JP2016537363A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016537363A5 JP2016537363A5 JP2016530933A JP2016530933A JP2016537363A5 JP 2016537363 A5 JP2016537363 A5 JP 2016537363A5 JP 2016530933 A JP2016530933 A JP 2016530933A JP 2016530933 A JP2016530933 A JP 2016530933A JP 2016537363 A5 JP2016537363 A5 JP 2016537363A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- item
- reacting
- produce
- 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
- 150000001875 compounds Chemical class 0.000 claims description 357
- 238000000034 method Methods 0.000 claims description 127
- 239000003960 organic solvent Substances 0.000 claims description 83
- 239000007800 oxidant agent Substances 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical class OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N methyl tert-butyl ether Substances COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 29
- -1 borane compound Chemical class 0.000 claims description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims description 20
- 239000003638 chemical reducing agent Substances 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 230000001590 oxidative effect Effects 0.000 claims description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 16
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical compound O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- 229910000085 borane Inorganic materials 0.000 claims description 10
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 10
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 claims description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- LDLRZFBSMOWZOS-FQEVSTJZSA-N (4s)-2-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine Chemical compound C1([C@@H]2NB(OC2(C=2C=CC=CC=2)C=2C=CC=CC=2)C)=CC=CC=C1 LDLRZFBSMOWZOS-FQEVSTJZSA-N 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- OHENQANLQNOMAO-UHFFFAOYSA-N oxaborole Chemical compound O1B=CC=C1 OHENQANLQNOMAO-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 5
- GXAMQZFEKIDKAP-JOCHJYFZSA-N (3ar)-1,3,3-triphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole Chemical compound N1([C@@H]2CCC1)B(C=1C=CC=CC=1)OC2(C=1C=CC=CC=1)C1=CC=CC=C1 GXAMQZFEKIDKAP-JOCHJYFZSA-N 0.000 description 4
- VMKAFJQFKBASMU-QGZVFWFLSA-N (r)-2-methyl-cbs-oxazaborolidine Chemical compound C([C@@H]12)CCN1B(C)OC2(C=1C=CC=CC=1)C1=CC=CC=C1 VMKAFJQFKBASMU-QGZVFWFLSA-N 0.000 description 4
- FVQDOKQWEOZEBQ-UHFFFAOYSA-N B1NCCO1 Chemical compound B1NCCO1 FVQDOKQWEOZEBQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HRBGUGQWTMBDTR-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)benzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C(C(C)C)=C1C(C)C HRBGUGQWTMBDTR-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361903730P | 2013-11-13 | 2013-11-13 | |
| US61/903,730 | 2013-11-13 | ||
| PCT/US2014/064519 WO2015073314A1 (en) | 2013-11-13 | 2014-11-07 | Amine salts of a prostacyclin analog |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016537363A JP2016537363A (ja) | 2016-12-01 |
| JP2016537363A5 true JP2016537363A5 (enExample) | 2017-12-14 |
| JP6373378B2 JP6373378B2 (ja) | 2018-08-15 |
Family
ID=51982791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016530933A Expired - Fee Related JP6373378B2 (ja) | 2013-11-13 | 2014-11-07 | プロスタサイクリン類似体のアミン塩 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9890104B2 (enExample) |
| EP (1) | EP3068752A1 (enExample) |
| JP (1) | JP6373378B2 (enExample) |
| KR (1) | KR20160086837A (enExample) |
| CN (1) | CN105722812B (enExample) |
| AU (1) | AU2014349000B2 (enExample) |
| CA (1) | CA2930574A1 (enExample) |
| IL (1) | IL245357B (enExample) |
| WO (1) | WO2015073314A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104837806A (zh) * | 2012-12-07 | 2015-08-12 | 开曼化学股份有限公司 | 前列环素类似物的合成方法 |
| EP3712142B1 (en) | 2013-01-11 | 2022-07-06 | Corsair Pharma, Inc. | Prodrugs of treprostinil |
| US9505737B2 (en) | 2013-01-11 | 2016-11-29 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| US9643911B2 (en) | 2015-06-17 | 2017-05-09 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| US9394227B1 (en) | 2015-06-17 | 2016-07-19 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| KR101830693B1 (ko) * | 2016-04-28 | 2018-02-21 | 연성정밀화학(주) | 트레프로스티닐의 제조방법 및 이를 위한 중간체 |
