JP2017508796A5 - - Google Patents
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- JP2017508796A5 JP2017508796A5 JP2016573684A JP2016573684A JP2017508796A5 JP 2017508796 A5 JP2017508796 A5 JP 2017508796A5 JP 2016573684 A JP2016573684 A JP 2016573684A JP 2016573684 A JP2016573684 A JP 2016573684A JP 2017508796 A5 JP2017508796 A5 JP 2017508796A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- substituted
- compound
- iron
- 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.)
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- 238000000034 method Methods 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims 10
- 125000003107 substituted aryl group Chemical group 0.000 claims 10
- -1 bicyclo [1.1.1] pentane compound Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000003153 chemical reaction reagent Substances 0.000 claims 7
- 150000004678 hydrides Chemical class 0.000 claims 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000005354 acylalkyl group Chemical group 0.000 claims 3
- 150000002506 iron compounds Chemical class 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- ZTXSPLGEGCABFL-UHFFFAOYSA-N 1.1.1-propellane Chemical compound C1C23CC31C2 ZTXSPLGEGCABFL-UHFFFAOYSA-N 0.000 claims 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 2
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 claims 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 150000003623 transition metal compounds Chemical class 0.000 claims 2
- JONIMGVUGJVFQD-UHFFFAOYSA-N (4-methylphenyl)sulfonylformonitrile Chemical compound CC1=CC=C(S(=O)(=O)C#N)C=C1 JONIMGVUGJVFQD-UHFFFAOYSA-N 0.000 claims 1
- RTAWPPLBLZFDNI-NTCAYCPXSA-N (e)-1-(benzenesulfonyl)-n-phenylmethoxymethanimine Chemical compound C=1C=CC=CC=1S(=O)(=O)\C=N\OCC1=CC=CC=C1 RTAWPPLBLZFDNI-NTCAYCPXSA-N 0.000 claims 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- 108010088249 Monogen Proteins 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 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
- MKCBRYIXFFGIKN-UHFFFAOYSA-N bicyclo[1.1.1]pentane Chemical group C1C2CC1C2 MKCBRYIXFFGIKN-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 claims 1
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 claims 1
- 230000026045 iodination Effects 0.000 claims 1
- 238000006192 iodination reaction Methods 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims 1
- CKFMJXZQTNRXGX-UHFFFAOYSA-L iron(2+);diperchlorate Chemical compound [Fe+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O CKFMJXZQTNRXGX-UHFFFAOYSA-L 0.000 claims 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims 1
- LNOZJRCUHSPCDZ-UHFFFAOYSA-L iron(ii) acetate Chemical compound [Fe+2].CC([O-])=O.CC([O-])=O LNOZJRCUHSPCDZ-UHFFFAOYSA-L 0.000 claims 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 claims 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 1
- 150000004843 oxaziridines Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims 1
- 229940116357 potassium thiocyanate Drugs 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical compound [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 claims 1
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical group CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- QFDUTPNKBRXHTC-UHFFFAOYSA-N zinc diazide Chemical compound [Zn++].[N-]=[N+]=[N-].[N-]=[N+]=[N-] QFDUTPNKBRXHTC-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461949733P | 2014-03-07 | 2014-03-07 | |
| US61/949,733 | 2014-03-07 | ||
| PCT/US2015/018886 WO2015134710A1 (en) | 2014-03-07 | 2015-03-05 | Propellane derivates and synthesis |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020038074A Division JP2020094059A (ja) | 2014-03-07 | 2020-03-05 | プロペラン誘導体および合成 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017508796A JP2017508796A (ja) | 2017-03-30 |
