JP2016514141A5 - - Google Patents
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- Publication number
- JP2016514141A5 JP2016514141A5 JP2016501568A JP2016501568A JP2016514141A5 JP 2016514141 A5 JP2016514141 A5 JP 2016514141A5 JP 2016501568 A JP2016501568 A JP 2016501568A JP 2016501568 A JP2016501568 A JP 2016501568A JP 2016514141 A5 JP2016514141 A5 JP 2016514141A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- methylquinolin
- oxymethyl
- methyl
- phenyl
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000009472 formulation Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- -1 4-Chloro-2-cyano-3-{[(2-methylquinolin-8-yl) oxy] methyl} phenyl Chemical group 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 208000028185 Angioedema Diseases 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 210000002381 plasma Anatomy 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 102000010183 Bradykinin receptor Human genes 0.000 claims description 6
- 108050001736 Bradykinin receptor Proteins 0.000 claims description 6
- 206010019860 Hereditary angioedema Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 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 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 102000055157 Complement C1 Inhibitor Human genes 0.000 claims description 4
- 108700040183 Complement C1 Inhibitor Proteins 0.000 claims description 4
- 101000975003 Homo sapiens Kallistatin Proteins 0.000 claims description 4
- 101001077723 Homo sapiens Serine protease inhibitor Kazal-type 6 Proteins 0.000 claims description 4
- 229940122920 Kallikrein inhibitor Drugs 0.000 claims description 4
- 102100023012 Kallistatin Human genes 0.000 claims description 4
- 206010030113 Oedema Diseases 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 239000004023 fresh frozen plasma Substances 0.000 claims description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 4
- 238000010922 spray-dried dispersion Methods 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- NBCISQDBUPJLTO-MDWZMJQESA-N (e)-3-(6-acetamidopyridin-3-yl)-n-[2-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]prop-2-enamide Chemical compound C1=NC(NC(=O)C)=CC=C1\C=C\C(=O)NCC(=O)NC1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1Cl NBCISQDBUPJLTO-MDWZMJQESA-N 0.000 claims description 2
- XCKWRUGRUFVXGC-NTEUORMPSA-N (e)-3-(6-acetamidopyridin-3-yl)-n-[2-[2,4-dichloro-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]prop-2-enamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CNC(=O)\C=C\C1=CC=C(NC(C)=O)N=C1 XCKWRUGRUFVXGC-NTEUORMPSA-N 0.000 claims description 2
- LRFPQMIXTRKWGR-RVDMUPIBSA-N (e)-n-[2-[4-chloro-2-cyano-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]-3-(3-methoxyphenyl)prop-2-enamide Chemical compound COC1=CC=CC(\C=C\C(=O)NCC(=O)N(C)C=2C(=C(COC=3C4=NC(C)=CC=C4C=CC=3)C(Cl)=CC=2)C#N)=C1 LRFPQMIXTRKWGR-RVDMUPIBSA-N 0.000 claims description 2
- HRMANULVIPULPC-OQLLNIDSSA-N (e)-n-[2-[4-chloro-2-cyano-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(C#N)C=1N(C)C(=O)CNC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1 HRMANULVIPULPC-OQLLNIDSSA-N 0.000 claims description 2