| CN107602376A (zh) * | 2017-10-30 | 2018-01-19 | 上海泰坦科技股份有限公司 | 一种曲列前尼尔的合成方法 |
| CA3112986C (en) * | 2018-09-18 | 2024-06-18 | Eli Lilly And Company | Erbumine salt of treprostinil |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306075A (en) | 1980-03-28 | 1981-12-15 | The Upjohn Company | Composition and process |
| JPH09100294A (ja) * | 1995-10-02 | 1997-04-15 | Tsumura & Co | 血管新生阻害剤 |
| US6441245B1 (en) | 1997-10-24 | 2002-08-27 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| US6700025B2 (en) | 2001-01-05 | 2004-03-02 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| KR20160048222A (ko) * | 2007-12-17 | 2016-05-03 | 유나이티드 세러퓨틱스 코오포레이션 | 레모둘린?의 활성 성분인 트레프로스티닐의 개선된 제조 방법 |
| CA2777070C (en) | 2010-06-03 | 2019-11-05 | United Therapeutics Corporation | Treprostinil production |
| CA2710726C (en) | 2010-07-22 | 2016-02-23 | Alphora Research Inc. | Synthesis of treprostinil and intermediates useful therein |
| EP2622354A1 (en) * | 2010-10-01 | 2013-08-07 | Rigshospitalet | Compounds capable of modulating/preserving endothelial integrity for use in prevention or treatment of acute traumatic coagulopathy and resuscitated cardiac arrest |
| CN104837806A (zh) * | 2012-12-07 | 2015-08-12 | 开曼化学股份有限公司 | 前列环素类似物的合成方法 |
-
2014
- 2014-11-07 EP EP14803019.0A patent/EP3068752A1/en not_active Withdrawn
- 2014-11-07 WO PCT/US2014/064519 patent/WO2015073314A1/en not_active Ceased
- 2014-11-07 KR KR1020167012739A patent/KR20160086837A/ko not_active Withdrawn
- 2014-11-07 CA CA2930574A patent/CA2930574A1/en not_active Abandoned
- 2014-11-07 AU AU2014349000A patent/AU2014349000B2/en not_active Ceased
- 2014-11-07 US US15/036,219 patent/US9890104B2/en not_active Expired - Fee Related
- 2014-11-07 CN CN201480062328.4A patent/CN105722812B/zh not_active Expired - Fee Related
- 2014-11-07 JP JP2016530933A patent/JP6373378B2/ja not_active Expired - Fee Related
-
2016
- 2016-05-01 IL IL24535716A patent/IL245357B/en not_active IP Right Cessation
-
2017
- 2017-12-22 US US15/852,922 patent/US10155716B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016537363A5 (enExample) | ||
| JP2018162250A5 (enExample) | ||
| JP2016504303A5 (enExample) | ||
| Tiecco et al. | New nitrogen containing chiral diselenides: synthesis and asymmetric addition reactions to olefins | |
| Gérard et al. | Application of N, S-chelating chiral ligands and zinc complexes in catalytic asymmetric hydrosilylation using polymethylhydrosiloxane | |
| JP4744507B2 (ja) | ビタミンｄ類似体の合成に有用な中間体の新規製造法 | |
| JP6584696B2 (ja) | ３−（（２ｓ，５ｓ）−４−メチレン−５−（３−オキソプロピル）テトラヒドロフラン−２−イル）プロパノール誘導体の製造方法及びそのための中間体 | |
| JP2013166728A (ja) | アセンジカルコゲノフェン誘導体用中間体及びその合成方法 | |
| Princival et al. | γ-Butyltelluro-2-butanol: a route to reactive 1, 4-dianion intermediates | |
| Knochel et al. | Preparation and applications of functionalized organozinc compounds | |
| Kadikova et al. | The efficient method for the preparation of alkenylsilanes from organoaluminums | |
| US7439400B2 (en) | Amino alcohol ligand and its use in preparation of chiral proparglic tertiary alcohols and tertiary amines via enantioselective addition reaction | |
| WO1993006110A1 (en) | Preparation and use of (2-butene-1,4-diyl)magnesium complexes in organic synthesis | |
| WO2013073596A1 (ja) | 光学活性ビスオキサゾリン化合物、不斉触媒およびそれを用いた光学活性シクロプロパン化合物の製造方法 | |
| CA2608232A1 (en) | Process for the production of statins | |
| CN102627571B (zh) | 一种手性铵盐的制备及合成方法 | |
| CN113637035A (zh) | 一种平面手性噁唑啉-醇二茂铁化合物及其制备、应用 | |
| JPH0561268B2 (enExample) | ||
| JP4807549B2 (ja) | シロキサン類，シラノール類及びシラン類，並びにその製造方法 | |
| CN1129567C (zh) | 环丙基乙炔衍生物的制备方法 | |
| Sasaki et al. | Brook rearrangement | |
| JP3762994B2 (ja) | アルキニルｓ，ｎ−アセタール誘導体及びその製造方法 | |
| CN114031487B (zh) | 一种2-芳基苯乙酮类化合物的合成方法 | |
| EP3969459B1 (en) | Process and intermediates for the preparation of eldecalcitol | |
| Andrés et al. | Diastereoselective synthesis of enantioenriched homopropargyl amino alcohols from α-dibenzylamino aldehydes and their use as chiral synthons |