CA2088490A1 - 3-substituted piperidine derivatives - Google Patents
3-substituted piperidine derivativesInfo
- Publication number
- CA2088490A1 CA2088490A1 CA002088490A CA2088490A CA2088490A1 CA 2088490 A1 CA2088490 A1 CA 2088490A1 CA 002088490 A CA002088490 A CA 002088490A CA 2088490 A CA2088490 A CA 2088490A CA 2088490 A1 CA2088490 A1 CA 2088490A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pentylpiperidine
- phenyl
- compounds
- pharmaceutically acceptable
- 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
- -1 3-substituted piperidine Chemical class 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005864 Sulphur Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 6
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims abstract 6
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 238000009825 accumulation Methods 0.000 claims description 4
- 210000004958 brain cell Anatomy 0.000 claims description 4
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- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- LELNJGJCQOJQBJ-UHFFFAOYSA-N 1-pentyl-3-[(2-phenylphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=CC=C1C1=CC=CC=C1 LELNJGJCQOJQBJ-UHFFFAOYSA-N 0.000 claims 1
- WWFYUVKNMOFGSR-UHFFFAOYSA-N 1-pentyl-3-[(3-phenylphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=CC(C=2C=CC=CC=2)=C1 WWFYUVKNMOFGSR-UHFFFAOYSA-N 0.000 claims 1
- PUZHRYBYNXAUEU-UHFFFAOYSA-N 1-pentyl-3-[(4-phenylmethoxyphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 PUZHRYBYNXAUEU-UHFFFAOYSA-N 0.000 claims 1
- CJPWBGLSTYJLCW-UHFFFAOYSA-N 1-pentyl-3-[(4-phenylphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=C(C=2C=CC=CC=2)C=C1 CJPWBGLSTYJLCW-UHFFFAOYSA-N 0.000 claims 1
- YITSLQRXVSYBCB-UHFFFAOYSA-N 1-pentyl-3-[(4-propan-2-ylphenoxy)methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=C(C(C)C)C=C1 YITSLQRXVSYBCB-UHFFFAOYSA-N 0.000 claims 1
- LJGCRYAMJZEMHR-UHFFFAOYSA-N 1-pentyl-3-[[3-(trifluoromethyl)phenoxy]methyl]piperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=CC(C(F)(F)F)=C1 LJGCRYAMJZEMHR-UHFFFAOYSA-N 0.000 claims 1
- IPXAFMGFFGVCIN-UHFFFAOYSA-N 3,4-dichloro-n-[(1-pentylpiperidin-3-yl)methyl]aniline Chemical compound C1N(CCCCC)CCCC1CNC1=CC=C(Cl)C(Cl)=C1 IPXAFMGFFGVCIN-UHFFFAOYSA-N 0.000 claims 1
- WDOHUEFGFMHWDK-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yloxymethyl)-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=C(OCO2)C2=C1 WDOHUEFGFMHWDK-UHFFFAOYSA-N 0.000 claims 1
- USDSIEIKHQQHER-UHFFFAOYSA-N 3-[(2-benzylphenoxy)methyl]-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=CC=C1CC1=CC=CC=C1 USDSIEIKHQQHER-UHFFFAOYSA-N 0.000 claims 1
- LNDNXWAZAZTURI-UHFFFAOYSA-N 3-[(3,4-dichlorophenoxy)methyl]-1-(3-phenylprop-2-enyl)piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OCC1CN(CC=CC=2C=CC=CC=2)CCC1 LNDNXWAZAZTURI-UHFFFAOYSA-N 0.000 claims 1
- QNGGMIAQIBEWLH-UHFFFAOYSA-N 3-[(4-benzylphenoxy)methyl]-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC(C=C1)=CC=C1CC1=CC=CC=C1 QNGGMIAQIBEWLH-UHFFFAOYSA-N 0.000 claims 1
- ZBFJCZSXXOVMTG-UHFFFAOYSA-N 3-[(4-fluorophenoxy)methyl]-1-pentylpiperidine Chemical compound C1N(CCCCC)CCCC1COC1=CC=C(F)C=C1 ZBFJCZSXXOVMTG-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 98
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
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- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
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- 239000000203 mixture Substances 0.000 description 20
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- LCDAPADGOWKBDM-UHFFFAOYSA-N (1-pentylpiperidin-3-yl)methanol Chemical compound CCCCCN1CCCC(CO)C1 LCDAPADGOWKBDM-UHFFFAOYSA-N 0.000 description 15
- 235000006408 oxalic acid Nutrition 0.000 description 13
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
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- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909017225A GB9017225D0 (en) | 1990-08-06 | 1990-08-06 | Compounds |
| GB9017225.5 | 1990-08-06 | ||
| GB909021852A GB9021852D0 (en) | 1990-10-08 | 1990-10-08 | Compounds |
| GB9021852.0 | 1990-10-08 | ||
| GB9107780.0 | 1991-04-12 | ||
| GB919107780A GB9107780D0 (en) | 1991-04-12 | 1991-04-12 | Compounds |
| PCT/GB1991/001339 WO1992002501A1 (en) | 1990-08-06 | 1991-08-05 | 3-substituted piperidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2088490A1 true CA2088490A1 (en) | 1992-02-07 |
Family
ID=27265217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002088490A Abandoned CA2088490A1 (en) | 1990-08-06 | 1991-08-05 | 3-substituted piperidine derivatives |
Country Status (14)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5290789A (en) * | 1992-11-20 | 1994-03-01 | Sterling Wintrop Inc. | Penta and tetrasubstituted piperidines and compositions and method of treating psychosis |
| GB9226111D0 (en) * | 1992-12-15 | 1993-02-10 | Smithkline Beecham Plc | Madicaments |
| GB9314973D0 (en) * | 1993-07-20 | 1993-09-01 | Smithkline Beecham Plc | Medicaments |
| GB9319534D0 (en) * | 1993-09-22 | 1993-11-10 | Boots Co Plc | Therapeutic agents |
| WO1995024390A1 (en) * | 1994-03-11 | 1995-09-14 | Smithkline Beecham Plc | Novel phenyl(-alkyl/alkoxy)-1-aminoalkyl-substituted piperidines and pyrrolidines as calcium channel antagonists |
| US5770575A (en) * | 1994-03-16 | 1998-06-23 | Ortho Pharmaceutical Corporation | Nipecotic acid derivatives as antithrombotic compounds |
| GB9411052D0 (en) * | 1994-06-02 | 1994-07-20 | Smithkline Beecham Plc | Medicaments |
| GB9411045D0 (en) * | 1994-06-02 | 1994-07-20 | Smithkline Beecham Plc | Compounds and use |
| US5843983A (en) * | 1996-02-15 | 1998-12-01 | Sankyo Company, Limited | Diphenylethane compounds containing a saturated heterocyclic group, their preparation, and their therapeutic use |
| US6110937A (en) * | 1997-04-03 | 2000-08-29 | Syntex Usa, Inc. | Phenoxymethyl piperidine derivatives for the treatment of neuropathic pain |
| CA2232147A1 (en) * | 1997-04-03 | 1998-10-03 | F. Hoffmann-La Roche Ag | Phenoxymethyl piperidine derivatives |
| US6251919B1 (en) | 1998-02-27 | 2001-06-26 | Warner-Lambert | Heterocyclic substituted aniline calcium channel blockers |
| US6166052A (en) * | 1998-03-11 | 2000-12-26 | Warner-Lambert Company | Heteroaryl alkyl alpha substituted peptidylamine calcium channel blockers |
| WO2000009491A1 (en) * | 1998-08-12 | 2000-02-24 | Smithkline Beecham Corporation | Calcilytic compounds |
| WO2004002483A1 (en) * | 2002-06-27 | 2004-01-08 | Actelion Pharmaceuticals Ltd | Substituted 3- and 4- aminomethylpiperidines for use as beta-secretase in the treatment of alzheimer’s disease |
| HK1260897A1 (zh) | 2015-08-21 | 2019-12-27 | Portola Pharmaceuticals, Inc. | 使用四氢异喹啉小分子来结合并调节pcsk9的蛋白活性的组合物和方法 |
| US10568882B2 (en) | 2015-08-21 | 2020-02-25 | Srx Cardio, Llc | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators and their use |
| WO2017034994A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate pcsk9 protein activity |
| WO2017147328A1 (en) | 2016-02-23 | 2017-08-31 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2310762A1 (fr) * | 1975-05-16 | 1976-12-10 | Roussel Uclaf | Nouveaux derives n-substitues de la phenyl piperidine et leurs sels, procede de preparation et application a titre de medicaments |
| DE2950135A1 (de) * | 1979-12-13 | 1981-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Basischer aether, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| FR2510112A1 (fr) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | Nouveaux derives du 2-oxo-pyrid-3-yl ou piperidin-3-yl indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| CA1260474A (en) * | 1984-12-03 | 1989-09-26 | Raymond A. Stokbroekx | Benzoxazol- and benzothiazolamine derivatives |
| NZ219646A (en) * | 1986-03-27 | 1990-10-26 | Merck Sharp & Dohme | Oxadiazole derivatives of azacyclics for treating cns disorders |
| IL83275A (en) * | 1986-09-08 | 1994-02-27 | Novo Nordisk As | Substituted 1, 2, 4- oxadiazolyl piperidine compounds, their preparation and pharmaceutical compositions containing them |
| EP0307141B1 (en) * | 1987-09-10 | 1993-01-13 | MERCK SHARP & DOHME LTD. | Oxazoles and thiazoles for the treatment of senile dementia |
| FR2636946B1 (fr) * | 1988-09-23 | 1990-11-02 | Lipha | ((diarylmethoxy)alcoyl)-1 pyrrolidines et piperidines, procedes de preparation et medicaments les contenant |
| DE3834860A1 (de) * | 1988-10-13 | 1990-04-19 | Basf Ag | Heterocyclisch substituierte alkoxycumarine, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
-
1991
- 1991-08-02 MX MX9100517A patent/MX9100517A/es unknown
- 1991-08-02 IE IE276091A patent/IE912760A1/en unknown
- 1991-08-04 IL IL99074A patent/IL99074A0/xx unknown
- 1991-08-05 NZ NZ239267A patent/NZ239267A/en unknown
- 1991-08-05 JP JP3513951A patent/JPH06500092A/ja active Pending
- 1991-08-05 CA CA002088490A patent/CA2088490A1/en not_active Abandoned
- 1991-08-05 TW TW080106122A patent/TW239860B/zh active
- 1991-08-05 MA MA22530A patent/MA22251A1/fr unknown
- 1991-08-05 EP EP91914530A patent/EP0542844A1/en not_active Withdrawn
- 1991-08-05 WO PCT/GB1991/001339 patent/WO1992002501A1/en not_active Application Discontinuation
- 1991-08-05 PT PT98575A patent/PT98575A/pt not_active Application Discontinuation
- 1991-08-05 CN CN91105944A patent/CN1062349A/zh active Pending
- 1991-08-05 AU AU83243/91A patent/AU649468B2/en not_active Ceased
- 1991-08-06 AP APAP/P/1991/000314A patent/AP236A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NZ239267A (en) | 1994-05-26 |
| CN1062349A (zh) | 1992-07-01 |
| AP236A (en) | 1993-02-24 |
| PT98575A (pt) | 1992-06-30 |
| AU649468B2 (en) | 1994-05-26 |
| JPH06500092A (ja) | 1994-01-06 |
| MX9100517A (es) | 1992-04-01 |
| IL99074A0 (en) | 1992-07-15 |
| TW239860B (enrdf_load_stackoverflow) | 1995-02-01 |
| IE912760A1 (en) | 1992-02-12 |
| AU8324391A (en) | 1992-03-02 |
| MA22251A1 (fr) | 1992-04-01 |
| WO1992002501A1 (en) | 1992-02-20 |
| EP0542844A1 (en) | 1993-05-26 |
| AP9100314A0 (en) | 1991-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |