SE456994B - Nya furo-(3,4-c)-pyridinderivat, saett foer framstaellning daerav och terapeutisk komposition innehaallande dem - Google Patents
Nya furo-(3,4-c)-pyridinderivat, saett foer framstaellning daerav och terapeutisk komposition innehaallande demInfo
- Publication number
- SE456994B SE456994B SE8200744A SE8200744A SE456994B SE 456994 B SE456994 B SE 456994B SE 8200744 A SE8200744 A SE 8200744A SE 8200744 A SE8200744 A SE 8200744A SE 456994 B SE456994 B SE 456994B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- carbon atoms
- formula
- alkoxy group
- hydroxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title claims 2
- GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical class C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 18
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 9
- -1 N-pyrrolidinyl Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 239000011677 pyridoxine Substances 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229940011671 vitamin b6 Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 229910052731 fluorine Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 7
- 239000011674 pyridoxal Substances 0.000 description 7
- 229960003581 pyridoxal Drugs 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000002934 diuretic Substances 0.000 description 4
- 229940030606 diuretics Drugs 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- XKIFTEHOCFPRJE-UHFFFAOYSA-N 2-(4-bromophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Br)C=C1 XKIFTEHOCFPRJE-UHFFFAOYSA-N 0.000 description 1
- MOVOYJFCKMYLHQ-UHFFFAOYSA-N 2-(4-bromophenoxy)-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=CC=C(Br)C=C1 MOVOYJFCKMYLHQ-UHFFFAOYSA-N 0.000 description 1
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- YDWKSSWZGXRQET-UHFFFAOYSA-N Pyrrolidine, 1-[2-(4-bromophenoxy)ethyl]- Chemical compound C1=CC(Br)=CC=C1OCCN1CCCC1 YDWKSSWZGXRQET-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 231100000064 subacute toxicity study Toxicity 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8104072 | 1981-02-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8200744L SE8200744L (sv) | 1982-08-11 |
| SE456994B true SE456994B (sv) | 1988-11-21 |
Family
ID=10519587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8200744A SE456994B (sv) | 1981-02-10 | 1982-02-09 | Nya furo-(3,4-c)-pyridinderivat, saett foer framstaellning daerav och terapeutisk komposition innehaallande dem |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4383998A (en, 2012) |
| JP (1) | JPS57150688A (en, 2012) |
| KR (1) | KR870000206B1 (en, 2012) |
| AR (1) | AR230284A1 (en, 2012) |
| AU (1) | AU545876B2 (en, 2012) |
| BE (1) | BE891797A (en, 2012) |
| CA (1) | CA1175837A (en, 2012) |
| CH (1) | CH649554A5 (en, 2012) |
| DE (1) | DE3204596A1 (en, 2012) |
| DK (1) | DK157551C (en, 2012) |
| DZ (1) | DZ376A1 (en, 2012) |
| ES (1) | ES509449A0 (en, 2012) |
| FI (1) | FI75347C (en, 2012) |
| FR (2) | FR2499406A1 (en, 2012) |
| GB (1) | GB2092586B (en, 2012) |
| GR (1) | GR75905B (en, 2012) |
| HK (1) | HK22485A (en, 2012) |
| HU (1) | HU185088B (en, 2012) |
| IE (1) | IE52376B1 (en, 2012) |
| IL (1) | IL64759A (en, 2012) |
| IN (1) | IN156817B (en, 2012) |
| IT (1) | IT1157252B (en, 2012) |
| LU (1) | LU83886A1 (en, 2012) |
| MA (1) | MA19378A1 (en, 2012) |
| MX (1) | MX6983E (en, 2012) |
| NL (1) | NL186697C (en, 2012) |
| NO (1) | NO156373C (en, 2012) |
| NZ (1) | NZ199528A (en, 2012) |
| OA (1) | OA07003A (en, 2012) |
| PT (1) | PT74408B (en, 2012) |
| SE (1) | SE456994B (en, 2012) |
| SG (1) | SG85384G (en, 2012) |
| YU (1) | YU44000B (en, 2012) |
| ZA (1) | ZA82158B (en, 2012) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4735950A (en) * | 1983-04-05 | 1988-04-05 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S) | Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing the same |
| IN160104B (en, 2012) * | 1983-04-05 | 1987-06-27 | Scras | |
| GB8327817D0 (en) * | 1983-10-18 | 1983-11-16 | Scras | 4-halo-furo-(3 4-c)-pyridine derivatives |
| GB8330517D0 (en) * | 1983-11-16 | 1983-12-21 | Scras | 6-vinyl-furo-(3,4-c)pyridine derivatives |
| GB8330658D0 (en) * | 1983-11-17 | 1983-12-29 | Scras | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| GB8414559D0 (en) * | 1984-06-07 | 1984-07-11 | Scras | Pyridine derivatives |
| GB8422379D0 (en) * | 1984-09-05 | 1984-10-10 | Scras | Derivatives |
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
| DE3519693A1 (de) * | 1985-06-01 | 1987-01-02 | Basf Ag | Pyridin-derivate, ihre herstellung und verwendung |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| DE3990349T1 (de) * | 1988-04-06 | 1990-04-26 | Scras | Stereospezifisches verfahren zur herstellung von enantiomeren von furo(3,4-c)pyridin, so erhaltene verbindungen und therapeutische zusammensetzungen auf basis dieser verbindungen |
| GB8907480D0 (en) * | 1989-04-03 | 1989-05-17 | Scaras Societe De Conseils De | Separation of insomers of furo(3,4-c)pyridine derivatives |
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| GB0221494D0 (en) * | 2002-09-16 | 2002-10-23 | Generics Uk Ltd | Novel processes for the preparation of 1.3-dihydro-6-methylfuro (3,4-c) pyndin derivatives |
| HUP0300990A2 (hu) * | 2003-04-15 | 2005-05-30 | SynoSens Kutató és Fejlesztő Kft. | Szinergista gyógyszer-kombináció a diabetesz megelőzésére vagy kezelésére |
| WO2005009446A1 (en) * | 2003-07-17 | 2005-02-03 | Cotherix, Inc. | Combination therapies for treatment of hypertension and complications in patients with diabetes or metabolic syndrome |
| US20060089374A1 (en) * | 2003-07-17 | 2006-04-27 | Glenn Cornett | Enantiomeric compositions of cicletanine, alone and in combination with other agents, for the treatment of disease |
| US20060153934A1 (en) * | 2005-01-13 | 2006-07-13 | Navitas Pharma | Combination therapies of cicletanine and magnesium |
| WO2006034510A2 (en) * | 2004-09-22 | 2006-03-30 | Glenn Cornett | Enantiomeric compositions of cicletanine, alone and in combination with other agents, for the treatment of disease |
| US20060154959A1 (en) * | 2005-01-13 | 2006-07-13 | Navitas Pharma | Combination therapies of cicletanine and carvedilol |
| US20070141174A1 (en) * | 2005-01-13 | 2007-06-21 | Navitas Pharma, Inc. | Enantiomeric compositions of cicletanine, in combination with other agents, for the treatment of hypertension |
| US20080096915A1 (en) * | 2005-01-13 | 2008-04-24 | Greenberg Traurig LLP | Compositions for the treatment of metabolic disorders |
| US20070105817A1 (en) * | 2005-11-09 | 2007-05-10 | Jim Page | Use of cicletanine and other furopyridines for treatment of systolic-predominant hypertension, isolated systolic hypertension, elevated pulse pressure, and general hypertension |
| AU2008203901A1 (en) * | 2007-01-03 | 2008-07-17 | Glenn V. Cornett | Cicletanine and PKC inhibitors in the treatment of pulmonary and cardiac disorders |
| AR073259A1 (es) * | 2008-07-29 | 2010-10-28 | Merck & Co Inc | Derivados de furosemida utiles como diureticos |
| US8214941B2 (en) | 2008-10-02 | 2012-07-10 | Kohler Co. | Slip-fit clamping system for mounting a fitting on a wall |
| EP2485734B1 (en) * | 2009-10-09 | 2014-07-02 | Merck Sharp & Dohme Corp. | Diuretics |
| EP2498605B1 (en) * | 2009-10-29 | 2014-08-27 | Merck Sharp & Dohme Corp. | Diuretics |
| US9522138B2 (en) * | 2013-12-31 | 2016-12-20 | Don C. Rockey | Systems, methods, techniques, and compounds in research and treatment of portal hypertension and other conditions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
-
1982
- 1982-01-06 IN IN11/DEL/82A patent/IN156817B/en unknown
- 1982-01-08 US US06/338,140 patent/US4383998A/en not_active Expired - Lifetime
- 1982-01-11 IL IL64759A patent/IL64759A/xx unknown
- 1982-01-11 ZA ZA82158A patent/ZA82158B/xx unknown
- 1982-01-12 GR GR66981A patent/GR75905B/el unknown
- 1982-01-15 BE BE0/207069A patent/BE891797A/fr not_active IP Right Cessation
- 1982-01-19 NL NLAANVRAGE8200180,A patent/NL186697C/xx not_active IP Right Cessation
- 1982-01-20 NZ NZ199528A patent/NZ199528A/en unknown
- 1982-01-21 AR AR288193A patent/AR230284A1/es active
- 1982-01-21 LU LU83886A patent/LU83886A1/fr unknown
- 1982-01-28 CH CH508/82A patent/CH649554A5/fr not_active IP Right Cessation
- 1982-01-28 OA OA57599A patent/OA07003A/xx unknown
- 1982-01-28 NO NO820253A patent/NO156373C/no not_active IP Right Cessation
- 1982-02-01 MA MA19583A patent/MA19378A1/fr unknown
- 1982-02-04 FI FI820353A patent/FI75347C/fi not_active IP Right Cessation
- 1982-02-05 YU YU253/82A patent/YU44000B/xx unknown
- 1982-02-07 DZ DZ826443A patent/DZ376A1/fr active
- 1982-02-08 GB GB8203522A patent/GB2092586B/en not_active Expired
- 1982-02-08 IT IT19502/82A patent/IT1157252B/it active
- 1982-02-09 AU AU80294/82A patent/AU545876B2/en not_active Expired
- 1982-02-09 DK DK054382A patent/DK157551C/da not_active IP Right Cessation
- 1982-02-09 IE IE288/82A patent/IE52376B1/en not_active IP Right Cessation
- 1982-02-09 ES ES509449A patent/ES509449A0/es active Granted
- 1982-02-09 SE SE8200744A patent/SE456994B/sv not_active IP Right Cessation
- 1982-02-09 PT PT74408A patent/PT74408B/pt unknown
- 1982-02-09 MX MX829909U patent/MX6983E/es unknown
- 1982-02-09 KR KR8200536A patent/KR870000206B1/ko not_active Expired
- 1982-02-09 CA CA000395857A patent/CA1175837A/en not_active Expired
- 1982-02-10 JP JP57019038A patent/JPS57150688A/ja active Granted
- 1982-02-10 HU HU82405A patent/HU185088B/hu unknown
- 1982-02-10 FR FR8202136A patent/FR2499406A1/fr active Granted
- 1982-02-10 DE DE19823204596 patent/DE3204596A1/de active Granted
- 1982-02-10 FR FR8202137A patent/FR2499574A1/fr active Granted
-
1984
- 1984-11-29 SG SG853/84A patent/SG85384G/en unknown
-
1985
- 1985-03-21 HK HK224/85A patent/HK22485A/xx not_active IP Right Cessation
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