CA2590898A1 - 3,4,(5)-substituted tetrahvdropyridines - Google Patents
3,4,(5)-substituted tetrahvdropyridines Download PDFInfo
- Publication number
- CA2590898A1 CA2590898A1 CA002590898A CA2590898A CA2590898A1 CA 2590898 A1 CA2590898 A1 CA 2590898A1 CA 002590898 A CA002590898 A CA 002590898A CA 2590898 A CA2590898 A CA 2590898A CA 2590898 A1 CA2590898 A1 CA 2590898A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- alkoxy
- 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.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 claims abstract description 281
- 150000001875 compounds Chemical class 0.000 claims abstract description 234
- -1 tetrahydropyridine compound Chemical class 0.000 claims abstract description 217
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 61
- 108090000783 Renin Proteins 0.000 claims abstract description 54
- 102100028255 Renin Human genes 0.000 claims abstract description 52
- 230000000694 effects Effects 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 47
- 201000010099 disease Diseases 0.000 claims abstract description 40
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 125000001424 substituent group Chemical group 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 20
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 17
- 241001465754 Metazoa Species 0.000 claims abstract description 10
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 204
- 229910052799 carbon Inorganic materials 0.000 claims description 202
- 239000000203 mixture Substances 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 70
- 125000001624 naphthyl group Chemical group 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000005843 halogen group Chemical group 0.000 claims description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000006239 protecting group Chemical group 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000004076 pyridyl group Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 125000003107 substituted aryl group Chemical group 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 19
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
- 125000001041 indolyl group Chemical group 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000002873 tetrahydrofuranonyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000005059 halophenyl group Chemical group 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001038 naphthoyl group Chemical class C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 4
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 4
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 20
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
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- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 1203
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- VIYXXANHGYSBLY-UHFFFAOYSA-N trimethylsilyl 2,2,2-trifluoroacetate Chemical compound C[Si](C)(C)OC(=O)C(F)(F)F VIYXXANHGYSBLY-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
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- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Psychiatry (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0500784.4A GB0500784D0 (en) | 2005-01-14 | 2005-01-14 | Organic compounds |
| GB0500784.4 | 2005-01-14 | ||
| PCT/EP2006/000216 WO2006074924A1 (en) | 2005-01-14 | 2006-01-12 | 3,4,(5)-substituted tetrahvdropyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2590898A1 true CA2590898A1 (en) | 2006-07-20 |
Family
ID=34224619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002590898A Abandoned CA2590898A1 (en) | 2005-01-14 | 2006-01-12 | 3,4,(5)-substituted tetrahvdropyridines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20100029647A1 (enExample) |
| EP (1) | EP1841740A1 (enExample) |
| JP (1) | JP2008526910A (enExample) |
| KR (1) | KR20070094918A (enExample) |
| CN (1) | CN101103002A (enExample) |
| AU (1) | AU2006205877B2 (enExample) |
| BR (1) | BRPI0606321A2 (enExample) |
| CA (1) | CA2590898A1 (enExample) |
| GB (1) | GB0500784D0 (enExample) |
| MX (1) | MX2007008558A (enExample) |
| RU (1) | RU2007130791A (enExample) |
