JP2016504303A5 - - Google Patents
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- JP2016504303A5 JP2016504303A5 JP2015545860A JP2015545860A JP2016504303A5 JP 2016504303 A5 JP2016504303 A5 JP 2016504303A5 JP 2015545860 A JP2015545860 A JP 2015545860A JP 2015545860 A JP2015545860 A JP 2015545860A JP 2016504303 A5 JP2016504303 A5 JP 2016504303A5
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- 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
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- 150000001875 compounds Chemical class 0.000 claims description 405
- 238000000034 method Methods 0.000 claims description 137
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- 239000003960 organic solvent Substances 0.000 claims description 68
- 239000007800 oxidant agent Substances 0.000 claims description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- -1 borane compound Chemical class 0.000 claims description 22
- 239000003638 chemical reducing agent Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 229910000085 borane Inorganic materials 0.000 claims description 9
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 28
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical compound O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical group [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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 6
- 238000006243 chemical reaction Methods 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
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 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 3
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PWVLBKIGYYBRLX-HSZRJFAPSA-N (6r)-6,7-bis[[tert-butyl(dimethyl)silyl]oxy]-1-(3-methoxy-2-prop-2-enylphenyl)hept-2-yn-1-one Chemical compound COC1=CC=CC(C(=O)C#CCC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1CC=C PWVLBKIGYYBRLX-HSZRJFAPSA-N 0.000 description 1
- CTKINSOISVBQLD-VKHMYHEASA-N (S)-Glycidol Chemical compound OC[C@H]1CO1 CTKINSOISVBQLD-VKHMYHEASA-N 0.000 description 1
- OQOUDZFBMYRNCD-UHFFFAOYSA-N 3-methoxy-2-prop-2-enylbenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1CC=C OQOUDZFBMYRNCD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IPGFEAXZBBFTFN-SECBINFHSA-N [(2r)-oxiran-2-yl]methyl 3,5-dinitrobenzoate Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)OC[C@@H]2OC2)=C1 IPGFEAXZBBFTFN-SECBINFHSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- IIJREXIVDSIOFR-UHFFFAOYSA-N dichloromethane;heptane Chemical compound ClCCl.CCCCCCC IIJREXIVDSIOFR-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261734672P | 2012-12-07 | 2012-12-07 | |
| US61/734,672 | 2012-12-07 | ||
| US201361777882P | 2013-03-12 | 2013-03-12 | |
| US61/777,882 | 2013-03-12 | ||
| PCT/US2013/073474 WO2014089385A2 (en) | 2012-12-07 | 2013-12-06 | Methods of synthesizing a prostacyclin analog |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018094605A Division JP2018162250A (ja) | 2012-12-07 | 2018-05-16 | プロスタサイクリン類似体を合成する方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016504303A JP2016504303A (ja) | 2016-02-12 |
| JP2016504303A5 true JP2016504303A5 (OSRAM) | 2017-01-26 |
| JP6342414B2 JP6342414B2 (ja) | 2018-06-13 |
Family
ID=49881039
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015545860A Expired - Fee Related JP6342414B2 (ja) | 2012-12-07 | 2013-12-06 | プロスタサイクリン類似体を合成する方法 |
| JP2018094605A Ceased JP2018162250A (ja) | 2012-12-07 | 2018-05-16 | プロスタサイクリン類似体を合成する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018094605A Ceased JP2018162250A (ja) | 2012-12-07 | 2018-05-16 | プロスタサイクリン類似体を合成する方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US20150315114A1 (OSRAM) |
| EP (2) | EP2928858B1 (OSRAM) |
| JP (2) | JP6342414B2 (OSRAM) |
| KR (1) | KR20150091170A (OSRAM) |
| CN (3) | CN104837806A (OSRAM) |
| AU (2) | AU2013355130B2 (OSRAM) |
| BR (1) | BR112015013085A2 (OSRAM) |
| CA (1) | CA2893604A1 (OSRAM) |
| CL (1) | CL2015001535A1 (OSRAM) |
| DK (1) | DK2928858T3 (OSRAM) |
| EA (1) | EA034309B1 (OSRAM) |
| ES (1) | ES2664026T3 (OSRAM) |
| IL (1) | IL239172B (OSRAM) |
| MX (2) | MX369094B (OSRAM) |
| NZ (1) | NZ708130A (OSRAM) |
| PE (1) | PE20160090A1 (OSRAM) |
| PH (2) | PH12015501258B1 (OSRAM) |
| SG (2) | SG11201504430TA (OSRAM) |
| TW (1) | TWI634104B (OSRAM) |
| WO (1) | WO2014089385A2 (OSRAM) |
Families Citing this family (19)
| 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 |
| EP3068752A1 (en) * | 2013-11-13 | 2016-09-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
| HU231184B1 (hu) * | 2014-10-08 | 2021-07-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Treprostinil-nátrium-monohidrát és eljárás ennek előállítására |
| 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 |
| JP7220650B2 (ja) | 2016-09-26 | 2023-02-10 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルプロドラッグ |
| EP3498283A1 (en) | 2017-12-14 | 2019-06-19 | Ipsol AG | Glycosidic derivatives of treprostinil |
| HU231296B1 (hu) | 2018-03-09 | 2022-09-28 | Chinoin Zrt | Eljárás treprostinil-dietanol-amin só B polimorf formájának előállítására |
| JP6503508B2 (ja) * | 2018-08-03 | 2019-04-17 | Ｊｘｔｇエネルギー株式会社 | テトラカルボン酸二無水物、ポリイミド前駆体樹脂、ポリイミド、ポリイミド前駆体樹脂溶液、ポリイミド溶液及びポリイミドフィルム |
| CN114616225A (zh) | 2019-08-23 | 2022-06-10 | 联合治疗公司 | 曲前列环素前药 |
| US11826327B2 (en) | 2020-04-17 | 2023-11-28 | United Therapeutics Corporation | Treatment for interstitial lung disease |
| WO2021252446A1 (en) | 2020-06-09 | 2021-12-16 | United Therapeutics Corporation | Fumaryl diketopiperidine prodrugs of treprostinil |
| KR20220030006A (ko) | 2020-09-02 | 2022-03-10 | 바이오플러스 주식회사 | 미용 조성물을 포함하는 마스크 및 그 제조 방법 |
| JP2023553989A (ja) | 2020-12-14 | 2023-12-26 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルプロドラッグで疾患を治療する方法 |
| AU2022229367A1 (en) | 2021-03-03 | 2023-09-14 | United Therapeutics Corporation | A dry powder composition of trestinil and its prodrug thereof and further comprising comprising (e)-3,6-bis[4-(n-carbonyl-2-propenyl)amidobutyl]-2,5-diketopiperazine (fdkp) |
| US11884640B2 (en) * | 2021-06-02 | 2024-01-30 | Chirogate International Inc. | Processes and intermediates for the preparations of benzoprostacyclin analogues and benzoprostacyclin analogues prepared therefrom |
| US11884613B2 (en) * | 2022-05-05 | 2024-01-30 | Chirogate International Inc. | Processes and intermediates for the preparation of carbaprostacyclin analogues |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306075A (en) | 1980-03-28 | 1981-12-15 | The Upjohn Company | Composition and process |
| CA2039857A1 (en) * | 1990-04-26 | 1991-10-27 | Wilfred Po-Sum Shum | Process for producing epoxyalcohols of high optical purity |
| 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 |
| CN101265226B (zh) * | 2003-05-22 | 2013-04-24 | 联合治疗公司 | 化合物和释放前列环素类似物的方法 |
| WO2009019868A1 (ja) * | 2007-08-06 | 2009-02-12 | Taisho Pharmaceutical Co., Ltd. | １０ａ、１２位架橋型１０ａ－アザライド化合物 |
| KR20160048222A (ko) | 2007-12-17 | 2016-05-03 | 유나이티드 세러퓨틱스 코오포레이션 | 레모둘린?의 활성 성분인 트레프로스티닐의 개선된 제조 방법 |
| US20110294815A1 (en) * | 2008-06-27 | 2011-12-01 | Harbeson Scott L | Prostacyclin analogs |
| WO2010039531A1 (en) * | 2008-09-23 | 2010-04-08 | Resolvyx Pharmaceuticals, Inc. | Therapeutic compounds |
| CN101891596B (zh) * | 2009-05-22 | 2013-12-11 | 上海天伟生物制药有限公司 | 一种化合物及其制备方法和用途 |
| 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 |
| CN103237780B (zh) * | 2010-11-30 | 2015-03-04 | 独立行政法人科学技术振兴机构 | 核苷类似物或其盐、寡核苷酸类似物、基因表达抑制剂和用于检测基因的核酸探针 |
| US8524939B2 (en) | 2011-08-24 | 2013-09-03 | Chirogate International Inc. | Intermediates for the synthesis of benzindene prostaglandins and preparations thereof |
| CN102796134B (zh) * | 2012-08-31 | 2015-07-01 | 甘肃皓天化学科技有限公司 | 一种马沙骨化醇中间体的制备方法 |
| 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 |
| EP3068752A1 (en) * | 2013-11-13 | 2016-09-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
-
2013
- 2013-12-06 CN CN201380064046.3A patent/CN104837806A/zh active Pending
- 2013-12-06 NZ NZ708130A patent/NZ708130A/en not_active IP Right Cessation
- 2013-12-06 TW TW102144990A patent/TWI634104B/zh not_active IP Right Cessation
- 2013-12-06 US US14/650,234 patent/US20150315114A1/en not_active Abandoned
- 2013-12-06 SG SG11201504430TA patent/SG11201504430TA/en unknown
- 2013-12-06 JP JP2015545860A patent/JP6342414B2/ja not_active Expired - Fee Related
- 2013-12-06 EP EP13812336.9A patent/EP2928858B1/en active Active
- 2013-12-06 EA EA201591093A patent/EA034309B1/ru not_active IP Right Cessation
- 2013-12-06 CA CA2893604A patent/CA2893604A1/en not_active Abandoned
- 2013-12-06 DK DK13812336.9T patent/DK2928858T3/en active
- 2013-12-06 EP EP18154039.4A patent/EP3398931B1/en active Active
- 2013-12-06 CN CN201910784017.3A patent/CN110590547A/zh active Pending
- 2013-12-06 WO PCT/US2013/073474 patent/WO2014089385A2/en not_active Ceased
- 2013-12-06 SG SG10201600303WA patent/SG10201600303WA/en unknown
- 2013-12-06 ES ES13812336.9T patent/ES2664026T3/es active Active
- 2013-12-06 KR KR1020157018095A patent/KR20150091170A/ko not_active Ceased
- 2013-12-06 CN CN201710389417.5A patent/CN107098925B/zh not_active Expired - Fee Related
- 2013-12-06 MX MX2015006972A patent/MX369094B/es active IP Right Grant
- 2013-12-06 BR BR112015013085A patent/BR112015013085A2/pt not_active Application Discontinuation
- 2013-12-06 AU AU2013355130A patent/AU2013355130B2/en not_active Ceased
- 2013-12-06 PE PE2015000742A patent/PE20160090A1/es unknown
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2015
- 2015-06-02 MX MX2019009102A patent/MX2019009102A/es unknown
- 2015-06-03 IL IL239172A patent/IL239172B/en not_active IP Right Cessation
- 2015-06-03 PH PH12015501258A patent/PH12015501258B1/en unknown
- 2015-06-05 CL CL2015001535A patent/CL2015001535A1/es unknown
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2017
- 2017-05-01 US US15/583,457 patent/US9908834B2/en not_active Expired - Fee Related
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2018
- 2018-01-18 US US15/874,093 patent/US10450257B2/en not_active Expired - Fee Related
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2019
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