JPWO2020030489A5 - - Google Patents
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- Publication number
- JPWO2020030489A5 JPWO2020030489A5 JP2021506326A JP2021506326A JPWO2020030489A5 JP WO2020030489 A5 JPWO2020030489 A5 JP WO2020030489A5 JP 2021506326 A JP2021506326 A JP 2021506326A JP 2021506326 A JP2021506326 A JP 2021506326A JP WO2020030489 A5 JPWO2020030489 A5 JP WO2020030489A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- compound
- nitrooxy
- ethyl
- methyl
- 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 41
- 150000003839 salts Chemical class 0.000 claims 17
- -1 (S)-(1-(4-(3-chloro-4-methoxybenzylamino)-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl)pyrrolidin-2-yl)methyl Chemical group 0.000 claims 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 230000004406 elevated intraocular pressure Effects 0.000 claims 5
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 4
- 206010030043 Ocular hypertension Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- SNPDKBFMQHFHFY-YFKPBYRVSA-N 3-[(2S)-2,3-dinitrooxypropoxy]propanoic acid Chemical compound [N+](=O)([O-])O[C@@H](COCCC(=O)O)CO[N+](=O)[O-] SNPDKBFMQHFHFY-YFKPBYRVSA-N 0.000 claims 2
- CBSFPBTYVIYRQZ-UHFFFAOYSA-N 6-nitrooxyhexanoic acid Chemical compound OC(=O)CCCCCO[N+]([O-])=O CBSFPBTYVIYRQZ-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 2
- 206010030348 Open-Angle Glaucoma Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims 2
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims 2
- 239000000048 adrenergic agonist Substances 0.000 claims 2
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 claims 2
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 claims 2
- 239000002876 beta blocker Substances 0.000 claims 2
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims 2
- 239000000064 cholinergic agonist Substances 0.000 claims 2
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 2
- WPYWMXNXEZFMAK-UHFFFAOYSA-N cinaciguat Chemical compound C=1C=C(C(O)=O)C=CC=1CN(CCCCC(=O)O)CCC1=CC=CC=C1OCC(C=C1)=CC=C1CCC1=CC=CC=C1 WPYWMXNXEZFMAK-UHFFFAOYSA-N 0.000 claims 2
- 229950002128 cinaciguat Drugs 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000003119 guanylate cyclase activator Substances 0.000 claims 2
- 239000003590 rho kinase inhibitor Substances 0.000 claims 2
- 150000003431 steroids Chemical class 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- XGBCQJBLBIYQGF-WLHGVMLRSA-N (e)-but-2-enedioic acid;hexanoic acid Chemical compound CCCCCC(O)=O.OC(=O)\C=C\C(O)=O XGBCQJBLBIYQGF-WLHGVMLRSA-N 0.000 claims 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims 1
- MAQKKKPGRLJDNV-UHFFFAOYSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 2-(2-nitrooxyethoxy)acetate Chemical compound [N+](=O)([O-])OCCOCC(=O)OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N=1)C(=CN2CC)CCC)=O MAQKKKPGRLJDNV-UHFFFAOYSA-N 0.000 claims 1
- YBTRCCSGPPOGHG-UHFFFAOYSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 3-(2,3-dinitrooxypropoxy)propanoate Chemical compound [N+](=O)([O-])OC(COCCC(=O)OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N=1)C(=CN2CC)CCC)=O)CO[N+](=O)[O-] YBTRCCSGPPOGHG-UHFFFAOYSA-N 0.000 claims 1
- DOJJOPKAHPWWPT-ASMAMLKCSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 3-[(2S)-2,3-dinitrooxypropoxy]propanoate dihydrochloride Chemical compound Cl.Cl.[N+](=O)([O-])O[C@@H](COCCC(=O)OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N1)C(=CN2CC)CCC)=O)CO[N+](=O)[O-] DOJJOPKAHPWWPT-ASMAMLKCSA-N 0.000 claims 1
- OKZLWXJJMYMSMI-UHFFFAOYSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 5,6-dinitrooxyhexanoate Chemical compound [N+](=O)([O-])OC(CCCC(=O)OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N=1)C(=CN2CC)CCC)=O)CO[N+](=O)[O-] OKZLWXJJMYMSMI-UHFFFAOYSA-N 0.000 claims 1
- YCAMBEZYYUGQGE-UHFFFAOYSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 6-nitrooxyhexanoate Chemical compound [N+](=O)([O-])OCCCCCC(=O)OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N=1)C(=CN2CC)CCC)=O YCAMBEZYYUGQGE-UHFFFAOYSA-N 0.000 claims 1
- WBDONDAAANGWPG-UHFFFAOYSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 6-nitrooxyhexanoate 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound CCCC1=CN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CCOC(=O)CCCCCO[N+](=O)[O-])OCCC)CC.C(C(=O)O)C(CC(=O)O)(C(=O)O)O WBDONDAAANGWPG-UHFFFAOYSA-N 0.000 claims 1
- IITVRWVPTKQOPC-UHFFFAOYSA-N 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl 6-nitrooxyhexyl carbonate Chemical compound C(OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N=1)C(=CN2CC)CCC)=O)(OCCCCCCO[N+](=O)[O-])=O IITVRWVPTKQOPC-UHFFFAOYSA-N 0.000 claims 1
- OPUKECCJFFBHHL-UHFFFAOYSA-N 2-[4-[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)phenyl]sulfonylpiperazin-1-yl]ethyl 5,6-dinitrooxyhexanoate Chemical compound CCCC1=CN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CCOC(=O)CCCC(CO[N+](=O)[O-])O[N+](=O)[O-])OCC)C OPUKECCJFFBHHL-UHFFFAOYSA-N 0.000 claims 1
- MILXNZLBBFVZCJ-UHFFFAOYSA-N 2-[4-[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)phenyl]sulfonylpiperazin-1-yl]ethyl 6-nitrooxyhexanoate Chemical compound CCCC1=CN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CCOC(=O)CCCCCO[N+](=O)[O-])OCC)C MILXNZLBBFVZCJ-UHFFFAOYSA-N 0.000 claims 1
- IICVPNIRHLOPNF-UHFFFAOYSA-N 5,6-dinitrooxyhexyl 2-[4-[3-(5-ethyl-4-oxo-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperazin-1-yl]ethyl carbonate Chemical compound C(OCCN1CCN(CC1)S(=O)(=O)C1=CC(=C(C=C1)OCCC)C=1NC(C2=C(N=1)C(=CN2CC)CCC)=O)(OCCCCC(CO[N+](=O)[O-])O[N+](=O)[O-])=O IICVPNIRHLOPNF-UHFFFAOYSA-N 0.000 claims 1
- XGBCQJBLBIYQGF-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C(CCCCC)(=O)O Chemical compound C(C=C/C(=O)O)(=O)O.C(CCCCC)(=O)O XGBCQJBLBIYQGF-UHFFFAOYSA-N 0.000 claims 1
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 1
- 206010074026 Exfoliation glaucoma Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 206010067013 Normal tension glaucoma Diseases 0.000 claims 1
- 206010035015 Pigmentary glaucoma Diseases 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 1
- JKKDPRJNUHCBCT-SFTDATJTSA-N [(2S)-1-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl]pyrrolidin-2-yl]methyl (5S)-5,6-dinitrooxyhexanoate Chemical compound COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4COC(=O)CCC[C@@H](CO[N+](=O)[O-])O[N+](=O)[O-])Cl JKKDPRJNUHCBCT-SFTDATJTSA-N 0.000 claims 1
- YXCZCBDZNPULHK-IBGZPJMESA-N [(2S)-1-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl]pyrrolidin-2-yl]methyl 2-(2-nitrooxyethoxy)acetate Chemical compound [N+](=O)([O-])OCCOCC(=O)OC[C@H]1N(CCC1)C1=NC=C(C(=N1)NCC1=CC(=C(C=C1)OC)Cl)C(NCC1=NC=CC=N1)=O YXCZCBDZNPULHK-IBGZPJMESA-N 0.000 claims 1
- PZDZSKCORVUHGH-BGERDNNASA-N [(2S)-1-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl]pyrrolidin-2-yl]methyl 3-(2,3-dinitrooxypropoxy)propanoate Chemical compound COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4COC(=O)CCOCC(CO[N+](=O)[O-])O[N+](=O)[O-])Cl PZDZSKCORVUHGH-BGERDNNASA-N 0.000 claims 1
- PZDZSKCORVUHGH-SFTDATJTSA-N [(2S)-1-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl]pyrrolidin-2-yl]methyl 3-[(2S)-2,3-dinitrooxypropoxy]propanoate Chemical compound [N+](=O)([O-])O[C@@H](COCCC(=O)OC[C@H]1N(CCC1)C1=NC=C(C(=N1)NCC1=CC(=C(C=C1)OC)Cl)C(NCC1=NC=CC=N1)=O)CO[N+](=O)[O-] PZDZSKCORVUHGH-SFTDATJTSA-N 0.000 claims 1
- JKKDPRJNUHCBCT-BGERDNNASA-N [(2S)-1-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5-(pyrimidin-2-ylmethylcarbamoyl)pyrimidin-2-yl]pyrrolidin-2-yl]methyl 5,6-dinitrooxyhexanoate Chemical compound [N+](=O)([O-])OC(CCCC(=O)OC[C@H]1N(CCC1)C1=NC=C(C(=N1)NCC1=CC(=C(C=C1)OC)Cl)C(NCC1=NC=CC=N1)=O)CO[N+](=O)[O-] JKKDPRJNUHCBCT-BGERDNNASA-N 0.000 claims 1
- 201000011190 diabetic macular edema Diseases 0.000 claims 1
- 201000004949 exfoliation syndrome Diseases 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- VMUPERDXQJQDOJ-UHFFFAOYSA-N hexanoic acid 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound C(CCCCC)(=O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O VMUPERDXQJQDOJ-UHFFFAOYSA-N 0.000 claims 1
- 201000002978 low tension glaucoma Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 208000004644 retinal vein occlusion Diseases 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024125823A JP2024150732A (ja) | 2018-08-06 | 2024-08-01 | 一酸化窒素放出性ホスホジエステラーゼ５型阻害薬 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18187482.7 | 2018-08-06 | ||
| EP18187482 | 2018-08-06 | ||
| EP18210147.7 | 2018-12-04 | ||
| EP18210147 | 2018-12-04 | ||
| PCT/EP2019/070597 WO2020030489A1 (en) | 2018-08-06 | 2019-07-31 | Nitric oxide releasing phosphodiesterase type 5 inhibitor |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024125823A Division JP2024150732A (ja) | 2018-08-06 | 2024-08-01 | 一酸化窒素放出性ホスホジエステラーゼ５型阻害薬 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021533152A JP2021533152A (ja) | 2021-12-02 |
| JP2021533152A5 JP2021533152A5 (https=) | 2022-08-08 |
| JPWO2020030489A5 true JPWO2020030489A5 (https=) | 2022-08-08 |
| JP7596257B2 JP7596257B2 (ja) | 2024-12-09 |
Family
ID=67539493
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021506326A Active JP7596257B2 (ja) | 2018-08-06 | 2019-07-31 | 一酸化窒素放出性ホスホジエステラーゼ５型阻害薬 |
| JP2024125823A Pending JP2024150732A (ja) | 2018-08-06 | 2024-08-01 | 一酸化窒素放出性ホスホジエステラーゼ５型阻害薬 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024125823A Pending JP2024150732A (ja) | 2018-08-06 | 2024-08-01 | 一酸化窒素放出性ホスホジエステラーゼ５型阻害薬 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US11980618B2 (https=) |
| EP (1) | EP3833395A1 (https=) |
| JP (2) | JP7596257B2 (https=) |
| KR (1) | KR102836746B1 (https=) |
| CN (2) | CN119350347A (https=) |
| AU (1) | AU2019319004B2 (https=) |
| BR (1) | BR112021001950A2 (https=) |
| CA (1) | CA3108551A1 (https=) |
| MX (2) | MX2021001503A (https=) |
| TW (1) | TWI839375B (https=) |
| WO (1) | WO2020030489A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7708771B2 (ja) * | 2020-02-05 | 2025-07-15 | ニコックス エス．エー． | 緑内障及び高眼圧症の処置のための組成物 |
| CN111217834B (zh) * | 2020-02-21 | 2021-10-26 | 维眸生物科技（上海）有限公司 | Rock激酶抑制剂的硝基氧衍生物 |
| WO2022022669A1 (en) * | 2020-07-30 | 2022-02-03 | Biofront Therapeutics (Beijing) Co., Ltd. | Dual-functional compounds and methods of use |
| KR102731727B1 (ko) * | 2020-07-30 | 2024-11-20 | 바이오프런트 쎄라퓨틱스 (베이징) 컴퍼니 리미티드 | 이중-기능성 화합물 및 이의 사용 방법 |
| CN116456963A (zh) * | 2020-11-02 | 2023-07-18 | 尼科斯股份有限公司 | 用于治疗干性年龄相关性黄斑变性、地图状萎缩和青光眼相关性神经变性的no-pde5抑制剂 |
| UY39509A (es) * | 2020-11-09 | 2022-01-31 | Ildong Pharmaceutical Co Ltd | Compuestos inhibidores de la pde-5 y/o la pde-6 donantes de óxido de nitrógeno, y usos de estos |
| WO2023005180A1 (en) * | 2021-07-30 | 2023-02-02 | Biofront Therapeutics (Beijing) Co., Ltd. | Dual-functional compounds and methods of use |
| JP2024541626A (ja) | 2021-12-02 | 2024-11-08 | ニコックス エス．エー． | 一酸化窒素放出ホスホジエステラーゼ５阻害剤を含有する眼科用医薬組成物及びその製造方法 |
| EP4233867B1 (en) | 2022-02-24 | 2025-09-03 | Nicox SA | Pde5 inhibitor for use in the treatment of anterior ischemic optic neuropathy |
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| JPS60149521A (ja) | 1984-01-18 | 1985-08-07 | Eisai Co Ltd | 高眼圧・緑内障治療・予防用点眼剤 |
| US4975428A (en) | 1988-05-31 | 1990-12-04 | Iolab Corporation | Treatment of glaucoma using phosphodiesterase inhibitors |
| GB9013750D0 (en) | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
| IL137429A0 (en) | 1999-07-28 | 2001-07-24 | Pfizer Prod Inc | Methods and compsitions for treating diseases and conditions of the eye |
| EP1219609B1 (en) | 1999-09-16 | 2007-04-04 | Tanabe Seiyaku Co., Ltd. | Aromatic nitrogenous six-membered ring compounds |
| KR100358083B1 (ko) * | 2000-02-17 | 2002-10-25 | 에스케이케미칼주식회사 | 피롤로피리미디논 유도체와 이의 제조방법, 그리고 이의용도 |
| US20020168424A1 (en) | 2002-07-31 | 2002-11-14 | Dr. Mohsen Shahinpoor | Nitric oxide (NO) donor+cGMP-PDE5 inhibitor as a topical drug for glaucoma |
| DE102005001989A1 (de) * | 2005-01-15 | 2006-07-20 | Bayer Healthcare Ag | Intravenöse Formulierungen von PDE-Inhibitoren |
| WO2008075152A1 (en) * | 2006-12-15 | 2008-06-26 | Pfizer Products Inc. | 1- [4- (sulfonyl) -phenyl] -5- (benzyl) -ih-i, 2, 4-triazol derivatives as inhibitors of carbonic anhydrase for treating glaucoma or ocular hypertension |
| US7993616B2 (en) | 2007-09-19 | 2011-08-09 | C-Quest Technologies LLC | Methods and devices for reducing hazardous air pollutants |
