LU85865A1 - Nouveaux derives du pyrane,leur preparation et compositions therapeutiques en contenant - Google Patents
Nouveaux derives du pyrane,leur preparation et compositions therapeutiques en contenant Download PDFInfo
- Publication number
- LU85865A1 LU85865A1 LU85865A LU85865A LU85865A1 LU 85865 A1 LU85865 A1 LU 85865A1 LU 85865 A LU85865 A LU 85865A LU 85865 A LU85865 A LU 85865A LU 85865 A1 LU85865 A1 LU 85865A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- formula
- tottoli
- insoluble
- water
- soluble
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 7
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 5
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 11
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 9
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims abstract description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000003085 diluting agent Substances 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 150000004880 oxines Chemical class 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 150000002243 furanoses Chemical class 0.000 abstract 1
- 150000003215 pyranoses Chemical class 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 150
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- 230000008018 melting Effects 0.000 description 79
- 238000002844 melting Methods 0.000 description 79
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 77
- 239000000843 powder Substances 0.000 description 56
- 230000035484 reaction time Effects 0.000 description 39
- 241000699670 Mus sp. Species 0.000 description 13
- 241000700605 Viruses Species 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 206010015150 Erythema Diseases 0.000 description 11
- 231100000321 erythema Toxicity 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 210000004072 lung Anatomy 0.000 description 10
- -1 pyrano- (2,3-c) pyrazole-dione Chemical compound 0.000 description 10
- 238000007596 consolidation process Methods 0.000 description 9
- 210000000416 exudates and transudate Anatomy 0.000 description 8
- 238000011081 inoculation Methods 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 6
- 229960004150 aciclovir Drugs 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 description 5
- RHALETUYNQUBKL-UHFFFAOYSA-N 1,7-dihydropyrano[2,3-d]pyrimidine-2,4-dione Chemical compound O1CC=CC2=C1NC(=O)NC2=O RHALETUYNQUBKL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010046555 Urinary retention Diseases 0.000 description 4
- 125000000328 arabinofuranosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
- SRBFZHDQGSBBOR-TXICZTDVSA-N beta-D-ribopyranose Chemical compound O[C@@H]1CO[C@@H](O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-TXICZTDVSA-N 0.000 description 4
- HMFHBZSHGGEWLO-KKQCNMDGSA-N beta-D-xylofuranose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-KKQCNMDGSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229940068196 placebo Drugs 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- TYNJDTZENDOQDO-UHFFFAOYSA-N 6,7-dihydro-1H-pyrano[2,3-d]pyrimidine-2,4,5-trione Chemical compound N1C(NC(C2=C1OCCC2=O)=O)=O TYNJDTZENDOQDO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010048461 Genital infection Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HMFHBZSHGGEWLO-SQOUGZDYSA-N beta-D-arabinofuranose Chemical compound OC[C@H]1O[C@@H](O)[C@@H](O)[C@@H]1O HMFHBZSHGGEWLO-SQOUGZDYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-SQOUGZDYSA-N beta-D-arabinopyranose Chemical compound O[C@@H]1CO[C@@H](O)[C@@H](O)[C@@H]1O SRBFZHDQGSBBOR-SQOUGZDYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-KKQCNMDGSA-N beta-D-xylose Chemical compound O[C@@H]1CO[C@@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-KKQCNMDGSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 208000009889 Herpes Simplex Diseases 0.000 description 2
- 101100176745 Mus musculus Gsc2 gene Proteins 0.000 description 2
- 241000700584 Simplexvirus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 238000000313 electron-beam-induced deposition Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- HFXRMQZCAIBURX-UHFFFAOYSA-N 7h-pyrano[2,3-d]pyrimidine Chemical compound C1=NC=C2C=CCOC2=N1 HFXRMQZCAIBURX-UHFFFAOYSA-N 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- 241001500351 Influenzavirus A Species 0.000 description 1
- 208000032376 Lung infection Diseases 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- SRBFZHDQGSBBOR-AIHAYLRMSA-N alpha-D-ribopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-AIHAYLRMSA-N 0.000 description 1
- HMFHBZSHGGEWLO-LECHCGJUSA-N alpha-D-xylofuranose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-LECHCGJUSA-N 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04H—BUILDINGS OR LIKE STRUCTURES FOR PARTICULAR PURPOSES; SWIMMING OR SPLASH BATHS OR POOLS; MASTS; FENCING; TENTS OR CANOPIES, IN GENERAL
- E04H1/00—Buildings or groups of buildings for dwelling or office purposes; General layout, e.g. modular co-ordination or staggered storeys
- E04H1/12—Small buildings or other erections for limited occupation, erected in the open air or arranged in buildings, e.g. kiosks, waiting shelters for bus stops or for filling stations, roofs for railway platforms, watchmen's huts or dressing cubicles
- E04H1/1272—Exhibition stands
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B2/00—Friction-grip releasable fastenings
- F16B2/20—Clips, i.e. with gripping action effected solely by the inherent resistance to deformation of the material of the fastening
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Architecture (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Civil Engineering (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Structural Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848410484A GB8410484D0 (en) | 1984-04-24 | 1984-04-24 | Antiviral and antibacterial compounds |
| GB8410484 | 1984-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85865A1 true LU85865A1 (fr) | 1985-12-16 |
Family
ID=10560013
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85864A LU85864A1 (fr) | 1984-04-24 | 1985-04-22 | Nouveaux derives du bornane,leur preparation et compositions therapeutiques en contenant |
| LU85865A LU85865A1 (fr) | 1984-04-24 | 1985-04-22 | Nouveaux derives du pyrane,leur preparation et compositions therapeutiques en contenant |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85864A LU85864A1 (fr) | 1984-04-24 | 1985-04-22 | Nouveaux derives du bornane,leur preparation et compositions therapeutiques en contenant |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4704454A (no) |
| JP (2) | JPS60233095A (no) |
| AR (2) | AR241916A1 (no) |
| AT (2) | AT388557B (no) |
| BE (2) | BE902231A (no) |
| CA (2) | CA1265129A (no) |
| CH (2) | CH665837A5 (no) |
| DE (2) | DE3514641A1 (no) |
| DK (2) | DK160832C (no) |
| DZ (1) | DZ772A1 (no) |
| ES (2) | ES8606379A1 (no) |
| FI (2) | FI78302C (no) |
| FR (3) | FR2563224B1 (no) |
| GB (3) | GB8410484D0 (no) |
| HK (2) | HK18788A (no) |
| IE (2) | IE58323B1 (no) |
| IT (2) | IT1201415B (no) |
| LU (2) | LU85864A1 (no) |
| MA (2) | MA20414A1 (no) |
| MY (1) | MY102313A (no) |
| NL (2) | NL193067C (no) |
| NO (2) | NO161121C (no) |
| OA (2) | OA08000A (no) |
| PT (2) | PT80324B (no) |
| SE (2) | SE462972B (no) |
| ZA (2) | ZA852367B (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622492B2 (en) | 2005-08-31 | 2009-11-24 | Hoffmann-La Roche Inc. | Pyrazolones as inhibitors of 11β-hydroxysteroid dehydrogenase |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868361A (en) * | 1973-03-12 | 1975-02-25 | Richard L Tolman | s-Triazolo{8 2,3-A{9 {0 pryimidine nucleosides |
| DE3019322A1 (de) * | 1980-05-21 | 1981-12-03 | Merck Patent Gmbh, 6100 Darmstadt | Psychopharmakon sowie verwendung von adenosinderivaten |
-
1984
- 1984-04-24 GB GB848410484A patent/GB8410484D0/en active Pending
-
1985
- 1985-03-28 ZA ZA852367A patent/ZA852367B/xx unknown
- 1985-03-28 ZA ZA852366A patent/ZA852366B/xx unknown
- 1985-04-01 US US06/718,064 patent/US4704454A/en not_active Expired - Fee Related
- 1985-04-01 US US06/718,065 patent/US4720487A/en not_active Expired - Fee Related
- 1985-04-10 AR AR85300028A patent/AR241916A1/es active
- 1985-04-10 AR AR85300029A patent/AR241917A1/es active
- 1985-04-17 SE SE8501884A patent/SE462972B/sv not_active IP Right Cessation
- 1985-04-17 SE SE8501885A patent/SE462973B/sv not_active IP Right Cessation
- 1985-04-18 BE BE0/214871A patent/BE902231A/fr not_active IP Right Cessation
- 1985-04-18 BE BE0/214872A patent/BE902232A/fr not_active IP Right Cessation
- 1985-04-18 CH CH1665/85A patent/CH665837A5/fr not_active IP Right Cessation
- 1985-04-18 CH CH1666/85A patent/CH664572A5/fr not_active IP Right Cessation
- 1985-04-19 MA MA20638A patent/MA20414A1/fr unknown
- 1985-04-19 MA MA20639A patent/MA20415A1/fr unknown
- 1985-04-22 IT IT20440/85A patent/IT1201415B/it active
- 1985-04-22 LU LU85864A patent/LU85864A1/fr unknown
- 1985-04-22 IT IT8520439A patent/IT1215265B/it active
- 1985-04-22 PT PT80324A patent/PT80324B/pt not_active IP Right Cessation
- 1985-04-22 LU LU85865A patent/LU85865A1/fr unknown
- 1985-04-22 FI FI851577A patent/FI78302C/fi not_active IP Right Cessation
- 1985-04-22 FI FI851576A patent/FI78301C/fi not_active IP Right Cessation
- 1985-04-22 PT PT80325A patent/PT80325B/pt not_active IP Right Cessation
- 1985-04-23 IE IE103085A patent/IE58323B1/en not_active IP Right Cessation
- 1985-04-23 NO NO851619A patent/NO161121C/no unknown
- 1985-04-23 DK DK181285A patent/DK160832C/da not_active IP Right Cessation
- 1985-04-23 ES ES542485A patent/ES8606379A1/es not_active Expired
- 1985-04-23 IE IE102985A patent/IE58322B1/en not_active IP Right Cessation
- 1985-04-23 GB GB08510328A patent/GB2157690B/en not_active Expired
- 1985-04-23 GB GB08510329A patent/GB2158436B/en not_active Expired
- 1985-04-23 DE DE19853514641 patent/DE3514641A1/de active Granted
- 1985-04-23 NO NO851620A patent/NO161122C/no unknown
- 1985-04-23 NL NL8501171A patent/NL193067C/nl not_active IP Right Cessation
- 1985-04-23 ES ES542486A patent/ES8606380A1/es not_active Expired
- 1985-04-23 DE DE19853514637 patent/DE3514637A1/de active Granted
- 1985-04-23 NL NL8501170A patent/NL193109B/xx not_active Application Discontinuation
- 1985-04-23 CA CA000479845A patent/CA1265129A/en not_active Expired - Fee Related
- 1985-04-23 CA CA000479844A patent/CA1241649A/en not_active Expired
- 1985-04-23 DZ DZ850084A patent/DZ772A1/fr active
- 1985-04-23 DK DK181385A patent/DK160833C/da not_active IP Right Cessation
- 1985-04-24 OA OA58577A patent/OA08000A/xx unknown
- 1985-04-24 AT AT0122585A patent/AT388557B/de not_active IP Right Cessation
- 1985-04-24 FR FR8506207A patent/FR2563224B1/fr not_active Expired
- 1985-04-24 FR FR8506204A patent/FR2563106B1/fr not_active Expired
- 1985-04-24 OA OA58576A patent/OA07999A/xx unknown
- 1985-04-24 FR FR8506206A patent/FR2563107B1/fr not_active Expired
- 1985-04-24 JP JP60086616A patent/JPS60233095A/ja active Granted
- 1985-04-24 JP JP60086617A patent/JPS60233096A/ja active Granted
- 1985-04-24 AT AT0122685A patent/AT388558B/de not_active IP Right Cessation
-
1988
- 1988-01-26 MY MYPI88000060A patent/MY102313A/en unknown
- 1988-03-10 HK HK187/88A patent/HK18788A/xx not_active IP Right Cessation
-
1989
- 1989-02-02 HK HK102/89A patent/HK10289A/xx not_active IP Right Cessation
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