JP2016540734A5 - - Google Patents
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- JP2016540734A5 JP2016540734A5 JP2016525531A JP2016525531A JP2016540734A5 JP 2016540734 A5 JP2016540734 A5 JP 2016540734A5 JP 2016525531 A JP2016525531 A JP 2016525531A JP 2016525531 A JP2016525531 A JP 2016525531A JP 2016540734 A5 JP2016540734 A5 JP 2016540734A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- linear
- alkyl
- prostacyclin compound
- patient
- 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
- -1 prostacyclin compound Chemical class 0.000 claims description 252
- 229960001123 epoprostenol Drugs 0.000 claims description 242
- 239000000203 mixture Substances 0.000 claims description 173
- 125000000217 alkyl group Chemical group 0.000 claims description 134
- 125000003342 alkenyl group Chemical group 0.000 claims description 62
- 210000004072 lung Anatomy 0.000 claims description 37
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- 230000000694 effects Effects 0.000 claims description 32
- 229960005032 treprostinil Drugs 0.000 claims description 32
- 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 description 31
- 150000002632 lipids Chemical class 0.000 claims description 26
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000006199 nebulizer Substances 0.000 claims description 22
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 claims description 18
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 9
- BLUGYPPOFIHFJS-UUFHNPECSA-N (2s)-n-[(2s)-1-[[(3r,4s,5s)-3-methoxy-1-[(2s)-2-[(1r,2r)-1-methoxy-2-methyl-3-oxo-3-[[(1s)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamid Chemical compound CN[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 BLUGYPPOFIHFJS-UUFHNPECSA-N 0.000 claims description 8
- 208000007934 ACTH-independent macronodular adrenal hyperplasia Diseases 0.000 claims description 8
- 239000000443 aerosol Substances 0.000 claims description 8
- 229960002240 iloprost Drugs 0.000 claims description 8
- HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 150000003815 prostacyclins Chemical class 0.000 claims description 8
- 208000026151 Chronic thromboembolic pulmonary hypertension Diseases 0.000 claims description 6
- 206010011224 Cough Diseases 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229940112141 dry powder inhaler Drugs 0.000 claims description 6
- 229940071648 metered dose inhaler Drugs 0.000 claims description 6
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 claims description 6
- 230000002685 pulmonary effect Effects 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 150000003505 terpenes Chemical class 0.000 claims description 6
- 235000007586 terpenes Nutrition 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- LVNGJLRDBYCPGB-UHFFFAOYSA-N 1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- NONFBHXKNNVFMO-UHFFFAOYSA-N [2-aminoethoxy(tetradecanoyloxy)phosphoryl] tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OP(=O)(OCCN)OC(=O)CCCCCCCCCCCCC NONFBHXKNNVFMO-UHFFFAOYSA-N 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003380 propellant Substances 0.000 claims description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical group CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000463 Poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol) Polymers 0.000 claims description 2
- 229920002560 Polyethylene Glycol 3000 Polymers 0.000 claims description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 2
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 description 2
- 150000005828 hydrofluoroalkanes Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002105 nanoparticle Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 229940032094 squalane Drugs 0.000 claims description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 description 62
- 239000002207 metabolite Substances 0.000 description 2
- 0 **C(**Oc1c(CC2C(C3)C(*)C(*)C2)c3ccc1)=O Chemical compound **C(**Oc1c(CC2C(C3)C(*)C(*)C2)c3ccc1)=O 0.000 description 1
- FISUNRXTXLFDTO-TYDDBILNSA-N CCCCC[C@@H](CC[C@@H]([C@@H](C1)O)[C@@H](Cc2ccc3)[C@H]1Cc2c3OCC(OC(CCCC)CCCC)=O)O Chemical compound CCCCC[C@@H](CC[C@@H]([C@@H](C1)O)[C@@H](Cc2ccc3)[C@H]1Cc2c3OCC(OC(CCCC)CCCC)=O)O FISUNRXTXLFDTO-TYDDBILNSA-N 0.000 description 1
- 108050006400 Cyclin Proteins 0.000 description 1
- 102000016736 Cyclin Human genes 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361895680P | 2013-10-25 | 2013-10-25 | |
| US61/895,680 | 2013-10-25 | ||
| US201361910703P | 2013-12-02 | 2013-12-02 | |
| US61/910,703 | 2013-12-02 | ||
| US201461950967P | 2014-03-11 | 2014-03-11 | |
| US61/950,967 | 2014-03-11 | ||
| US201462028758P | 2014-07-24 | 2014-07-24 | |
| US62/028,758 | 2014-07-24 | ||
| US201462042123P | 2014-08-26 | 2014-08-26 | |
| US62/042,123 | 2014-08-26 | ||
| PCT/US2014/062232 WO2015061720A2 (en) | 2013-10-25 | 2014-10-24 | Prostacyclin compounds, compositions and methods of use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018248772A Division JP6722268B2 (ja) | 2013-10-25 | 2018-12-29 | プロスタサイクリン化合物、組成物およびその使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016540734A JP2016540734A (ja) | 2016-12-28 |
| JP2016540734A5 true JP2016540734A5 (https=) | 2017-11-30 |
| JP6491203B2 JP6491203B2 (ja) | 2019-03-27 |
Family
ID=52993757
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016525531A Active JP6491203B2 (ja) | 2013-10-25 | 2014-10-24 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2018248772A Active JP6722268B2 (ja) | 2013-10-25 | 2018-12-29 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2020085701A Active JP6967111B2 (ja) | 2013-10-25 | 2020-05-15 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2021146084A Active JP7190011B2 (ja) | 2013-10-25 | 2021-09-08 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2022177999A Active JP7430766B2 (ja) | 2013-10-25 | 2022-11-07 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2023197454A Active JP7618009B2 (ja) | 2013-10-25 | 2023-11-21 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2024216284A Active JP7777660B2 (ja) | 2013-10-25 | 2024-12-11 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2025156037A Pending JP2025181916A (ja) | 2013-10-25 | 2025-09-19 | プロスタサイクリン化合物、組成物およびその使用方法 |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018248772A Active JP6722268B2 (ja) | 2013-10-25 | 2018-12-29 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2020085701A Active JP6967111B2 (ja) | 2013-10-25 | 2020-05-15 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2021146084A Active JP7190011B2 (ja) | 2013-10-25 | 2021-09-08 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2022177999A Active JP7430766B2 (ja) | 2013-10-25 | 2022-11-07 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2023197454A Active JP7618009B2 (ja) | 2013-10-25 | 2023-11-21 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2024216284A Active JP7777660B2 (ja) | 2013-10-25 | 2024-12-11 | プロスタサイクリン化合物、組成物およびその使用方法 |
| JP2025156037A Pending JP2025181916A (ja) | 2013-10-25 | 2025-09-19 | プロスタサイクリン化合物、組成物およびその使用方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (9) | US9469600B2 (https=) |
| EP (2) | EP3808731A1 (https=) |
| JP (8) | JP6491203B2 (https=) |
| KR (2) | KR102427785B1 (https=) |
| CN (2) | CN105848479B (https=) |
| AU (3) | AU2014339866C1 (https=) |
| BR (1) | BR112016009207B1 (https=) |
| CA (1) | CA2927788C (https=) |
| CY (1) | CY1123944T1 (https=) |
| DK (1) | DK3060041T3 (https=) |
| EA (1) | EA031604B1 (https=) |
| ES (1) | ES2860975T3 (https=) |
| HR (1) | HRP20210351T1 (https=) |
| IL (1) | IL245184B (https=) |
| LT (1) | LT3060041T (https=) |
| MX (2) | MX382833B (https=) |
| PL (1) | PL3060041T3 (https=) |
| PT (1) | PT3060041T (https=) |
| SI (1) | SI3060041T1 (https=) |
| WO (1) | WO2015061720A2 (https=) |
Families Citing this family (35)
| 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 |
| EP3712142B1 (en) | 2013-01-11 | 2022-07-06 | Corsair Pharma, Inc. | Prodrugs of treprostinil |
| ES2860975T3 (es) | 2013-10-25 | 2021-10-05 | Insmed Inc | Compuestos de prostaciclina |
| AU2015349969B2 (en) * | 2014-11-18 | 2020-02-06 | Insmed Incorporated | Methods of manufacturing treprostinil and treprostinil derivative prodrugs |
| 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 |
| CA3012679C (en) * | 2016-01-29 | 2023-12-12 | Mannkind Corporation | Dry powder inhaler |
| IL262720B2 (en) | 2016-05-05 | 2024-06-01 | Liquidia Tech Inc | Dry powder treprostinil for the treatment of pulmonary hypertension |
| WO2017223400A1 (en) * | 2016-06-24 | 2017-12-28 | Insmed Incorporated | Prostacyclin compounds and compositions for treating sarcoidosis |
| 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 |
| CN114072136B (zh) * | 2019-04-29 | 2024-11-29 | 英斯梅德股份有限公司 | 曲前列素前药的干粉组合物及其使用方法 |
| EP4017588A1 (en) | 2019-08-23 | 2022-06-29 | 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 |
| US20240238309A1 (en) * | 2020-03-25 | 2024-07-18 | Insmed Incorporated | Pharmaceutical formulations of treprostinil prodrugs and methods of use thereof |
| 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 |
| IL298591A (en) | 2020-06-09 | 2023-01-01 | United Therapeutics Corp | Pomeryl dictopiperidine prodrugs of treprostinil |
| WO2022094100A1 (en) | 2020-10-28 | 2022-05-05 | Insmed Incorporated | Dry powder compositions of treprostinil prodrugs and methods of use thereof |
| US11447440B2 (en) | 2020-10-29 | 2022-09-20 | Chirogate International Inc. | Treprostinil monohydrate crystals and methods for preparation thereof |
| KR20250133451A (ko) | 2020-12-14 | 2025-09-05 | 유나이티드 쎄러퓨틱스 코포레이션 | 트레프로스티닐 프로드러그로 질환을 치료하는 방법 |
| JP2024510930A (ja) | 2021-03-03 | 2024-03-12 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニル及びそのプロドラッグの乾燥粉末組成物、及び、さらに（ｅ）－３，６－ビス［４－（ｎ－カルボニル－２－プロペニル）アミドブチル］－２，５－ジケトピペラジン（ｆｄｋｐ）を含む乾燥粉末組成物 |
| WO2022194195A1 (zh) * | 2021-03-16 | 2022-09-22 | 江苏恒瑞医药股份有限公司 | 一种曲前列环素衍生物及其用途 |
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