| JP2017508796A5 true JP2017508796A5 (enExample) | 2018-04-12 |
| JP6741343B2 JP6741343B2 (ja) | 2020-08-19 |
Family
ID=54055863
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016573684A Active JP6741343B2 (ja) | 2014-03-07 | 2015-03-05 | プロペラン誘導体および合成 |
| JP2020038074A Withdrawn JP2020094059A (ja) | 2014-03-07 | 2020-03-05 | プロペラン誘導体および合成 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020038074A Withdrawn JP2020094059A (ja) | 2014-03-07 | 2020-03-05 | プロペラン誘導体および合成 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10654812B2 (enExample) |
| EP (1) | EP3114107B1 (enExample) |
| JP (2) | JP6741343B2 (enExample) |
| KR (1) | KR102401840B1 (enExample) |
| CN (2) | CN106232567B (enExample) |
| CA (1) | CA2942144C (enExample) |
| TW (1) | TWI671281B (enExample) |
| WO (1) | WO2015134710A1 (enExample) |
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| JP6506248B2 (ja) | 2013-03-14 | 2019-04-24 | ゾーン・ロイヤリティズ・アンド・マイルストーンズ・エルエルシー | 二環式鎮痛化合物 |
| KR102380609B1 (ko) | 2013-12-12 | 2022-03-30 | 리커리엄 아이피 홀딩스, 엘엘씨 | 바이사이클릭 알킬 화합물 및 합성 |
| US10654812B2 (en) | 2014-03-07 | 2020-05-19 | Recurium Ip Holdings Llc | Propellane derivates and synthesis |
| KR20170048588A (ko) * | 2014-09-17 | 2017-05-08 | 카리라 파마슈티컬스, 아이앤씨. | 바이사이클릭 화합물 |
| CN109879859B (zh) | 2015-07-06 | 2022-01-25 | 吉利德科学公司 | Cot调节剂及其使用方法 |
| NZ750265A (en) | 2016-08-23 | 2021-03-26 | Recurium Ip Holdings Llc | Methods for cross coupling |
| WO2018107072A1 (en) | 2016-12-08 | 2018-06-14 | Board Of Regents, The University Of Texas System | Bicyclo[1.1.1]pentane inhibitors of dual leucine zipper (dlk) kinase for the treatment of disease |
| MX389668B (es) | 2017-05-15 | 2025-03-20 | Recurium Ip Holdings Llc | Compuestos biciclo[1.1.1]pentilo sustituidos y uso de los mismos para el tratamiento del dolor y fiebre. |
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| CN113264843B (zh) * | 2021-04-15 | 2022-09-27 | 台州学院 | 一种3-氨基二环[1.1.1]戊烷-1-羧酸酯类衍生物的合成方法 |
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| TW201609671A (zh) | 2013-12-20 | 2016-03-16 | 標誌製藥公司 | 經取代之二胺基嘧啶基化合物、其組合物及使用其之治療方法 |
| US10654812B2 (en) | 2014-03-07 | 2020-05-19 | Recurium Ip Holdings Llc | Propellane derivates and synthesis |
| US9603850B2 (en) | 2014-04-11 | 2017-03-28 | The University Of North Carolina At Chapel Hill | MerTK-specific pyrazolopyrimidine compounds |
| EP3131891A1 (en) | 2014-04-15 | 2017-02-22 | Pfizer Inc. | Tropomyosin-related kinase inhibitors containing both a 1h-pyrazole and a pyrimidine moiety |
| MX2016013812A (es) | 2014-04-24 | 2017-03-09 | Novartis Ag | Derivados de amino-pirazina como inhibidores de fosfatidil-inositol-3-cinasa. |
| BR112017002001B1 (pt) | 2014-07-31 | 2022-10-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Compostos e composição farmacêutica |
| KR20170048588A (ko) | 2014-09-17 | 2017-05-08 | 카리라 파마슈티컬스, 아이앤씨. | 바이사이클릭 화합물 |
-
2015
- 2015-03-05 US US15/123,898 patent/US10654812B2/en active Active
- 2015-03-05 CN CN201580020861.9A patent/CN106232567B/zh active Active
- 2015-03-05 CA CA2942144A patent/CA2942144C/en active Active
- 2015-03-05 JP JP2016573684A patent/JP6741343B2/ja active Active
- 2015-03-05 EP EP15757721.4A patent/EP3114107B1/en active Active
- 2015-03-05 CN CN202110430501.3A patent/CN113336653A/zh active Pending
- 2015-03-05 WO PCT/US2015/018886 patent/WO2015134710A1/en not_active Ceased
- 2015-03-05 KR KR1020167027508A patent/KR102401840B1/ko active Active
- 2015-03-06 TW TW104107323A patent/TWI671281B/zh active
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2020
- 2020-03-05 JP JP2020038074A patent/JP2020094059A/ja not_active Withdrawn
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