JP2010526136A5 - - Google Patents
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- Publication number
- JP2010526136A5 JP2010526136A5 JP2010507348A JP2010507348A JP2010526136A5 JP 2010526136 A5 JP2010526136 A5 JP 2010526136A5 JP 2010507348 A JP2010507348 A JP 2010507348A JP 2010507348 A JP2010507348 A JP 2010507348A JP 2010526136 A5 JP2010526136 A5 JP 2010526136A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- compound according
- inhibitor
- treating
- formula
- 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 44
- 238000000034 method Methods 0.000 claims 17
- 239000003814 drug Substances 0.000 claims 12
- 238000004519 manufacturing process Methods 0.000 claims 7
- 239000000556 agonist Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 102000002723 Atrial Natriuretic Factor Human genes 0.000 claims 4
- 101800001288 Atrial natriuretic factor Proteins 0.000 claims 4
- 101800001890 Atrial natriuretic peptide Proteins 0.000 claims 4
- 102000003729 Neprilysin Human genes 0.000 claims 4
- 108090000028 Neprilysin Proteins 0.000 claims 4
- 102000008052 Nitric Oxide Synthase Type III Human genes 0.000 claims 4
- 108010075520 Nitric Oxide Synthase Type III Proteins 0.000 claims 4
- 239000002876 beta blocker Substances 0.000 claims 4
- 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 4
- 229940079593 drug Drugs 0.000 claims 4
- 239000003623 enhancer Substances 0.000 claims 4
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- -1 nitro, amino Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 238000005932 reductive alkylation reaction Methods 0.000 claims 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- 229940121819 ATPase inhibitor Drugs 0.000 claims 2
- 229940124258 Adenosine A1 receptor antagonist Drugs 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 2
- 102000013602 Cardiac Myosins Human genes 0.000 claims 2
- 108010051609 Cardiac Myosins Proteins 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229940119334 Chymase inhibitor Drugs 0.000 claims 2
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims 2
- 102100038018 Corticotropin-releasing factor receptor 1 Human genes 0.000 claims 2
- 108030001679 Endothelin-converting enzyme 1 Proteins 0.000 claims 2
- 102000048186 Endothelin-converting enzyme 1 Human genes 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 229940098712 Myosin activator Drugs 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 2
- 102100028646 Nociceptin receptor Human genes 0.000 claims 2
- 101710176384 Peptide 1 Proteins 0.000 claims 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims 2
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 2
- 229940116211 Vasopressin antagonist Drugs 0.000 claims 2
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims 2
- 239000002598 adenosine A1 receptor antagonist Substances 0.000 claims 2
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims 2
- 239000000048 adrenergic agonist Substances 0.000 claims 2
- 239000000674 adrenergic antagonist Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000002160 alpha blocker Substances 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 239000003416 antiarrhythmic agent Substances 0.000 claims 2
- 239000003524 antilipemic agent Substances 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 230000006793 arrhythmia Effects 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 239000000759 benzodiazepine receptor stimulating agent Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000000480 calcium channel blocker Substances 0.000 claims 2
- 229940097217 cardiac glycoside Drugs 0.000 claims 2
- 239000002368 cardiac glycoside Substances 0.000 claims 2
- 239000002738 chelating agent Substances 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 239000003601 chymase inhibitor Substances 0.000 claims 2
- 238000004132 cross linking Methods 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002934 diuretic Substances 0.000 claims 2
- 229940030606 diuretics Drugs 0.000 claims 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 2
- 230000009977 dual effect Effects 0.000 claims 2
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 230000036252 glycation Effects 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 108010020615 nociceptin receptor Proteins 0.000 claims 2
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims 2
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 2
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 claims 2
- 239000004036 potassium channel stimulating agent Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000002461 renin inhibitor Substances 0.000 claims 2
- 229940086526 renin-inhibitors Drugs 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 claims 2
- 229930002534 steroid glycoside Natural products 0.000 claims 2
- 238000013518 transcription Methods 0.000 claims 2
- 230000035897 transcription Effects 0.000 claims 2
- 229960005486 vaccine Drugs 0.000 claims 2
- 229940124549 vasodilator Drugs 0.000 claims 2
- 239000003071 vasodilator agent Substances 0.000 claims 2
- 239000003038 vasopressin antagonist Substances 0.000 claims 2
- 239000003064 xanthine oxidase inhibitor Substances 0.000 claims 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- CWWWTTYMUOYSQA-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 CWWWTTYMUOYSQA-LLVKDONJSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 108010015720 Dopamine beta-Hydroxylase Proteins 0.000 claims 1
- 102100033156 Dopamine beta-hydroxylase Human genes 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229960003638 dopamine Drugs 0.000 claims 1
- 150000002222 fluorine compounds Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000033444 hydroxylation Effects 0.000 claims 1
- 238000005805 hydroxylation reaction Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229960002748 norepinephrine Drugs 0.000 claims 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical group [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0708818.0A GB0708818D0 (en) | 2007-05-08 | 2007-05-08 | Compounds |
| GB0708818.0 | 2007-05-08 | ||
| PCT/PT2008/000019 WO2008136695A1 (en) | 2007-05-08 | 2008-05-06 | 1, 3-dihydroimidazole- 2 -thione derivatives as inhibitors of dopamine-beta-hydroxylase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010526136A JP2010526136A (ja) | 2010-07-29 |
| JP2010526136A5 true JP2010526136A5 (enExample) | 2011-06-23 |
| JP5559677B2 JP5559677B2 (ja) | 2014-07-23 |
Family
ID=38198874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010507348A Expired - Fee Related JP5559677B2 (ja) | 2007-05-08 | 2008-05-06 | ドーパミン−β−ヒドロキシラーゼの阻害剤としての１，３−ジヒドロイミダゾール−２−チオン誘導体 |
Country Status (29)
| Country | Link |
|---|---|
| US (5) | US8481582B2 (enExample) |
| EP (1) | EP2155731B1 (enExample) |
| JP (1) | JP5559677B2 (enExample) |
| KR (1) | KR101598482B1 (enExample) |
| CN (1) | CN101687858B (enExample) |
| AR (2) | AR066457A1 (enExample) |
| AT (1) | ATE499367T1 (enExample) |
| AU (1) | AU2008246443B2 (enExample) |
| BR (1) | BRPI0811275B8 (enExample) |
| CA (1) | CA2686387C (enExample) |
| CL (1) | CL2008001321A1 (enExample) |
| CY (1) | CY1111517T1 (enExample) |
| DE (1) | DE602008005141D1 (enExample) |
| DK (1) | DK2155731T3 (enExample) |
| ES (1) | ES2360841T3 (enExample) |
| GB (1) | GB0708818D0 (enExample) |
| HR (1) | HRP20110253T1 (enExample) |
| IL (1) | IL201921A (enExample) |
| MX (1) | MX2009012041A (enExample) |
| NO (1) | NO20093275L (enExample) |
| NZ (1) | NZ580962A (enExample) |
| PL (1) | PL2155731T3 (enExample) |
| RS (1) | RS51692B (enExample) |
| RU (1) | RU2501796C2 (enExample) |
| SI (1) | SI2155731T1 (enExample) |
| TW (1) | TWI458722B (enExample) |
| UA (1) | UA104844C2 (enExample) |
| WO (1) | WO2008136695A1 (enExample) |
| ZA (1) | ZA200908612B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0708818D0 (en) | 2007-05-08 | 2007-06-13 | Portela & Ca Sa | Compounds |
| US9212130B2 (en) * | 2010-08-10 | 2015-12-15 | Shionogi & Co., Ltd. | Heterocyclic derivative and pharmaceutical composition comprising the same |
| BR112013015864B1 (pt) | 2010-12-22 | 2021-11-09 | Bial - Portela & C.A., S.A. | Processo para purificar um composto de forma cristalina a de (r)-5-(2-benzilamino)etil)-1- (6,8-difluorocroman-3-il)-1h-imidazol-2(3h)-tiona |
| US9346751B2 (en) | 2011-06-29 | 2016-05-24 | Bial-Portela & Ca, S.A. | Process for preparing 1, 3-Dihydroimidazole-2-Thione Derivatives |
| EP2919780B1 (en) | 2012-11-14 | 2018-08-01 | BIAL - Portela & CA., S.A. | 1,3-dihydroimidazole-2-thione derivatives for use in the treatment of pulmonary arterial hypertension and lung injury |
| CN103356671B (zh) * | 2013-06-24 | 2015-11-25 | 顾祥茂 | Houttuynoid C在制备治疗或预防慢性心衰的药物中的应用 |
| GB201316410D0 (en) | 2013-09-13 | 2013-10-30 | Bial Portela & Ca Sa | Processes for preparing peripherally-selective inhibitors of dopamine-?-hydroxylase and intermediates for use therein |
| JOP20190049A1 (ar) * | 2016-09-23 | 2019-03-20 | Bial Portela & C? S A | مثبطات دوبامين-b-هيدروكسيلاز |
| BR112020004800A2 (pt) | 2017-09-13 | 2020-09-24 | Amgen Inc. | compostos de bisamida ativantes do sarcômero e seus usos |
| WO2019112457A1 (en) * | 2017-12-04 | 2019-06-13 | BIAL - PORTELA & Cª, S.A. | Dopamine-β-hydroxylase inhibitors |
| GB201810395D0 (en) | 2018-06-25 | 2018-08-08 | Bial Portela & Ca Sa | Formulations comprising dopamine-beta-hydroxylase inhibitors and methods for their preparation |
| CN113166053A (zh) * | 2018-11-12 | 2021-07-23 | 伊缪诺金公司 | 制备细胞毒性苯二氮䓬衍生物的方法 |
| GB201908044D0 (en) | 2019-06-05 | 2019-07-17 | Bial Portela & Ca Sa | Dopamine-B-Hydroxylase inhibitors |
| AU2022213938A1 (en) * | 2021-01-26 | 2023-09-07 | Asieris Pharmaceuticals (Shanghai) Co., Ltd. | Pathway modulator, pharmaceutical composition having same, use thereof, and therapeutic method using same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217347A (en) * | 1977-12-27 | 1980-08-12 | E. R. Squibb & Sons, Inc. | Method of treating hypertension and medicaments therefor |
| US4962128A (en) * | 1989-11-02 | 1990-10-09 | Pfizer Inc. | Method of treating anxiety-related disorders using sertraline |
| US5298497A (en) * | 1990-05-15 | 1994-03-29 | E. R. Squibb & Sons, Inc. | Method for preventing onset of hypertension employing a cholesterol lowering drug |
| EP0757677B1 (en) | 1994-04-26 | 2003-06-18 | Syntex (U.S.A.) LLC | Benzocyclohexylimidazolethione derivatives |
| AR032711A1 (es) | 2001-02-21 | 2003-11-19 | Solvay Pharm Bv | Derivados de fenilpiperazina, un metodo para la preparacion de los mismos y una composicion farmaceutica que los contiene |
| GB2393958A (en) * | 2002-10-11 | 2004-04-14 | Portela & Ca Sa | Peripherally-selective imidazole inhibitors of dopamine-beta-hydroxylase |
| US7125904B2 (en) * | 2002-10-11 | 2006-10-24 | Portela & C.A., S.A. | Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation |
| GB0708818D0 (en) | 2007-05-08 | 2007-06-13 | Portela & Ca Sa | Compounds |
-
2007
- 2007-05-08 GB GBGB0708818.0A patent/GB0708818D0/en not_active Ceased
-
2008
- 2008-05-06 UA UAA200912720A patent/UA104844C2/uk unknown
- 2008-05-06 PL PL08741778T patent/PL2155731T3/pl unknown
- 2008-05-06 BR BRPI0811275A patent/BRPI0811275B8/pt not_active IP Right Cessation
- 2008-05-06 JP JP2010507348A patent/JP5559677B2/ja not_active Expired - Fee Related
- 2008-05-06 RU RU2009145270/04A patent/RU2501796C2/ru active
- 2008-05-06 CA CA2686387A patent/CA2686387C/en active Active
- 2008-05-06 EP EP08741778A patent/EP2155731B1/en active Active
- 2008-05-06 WO PCT/PT2008/000019 patent/WO2008136695A1/en not_active Ceased
- 2008-05-06 US US12/599,014 patent/US8481582B2/en not_active Expired - Fee Related
- 2008-05-06 HR HR20110253T patent/HRP20110253T1/hr unknown
- 2008-05-06 AR ARP080101912A patent/AR066457A1/es not_active Application Discontinuation
- 2008-05-06 SI SI200830191T patent/SI2155731T1/sl unknown
- 2008-05-06 CN CN2008800151606A patent/CN101687858B/zh not_active Expired - Fee Related
- 2008-05-06 DK DK08741778.8T patent/DK2155731T3/da active
- 2008-05-06 RS RS20110165A patent/RS51692B/sr unknown
- 2008-05-06 KR KR1020097025071A patent/KR101598482B1/ko not_active Expired - Fee Related
- 2008-05-06 AT AT08741778T patent/ATE499367T1/de active
- 2008-05-06 MX MX2009012041A patent/MX2009012041A/es active IP Right Grant
- 2008-05-06 ES ES08741778T patent/ES2360841T3/es active Active
- 2008-05-06 DE DE602008005141T patent/DE602008005141D1/de active Active
- 2008-05-06 NZ NZ580962A patent/NZ580962A/en not_active IP Right Cessation
- 2008-05-06 AU AU2008246443A patent/AU2008246443B2/en not_active Ceased
- 2008-05-07 CL CL2008001321A patent/CL2008001321A1/es unknown
- 2008-05-07 TW TW097116854A patent/TWI458722B/zh not_active IP Right Cessation
-
2009
- 2009-11-03 NO NO20093275A patent/NO20093275L/no not_active Application Discontinuation
- 2009-11-04 IL IL201921A patent/IL201921A/en active IP Right Grant
- 2009-12-04 ZA ZA2009/08612A patent/ZA200908612B/en unknown
-
2011
- 2011-04-26 CY CY20111100414T patent/CY1111517T1/el unknown
-
2013
- 2013-06-13 US US13/917,385 patent/US9630951B2/en not_active Expired - Fee Related
-
2017
- 2017-03-09 US US15/454,201 patent/US20170369478A1/en not_active Abandoned
-
2018
- 2018-09-05 AR ARP180102520A patent/AR112789A2/es unknown
-
2019
- 2019-05-03 US US16/402,454 patent/US20190322648A1/en not_active Abandoned
-
2021
- 2021-05-10 US US17/315,791 patent/US20210261533A1/en not_active Abandoned
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