2018510218A5 (ja) | 2019-04-25 |
Family
ID=56919959
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018500267A Pending JP2018510218A (ja) | 2015-03-18 | 2016-03-18 | ピロールで結合している二価の化合物の化学合成方法、及びその組成物 |
Country Status (8)
Country | Link |
---|---|
US (2) | US10253034B2 (ja) |
EP (1) | EP3270916A4 (ja) |
JP (1) | JP2018510218A (ja) |
CN (1) | CN107613973A (ja) |
CA (1) | CA2978097A1 (ja) |
HK (1) | HK1250020A1 (ja) |
IL (1) | IL254454B (ja) |
WO (1) | WO2016149608A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10253034B2 (en) * | 2015-03-18 | 2019-04-09 | Avekshan, Llc. | Methods for the chemical synthesis of pyrrole-linked bivalent compounds, and compositions thereof |
WO2017038728A1 (ja) | 2015-08-28 | 2017-03-09 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4649200A (en) | 1986-05-08 | 1987-03-10 | Regents Of The University Of Minnesota | Substituted pyrroles with opioid receptor activity |
DE10218582A1 (de) | 2002-04-26 | 2003-11-06 | Bayer Ag | Zimtsäureamide |
US10226428B2 (en) | 2003-09-19 | 2019-03-12 | Sun Pharma Advanced Research Company Ltd. | Oral drug delivery system |
US9623023B2 (en) | 2012-10-22 | 2017-04-18 | The Florida State University Research Foundation, Incorporated | Class of non-stimulant treatment and ADHD and related disorders |
US10253034B2 (en) * | 2015-03-18 | 2019-04-09 | Avekshan, Llc. | Methods for the chemical synthesis of pyrrole-linked bivalent compounds, and compositions thereof |
-
2016
- 2016-03-18 US US15/558,808 patent/US10253034B2/en active Active
- 2016-03-18 CA CA2978097A patent/CA2978097A1/en not_active Abandoned
- 2016-03-18 WO PCT/US2016/023107 patent/WO2016149608A1/en active Application Filing
- 2016-03-18 JP JP2018500267A patent/JP2018510218A/ja active Pending
- 2016-03-18 CN CN201680016569.4A patent/CN107613973A/zh active Pending
- 2016-03-18 EP EP16765818.6A patent/EP3270916A4/en not_active Withdrawn
-
2017
- 2017-09-12 IL IL254454A patent/IL254454B/en not_active IP Right Cessation
-
2018
- 2018-07-23 HK HK18109533.5A patent/HK1250020A1/zh unknown
-
2019
- 2019-02-01 US US16/265,286 patent/US10654862B2/en active Active
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