RU2020119175A - Гликозидные производные трепростинила - Google Patents
Гликозидные производные трепростинила Download PDFInfo
- Publication number
- RU2020119175A RU2020119175A RU2020119175A RU2020119175A RU2020119175A RU 2020119175 A RU2020119175 A RU 2020119175A RU 2020119175 A RU2020119175 A RU 2020119175A RU 2020119175 A RU2020119175 A RU 2020119175A RU 2020119175 A RU2020119175 A RU 2020119175A
- Authority
- RU
- Russia
- Prior art keywords
- treprostinil
- derivative
- minutes
- ester
- benzyl
- Prior art date
Links
- -1 Treprostinil Glycoside Chemical class 0.000 title claims 6
- 229960005032 treprostinil Drugs 0.000 title claims 3
- 229930182470 glycoside Natural products 0.000 title claims 2
- PAJMKGZZBBTTOY-ZFORQUDYSA-N treprostinil Chemical class 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 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims 3
- 150000001720 carbohydrates Chemical class 0.000 claims 3
- 229930182830 galactose Natural products 0.000 claims 3
- 239000008103 glucose Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 claims 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000002772 monosaccharides Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-CBPJZXOFSA-N 2-amino-2-deoxy-D-mannopyranose Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-CBPJZXOFSA-N 0.000 claims 1
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical compound OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 claims 1
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 claims 1
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims 1
- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 claims 1
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 claims 1
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 claims 1
- 229930091371 Fructose Natural products 0.000 claims 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 1
- 239000005715 Fructose Substances 0.000 claims 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 claims 1
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 claims 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 150000001320 aldopentoses Chemical class 0.000 claims 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 1
- 150000002016 disaccharides Chemical class 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 229960002442 glucosamine Drugs 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 150000002337 glycosamines Chemical class 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 150000008273 hexosamines Chemical class 0.000 claims 1
- 125000002951 idosyl group Chemical class C1([C@@H](O)[C@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims 1
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 claims 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 claims 1
- 150000002581 ketopentoses Chemical class 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229950006780 n-acetylglucosamine Drugs 0.000 claims 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 claims 1
- 229920001542 oligosaccharide Polymers 0.000 claims 1
- 150000002482 oligosaccharides Chemical class 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 150000005846 sugar alcohols Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical class [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
Claims (27)
1. Гликозидное производное трепростинила общей формулы I
в которой R1, R2 и R3 представляют собой независимо друг от друга Н или углевод, и в которой, по меньшей мере, один из R1, R2 и R3 не является Н.
2. Производное трепростинила по п.1, в котором углевод представляет собой моносахарид, дисахарид, олигосахарид, аминосахар или альдит.
3. Производное трепростинила по п.2, в котором моносахарид представляет собой пиранозид или фуранозид.
4. Производное трепростинила по п.2, в котором углевод выбран из гексоальдоз, таких как аллоза, альтроза, глюкоза, манноза, гулоза, идоза, галактоза и талоза, из гексокетоз, таких как псикоза, фруктоза, сорбоза и тагатоза, из альдопентоз, таких как рибоза, арабиноза, ксилоза и ликсоза, из кетопентоз, таких как рибулоза и ксилулоза, или из гексозаминов, таких как галактозамин, глюкозамин, маннозамин, нейраминовая кислота, мураминовая кислота и N-ацетилглюкозамин.
5. Производное трепростинила по п.4, в котором пиранозид представляет собой глюкозу или галактозу.
6. Производное трепростинила по любому одному из пп.1-5, в котором указанное производное трепростинила имеет период полувыведения из плазмы, по меньшей мере, 60 мин, в частности 70 мин, 80 мин, 90 мин, в частности 100 мин±20 мин.
7. Производное трепростинила по любому одному из пп.1-5, в котором указанное производное трепростинила расщепляется в плазме в течение 20 ч±5 ч, по меньшей мере, на 50%, в частности, по меньшей мере, на 60%, 70%, 80%, более определенно, по меньшей мере, на 90%.
8. Композиция, содержащая гликозидное производное трепростинила по любому из пп.1-7.
9. Фармацевтическая композиция, содержащая гликозидное производное трепростинила по любому из пп.1-7.
10. Фармацевтическая композиция по п.9, в которой производное трепростинила выбрано из
и 
111. Способ получения соединения формулы I, в котором, по меньшей мере, один из R1, R2 или R3 представляет собой Н, включающий следующие стадии реакции
в котором PG представляет собой защитную группу,
R1, R2 и R3 представляют собой, как определено в п.1.
12. Способ по п.11, в котором защитная группа представляет собой бензил, бензиловый эфир, выбранный из группы, состоящей из замещенного метилового эфира, замещенного этилового эфира, замещенного бензилового эфира, различных силиловых эфиров, сложного эфира, выбранного из группы, состоящей из ацетата, замещенного ацетата, бензоата, карбоната, сульфоната, циклического ацеталя, ацеталя из кетонов, сложного эфира, амида, гидразида, бензилового эфира.
13. Способ по п.11 или 12, в котором гликозид представляет собой пиранозид, в частности глюкозу или галактозу.
14. Промежуточное соединение формулы II
в которой Bn представляет собой бензильный фрагмент.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17207329.8 | 2017-12-14 | ||
| EP17207329.8A EP3498283A1 (en) | 2017-12-14 | 2017-12-14 | Glycosidic derivatives of treprostinil |
| PCT/EP2018/084779 WO2019115702A1 (en) | 2017-12-14 | 2018-12-13 | Glycosidic derivatives of treprostinil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2020119175A3 RU2020119175A3 (ru) | 2022-01-14 |
| RU2020119175A true RU2020119175A (ru) | 2022-01-14 |
Family
ID=60673569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020119175A RU2020119175A (ru) | 2017-12-14 | 2018-12-13 | Гликозидные производные трепростинила |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US11427609B2 (ru) |
| EP (2) | EP3498283A1 (ru) |
| JP (1) | JP7295877B2 (ru) |
| KR (1) | KR20200099134A (ru) |
| CN (1) | CN111447933A (ru) |
| AU (1) | AU2018382556B2 (ru) |
| BR (1) | BR112020010945A2 (ru) |
| CA (1) | CA3085398A1 (ru) |
| CL (1) | CL2020001559A1 (ru) |
| IL (1) | IL275127B2 (ru) |
| MX (1) | MX2020006173A (ru) |
| RU (1) | RU2020119175A (ru) |
| SG (1) | SG11202005360TA (ru) |
| WO (1) | WO2019115702A1 (ru) |
| ZA (1) | ZA202002725B (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11793780B2 (en) | 2020-06-09 | 2023-10-24 | United Therapeutics Corporation | Prodrugs of treprosiinil |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8814438D0 (en) | 1988-06-17 | 1988-07-20 | Wellcome Found | Compounds for use in medicine |
| US6521212B1 (en) | 1999-03-18 | 2003-02-18 | United Therapeutics Corporation | Method for treating peripheral vascular disease by administering benzindene prostaglandins by inhalation |
| AU4327300A (en) | 1999-03-31 | 2000-10-16 | United Therapeutics Corporation | Prostaglandin compounds, compositions and methods of treating peripheral vascular disease and pulmonary hypertension |
| US20030108512A1 (en) | 2001-12-10 | 2003-06-12 | Robert Shorr | Modified prostaglandin compounds and analogs thereof, compositions containing the same useful for the treatment of cancer |
| EP1628654B2 (en) * | 2003-05-22 | 2019-12-04 | United Therapeutics Corporation | Compounds and methods for delivery of prostacyclin analogs |
| WO2009019534A2 (en) | 2006-10-12 | 2009-02-12 | Bellus Health (International) Limited | Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid |
| RS55624B1 (sr) | 2011-02-07 | 2017-06-30 | Scipharm Sàrl | Nova kompozicija za lečenje cistične fibroze |
| CN103857413A (zh) | 2011-08-12 | 2014-06-11 | 阿森迪斯药物股份有限公司 | 载体连接的曲罗尼尔前药 |
| SI2674413T1 (sl) | 2012-06-15 | 2017-10-30 | Scipharm Sarl | Postopek za pripravo treprostinila in derivatov le-tega |
| EP3398931B1 (en) | 2012-12-07 | 2020-04-08 | Cayman Chemical Company, Incorporated | Methods of synthesizing a prostacyclin analog |
| 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 |
| BR112017016084A2 (pt) | 2015-01-27 | 2018-03-27 | Scipharm Sarl | composição e método para o tratamento da doença veno-oclusiva hepática |
| 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 |
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2017
- 2017-12-14 EP EP17207329.8A patent/EP3498283A1/en not_active Withdrawn
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2018
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- 2018-12-13 EP EP18829270.0A patent/EP3723769A1/en active Pending
- 2018-12-13 RU RU2020119175A patent/RU2020119175A/ru unknown
- 2018-12-13 WO PCT/EP2018/084779 patent/WO2019115702A1/en active Application Filing
- 2018-12-13 SG SG11202005360TA patent/SG11202005360TA/en unknown
- 2018-12-13 US US16/771,741 patent/US11427609B2/en active Active
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| RU2020119175A3 (ru) | 2022-01-14 |
| WO2019115702A1 (en) | 2019-06-20 |
| US11427609B2 (en) | 2022-08-30 |
| IL275127B1 (en) | 2023-07-01 |
| AU2018382556B2 (en) | 2024-03-14 |
| CN111447933A (zh) | 2020-07-24 |
| US20210087216A1 (en) | 2021-03-25 |
| MX2020006173A (es) | 2020-10-12 |
| IL275127B2 (en) | 2023-11-01 |
| EP3498283A1 (en) | 2019-06-19 |
| CA3085398A1 (en) | 2019-06-20 |
| JP2021506959A (ja) | 2021-02-22 |
| EP3723769A1 (en) | 2020-10-21 |
| ZA202002725B (en) | 2021-08-25 |
| SG11202005360TA (en) | 2020-07-29 |
| BR112020010945A2 (pt) | 2020-11-17 |
| KR20200099134A (ko) | 2020-08-21 |
| CL2020001559A1 (es) | 2021-03-12 |
| JP7295877B2 (ja) | 2023-06-21 |
| IL275127A (en) | 2020-07-30 |
| AU2018382556A1 (en) | 2020-05-28 |
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