CA2521898A1 - Diazabicyclononene derivatives - Google Patents
Diazabicyclononene derivatives Download PDFInfo
- Publication number
- CA2521898A1 CA2521898A1 CA002521898A CA2521898A CA2521898A1 CA 2521898 A1 CA2521898 A1 CA 2521898A1 CA 002521898 A CA002521898 A CA 002521898A CA 2521898 A CA2521898 A CA 2521898A CA 2521898 A1 CA2521898 A1 CA 2521898A1
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- mixtures
- general formula
- compounds
- diastereomers
- 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.)
- Abandoned
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- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical class C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 26
- -1 racemates Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000002904 solvent Chemical class 0.000 claims description 20
- 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 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 230000036454 renin-angiotensin system Effects 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 201000006370 kidney failure Diseases 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 206010019280 Heart failures Diseases 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000012876 carrier material Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 206010020772 Hypertension Diseases 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
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- 239000005541 ACE inhibitor Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000006193 alkinyl group Chemical group 0.000 claims description 7
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
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- 125000004104 aryloxy group Chemical group 0.000 claims description 4
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- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
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- 230000000948 sympatholitic effect Effects 0.000 claims description 2
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- 229940125721 immunosuppressive agent Drugs 0.000 claims 3
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- CYLMWXHNKGDKEL-REZFCLSBSA-N (1r,5s)-n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-7-[4-[(2s)-2-methyl-3-(2,3,6-trifluorophenoxy)propoxy]phenyl]-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxamide Chemical compound C=1([C@@]2([H])CNC[C@](N2)(CC=1C=1C=CC(OC[C@H](C)COC=2C(=C(F)C=CC=2F)F)=CC=1)[H])C(=O)N(C1CC1)CC1=CC=CC(Cl)=C1Cl CYLMWXHNKGDKEL-REZFCLSBSA-N 0.000 claims 2
- CYLMWXHNKGDKEL-NRVKVJMMSA-N (1s,5r)-n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-7-[4-[(2s)-2-methyl-3-(2,3,6-trifluorophenoxy)propoxy]phenyl]-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxamide Chemical compound C=1([C@]2([H])CNC[C@@](N2)(CC=1C=1C=CC(OC[C@H](C)COC=2C(=C(F)C=CC=2F)F)=CC=1)[H])C(=O)N(C1CC1)CC1=CC=CC(Cl)=C1Cl CYLMWXHNKGDKEL-NRVKVJMMSA-N 0.000 claims 2
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims 1
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 108090000783 Renin Proteins 0.000 abstract description 7
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- 239000004480 active ingredient Substances 0.000 abstract description 2
- YJTZZSKGEPHUTF-UHFFFAOYSA-N 3,9-diazabicyclo[3.3.1]non-4-ene Chemical class C1NC=C2CCCC1N2 YJTZZSKGEPHUTF-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 9
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP03/04622 | 2003-05-02 | ||
| EP0304622 | 2003-05-02 | ||
| PCT/EP2004/004372 WO2004096116A2 (en) | 2003-05-02 | 2004-04-26 | Diazabicyclononene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2521898A1 true CA2521898A1 (en) | 2004-11-11 |
Family
ID=33395698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002521898A Abandoned CA2521898A1 (en) | 2003-05-02 | 2004-04-26 | Diazabicyclononene derivatives |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1622564A2 (ko) |
| JP (1) | JP2006525259A (ko) |
| KR (1) | KR20060015573A (ko) |
| CN (1) | CN1780838A (ko) |
| AU (1) | AU2004233577A1 (ko) |
| BR (1) | BRPI0409882A (ko) |
| CA (1) | CA2521898A1 (ko) |
| MX (1) | MXPA05011711A (ko) |
