JP2018507207A5 - - Google Patents
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- Publication number
- JP2018507207A5 JP2018507207A5 JP2017543772A JP2017543772A JP2018507207A5 JP 2018507207 A5 JP2018507207 A5 JP 2018507207A5 JP 2017543772 A JP2017543772 A JP 2017543772A JP 2017543772 A JP2017543772 A JP 2017543772A JP 2018507207 A5 JP2018507207 A5 JP 2018507207A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorobiphenyl
- chloro
- amino
- compound
- item
- 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 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 208000017169 kidney disease Diseases 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000006186 oral dosage form Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 206010019280 Heart failures Diseases 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 9
- RRCIEZCEOIRHEB-VQIMIIECSA-N (2R,4R)-5-[4-(5-chloro-2-fluorophenyl)phenyl]-2-hydroxy-4-[(5-methyl-1,3-oxazole-2-carbonyl)amino]pentanoic acid Chemical compound ClC=1C=CC(=C(C=1)C1=CC=C(C=C1)C[C@H](C[C@H](C(=O)O)O)NC(=O)C=1OC(=CN=1)C)F RRCIEZCEOIRHEB-VQIMIIECSA-N 0.000 claims description 8
- -1 7-azabenzotriazol-1-yl Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 102000002723 Atrial Natriuretic Factor Human genes 0.000 claims description 6
- 101800001288 Atrial natriuretic factor Proteins 0.000 claims description 6
- 101800001890 Atrial natriuretic peptide Proteins 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- NSQLIUXCMFBZME-MPVJKSABSA-N carperitide Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)=O)[C@@H](C)CC)C1=CC=CC=C1 NSQLIUXCMFBZME-MPVJKSABSA-N 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- WDBBEKDVFVFYRC-CRAIPNDOSA-N ethyl (2r,4r)-4-amino-5-[4-(5-chloro-2-fluorophenyl)phenyl]-2-hydroxypentanoate Chemical compound C1=CC(C[C@@H](N)C[C@@H](O)C(=O)OCC)=CC=C1C1=CC(Cl)=CC=C1F WDBBEKDVFVFYRC-CRAIPNDOSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- HGZMWZLQUPTYSX-UHFFFAOYSA-N 2-methyl-3H-1,3-oxazole-2-carboxylic acid Chemical compound CC1(OC=CN1)C(=O)O HGZMWZLQUPTYSX-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 4
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 229920001059 synthetic polymer Polymers 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 239000005541 ACE inhibitor Substances 0.000 claims description 2
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 2
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- 239000007821 HATU Substances 0.000 claims description 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 2
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 208000020832 chronic kidney disease Diseases 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims description 2
- 238000013270 controlled release Methods 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 230000001882 diuretic effect Effects 0.000 claims description 2
- 230000024924 glomerular filtration Effects 0.000 claims description 2
- 239000007902 hard capsule Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000006207 intravenous dosage form Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000002461 renin inhibitor Substances 0.000 claims description 2
- 229940086526 renin-inhibitors Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- VIIDTFSZAWAMNW-UHFFFAOYSA-M sodium 5-methyl-1,3-oxazole-2-carboxylate Chemical compound CC1=CN=C(O1)C(=O)[O-].[Na+] VIIDTFSZAWAMNW-UHFFFAOYSA-M 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 210000002700 urine Anatomy 0.000 claims description 2
- 125000005500 uronium group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 102000003729 Neprilysin Human genes 0.000 description 2
- 108090000028 Neprilysin Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562118067P | 2015-02-19 | 2015-02-19 | |
| US62/118,067 | 2015-02-19 | ||
| PCT/US2016/017699 WO2016133803A1 (en) | 2015-02-19 | 2016-02-12 | (2r,4r)-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-2-hydroxy-4-[(5-methyloxazole-2-carbonyl)amino]pentanoic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018507207A JP2018507207A (ja) | 2018-03-15 |
| JP2018507207A5 true JP2018507207A5 (enExample) | 2019-02-14 |
| JP6714009B2 JP6714009B2 (ja) | 2020-06-24 |
Family