| WO (1) | WO2006074924A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009135299A1 (en) * | 2008-05-05 | 2009-11-12 | Merck Frosst Canada Ltd. | 3, 4 - substituted piperidine derivatives as renin inhibitors |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0505969D0 (en) * | 2005-03-23 | 2005-04-27 | Novartis Ag | Organic compounds |
| GB0514203D0 (en) | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
| US8129411B2 (en) | 2005-12-30 | 2012-03-06 | Novartis Ag | Organic compounds |
| EP1908471A1 (en) * | 2006-10-04 | 2008-04-09 | Speedel Experimenta AG | Tetrahydropyridines as renin inhibitors |
| US8129538B1 (en) | 2007-03-28 | 2012-03-06 | Takeda Pharmaceutical Company Limited | Renin inhibitors |
| CA2689109A1 (en) | 2007-06-25 | 2008-12-31 | Novartis Ag | N5-(2-ethoxyethyl)-n3-(2-pyridinyl) -3,5-piperidinedicarboxamide derivatives for use as renin inhibitors |
| US8586776B2 (en) | 2009-11-05 | 2013-11-19 | Fibrostatin, S.L. | GPBP inhibition using Q2 peptidomimetics |
| CN103502221B (zh) | 2011-03-18 | 2016-03-30 | 拜耳知识产权有限责任公司 | N-(3-氨甲酰基苯基)-1h-吡唑-5-甲酰胺衍生物及其用于防治动物害虫的用途 |
| EP2933248B1 (en) * | 2012-09-14 | 2018-01-31 | Mitsubishi Tanabe Pharma Corporation | Novel renin inhibitor |
| WO2016114312A1 (ja) | 2015-01-13 | 2016-07-21 | 日産化学工業株式会社 | 反応混合物中のスズ化合物の処理方法 |
| CN110577974B (zh) * | 2019-09-10 | 2021-07-20 | 杭州澳赛诺生物科技有限公司 | 手性3-羟基-1,2,3,6-四氢吡啶的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE242213T1 (de) * | 1995-09-07 | 2003-06-15 | Hoffmann La Roche | Neue 4-(oxyalkoxyphenyl)-3-oxy-piperidine zur behandlung von herz- und niereninsuffizienz |
| US6376672B1 (en) * | 1999-04-27 | 2002-04-23 | Hoffmann-La Roche Inc. | Naphthalenylmethoxypiperidines as renin inhibitors |
| US6197959B1 (en) * | 1999-04-27 | 2001-03-06 | Hoffmann-La Roche Inc. | Piperidine derivatives |
| EP1505945B1 (en) * | 2002-05-20 | 2008-11-05 | Bristol-Myers Squibb Company | Substituted cycloalkyl p1' hepatitis c virus inhibitors |
| CA2490138A1 (en) * | 2002-06-27 | 2004-01-08 | Actelion Pharmaceuticals Ltd. | Novel tetrahydropyridine derivatives as renin inhibitors |
| MXPA05011478A (es) * | 2003-04-29 | 2005-12-12 | Actelion Pharmaceuticals Ltd | Derivados de 1,2,3,6-tetrahidropiridina 3,4-disustituidos novedosos. |
| WO2005040120A1 (en) * | 2003-10-09 | 2005-05-06 | Actelion Pharmaceuticals Ltd | Tetrahydropyridine derivatives |
-
2005
- 2005-01-14 GB GBGB0500784.4A patent/GB0500784D0/en not_active Ceased
-
2006
- 2006-01-12 EP EP06700380A patent/EP1841740A1/en not_active Withdrawn
- 2006-01-12 CN CNA2006800023806A patent/CN101103002A/zh active Pending
- 2006-01-12 MX MX2007008558A patent/MX2007008558A/es not_active Application Discontinuation
- 2006-01-12 RU RU2007130791/04A patent/RU2007130791A/ru not_active Application Discontinuation
- 2006-01-12 BR BRPI0606321-7A patent/BRPI0606321A2/pt not_active IP Right Cessation
- 2006-01-12 JP JP2007550751A patent/JP2008526910A/ja active Pending
- 2006-01-12 US US11/722,398 patent/US20100029647A1/en not_active Abandoned
- 2006-01-12 AU AU2006205877A patent/AU2006205877B2/en not_active Expired - Fee Related
- 2006-01-12 WO PCT/EP2006/000216 patent/WO2006074924A1/en not_active Ceased
- 2006-01-12 CA CA002590898A patent/CA2590898A1/en not_active Abandoned
- 2006-01-12 KR KR1020077016005A patent/KR20070094918A/ko not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009135299A1 (en) * | 2008-05-05 | 2009-11-12 | Merck Frosst Canada Ltd. | 3, 4 - substituted piperidine derivatives as renin inhibitors |
| EA020853B1 (ru) * | 2008-05-05 | 2015-02-27 | Мерк Кэнэда Инк. | 3,4-замещенные пиперидиновые производные в качестве ингибиторов ренина |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101103002A (zh) | 2008-01-09 |
| AU2006205877A1 (en) | 2006-07-20 |
| WO2006074924A1 (en) | 2006-07-20 |
| US20100029647A1 (en) | 2010-02-04 |
| GB0500784D0 (en) | 2005-02-23 |
| EP1841740A1 (en) | 2007-10-10 |
| AU2006205877B2 (en) | 2010-01-07 |
| WO2006074924A8 (en) | 2007-04-19 |
| KR20070094918A (ko) | 2007-09-27 |
| MX2007008558A (es) | 2007-08-14 |
| RU2007130791A (ru) | 2009-02-20 |
| BRPI0606321A2 (pt) | 2009-06-16 |
| JP2008526910A (ja) | 2008-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |