JP2017510576A5 - - Google Patents
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- Publication number
- JP2017510576A5 JP2017510576A5 JP2016558222A JP2016558222A JP2017510576A5 JP 2017510576 A5 JP2017510576 A5 JP 2017510576A5 JP 2016558222 A JP2016558222 A JP 2016558222A JP 2016558222 A JP2016558222 A JP 2016558222A JP 2017510576 A5 JP2017510576 A5 JP 2017510576A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- carbonyl
- pyridine
- diazepine
- carboxylate
- 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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- -1 2,3-dihydro-1H-isoindol-2-yl Chemical group 0.000 claims 59
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 11
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- HCDJQBTVYWELRZ-UHFFFAOYSA-N 1h-diazepine-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC=NN1 HCDJQBTVYWELRZ-UHFFFAOYSA-N 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 206010052779 Transplant rejections Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 230000003176 fibrotic effect Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 208000017169 kidney disease Diseases 0.000 claims 3
- 208000019423 liver disease Diseases 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- GMBGJLJXWMRPIE-UHFFFAOYSA-N 1-[2-(1,2,3,3a,4,6,7,7a-octahydrotriazolo[4,5-c]pyridine-5-carbonyl)-4,5,7,8-tetrahydropyrazolo[1,5-d][1,4]diazepin-6-yl]-3-[4-(trifluoromethoxy)phenyl]propan-1-one Chemical compound C1CN(CC2C1NNN2)C(=O)C3=NN4CCN(CCC4=C3)C(=O)CCC5=CC=C(C=C5)OC(F)(F)F GMBGJLJXWMRPIE-UHFFFAOYSA-N 0.000 claims 2
- YUOJULDAKIAAMA-UHFFFAOYSA-N CCC1=C(OCC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=CC(=C1)C#N Chemical compound CCC1=C(OCC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=CC(=C1)C#N YUOJULDAKIAAMA-UHFFFAOYSA-N 0.000 claims 2
- PRWLPVCFKAAQDK-UHFFFAOYSA-N FC(F)OC1=C(F)C=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound FC(F)OC1=C(F)C=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 PRWLPVCFKAAQDK-UHFFFAOYSA-N 0.000 claims 2
- ZVBXGHZQUZNITD-DUXPYHPUSA-N FC(F)OC1=C(F)C=C(\C=C\C(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound FC(F)OC1=C(F)C=C(\C=C\C(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 ZVBXGHZQUZNITD-DUXPYHPUSA-N 0.000 claims 2
- XYXJKFGZOCUJAV-UHFFFAOYSA-N FC1=C(C=CC(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)=C1)C#N Chemical compound FC1=C(C=CC(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)=C1)C#N XYXJKFGZOCUJAV-UHFFFAOYSA-N 0.000 claims 2
- FCDVKPXUJSOLBD-UHFFFAOYSA-N FC1=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=CC(=C1)C#N Chemical compound FC1=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=CC(=C1)C#N FCDVKPXUJSOLBD-UHFFFAOYSA-N 0.000 claims 2
- VKVXAFZJLAELDA-UHFFFAOYSA-N FC1=C(OC(F)(F)F)C=CC(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)=C1 Chemical compound FC1=C(OC(F)(F)F)C=CC(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)=C1 VKVXAFZJLAELDA-UHFFFAOYSA-N 0.000 claims 2
- JZZLUZUCQVQRBW-UHFFFAOYSA-N N1N=NC=2CN(CCC21)C(=O)C2=NN1CCN(CCC1=C2)C(=O)OCC2=CC=CC=C2 Chemical compound N1N=NC=2CN(CCC21)C(=O)C2=NN1CCN(CCC1=C2)C(=O)OCC2=CC=CC=C2 JZZLUZUCQVQRBW-UHFFFAOYSA-N 0.000 claims 2
- TTWYWZFETSEMJI-UHFFFAOYSA-N O=C(COC1=C(C=C(C=C1)C#N)C1CC1)N1CCN2N=C(C=C2CC1)C(=O)N1CCC2=C(C1)N=NN2 Chemical compound O=C(COC1=C(C=C(C=C1)C#N)C1CC1)N1CCN2N=C(C=C2CC1)C(=O)N1CCC2=C(C1)N=NN2 TTWYWZFETSEMJI-UHFFFAOYSA-N 0.000 claims 2
- RLQNNQXQAXRJKB-UHFFFAOYSA-N O=C(OCC1=CC=C(C=C1)C#N)N1CCN2N=C(C=C2CC1)C(=O)N1CCC2=C(C1)N=NN2 Chemical compound O=C(OCC1=CC=C(C=C1)C#N)N1CCN2N=C(C=C2CC1)C(=O)N1CCC2=C(C1)N=NN2 RLQNNQXQAXRJKB-UHFFFAOYSA-N 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 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
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- XSRSXIBAUWUKJZ-UHFFFAOYSA-N (4-methoxyphenyl)methyl 2-(1,2,3,3a,4,6,7,7a-octahydrotriazolo[4,5-c]pyridine-5-carbonyl)-4,5,7,8-tetrahydropyrazolo[1,5-d][1,4]diazepine-6-carboxylate Chemical compound COC1=CC=C(C=C1)COC(=O)N2CCC3=CC(=NN3CC2)C(=O)N4CCC5C(C4)NNN5 XSRSXIBAUWUKJZ-UHFFFAOYSA-N 0.000 claims 1
- FEEDXFJJEWKDQS-UHFFFAOYSA-N 1,2,3,5,6,8-hexahydroimidazo[1,2-d][1,4]diazepine-7-carboxylic acid Chemical compound C1CN2CCN(CC=C2N1)C(=O)O FEEDXFJJEWKDQS-UHFFFAOYSA-N 0.000 claims 1
- ZMJNNPMURGKLLB-UHFFFAOYSA-N 1-[2-(1,2,3,3a,4,6,7,7a-octahydrotriazolo[4,5-c]pyridine-5-carbonyl)-4,5,7,8-tetrahydropyrazolo[1,5-d][1,4]diazepin-6-yl]-3-[4-(difluoromethoxy)-3-fluorophenyl]propan-1-one Chemical compound C1CN(CC2C1NNN2)C(=O)C3=NN4CCN(CCC4=C3)C(=O)CCC5=CC(=C(C=C5)OC(F)F)F ZMJNNPMURGKLLB-UHFFFAOYSA-N 0.000 claims 1
- ICVXGVGABINVHF-UHFFFAOYSA-N COC1=C(F)C=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound COC1=C(F)C=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 ICVXGVGABINVHF-UHFFFAOYSA-N 0.000 claims 1
- NSYSENPPXUMHGR-UHFFFAOYSA-N COC1=CC(C)=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound COC1=CC(C)=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 NSYSENPPXUMHGR-UHFFFAOYSA-N 0.000 claims 1
- KCCXZLKJIBUZJK-UHFFFAOYSA-N COC1=CC=C(C=C1)CCC(=O)N1CCN2C(CC1)=CC(=N2)C(=O)N2CC1=C(CC2)NN=N1 Chemical compound COC1=CC=C(C=C1)CCC(=O)N1CCN2C(CC1)=CC(=N2)C(=O)N2CC1=C(CC2)NN=N1 KCCXZLKJIBUZJK-UHFFFAOYSA-N 0.000 claims 1
- JGLOZZNBXVELFE-UHFFFAOYSA-N FC(F)(F)OC1=C(Cl)C=C(CCC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound FC(F)(F)OC1=C(Cl)C=C(CCC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 JGLOZZNBXVELFE-UHFFFAOYSA-N 0.000 claims 1
- AHXVDAZHUDPKLC-UHFFFAOYSA-N FC(F)(F)OC1=CC=C(CCC(=O)N2CCN3N=C(N=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound FC(F)(F)OC1=CC=C(CCC(=O)N2CCN3N=C(N=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 AHXVDAZHUDPKLC-UHFFFAOYSA-N 0.000 claims 1
- MXSFTQSOVZLBEH-UHFFFAOYSA-N FC1=CC=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 Chemical compound FC1=CC=C(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)C=C1 MXSFTQSOVZLBEH-UHFFFAOYSA-N 0.000 claims 1
- NBUPLPLOLPUNAJ-UHFFFAOYSA-N FC1=CC=CC(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)=C1 Chemical compound FC1=CC=CC(COC(=O)N2CCN3N=C(C=C3CC2)C(=O)N2CCC3=C(C2)N=NN3)=C1 NBUPLPLOLPUNAJ-UHFFFAOYSA-N 0.000 claims 1
- BJMFVUKWCFELMG-UHFFFAOYSA-N O=C(OCC1=CC=C(C=C1)C1CC1)N1CCN2N=C(C=C2CC1)C(=O)N1CCC2=C(C1)N=NN2 Chemical compound O=C(OCC1=CC=C(C=C1)C1CC1)N1CCN2N=C(C=C2CC1)C(=O)N1CCC2=C(C1)N=NN2 BJMFVUKWCFELMG-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14161756 | 2014-03-26 | ||
| EP14161756.3 | 2014-03-26 | ||
| PCT/EP2015/056041 WO2015144609A1 (en) | 2014-03-26 | 2015-03-23 | Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017510576A JP2017510576A (ja) | 2017-04-13 |
| JP2017510576A5 true JP2017510576A5 (enExample) | 2018-04-26 |
| JP6554481B2 JP6554481B2 (ja) | 2019-07-31 |
Family
ID=50389847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016558222A Expired - Fee Related JP6554481B2 (ja) | 2014-03-26 | 2015-03-23 | オートタキシン（ａｔｘ）及びリゾホスファチジン酸（ｌｐａ）産生の阻害剤としての縮合［１，４］ジアゼピン化合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US10669285B2 (enExample) |
| EP (1) | EP3122751B1 (enExample) |
| JP (1) | JP6554481B2 (enExample) |
| KR (1) | KR20160128428A (enExample) |
| CN (1) | CN106029667B (enExample) |
| AR (1) | AR099823A1 (enExample) |
| AU (1) | AU2015238541B2 (enExample) |
| CA (1) | CA2935612A1 (enExample) |
| CL (1) | CL2016002317A1 (enExample) |
| CR (1) | CR20160418A (enExample) |
| EA (1) | EA032357B1 (enExample) |
| IL (1) | IL246501B (enExample) |
| MX (1) | MX373236B (enExample) |
| PE (1) | PE20161223A1 (enExample) |
| PH (1) | PH12016501633A1 (enExample) |
| SG (1) | SG11201607845RA (enExample) |
| TW (1) | TWI678370B (enExample) |
| UA (1) | UA119347C2 (enExample) |
| WO (1) | WO2015144609A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013186159A1 (en) | 2012-06-13 | 2013-12-19 | F. Hoffmann-La Roche Ag | New diazaspirocycloalkane and azaspirocycloalkane |
| HRP20191937T1 (hr) | 2012-09-25 | 2020-01-10 | F. Hoffmann - La Roche Ag | Derivati heksahidropirolo [3,4-c]pirola i srodni spojevi kao inhibitori autotaksina (atx) i kao inhibitori proizvodnje lizofosfatidne kiseline (lpa) za liječenje npr. bubrežnih bolesti |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| RS56776B1 (sr) | 2013-11-26 | 2018-04-30 | Hoffmann La Roche | Derivati oktahidro-ciklobuta [1,2-c;3,4-c']dipirola kao inhibitori autotaksina |
| CA2938311C (en) | 2014-02-03 | 2023-03-07 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ror-gamma |
| CA2935612A1 (en) | 2014-03-26 | 2015-10-01 | F. Hoffmann-La Roche Ag | Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
| UA118582C2 (uk) | 2014-03-26 | 2019-02-11 | Ф. Хоффманн-Ля Рош Аг | Біциклічні сполуки як інгібітори продукції аутотаксину (atx) і лізофосфатидилової кислоти (lpa) |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| ES2856931T3 (es) | 2015-08-05 | 2021-09-28 | Vitae Pharmaceuticals Llc | Moduladores de ROR-gamma |
| CR20180058A (es) | 2015-09-04 | 2018-02-26 | Hoffmann La Roche | Nuevos derivados de fenoximetilo |
| EP3353180B1 (en) | 2015-09-24 | 2022-03-16 | F. Hoffmann-La Roche AG | Bicyclic compounds as atx inhibitors |
| PE20180552A1 (es) | 2015-09-24 | 2018-04-02 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores duales de atx/ca |
| EP3353176B1 (en) | 2015-09-24 | 2022-01-19 | F. Hoffmann-La Roche AG | Bicyclic compounds as atx inhibitors |
| BR112017026682A2 (pt) | 2015-09-24 | 2018-08-14 | Hoffmann La Roche | novos compostos bicíclicos como inibidores de dupla ação de atx/ca |
| BR112018010018A2 (pt) | 2015-11-20 | 2018-11-21 | Vitae Pharmaceuticals Inc | moduladores de ror-gama |
| TWI757266B (zh) | 2016-01-29 | 2022-03-11 | 美商維它藥物有限責任公司 | ＲＯＲ－γ調節劑 |
| EP3548484B1 (en) | 2016-12-02 | 2025-04-30 | F. Hoffmann-La Roche AG | Bicyclic amide compounds and methods of use thereof |
| BR112019019017A2 (pt) * | 2017-03-16 | 2020-04-14 | Hoffmann La Roche | compostos heterocíclicos de utilidade como inibidores duplos de atx/ca |
| EP3596060B1 (en) * | 2017-03-16 | 2023-09-20 | F. Hoffmann-La Roche AG | New bicyclic compounds as atx inhibitors |
| CA3067944C (en) | 2017-07-14 | 2023-03-14 | F. Hoffmann-La Roche Ag | Bicyclic ketone compounds and methods of use thereof |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| MA49685A (fr) | 2017-07-24 | 2021-04-14 | Vitae Pharmaceuticals Llc | INHIBITEURS DE ROR gamma |
| MX2020003451A (es) | 2017-10-31 | 2020-08-03 | Hoffmann La Roche | Sulfonas y sulfoxidos biciclicos y metodos de uso de los mismos. |
| EP3908586B1 (en) | 2019-01-11 | 2022-12-21 | F. Hoffmann-La Roche AG | Bicyclic pyrrolotriazolr ketone compounds and methods of use thereof |
| KR102524669B1 (ko) * | 2021-10-01 | 2023-04-21 | 주식회사 넥스트젠바이오사이언스 | 신규한 피페리딘 유도체 및 이를 포함하는 오토탁신 저해용 약학 조성물 |
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| US5240928A (en) | 1989-07-03 | 1993-08-31 | Merck & Co., Inc. | Substituted quinazolinones as angiotensin II antagonists |
| DE3930262A1 (de) | 1989-09-11 | 1991-03-21 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CA2037630C (en) | 1990-03-07 | 2001-07-03 | Akira Morimoto | Nitrogen-containing heterocylic compounds, their production and use |
| US5470975A (en) | 1990-10-16 | 1995-11-28 | E.R. Squibb & Sons, Inc. | Dihydropyrimidine derivatives |
| US5290780A (en) | 1991-01-30 | 1994-03-01 | American Cyanamid Co. | Angiotensin II receptor blocking 2,3,6 substituted quinazolinones |
| US5238942A (en) | 1991-05-10 | 1993-08-24 | Merck & Co., Inc. | Substituted quinazolinones bearing acidic functional groups as angiotensin ii antagonists |
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| DE4407047A1 (de) | 1994-03-03 | 1995-09-07 | Merck Patent Gmbh | Acetamide |
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-
2015
- 2015-03-23 CA CA2935612A patent/CA2935612A1/en not_active Abandoned
- 2015-03-23 CN CN201580008228.8A patent/CN106029667B/zh not_active Expired - Fee Related
- 2015-03-23 EP EP15711207.9A patent/EP3122751B1/en active Active
- 2015-03-23 UA UAA201610688A patent/UA119347C2/uk unknown
- 2015-03-23 EA EA201691794A patent/EA032357B1/ru not_active IP Right Cessation
- 2015-03-23 CR CR20160418A patent/CR20160418A/es unknown
- 2015-03-23 AU AU2015238541A patent/AU2015238541B2/en not_active Ceased
- 2015-03-23 PE PE2016001541A patent/PE20161223A1/es active IP Right Grant
- 2015-03-23 KR KR1020167029704A patent/KR20160128428A/ko not_active Ceased
- 2015-03-23 JP JP2016558222A patent/JP6554481B2/ja not_active Expired - Fee Related
- 2015-03-23 WO PCT/EP2015/056041 patent/WO2015144609A1/en not_active Ceased
- 2015-03-23 MX MX2016010675A patent/MX373236B/es active IP Right Grant
- 2015-03-23 SG SG11201607845RA patent/SG11201607845RA/en unknown
- 2015-03-25 AR ARP150100864A patent/AR099823A1/es unknown
- 2015-03-25 TW TW104109652A patent/TWI678370B/zh not_active IP Right Cessation
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2016
- 2016-06-28 IL IL246501A patent/IL246501B/en active IP Right Grant
- 2016-08-16 PH PH12016501633A patent/PH12016501633A1/en unknown
- 2016-09-14 CL CL2016002317A patent/CL2016002317A1/es unknown
- 2016-09-21 US US15/272,085 patent/US10669285B2/en active Active
-
2020
- 2020-03-02 US US16/806,302 patent/US20200199155A1/en not_active Abandoned
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