NO771926L - Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveol - Google Patents
Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveolInfo
- Publication number
- NO771926L NO771926L NO771926A NO771926A NO771926L NO 771926 L NO771926 L NO 771926L NO 771926 A NO771926 A NO 771926A NO 771926 A NO771926 A NO 771926A NO 771926 L NO771926 L NO 771926L
- Authority
- NO
- Norway
- Prior art keywords
- pinocarveol
- myrtenal
- verbenone
- treatment
- pharmaceutical composition
- Prior art date
Links
- 229930006721 pinocarveol Natural products 0.000 title claims description 31
- LCYXQUJDODZYIJ-UHFFFAOYSA-N pinocarveol Chemical compound C1C2C(C)(C)C1CC(O)C2=C LCYXQUJDODZYIJ-UHFFFAOYSA-N 0.000 title claims description 30
- KMRMUZKLFIEVAO-RKDXNWHRSA-N Myrtenal Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2C=O KMRMUZKLFIEVAO-RKDXNWHRSA-N 0.000 title claims description 29
- KMRMUZKLFIEVAO-UHFFFAOYSA-N 7,7-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde Chemical compound C1C2C(C)(C)C1CC=C2C=O KMRMUZKLFIEVAO-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-N 0.000 claims description 29
- DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 claims description 29
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 235000007586 terpenes Nutrition 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000003505 terpenes Chemical class 0.000 claims description 17
- RXBQNMWIQKOSCS-UHFFFAOYSA-N (7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol Chemical compound C1C2C(C)(C)C1CC=C2CO RXBQNMWIQKOSCS-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 7
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052753 mercury Inorganic materials 0.000 claims description 7
- 238000004508 fractional distillation Methods 0.000 claims description 6
- RXBQNMWIQKOSCS-RKDXNWHRSA-N Myrtenol Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2CO RXBQNMWIQKOSCS-RKDXNWHRSA-N 0.000 claims description 5
- 210000002345 respiratory system Anatomy 0.000 claims description 5
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 5
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 4
- 229940117975 chromium trioxide Drugs 0.000 claims description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 4
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims 1
- 229930006722 beta-pinene Natural products 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 230000001148 spastic effect Effects 0.000 claims 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 claims 1
- OMDMTHRBGUBUCO-IUCAKERBSA-N (1s,5s)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol Chemical compound CC1=CC[C@H](C(C)(C)O)C[C@@H]1O OMDMTHRBGUBUCO-IUCAKERBSA-N 0.000 description 38
- 229960000230 sobrerol Drugs 0.000 description 19
- OMDMTHRBGUBUCO-UHFFFAOYSA-N trans-sobrerol Natural products CC1=CCC(C(C)(C)O)CC1O OMDMTHRBGUBUCO-UHFFFAOYSA-N 0.000 description 19
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 238000000338 in vitro Methods 0.000 description 14
- 230000037396 body weight Effects 0.000 description 11
- 241000700159 Rattus Species 0.000 description 9
- WONIGEXYPVIKFS-UHFFFAOYSA-N Verbenol Chemical class CC1=CC(O)C2C(C)(C)C1C2 WONIGEXYPVIKFS-UHFFFAOYSA-N 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000003182 bronchodilatating effect Effects 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002744 anti-aggregatory effect Effects 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 4
- IRZWAJHUWGZMMT-UHFFFAOYSA-N Chrysanthenol Natural products CC1=CCC2C(C)(C)C1C2O IRZWAJHUWGZMMT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 206010018910 Haemolysis Diseases 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 230000008588 hemolysis Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 3
- 208000014181 Bronchial disease Diseases 0.000 description 3
- 206010006482 Bronchospasm Diseases 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000002587 anti-hemolytic effect Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 210000003743 erythrocyte Anatomy 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 241000021559 Dicerandra Species 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- 235000010654 Melissa officinalis Nutrition 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- NQFUSWIGRKFAHK-BDNRQGISSA-N alpha-Pinene epoxide Natural products C([C@@H]1O[C@@]11C)[C@@H]2C(C)(C)[C@H]1C2 NQFUSWIGRKFAHK-BDNRQGISSA-N 0.000 description 2
- 229930006723 alpha-pinene oxide Natural products 0.000 description 2
- 125000003425 alpha-pinene oxide group Chemical group 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 230000003555 analeptic effect Effects 0.000 description 2
- 230000002322 anti-exudative effect Effects 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000865 liniment Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 terpene compounds Chemical class 0.000 description 2
- 230000002446 thrombocytic effect Effects 0.000 description 2
- 210000005090 tracheal smooth muscle Anatomy 0.000 description 2
- DCSCXTJOXBUFGB-MQWKRIRWSA-N (5r)-2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one Chemical compound CC1=CC(=O)[C@H]2C(C)(C)C1C2 DCSCXTJOXBUFGB-MQWKRIRWSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Chemical class 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000000001 effect on platelet aggregation Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/11—Aldehydes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH704276A CH625197A5 (en) | 1976-06-03 | 1976-06-03 | Process for preparing verbenone, myrtenal and pinocarveol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771926L true NO771926L (no) | 1977-12-06 |
Family
ID=4319020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771926A NO771926L (no) | 1976-06-03 | 1977-06-01 | Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveol |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS52151156A (nl) |
| AR (1) | AR214200A1 (nl) |
| AT (1) | AT351520B (nl) |
| AU (1) | AU519521B2 (nl) |
| BE (1) | BE855297A (nl) |
| CA (1) | CA1099214A (nl) |
| CH (1) | CH625197A5 (nl) |
| CS (1) | CS251755B2 (nl) |
| DD (1) | DD130475A1 (nl) |
| DE (2) | DE2760410C2 (nl) |
| DK (1) | DK244277A (nl) |
| ES (1) | ES459425A1 (nl) |
| FI (1) | FI771765A (nl) |
| FR (2) | FR2416878A1 (nl) |
| GB (2) | GB1585832A (nl) |
| HU (1) | HU178205B (nl) |
| IT (1) | IT1074511B (nl) |
| NL (1) | NL7705934A (nl) |
| NO (1) | NO771926L (nl) |
| OA (1) | OA05678A (nl) |
| PL (1) | PL116550B1 (nl) |
| PT (1) | PT66619B (nl) |
| SE (2) | SE424723B (nl) |
| SU (1) | SU816396A3 (nl) |
| ZA (1) | ZA773345B (nl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04239414A (ja) * | 1991-01-24 | 1992-08-27 | Sekisui Chem Co Ltd | 粘着テープを使用した結束装置及び結束方法 |
| IT1251615B (it) * | 1991-10-04 | 1995-05-17 | Golgi Sa | Medicamento ad attivita' antielastasica. |
| IT1312537B1 (it) * | 1999-04-16 | 2002-04-22 | Euphar Group Srl | Derivati del (-)- verbenone. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1103814A (fr) * | 1953-04-30 | 1955-11-07 | Glidden Co | Perfectionnements relatifs au traitement des mélanges et produits d'auto-oxydation du terpène |
| US2911442A (en) * | 1953-04-30 | 1959-11-03 | Glidden Co | Production of oxygenated terpenes from alpha-pinene |
| FR1377525A (fr) * | 1963-09-25 | 1964-11-06 | Centre Nat Rech Scient | Procédé de préparation de cétones terpéniques |
| FR1572146A (nl) * | 1967-05-10 | 1969-06-27 | ||
| US3673066A (en) * | 1969-02-14 | 1972-06-27 | Lab De L Ozothine | Process for the accelerated obtaining of terpenic oxides using ultraviolet light |
| CH523962A (fr) * | 1969-08-18 | 1972-06-15 | Int Flavors & Fragrances Inc | Utilisation de dérivés d'indane comme principes odorants |
| CH542163A (fr) * | 1971-06-14 | 1973-09-30 | Buskine Sa | Procédé de production d'un mélange terpénique |
| FR2267296A1 (en) * | 1974-04-12 | 1975-11-07 | Anvar | Myrtenol synthesis - by isomerisation of beta-pinene epoxide |
-
1976
- 1976-06-03 CH CH704276A patent/CH625197A5/it not_active IP Right Cessation
-
1977
- 1977-05-25 GB GB1504/80A patent/GB1585832A/en not_active Expired
- 1977-05-25 GB GB22089/77A patent/GB1585831A/en not_active Expired
- 1977-05-31 PT PT66619A patent/PT66619B/pt unknown
- 1977-05-31 NL NL7705934A patent/NL7705934A/nl not_active Application Discontinuation
- 1977-05-31 CS CS773586A patent/CS251755B2/cs unknown
- 1977-06-01 SE SE7706385A patent/SE424723B/xx unknown
- 1977-06-01 BE BE178116A patent/BE855297A/xx unknown
- 1977-06-01 NO NO771926A patent/NO771926L/no unknown
- 1977-06-01 AU AU25732/77A patent/AU519521B2/en not_active Expired
- 1977-06-01 CA CA279,610A patent/CA1099214A/en not_active Expired
- 1977-06-02 SU SU772494040A patent/SU816396A3/ru active
- 1977-06-02 FI FI771765A patent/FI771765A/fi not_active Application Discontinuation
- 1977-06-02 JP JP6404177A patent/JPS52151156A/ja active Pending
- 1977-06-02 ES ES459425A patent/ES459425A1/es not_active Expired
- 1977-06-02 HU HU77CO341A patent/HU178205B/hu unknown
- 1977-06-02 DK DK244277A patent/DK244277A/da not_active Application Discontinuation
- 1977-06-02 PL PL1977198600A patent/PL116550B1/pl unknown
- 1977-06-03 OA OA56187A patent/OA05678A/xx unknown
- 1977-06-03 DE DE2760410A patent/DE2760410C2/de not_active Expired - Fee Related
- 1977-06-03 DE DE2725247A patent/DE2725247C2/de not_active Expired
- 1977-06-03 AT AT394077A patent/AT351520B/de not_active IP Right Cessation
- 1977-06-03 FR FR7717088A patent/FR2416878A1/fr not_active Withdrawn
- 1977-06-03 ZA ZA00773345A patent/ZA773345B/xx unknown
- 1977-06-03 DD DD7700199291A patent/DD130475A1/xx unknown
- 1977-06-03 IT IT24385/77A patent/IT1074511B/it active Protection Beyond IP Right Term
- 1977-06-08 AR AR267933A patent/AR214200A1/es active
-
1981
- 1981-05-06 FR FR8108999A patent/FR2479804A1/fr not_active Withdrawn
- 1981-09-25 SE SE8105687A patent/SE8105687L/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CH625197A5 (en) | 1981-09-15 |
| CA1099214A (en) | 1981-04-14 |
| OA05678A (fr) | 1981-05-31 |
| FR2479804A1 (fr) | 1981-10-09 |
| DE2725247C2 (de) | 1987-02-12 |
| AU2573277A (en) | 1978-12-07 |
| PT66619B (fr) | 1978-10-27 |
| BE855297A (fr) | 1977-10-03 |
| JPS52151156A (en) | 1977-12-15 |
| DK244277A (da) | 1977-12-04 |
| AU519521B2 (en) | 1981-12-10 |
| DE2760410C2 (nl) | 1990-08-16 |
| PT66619A (fr) | 1977-06-01 |
| HU178205B (en) | 1982-03-28 |
| CS251755B2 (en) | 1987-08-13 |
| FR2416878A1 (fr) | 1979-09-07 |
| GB1585832A (en) | 1981-03-11 |
| PL116550B1 (en) | 1981-06-30 |
| AR214200A1 (es) | 1979-05-15 |
| SU816396A3 (ru) | 1981-03-23 |
| IT1074511B (it) | 1985-04-20 |
| GB1585831A (en) | 1981-03-11 |
| AT351520B (de) | 1979-07-25 |
| DE2725247A1 (de) | 1977-12-22 |
| FI771765A (nl) | 1977-12-04 |
| DD130475A1 (de) | 1978-04-05 |
| NL7705934A (nl) | 1977-12-06 |
| ATA394077A (de) | 1979-01-15 |
| SE7706385L (sv) | 1977-12-04 |
| ZA773345B (en) | 1978-04-26 |
| ES459425A1 (es) | 1978-04-01 |
| SE8105687L (sv) | 1981-09-25 |
| PL198600A1 (pl) | 1978-06-19 |
| SE424723B (sv) | 1982-08-09 |
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