HRP980313A2 - Novel pentaerythrite derivatives, the production and use thereof and intermediate products for the synthesis of the same - Google Patents
Novel pentaerythrite derivatives, the production and use thereof and intermediate products for the synthesis of the sameInfo
- Publication number
- HRP980313A2 HRP980313A2 HR19725340.7A HRP980313A HRP980313A2 HR P980313 A2 HRP980313 A2 HR P980313A2 HR P980313 A HRP980313 A HR P980313A HR P980313 A2 HRP980313 A2 HR P980313A2
- Authority
- HR
- Croatia
- Prior art keywords
- compounds
- formula
- propyl
- image
- well
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 230000015572 biosynthetic process Effects 0.000 title description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 title description 7
- 238000003786 synthesis reaction Methods 0.000 title description 6
- 239000013067 intermediate product Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 99
- -1 n-octyl Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 239000013543 active substance Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 210000003038 endothelium Anatomy 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
- 230000017531 blood circulation Effects 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- 210000004204 blood vessel Anatomy 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
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- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 2
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- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims description 2
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- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 2
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 2
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
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- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
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- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 2
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- 208000019622 heart disease Diseases 0.000 claims 1
- 230000000304 vasodilatating effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- BRBAEHHXGZRCBK-UHFFFAOYSA-N pentrinitrol Chemical compound [O-][N+](=O)OCC(CO)(CO[N+]([O-])=O)CO[N+]([O-])=O BRBAEHHXGZRCBK-UHFFFAOYSA-N 0.000 description 14
- 229950006286 pentrinitrol Drugs 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 229910017604 nitric acid Inorganic materials 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000026 Pentaerythritol tetranitrate Substances 0.000 description 10
- 229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LHSHCLPXMPQXCS-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-nitrooxypropyl] nitrate Chemical compound [O-][N+](=O)OCC(CO)(CO)CO[N+]([O-])=O LHSHCLPXMPQXCS-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 235000011149 sulphuric acid Nutrition 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- RHVYBZNTBGYKKV-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] nitrate Chemical class OCC(CO)(CO)CO[N+]([O-])=O RHVYBZNTBGYKKV-UHFFFAOYSA-N 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
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- 235000019198 oils Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 229910002651 NO3 Inorganic materials 0.000 description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
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- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
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- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- 150000001413 amino acids Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 150000002823 nitrates Chemical class 0.000 description 4
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- 239000003826 tablet Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
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- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
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- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
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- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- CYJWLKOSJIAOAI-UHFFFAOYSA-N 4-butyl-1,2,4-oxadiazolidine-3,5-dione Chemical compound CCCCN1C(O)=NOC1=O CYJWLKOSJIAOAI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 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 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WNDKQMVUVHIESB-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol hydrate Chemical compound O.OCC(CO)(CO)CO WNDKQMVUVHIESB-UHFFFAOYSA-N 0.000 description 1
- KTGAFVGVECOGCK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propanedioic acid Chemical compound OCC(CO)(C(O)=O)C(O)=O KTGAFVGVECOGCK-UHFFFAOYSA-N 0.000 description 1
- PPVBGPLECSKJDX-UHFFFAOYSA-N 2-(hydroxymethyl)propanedioic acid Chemical compound OCC(C(O)=O)C(O)=O PPVBGPLECSKJDX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19725340 | 1997-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980313A2 true HRP980313A2 (en) | 1999-04-30 |
Family
ID=7832585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19725340.7A HRP980313A2 (en) | 1997-06-11 | 1998-06-11 | Novel pentaerythrite derivatives, the production and use thereof and intermediate products for the synthesis of the same |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6365611B1 (bg) |
| EP (1) | EP0988282A2 (bg) |
| JP (1) | JP2002504903A (bg) |
| CN (1) | CN1266429A (bg) |
| AU (1) | AU8532198A (bg) |
| BG (1) | BG104021A (bg) |
| CA (1) | CA2293407A1 (bg) |
| DE (2) | DE19826781A1 (bg) |
| EA (1) | EA200000006A1 (bg) |
| EE (1) | EE9900568A (bg) |
| HR (1) | HRP980313A2 (bg) |
| HU (1) | HUP0002925A3 (bg) |
| IL (1) | IL133410A0 (bg) |
| NO (1) | NO996128D0 (bg) |
| NZ (1) | NZ501414A (bg) |
| PL (1) | PL337775A1 (bg) |
| SK (1) | SK169599A3 (bg) |
| TR (2) | TR199903054T2 (bg) |
| WO (1) | WO1998056759A2 (bg) |
| ZA (1) | ZA985064B (bg) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1306184B1 (it) * | 1999-08-05 | 2001-05-30 | Sigma Tau Ind Farmaceuti | Nitrilossi derivati della (r) e (s)-carnitina. |
| DE19950483A1 (de) * | 1999-10-19 | 2001-05-10 | Isis Pharma Gmbh | Verfahren zur Herstellung von 3-Nitryloxy-2,2-bis(nitryloxymethyl)-propanal |
| US20040013649A1 (en) * | 2002-05-10 | 2004-01-22 | Inex Pharmaceuticals Corporation | Cancer vaccines and methods of using the same |
| US20040009944A1 (en) * | 2002-05-10 | 2004-01-15 | Inex Pharmaceuticals Corporation | Methylated immunostimulatory oligonucleotides and methods of using the same |
| WO2005034979A2 (en) * | 2003-10-11 | 2005-04-21 | Inex Pharmaceuticals Corporation | Methods and compositions for enhancing innate immunity and antibody dependent cellular cytotoxicity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419571A (en) * | 1966-04-06 | 1968-12-31 | Warner Lambert Pharmaceutical | Method for relieving coronary insufficiency |
| DE3836021A1 (de) | 1988-10-22 | 1990-05-03 | Boehringer Mannheim Gmbh | Arzneimittel enthaltend nitroxyalkylamine mit amidfunktion und verfahren zur herstellung dieser verbindungen |
| DE19515970A1 (de) * | 1995-05-02 | 1996-11-07 | Bayer Ag | Acetylsalicylsäurenitrate |
| SK43499A3 (en) | 1996-10-10 | 2000-02-14 | Isis Pharma Gmbh | New pentaerythritol derivatives, their production and use and intermediates for their synthesis |
-
1998
- 1998-06-11 NZ NZ501414A patent/NZ501414A/en unknown
- 1998-06-11 ZA ZA985064A patent/ZA985064B/xx unknown
- 1998-06-11 HR HR19725340.7A patent/HRP980313A2/hr not_active Application Discontinuation
- 1998-06-11 DE DE19826781A patent/DE19826781A1/de not_active Withdrawn
- 1998-06-11 EA EA200000006A patent/EA200000006A1/ru unknown
- 1998-06-11 CA CA002293407A patent/CA2293407A1/en not_active Abandoned
- 1998-06-11 US US09/445,782 patent/US6365611B1/en not_active Expired - Fee Related
- 1998-06-11 WO PCT/DE1998/001635 patent/WO1998056759A2/de not_active Application Discontinuation
- 1998-06-11 EE EEP199900568A patent/EE9900568A/xx unknown
- 1998-06-11 SK SK1695-99A patent/SK169599A3/sk unknown
- 1998-06-11 JP JP50133099A patent/JP2002504903A/ja active Pending
- 1998-06-11 AU AU85321/98A patent/AU8532198A/en not_active Abandoned
- 1998-06-11 TR TR1999/03054T patent/TR199903054T2/xx unknown
- 1998-06-11 EP EP98936180A patent/EP0988282A2/de not_active Withdrawn
- 1998-06-11 TR TR2000/03352T patent/TR200003352T2/xx unknown
- 1998-06-11 CN CN98808056A patent/CN1266429A/zh active Pending
- 1998-06-11 PL PL98337775A patent/PL337775A1/xx unknown
- 1998-06-11 HU HU0002925A patent/HUP0002925A3/hu unknown
- 1998-06-11 IL IL13341098A patent/IL133410A0/xx unknown
- 1998-06-11 DE DE19880813T patent/DE19880813D2/de not_active Expired - Lifetime
-
1999
- 1999-12-10 NO NO996128A patent/NO996128D0/no not_active Application Discontinuation
- 1999-12-16 BG BG104021A patent/BG104021A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EE9900568A (et) | 2000-08-15 |
| WO1998056759A3 (de) | 1999-09-16 |
| NO996128L (no) | 1999-12-10 |
| IL133410A0 (en) | 2001-04-30 |
| BG104021A (bg) | 2000-07-31 |
| CA2293407A1 (en) | 1998-12-17 |
| DE19880813D2 (de) | 2000-05-31 |
| EP0988282A2 (de) | 2000-03-29 |
| ZA985064B (en) | 1998-08-28 |
| US6365611B1 (en) | 2002-04-02 |
| JP2002504903A (ja) | 2002-02-12 |
| CN1266429A (zh) | 2000-09-13 |
| PL337775A1 (en) | 2000-09-11 |
| EA200000006A1 (ru) | 2000-08-28 |
| NZ501414A (en) | 2001-12-21 |
| WO1998056759A2 (de) | 1998-12-17 |
| SK169599A3 (en) | 2000-11-07 |
| HUP0002925A3 (en) | 2002-11-28 |
| TR200003352T2 (tr) | 2001-02-21 |
| TR199903054T2 (xx) | 2000-07-21 |
| NO996128D0 (no) | 1999-12-10 |
| AU8532198A (en) | 1998-12-30 |
| HUP0002925A2 (hu) | 2001-07-30 |
| DE19826781A1 (de) | 1998-12-17 |
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