| RU (1) | RU2005137571A (ko) |
| WO (1) | WO2004096116A2 (ko) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004283821A1 (en) * | 2003-10-13 | 2005-05-06 | Actelion Pharmaceuticals Ltd. | Diazabicyclononene derivatives and their use as renin inhibitors |
| JP2007509099A (ja) * | 2003-10-23 | 2007-04-12 | アクテリオン ファマシューティカルズ リミテッド | 新規ジアザビシクロノネンおよび新規極性側鎖を有するテトラヒドロピリジン誘導体 |
| AU2004295092A1 (en) * | 2003-12-05 | 2005-06-16 | Actelion Pharmaceuticals Ltd. | Azabicyclooctene and other tetrahydropyridine derivatives with a new side-chain |
| WO2006021403A1 (en) * | 2004-08-25 | 2006-03-02 | Actelion Pharmaceuticals Ltd | Bicyclononene derivatives |
| US8138340B2 (en) | 2004-08-25 | 2012-03-20 | Actelion Pharmaceuticals Ltd. | Bicyclononene derivatives |
| WO2006058546A1 (en) * | 2004-12-01 | 2006-06-08 | Actelion Pharmaceuticals Ltd | Novel lactame derivatives as renin inhibitors |
| WO2006063610A1 (en) * | 2004-12-17 | 2006-06-22 | Actelion Pharmaceuticals Ltd | Heteroaryl substituted diazabicyclononene derivatives |
| GB0428526D0 (en) | 2004-12-30 | 2005-02-09 | Novartis Ag | Organic compounds |
| US7915259B2 (en) * | 2005-01-28 | 2011-03-29 | Actelion Pharmaceuticals Ltd. | Diazabicyclononene derivatives and use thereof |
| WO2006131884A2 (en) * | 2005-06-07 | 2006-12-14 | Actelion Pharmaceuticals Ltd | Thiazole substituted diazabicyclononane or-nonene derivatives as renin inhibitors |
| GB0514203D0 (en) | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
| ES2430139T3 (es) | 2005-12-30 | 2013-11-19 | Novartis Ag | Compuestos de piperidina 3,5-sustituido como inhibidores de renina |
| US20100166839A1 (en) * | 2006-03-16 | 2010-07-01 | Nicox S.A | Non peptidic renin inhibitors nitroderivatives |
| WO2008141462A1 (en) | 2007-05-24 | 2008-11-27 | Merck Frosst Canada Ltd. | Novel case of renin inhibitors |
| CN101687847B (zh) | 2007-06-25 | 2013-11-06 | 诺华股份有限公司 | 用作肾素抑制剂的n5-(2-乙氧基乙基)-n3-(2-吡啶基)-3，5-哌啶二甲酰胺衍生物 |
| US8334308B2 (en) | 2007-08-20 | 2012-12-18 | Merck Sharp & Dohme Corp. | Renin inhibitors |
| SG192543A1 (en) | 2008-05-05 | 2013-08-30 | Merck Canada Inc | 3, 4 - substituted piperidine derivatives as renin inhibitors |
| WO2013038936A1 (ja) * | 2011-09-13 | 2013-03-21 | タカラバイオ株式会社 | ペルオキシダーゼ反応の停止方法及び反応停止剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3509161A (en) * | 1967-07-10 | 1970-04-28 | Boehringer & Soehne Gmbh | 3-phenyl-granatene-(2)-derivatives |
| WO1997009311A1 (de) * | 1995-09-07 | 1997-03-13 | F. Hoffmann-La Roche Ag | Neue 4-(oxyalkoxyphenyl)-3-oxy-piperidine zur behandlung von herz- und niereninsuffizienz |
| EP1501830B1 (en) * | 2002-04-29 | 2011-10-05 | Actelion Pharmaceuticals Ltd. | 7-aryl-3,9-diazabicyclo[3.3.1]non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases |
| EP1519920A1 (en) * | 2002-06-27 | 2005-04-06 | Actelion Pharmaceuticals Ltd. | Novel tetrahydropyridine derivatives as renin inhibitors |
-
2004
- 2004-04-26 RU RU2005137571/04A patent/RU2005137571A/ru not_active Application Discontinuation
- 2004-04-26 CA CA002521898A patent/CA2521898A1/en not_active Abandoned
- 2004-04-26 WO PCT/EP2004/004372 patent/WO2004096116A2/en active Application Filing
- 2004-04-26 MX MXPA05011711A patent/MXPA05011711A/es not_active Application Discontinuation
- 2004-04-26 JP JP2006505261A patent/JP2006525259A/ja active Pending
- 2004-04-26 BR BRPI0409882-0A patent/BRPI0409882A/pt not_active Application Discontinuation
- 2004-04-26 EP EP04729414A patent/EP1622564A2/en not_active Withdrawn
- 2004-04-26 AU AU2004233577A patent/AU2004233577A1/en not_active Abandoned
- 2004-04-26 CN CNA2004800116500A patent/CN1780838A/zh active Pending
- 2004-04-26 KR KR1020057020788A patent/KR20060015573A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060015573A (ko) | 2006-02-17 |
| WO2004096116A2 (en) | 2004-11-11 |
| EP1622564A2 (en) | 2006-02-08 |
| AU2004233577A1 (en) | 2004-11-11 |
| JP2006525259A (ja) | 2006-11-09 |
| RU2005137571A (ru) | 2006-05-10 |
| CN1780838A (zh) | 2006-05-31 |
| BRPI0409882A (pt) | 2006-05-23 |
| WO2004096116A3 (en) | 2005-03-24 |
| MXPA05011711A (es) | 2006-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |