JP2017531661A5 - - Google Patents
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- JP2017531661A5 JP2017531661A5 JP2017518846A JP2017518846A JP2017531661A5 JP 2017531661 A5 JP2017531661 A5 JP 2017531661A5 JP 2017518846 A JP2017518846 A JP 2017518846A JP 2017518846 A JP2017518846 A JP 2017518846A JP 2017531661 A5 JP2017531661 A5 JP 2017531661A5
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- Prior art keywords
- compound
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- general formula
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- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- -1 salt anhydride Chemical class 0.000 claims 15
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 6
- 239000002585 base Substances 0.000 claims 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 4
- 229910000085 borane Inorganic materials 0.000 claims 4
- 229910052710 silicon Inorganic materials 0.000 claims 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000010703 silicon Substances 0.000 claims 3
- 239000007818 Grignard reagent Substances 0.000 claims 2
- 241000282376 Panthera tigris Species 0.000 claims 2
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 2
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 claims 2
- 150000004795 grignard reagents Chemical class 0.000 claims 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 2
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 150000003839 salts Chemical group 0.000 claims 2
- PAJMKGZZBBTTOY-ZFORQUDYSA-N treprostinil Chemical compound C1=CC=C(OCC(O)=O)C2=C1C[C@@H]1[C@@H](CC[C@@H](O)CCCCC)[C@H](O)C[C@@H]1C2 PAJMKGZZBBTTOY-ZFORQUDYSA-N 0.000 claims 2
- 229960005032 treprostinil Drugs 0.000 claims 2
- 150000003751 zinc Chemical class 0.000 claims 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 238000006859 Swern oxidation reaction Methods 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims 1
- KHYAFFAGZNCWPT-UHFFFAOYSA-N boron;n,n-diethylaniline Chemical compound [B].CCN(CC)C1=CC=CC=C1 KHYAFFAGZNCWPT-UHFFFAOYSA-N 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 claims 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
- GFTXWCQFWLOXAT-UHFFFAOYSA-M magnesium;cyclohexane;bromide Chemical compound [Mg+2].[Br-].C1CC[CH-]CC1 GFTXWCQFWLOXAT-UHFFFAOYSA-M 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006140 methanolysis reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 claims 1
- 0 *O[C@](C1)C(C*O)[C@@](C2)[C@]1Cc1c2cccc1O* Chemical compound *O[C@](C1)C(C*O)[C@@](C2)[C@]1Cc1c2cccc1O* 0.000 description 3
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019165225A JP6898401B2 (ja) | 2014-10-08 | 2019-09-11 | トレプロスチニルの製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP1400475 | 2014-10-08 | ||
| HU1400475A HU231186B1 (hu) | 2014-10-08 | 2014-10-08 | Új eljárás treprostinil és sói előállítására |
| PCT/HU2015/000065 WO2016055819A1 (en) | 2014-10-08 | 2015-09-28 | Process for the preparation of treprostinil |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019165225A Division JP6898401B2 (ja) | 2014-10-08 | 2019-09-11 | トレプロスチニルの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017531661A JP2017531661A (ja) | 2017-10-26 |
| JP2017531661A5 true JP2017531661A5 (enExample) | 2020-06-11 |
| JP6820255B2 JP6820255B2 (ja) | 2021-01-27 |
Family
ID=89991608
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017518846A Active JP6820255B2 (ja) | 2014-10-08 | 2015-09-28 | トレプロスチニルの製造方法 |
| JP2019165225A Active JP6898401B2 (ja) | 2014-10-08 | 2019-09-11 | トレプロスチニルの製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019165225A Active JP6898401B2 (ja) | 2014-10-08 | 2019-09-11 | トレプロスチニルの製造方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US10322990B2 (enExample) |
| EP (1) | EP3204349A1 (enExample) |
| JP (2) | JP6820255B2 (enExample) |
| KR (2) | KR102651020B1 (enExample) |
| CN (2) | CN113292419A (enExample) |
| AU (1) | AU2015329740B2 (enExample) |
| CA (1) | CA2963844C (enExample) |
| HU (2) | HU231184B1 (enExample) |
| IL (1) | IL251613B (enExample) |
| MX (1) | MX384201B (enExample) |
| RU (1) | RU2709200C2 (enExample) |
| SG (1) | SG11201702790YA (enExample) |
| TW (2) | TWI761731B (enExample) |
| WO (1) | WO2016055819A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9505737B2 (en) | 2013-01-11 | 2016-11-29 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| US9371264B2 (en) | 2013-01-11 | 2016-06-21 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| US9394227B1 (en) | 2015-06-17 | 2016-07-19 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| US9643911B2 (en) | 2015-06-17 | 2017-05-09 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| EP3408252B1 (en) | 2016-01-27 | 2022-03-02 | Emcure Pharmaceuticals Limited | Process for preparation of prostacyclin derivatives |
| KR101830693B1 (ko) | 2016-04-28 | 2018-02-21 | 연성정밀화학(주) | 트레프로스티닐의 제조방법 및 이를 위한 중간체 |
| AU2017330099B2 (en) | 2016-09-26 | 2023-08-10 | United Therapeutics Corporation | Treprostinil prodrugs |
| HU231296B1 (hu) * | 2018-03-09 | 2022-09-28 | Chinoin Zrt | Eljárás treprostinil-dietanol-amin só B polimorf formájának előállítására |
| KR102084044B1 (ko) * | 2018-12-24 | 2020-03-03 | 주식회사 세미부스터 | 인산용액 중의 실리콘 농도 분석방법 |
| CA3141164C (en) | 2019-05-21 | 2023-09-05 | Jiangsu Forefront Pharmaceutical Co., Ltd. | New crystal form of treprostinil sodium salt and preparation method therefor |
| US11634443B2 (en) | 2019-08-23 | 2023-04-25 | United Therapeutics Corporation | Treprostinil prodrugs |
| US10781160B1 (en) * | 2019-10-04 | 2020-09-22 | Chirogate International Inc. | Hexadecyl Treprostinil crystals and methods for preparation thereof |
| US11339110B2 (en) * | 2019-12-19 | 2022-05-24 | Chirogate International Inc. | Efficient crystallization process for preparing ultrapure Treprostinil and crystal prepared therefrom |
| JP2023523557A (ja) | 2020-04-17 | 2023-06-06 | ユナイテッド セラピューティクス コーポレイション | 間質性肺疾患の治療における使用のためのトレプロスチニル |
| AU2021289336B2 (en) | 2020-06-09 | 2025-08-28 | Mannkind Corporation | Fumaryl diketopiperidine prodrugs of treprostinil |
| US11447440B2 (en) * | 2020-10-29 | 2022-09-20 | Chirogate International Inc. | Treprostinil monohydrate crystals and methods for preparation thereof |
| CN117062605A (zh) | 2020-12-14 | 2023-11-14 | 联合治疗公司 | 使用曲前列环素前药治疗疾病的方法 |
| US12168071B2 (en) | 2021-03-03 | 2024-12-17 | United Therapeutics Corporation | Treprostinil derivatives and their use in pharmaceutical compositions |
| WO2023154705A1 (en) | 2022-02-08 | 2023-08-17 | United Therapeutics Corporation | Treprostinil iloprost combination therapy |
| AU2024208919A1 (en) | 2023-01-19 | 2025-07-17 | United Therapeutics Corporation | Treprostinil analogs |
| WO2025101824A1 (en) | 2023-11-09 | 2025-05-15 | United Therapeutics Corporation | Syntheses of compounds useful for producing treprostinil |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338457A (en) | 1980-02-28 | 1982-07-06 | The Upjohn Company | Composition and process |
| CA1313670C (en) | 1980-02-28 | 1993-02-16 | Robert Charles Kelly | Carbacyclin analogs |
| DE69816642T2 (de) * | 1997-10-24 | 2004-06-09 | United Therapeutics Corp. | Verfahren zur stereoselektiven synthese von prostacyclin-derivaten |