- ISROIASQKHGIJZ-UHFFFAOYSA-N 2-(4-aminobutylcarbamoylamino)-n-[4-chloro-2-cyano-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound NCCCCNC(=O)NCC(=O)N(C)C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1C#N ISROIASQKHGIJZ-UHFFFAOYSA-N 0.000 claims description 2
- QMOFUAFIOXKKNA-UHFFFAOYSA-N 2-(5-benzoyl-1-methylpyrrol-2-yl)-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC(N1C)=CC=C1C(=O)C1=CC=CC=C1 QMOFUAFIOXKKNA-UHFFFAOYSA-N 0.000 claims description 2
- IKBZKTIWBYTIOT-UHFFFAOYSA-N 2-[5-(4-aminobenzoyl)-1-methylpyrrol-2-yl]-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC(N1C)=CC=C1C(=O)C1=CC=C(N)C=C1 IKBZKTIWBYTIOT-UHFFFAOYSA-N 0.000 claims description 2
- NYIKMJQJOYNHLK-UHFFFAOYSA-N 2-[5-(4-cyanobenzoyl)-1-methylpyrrol-2-yl]-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]acetamide Chemical compound C12=NC(C)=CC=C2C=CC=C1OCC(C=1Cl)=C(Cl)C=CC=1NC(=O)CC(N1C)=CC=C1C(=O)C1=CC=C(C#N)C=C1 NYIKMJQJOYNHLK-UHFFFAOYSA-N 0.000 claims description 2
- XFTJDGAYMRFSDJ-UHFFFAOYSA-N 2-[5-(4-cyanobenzoyl)-1h-pyrrol-2-yl]-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC(N1)=CC=C1C(=O)C1=CC=C(C#N)C=C1 XFTJDGAYMRFSDJ-UHFFFAOYSA-N 0.000 claims description 2
- DMHZOSVTCZAJGP-UHFFFAOYSA-N 2-[5-(6-cyanopyridine-3-carbonyl)-1-methylpyrrol-2-yl]-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC(N1C)=CC=C1C(=O)C1=CC=C(C#N)N=C1 DMHZOSVTCZAJGP-UHFFFAOYSA-N 0.000 claims description 2
- VYYSWHWZVWPBKK-UHFFFAOYSA-N 2-[5-(cyclohexanecarbonyl)-1-methylpyrrol-2-yl]-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC(N1C)=CC=C1C(=O)C1CCCCC1 VYYSWHWZVWPBKK-UHFFFAOYSA-N 0.000 claims description 2
- HRLBCSJZOFMEKH-BKKLXTLSSA-N 4-[(e)-3-[[(z)-3-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]prop-2-enyl]amino]-3-oxoprop-1-enyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1\C=C\C(=O)NC\C=C/C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1Cl HRLBCSJZOFMEKH-BKKLXTLSSA-N 0.000 claims description 2
- XZERMVBWFJENLS-MHWRWJLKSA-N 4-[(e)-3-[[2-[2,4-dichloro-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]amino]-3-oxoprop-1-enyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1\C=C\C(=O)NCC(=O)N(C)C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1Cl XZERMVBWFJENLS-MHWRWJLKSA-N 0.000 claims description 2
- YAOHXRHHUWDNDM-UHFFFAOYSA-N 4-[[2-[4-chloro-2-cyano-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]carbamoylamino]butanoic acid Chemical compound OC(=O)CCCNC(=O)NCC(=O)N(C)C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1C#N YAOHXRHHUWDNDM-UHFFFAOYSA-N 0.000 claims description 2
- 101800004538 Bradykinin Proteins 0.000 claims description 2
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims description 2
- 102100035792 Kininogen-1 Human genes 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- KTUYWPXXZRLSON-UHFFFAOYSA-N n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-2-[5-(2,2-dimethylpropanoyl)-1-methylpyrrol-2-yl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC1=CC=C(C(=O)C(C)(C)C)N1C KTUYWPXXZRLSON-UHFFFAOYSA-N 0.000 claims description 2