ID=55456914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017543772A Active JP6714009B2 (ja) | 2015-02-19 | 2016-02-12 | （２ｒ，４ｒ）−５−（５’−クロロ−２’−フルオロビフェニル−４−イル）−２−ヒドロキシ−４−［（５−メチルオキサゾール−２−カルボニル）アミノ］ペンタン酸 |
Country Status (29)
| Country | Link |
|---|---|
| US (6) | US9533962B2 (enExample) |
| EP (1) | EP3259255B1 (enExample) |
| JP (1) | JP6714009B2 (enExample) |
| KR (1) | KR102573351B1 (enExample) |
| CN (1) | CN107250119B (enExample) |
| AU (1) | AU2016220348B2 (enExample) |
| BR (1) | BR112017017783A2 (enExample) |
| CA (1) | CA2975269C (enExample) |
| CO (1) | CO2017008426A2 (enExample) |
| CY (1) | CY1123728T1 (enExample) |
| DK (1) | DK3259255T3 (enExample) |
| ES (1) | ES2857101T3 (enExample) |
| HR (1) | HRP20210040T1 (enExample) |
| HU (1) | HUE052732T2 (enExample) |
| IL (1) | IL253759B (enExample) |
| LT (1) | LT3259255T (enExample) |
| MX (1) | MX370065B (enExample) |
| MY (1) | MY191183A (enExample) |
| PH (1) | PH12017501444A1 (enExample) |
| PL (1) | PL3259255T3 (enExample) |
| PT (1) | PT3259255T (enExample) |
| RS (1) | RS61325B1 (enExample) |
| RU (1) | RU2715241C2 (enExample) |
| SG (1) | SG11201706662YA (enExample) |
| SI (1) | SI3259255T1 (enExample) |
| SM (1) | SMT202100028T1 (enExample) |
| TW (1) | TWI707846B (enExample) |
| WO (1) | WO2016133803A1 (enExample) |
| ZA (1) | ZA201705487B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112014030743B1 (pt) * | 2012-06-08 | 2022-09-06 | Theravance Biopharma R&D Ip, Llc | Composto inibidor de neprilisina, processo para a preparação do referido composto, composição farmacêutica e uso do referido composto |
| LT3259255T (lt) | 2015-02-19 | 2021-04-26 | Theravance Biopharma R&D Ip, Llc | (2r,4r)-5-(5`-chlor-2`-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentano rūgštis |
| KR102238177B1 (ko) | 2017-09-15 | 2021-04-07 | 주식회사 엘지화학 | 전지셀 및 전극 리드 제조방법 |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
| EP3994134B9 (en) * | 2019-07-03 | 2024-06-26 | Merck Patent GmbH | Process for manufacturing (s)-3-hydroxy-1-(1h-indol-5-yl)-2-oxo-pyrrolidine-3-carboxylic acid 3,5-difluoro-benzylamide |
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| US4206232A (en) | 1976-05-10 | 1980-06-03 | E. R. Squibb & Sons, Inc. | Relieving hypertension with carboxyalkylacylamino acids |
| IL58849A (en) | 1978-12-11 | 1983-03-31 | Merck & Co Inc | Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them |
| FR2480747A1 (fr) | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
| US4906615A (en) | 1980-12-18 | 1990-03-06 | Schering Corporation | Substituted dipeptides as inhibitors of enkephalinases |
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| EP0225292A3 (en) | 1985-12-06 | 1988-11-30 | Ciba-Geigy Ag | Certain n-substituted butyramide derivatives |
| US4929641B1 (en) | 1988-05-11 | 1994-08-30 | Schering Corp | Mercapto-acylamino acid antihypertensives |
| KR880007441A (ko) | 1986-12-11 | 1988-08-27 | 알렌 제이.스피겔 | 스피로-치환된 글루타르아미드 이뇨제 |
| FR2623498B1 (fr) | 1987-11-24 | 1990-04-06 | Bioprojet Soc Civ | Nouveaux composes enantiomeres derives d'amino-acides, leur procede de preparation et leurs applications therapeutiques |
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| US5508272A (en) | 1993-06-15 | 1996-04-16 | Bristol-Myers Squibb Company | Compounds containing a fused bicycle ring and processes therefor |
| DE19510566A1 (de) | 1995-03-23 | 1996-09-26 | Kali Chemie Pharma Gmbh | Benzazepin-, Benzoxazepin- und Benzothiazepin-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JPH11505522A (ja) | 1995-04-21 | 1999-05-21 | ノバルティス・アクチエンゲゼルシャフト | エンドセリン阻害剤としてのｎ−アロイルアミノ酸アミド |
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| WO2007106708A2 (en) | 2006-03-10 | 2007-09-20 | Novartis Ag | Combinations of the angiotensin ii antagonist valsartan and the nep inhibitor daglutril |
| PT2121578T (pt) | 2007-01-12 | 2016-11-14 | Novartis Ag | Processo de preparação de ácido 5-bifenil-4-amino-2-metil-pentanoico |
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| PE20091364A1 (es) | 2008-01-17 | 2009-10-13 | Novartis Ag | Proceso para la preparacion de inhibidores de nep |
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| HRP20151061T1 (hr) | 2010-01-22 | 2015-12-04 | Novartis Ag | Posrednici inhibitora neutralne endopeptidaze i postupak njihove pripreme |
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| SG191175A1 (en) | 2010-12-15 | 2013-07-31 | Theravance Inc | Neprilysin inhibitors |
| CN103380119B (zh) | 2011-02-17 | 2016-02-17 | 施万生物制药研发Ip有限责任公司 | 作为脑啡肽酶抑制剂的经取代的氨基丁酸衍生物 |
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| CN103596928B (zh) | 2011-05-31 | 2017-02-15 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| CA2835281A1 (en) | 2011-05-31 | 2012-12-06 | Theravance, Inc. | Neprilysin inhibitors |
| US9499487B2 (en) | 2011-05-31 | 2016-11-22 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| TWI560172B (en) | 2011-11-02 | 2016-12-01 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| CA2871292A1 (en) | 2012-05-31 | 2013-12-05 | Theravance Biopharma R&D Ip, Llc | Nitric oxide donor neprilysin inhibitors |
| ES2710932T3 (es) | 2012-06-08 | 2019-04-29 | Theravance Biopharma R&D Ip Llc | Inhibidores de neprilisina |
| BR112014030743B1 (pt) | 2012-06-08 | 2022-09-06 | Theravance Biopharma R&D Ip, Llc | Composto inibidor de neprilisina, processo para a preparação do referido composto, composição farmacêutica e uso do referido composto |
| KR102104954B1 (ko) | 2012-08-08 | 2020-04-27 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | 네프릴리신 억제제 |
| HUE034210T2 (hu) | 2013-03-05 | 2018-02-28 | Theravance Biopharma R&D Ip Llc | Neprilizininhibitorok |
| MX2016009759A (es) * | 2014-01-30 | 2016-11-17 | Theravance Biopharma R&D Ip Llc | Inhibidores de neprilisina. |
| MY187899A (en) | 2015-02-11 | 2021-10-27 | Theravance Biopharma R&D Ip Llc | (2s,4r)-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-4-(ethoxyoxalylamino)-2-hydroxymethyl-2-methylpentanoic acid as neprilysin inhibitor |
| LT3259255T (lt) | 2015-02-19 | 2021-04-26 | Theravance Biopharma R&D Ip, Llc | (2r,4r)-5-(5`-chlor-2`-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentano rūgštis |
-
2016
- 2016-02-12 LT LTEP16708268.4T patent/LT3259255T/lt unknown
- 2016-02-12 ES ES16708268T patent/ES2857101T3/es active Active
- 2016-02-12 RS RS20210057A patent/RS61325B1/sr unknown
- 2016-02-12 RU RU2017132430A patent/RU2715241C2/ru active
- 2016-02-12 US US15/042,391 patent/US9533962B2/en active Active
- 2016-02-12 WO PCT/US2016/017699 patent/WO2016133803A1/en not_active Ceased
- 2016-02-12 BR BR112017017783-8A patent/BR112017017783A2/pt not_active Application Discontinuation
- 2016-02-12 SI SI201631051T patent/SI3259255T1/sl unknown
- 2016-02-12 MY MYPI2017702772A patent/MY191183A/en unknown
- 2016-02-12 SM SM20210028T patent/SMT202100028T1/it unknown
- 2016-02-12 EP EP16708268.4A patent/EP3259255B1/en active Active
- 2016-02-12 PL PL16708268T patent/PL3259255T3/pl unknown
- 2016-02-12 PT PT167082684T patent/PT3259255T/pt unknown
- 2016-02-12 JP JP2017543772A patent/JP6714009B2/ja active Active
- 2016-02-12 SG SG11201706662YA patent/SG11201706662YA/en unknown
- 2016-02-12 DK DK16708268.4T patent/DK3259255T3/da active
- 2016-02-12 MX MX2017010666A patent/MX370065B/es active IP Right Grant
- 2016-02-12 HR HRP20210040TT patent/HRP20210040T1/hr unknown
- 2016-02-12 HU HUE16708268A patent/HUE052732T2/hu unknown
- 2016-02-12 CA CA2975269A patent/CA2975269C/en active Active
- 2016-02-12 CN CN201680011254.0A patent/CN107250119B/zh active Active
- 2016-02-12 KR KR1020177026454A patent/KR102573351B1/ko active Active
- 2016-02-12 AU AU2016220348A patent/AU2016220348B2/en not_active Ceased
- 2016-02-19 TW TW105104991A patent/TWI707846B/zh active
- 2016-11-21 US US15/357,269 patent/US9872855B2/en active Active
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2017
- 2017-07-31 IL IL253759A patent/IL253759B/en active IP Right Grant
- 2017-08-10 PH PH12017501444A patent/PH12017501444A1/en unknown
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- 2017-08-18 CO CONC2017/0008426A patent/CO2017008426A2/es unknown
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2018
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2019
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2021
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- 2021-05-14 US US17/302,877 patent/US11642332B2/en active Active
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