| US6441245B1 (en) | 1997-10-24 | 2002-08-27 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| EP1045695B1 (en) | 1997-11-14 | 2004-03-24 | United Therapeutics Corporation | Use of 9-deoxy-2', 9-alpha-methano-3- oxa-4,5,6- trinor-3, 7-(1',3'-interphenylene) -13,14-dihydro- prostaglandin f 1? to treat peripheral vascular disease |
| EP1628654B2 (en) | 2003-05-22 | 2019-12-04 | United Therapeutics Corporation | Compounds and methods for delivery of prostacyclin analogs |
| JP5038031B2 (ja) | 2006-07-11 | 2012-10-03 | キヤノン株式会社 | 放射線撮影装置、その駆動方法及び放射線撮影システム |
| JP5851691B2 (ja) | 2007-12-17 | 2016-02-03 | ユナイテッド セラピューティクス コーポレーション | リモジュリンの活性成分であるトレプロスチニルを製造する改良方法 |
| WO2009137066A1 (en) * | 2008-05-08 | 2009-11-12 | United Therapeutics Corporation | Treprostinil monohydrate |
| WO2009158010A1 (en) * | 2008-06-27 | 2009-12-30 | Concert Pharmaceuticals, Inc. | Prostacyclin analogs |
| CN102040618B (zh) | 2009-04-30 | 2013-09-04 | 上海天伟生物制药有限公司 | 一种PGF2a类似物的制备方法及其相关中间体 |
| CA3029711A1 (en) * | 2010-06-03 | 2011-12-08 | United Therapeutics Corporation | Treprostinil production |
| CA2710726C (en) * | 2010-07-22 | 2016-02-23 | Alphora Research Inc. | Synthesis of treprostinil and intermediates useful therein |
| CN102906520B (zh) | 2010-11-19 | 2014-11-12 | 岛产业株式会社 | 干燥减容处理装置 |
| CA2726599C (en) * | 2010-12-30 | 2017-07-25 | Alphora Research Inc. | Process for treprostinil salt preparation |
| EP2495235B1 (en) * | 2011-03-04 | 2015-08-05 | Newchem S.p.A. | Process for the synthesis of prostaglandins and intermediates thereof |
| US8524939B2 (en) * | 2011-08-24 | 2013-09-03 | Chirogate International Inc. | Intermediates for the synthesis of benzindene prostaglandins and preparations thereof |
| CN103193627B (zh) * | 2012-01-10 | 2016-04-20 | 上海天伟生物制药有限公司 | 一种前列腺素类似物的晶型及其制备方法和用途 |
| EP2674413B1 (en) * | 2012-06-15 | 2017-06-07 | SciPharm SàRL | Process for the preparation of treprostinil and derivatives thereof |
| JP6342414B2 (ja) * | 2012-12-07 | 2018-06-13 | ケイマン ケミカル カンパニー， インコーポレーテッド | プロスタサイクリン類似体を合成する方法 |
| US9371264B2 (en) * | 2013-01-11 | 2016-06-21 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| CN109608326A (zh) * | 2013-03-15 | 2019-04-12 | 联合治疗公司 | 曲前列环素的盐 |
| JP6561109B2 (ja) * | 2014-07-16 | 2019-08-14 | コルセア ファーマ インコーポレイテッド | トレプロスチニル誘導体化合物およびその使用方法 |
-
2014
- 2014-10-08 HU HU1900346A patent/HU231184B1/hu unknown
- 2014-10-08 HU HU1400475A patent/HU231186B1/hu unknown
-
2015
- 2015-09-28 SG SG11201702790YA patent/SG11201702790YA/en unknown
- 2015-09-28 US US15/518,096 patent/US10322990B2/en active Active
- 2015-09-28 CA CA2963844A patent/CA2963844C/en active Active
- 2015-09-28 AU AU2015329740A patent/AU2015329740B2/en active Active
- 2015-09-28 MX MX2017004672A patent/MX384201B/es unknown
- 2015-09-28 KR KR1020177012210A patent/KR102651020B1/ko active Active
- 2015-09-28 EP EP15787660.8A patent/EP3204349A1/en active Pending
- 2015-09-28 CN CN202110561010.2A patent/CN113292419A/zh active Pending
- 2015-09-28 RU RU2017115930A patent/RU2709200C2/ru active
- 2015-09-28 JP JP2017518846A patent/JP6820255B2/ja active Active
- 2015-09-28 WO PCT/HU2015/000065 patent/WO2016055819A1/en not_active Ceased
- 2015-09-28 KR KR1020247009377A patent/KR102841902B1/ko active Active
- 2015-09-28 CN CN201580066416.6A patent/CN107001221B/zh active Active
- 2015-10-06 TW TW108142477A patent/TWI761731B/zh active
- 2015-10-06 TW TW104132764A patent/TWI761299B/zh active
-
2017
- 2017-04-06 IL IL251613A patent/IL251613B/en active IP Right Grant
-
2019
- 2019-04-29 US US16/397,139 patent/US11098001B2/en active Active
- 2019-09-11 JP JP2019165225A patent/JP6898401B2/ja active Active
-
2021
- 2021-07-15 US US17/377,125 patent/US11724979B2/en active Active
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