- KTAARZWLIWWBTL-UHFFFAOYSA-N n-[4-chloro-2-cyano-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-2-(ethylcarbamoylamino)-n-methylacetamide Chemical compound CCNC(=O)NCC(=O)N(C)C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1C#N KTAARZWLIWWBTL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- ZTMFMJMJGDWCGD-UHFFFAOYSA-N 1-[[4-chloro-3-[[4-(4-fluoropyrazol-1-yl)-2-methylquinolin-8-yl]oxymethyl]-6-methylpyridin-2-yl]methyl]-2-oxopyridine-3-carbonitrile Chemical compound C1=CC=C(C#N)C(=O)N1CC1=NC(C)=CC(Cl)=C1COC(C1=NC(C)=C2)=CC=CC1=C2N1C=C(F)C=N1 ZTMFMJMJGDWCGD-UHFFFAOYSA-N 0.000 claims 1
- XDSJSAQKNVFGCS-UHFFFAOYSA-N 2-[5-(4-cyanobenzoyl)-1-methylpyrrol-2-yl]-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CC(N1C)=CC=C1C(=O)C1=CC=C(C#N)C=C1 XDSJSAQKNVFGCS-UHFFFAOYSA-N 0.000 claims 1
- HRLBCSJZOFMEKH-TWYFDOCPSA-N 4-[(e)-3-[[(e)-3-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]prop-2-enyl]amino]-3-oxoprop-1-enyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1\C=C\C(=O)NC\C=C\C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1Cl HRLBCSJZOFMEKH-TWYFDOCPSA-N 0.000 claims 1
- 102100028519 B2 bradykinin receptor Human genes 0.000 claims 1
- 101710085045 B2 bradykinin receptor Proteins 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 24
- 239000012453 solvate Substances 0.000 description 8
- 0 C*c(c(*)c1C)ccc1Cl Chemical compound C*c(c(*)c1C)ccc1Cl 0.000 description 3
- 206010015866 Extravasation Diseases 0.000 description 3
- 230000036251 extravasation Effects 0.000 description 3
- 241000238366 Cephalopoda Species 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- AOZUWOHAZYLXRV-CLNHMMGSSA-N (e)-n-[2-[2,4-dichloro-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]-3-phenylprop-2-enamide;hydrochloride Chemical compound Cl.C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CNC(=O)\C=C\C1=CC=CC=C1 AOZUWOHAZYLXRV-CLNHMMGSSA-N 0.000 description 1
- NIVXTZDYYCIGNY-UHFFFAOYSA-N 2-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-N-methylacetamide Chemical compound ClC1=C(C=CC(=C1COC=1C=CC=C2C=CC(=NC=12)C)Cl)CC(=O)NC NIVXTZDYYCIGNY-UHFFFAOYSA-N 0.000 description 1
- FSOOSGIZMQWMPQ-UHFFFAOYSA-N C[n]1ncc(F)c1 Chemical compound C[n]1ncc(F)c1 FSOOSGIZMQWMPQ-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361786126P | 2013-03-14 | 2013-03-14 | |
| US61/786,126 | 2013-03-14 | ||
| PCT/US2014/024540 WO2014159637A1 (en) | 2013-03-14 | 2014-03-12 | Methods of treating b2-bradykinin receptor mediated angioedema |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016514141A JP2016514141A (ja) | 2016-05-19 |
| JP2016514141A5 true JP2016514141A5 (https=) | 2017-04-13 |
Family
ID=51625217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016501568A Pending JP2016514141A (ja) | 2013-03-14 | 2014-03-12 | Ｂ２−ブラジキニン受容体媒介の血管浮腫の治療方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20160030416A1 (https=) |
| EP (1) | EP2968308A4 (https=) |
| JP (1) | JP2016514141A (https=) |
| KR (1) | KR20150127718A (https=) |
| CN (1) | CN105228623A (https=) |
| AU (1) | AU2014244592A1 (https=) |
| BR (1) | BR112015022846A2 (https=) |
| CA (1) | CA2904052A1 (https=) |
| HK (1) | HK1220136A1 (https=) |
| MX (1) | MX2015012650A (https=) |
| RU (1) | RU2015138443A (https=) |
| WO (1) | WO2014159637A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2017325986B2 (en) * | 2016-09-16 | 2023-12-14 | Takeda Pharmaceutical Company Limited | Metabolite biomarkers for diseases associated with the contact activation system |
| WO2019101906A1 (en) | 2017-11-24 | 2019-05-31 | Pharvaris B.V. | Novel bradykinin b2 receptor antagonists |
| US12163956B2 (en) | 2019-02-21 | 2024-12-10 | Takeda Pharmaceutical Company Limited | Lateral flow immunoassay for measuring functional C1-esterase inhibitor (C1-INH) in plasma samples |
| UY38706A (es) * | 2019-05-23 | 2020-12-31 | Pharvaris Gmbh | Antagonistas cíclicos del receptor b2 de bradiquinina |
| UY38707A (es) * | 2019-05-23 | 2020-12-31 | Pharvaris Gmbh | Nuevos antagonistas cíclicos del receptor b2 de bradiquinina |
| US11401303B2 (en) | 2020-06-15 | 2022-08-02 | Taian City Qihang Biotechnology Co. | Synthetic peptide BRAP and application in preparation of anti-inflammatory drug for COVID-19 thereof |
| RS65427B1 (sr) | 2021-08-05 | 2024-05-31 | Pharvaris Gmbh | Kompozicija na bazi lipida za oralnu primenu antagonista receptora bradikinina b2 |
| EP4499100A1 (en) | 2022-03-25 | 2025-02-05 | Pharvaris GmbH | Therapeutic uses of bradykinin b2-receptor antagonists |
| TW202345810A (zh) | 2022-03-25 | 2023-12-01 | 瑞士商帕法瑞斯有限責任公司 | 包含緩激肽ｂ２受體拮抗劑之固態延長釋放組成物 |
| IL315699A (en) | 2022-03-25 | 2024-11-01 | Pharvaris Gmbh | A solid composition comprising dissolved bradykinin B2 receptor antagonists |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU680870B2 (en) * | 1993-04-28 | 1997-08-14 | Astellas Pharma Inc. | New heterocyclic compounds |
| KR20040011549A (ko) * | 2001-06-22 | 2004-02-05 | 화이자 프로덕츠 인크. | 저용해도 및(또는) 산-민감성 약물 및 중화된 산성중합체를 포함하는 제약 조성물 |
| WO2003087090A2 (en) * | 2002-04-10 | 2003-10-23 | Ortho-Mcneil Pharmaceutical,Inc. | Novel heteroaryl alkylamide derivatives useful as bradykinin receptor modulators |
| US20100068301A1 (en) * | 2006-11-30 | 2010-03-18 | Hutchinson John H | Compositions and treatments comprising 5-lipoxygenase-activating protein inhibitors and nitric oxide modulators |
| TWI407960B (zh) * | 2007-03-23 | 2013-09-11 | Jerini Ag | 小分子緩激肽ｂ２受體調節劑 |
| IT1391236B1 (it) * | 2008-07-11 | 2011-12-01 | St Luso Farm D'italia Spa | Composizioni farmaceutiche a base di antagonisti del recettore b2 delle chinine e corticosteroidi e loro uso |
| EP2316820A1 (en) * | 2009-10-28 | 2011-05-04 | Dompe S.p.A. | 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them |
-
2014
- 2014-03-12 CA CA2904052A patent/CA2904052A1/en not_active Abandoned
- 2014-03-12 WO PCT/US2014/024540 patent/WO2014159637A1/en not_active Ceased
- 2014-03-12 KR KR1020157029035A patent/KR20150127718A/ko not_active Withdrawn
- 2014-03-12 HK HK16108272.4A patent/HK1220136A1/zh unknown
- 2014-03-12 CN CN201480027533.7A patent/CN105228623A/zh active Pending
- 2014-03-12 MX MX2015012650A patent/MX2015012650A/es unknown
- 2014-03-12 AU AU2014244592A patent/AU2014244592A1/en not_active Abandoned
- 2014-03-12 RU RU2015138443A patent/RU2015138443A/ru not_active Application Discontinuation
- 2014-03-12 US US14/776,542 patent/US20160030416A1/en not_active Abandoned
- 2014-03-12 EP EP14776198.5A patent/EP2968308A4/en not_active Withdrawn
- 2014-03-12 JP JP2016501568A patent/JP2016514141A/ja active Pending
- 2014-03-12 BR BR112015022846A patent/BR112015022846A2/pt active Search and Examination
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