| ES2393049T3 (es) | 2008-02-07 | 2012-12-18 | Nicox S.A. | Compuestos donantes de óxido nítrico |
| EP2398761A4 (en) * | 2009-02-18 | 2015-11-04 | Bezwada Biomedical Llc | CONTROLLED RELEASE OF NITRIC OXIDE AND MEDICINES FROM FUNCTIONALIZED MACROMERS AND OLIGOMERS |
| CN102498088A (zh) * | 2009-09-15 | 2012-06-13 | 帝斯曼知识产权资产管理有限公司 | 硝基氧基酯及其制备和用途 |
| AU2010330813B2 (en) * | 2009-12-18 | 2016-04-28 | Exodos Life Sciences Limited Partnership | Methods and compositions for treating peripheral vascular disease |
| US9446015B2 (en) | 2012-10-23 | 2016-09-20 | Nicox Science Ireland | Quinone based nitric oxide donating compounds for ophthalmic use |
| EP2826491A1 (en) * | 2013-07-15 | 2015-01-21 | Nicox Science Ireland | Ophthalmic compositions containing a nitric oxide donor |
| TW201625584A (zh) | 2014-07-02 | 2016-07-16 | 諾華公司 | 茚滿及吲哚啉衍生物及其作為可溶性鳥苷酸環化酶活化劑之用途 |
| ES2632808T3 (es) | 2014-09-04 | 2017-09-15 | Nicox Science Ireland | Compuestos de carnosina donadores de óxido nítrico |
| US10610509B2 (en) | 2014-11-19 | 2020-04-07 | Nicox S.A. | Combinations of prostaglandins and nitric oxide donors |
| US10280138B2 (en) * | 2015-03-31 | 2019-05-07 | Nicox S.A. | Nitric oxide donating derivatives of fluprostenol |
| US10047047B2 (en) | 2015-03-31 | 2018-08-14 | Nicox S.A. | Nitric oxide donating derivatives of latanoprost free acid |
| EP3088388A1 (en) * | 2015-04-30 | 2016-11-02 | NicOx S.A. | Nitric oxide donating derivatives of prostaglandins |
| PL3377495T3 (pl) * | 2015-11-16 | 2022-05-16 | Topadur Pharma Ag | Pochodne 2-fenylo-3,4-dihydropirolo[2,1-f] [1,2,4]triazynonu jako inhibitory fosfodiesterazy i ich zastosowania |
| KR102670626B1 (ko) | 2017-05-22 | 2024-05-29 | 토파두르 파마 아게 | 가용성 구아닐레이트 사이클라제 활성제 및 포스포디에스테라제 억제제의 신규한 이중 작용 방식 및 이의 용도 |
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2019
- 2019-07-31 JP JP2021506326A patent/JP7596257B2/ja active Active
- 2019-07-31 CN CN202411482883.4A patent/CN119350347A/zh active Pending
- 2019-07-31 KR KR1020217006735A patent/KR102836746B1/ko active Active
- 2019-07-31 CN CN201980052271.2A patent/CN112566670B/zh active Active
- 2019-07-31 AU AU2019319004A patent/AU2019319004B2/en active Active
- 2019-07-31 BR BR112021001950-2A patent/BR112021001950A2/pt unknown
- 2019-07-31 US US17/265,134 patent/US11980618B2/en active Active
- 2019-07-31 MX MX2021001503A patent/MX2021001503A/es unknown
- 2019-07-31 EP EP19749305.9A patent/EP3833395A1/en active Pending
- 2019-07-31 WO PCT/EP2019/070597 patent/WO2020030489A1/en not_active Ceased
- 2019-07-31 CA CA3108551A patent/CA3108551A1/en active Pending
- 2019-08-02 TW TW108127595A patent/TWI839375B/zh active
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2021
- 2021-02-05 MX MX2023012941A patent/MX2023012941A/es unknown
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2024
- 2024-03-22 US US18/614,143 patent/US20240245684A1/en active Pending
- 2024-08-01 JP JP2024125823A patent/JP2024150732A/ja active Pending
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