NO771926L - Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveol - Google Patents

Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveol

Info

Publication number: NO771926L
Authority: NO; Norway
Prior art keywords: pinocarveol; myrtenal; verbenone; treatment; pharmaceutical composition
Prior art date: 1976-06-03

Application number

NO771926A

Other languages

English (en)

Norwegian (no)

Inventor

Davide Vegezzi

Original Assignee

Corvi Mora E

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-03

Filing date

1977-06-01

Publication date

1977-12-06

1977-06-01 Application filed by Corvi Mora E filed Critical Corvi Mora E

1977-12-06 Publication of NO771926L publication Critical patent/NO771926L/no

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)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Rheumatology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Communicable Diseases (AREA)
Pulmonology (AREA)
Crystallography & Structural Chemistry (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Medicines Containing Plant Substances (AREA)

NO771926A 1976-06-03 1977-06-01 Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveol NO771926L (no)

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 (xx)
AR (1)	AR214200A1 (xx)
AT (1)	AT351520B (xx)
AU (1)	AU519521B2 (xx)
BE (1)	BE855297A (xx)
CA (1)	CA1099214A (xx)
CH (1)	CH625197A5 (xx)
CS (1)	CS251755B2 (xx)
DD (1)	DD130475A1 (xx)
DE (2)	DE2725247A1 (xx)
DK (1)	DK244277A (xx)
ES (1)	ES459425A1 (xx)
FI (1)	FI771765A (xx)
FR (2)	FR2416878A1 (xx)
GB (2)	GB1585832A (xx)
HU (1)	HU178205B (xx)
IT (1)	IT1074511B (xx)
NL (1)	NL7705934A (xx)
NO (1)	NO771926L (xx)
OA (1)	OA05678A (xx)
PL (1)	PL116550B1 (xx)
PT (1)	PT66619B (xx)
SE (2)	SE424723B (xx)
SU (1)	SU816396A3 (xx)
ZA (1)	ZA773345B (xx)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (xx) *	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 NL NL7705934A patent/NL7705934A/xx not_active Application Discontinuation
- 1977-05-31 PT PT66619A patent/PT66619B/pt unknown
- 1977-05-31 CS CS773586A patent/CS251755B2/cs 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 SE SE7706385A patent/SE424723B/xx unknown
- 1977-06-01 BE BE178116A patent/BE855297A/xx unknown
- 1977-06-01 CA CA279,610A patent/CA1099214A/en not_active Expired
- 1977-06-02 PL PL1977198600A patent/PL116550B1/pl unknown
- 1977-06-02 SU SU772494040A patent/SU816396A3/ru active
- 1977-06-02 ES ES459425A patent/ES459425A1/es not_active Expired
- 1977-06-02 DK DK244277A patent/DK244277A/da not_active Application Discontinuation
- 1977-06-02 JP JP6404177A patent/JPS52151156A/ja active Pending
- 1977-06-02 HU HU77CO341A patent/HU178205B/hu unknown
- 1977-06-02 FI FI771765A patent/FI771765A/fi not_active Application Discontinuation
- 1977-06-03 DD DD7700199291A patent/DD130475A1/xx unknown
- 1977-06-03 DE DE19772725247 patent/DE2725247A1/de active Granted
- 1977-06-03 AT AT394077A patent/AT351520B/de not_active IP Right Cessation
- 1977-06-03 IT IT24385/77A patent/IT1074511B/it active Protection Beyond IP Right Term
- 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 FR FR7717088A patent/FR2416878A1/fr not_active Withdrawn
- 1977-06-03 ZA ZA00773345A patent/ZA773345B/xx unknown
- 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
FR2479804A1 (fr)	1981-10-09
PL116550B1 (en)	1981-06-30
DK244277A (da)	1977-12-04
PT66619A (fr)	1977-06-01
AR214200A1 (es)	1979-05-15
GB1585832A (en)	1981-03-11
DD130475A1 (de)	1978-04-05
CH625197A5 (en)	1981-09-15
CA1099214A (en)	1981-04-14
SE8105687L (sv)	1981-09-25
DE2760410C2 (xx)	1990-08-16
SE7706385L (sv)	1977-12-04
AT351520B (de)	1979-07-25
GB1585831A (en)	1981-03-11
SU816396A3 (ru)	1981-03-23
DE2725247C2 (xx)	1987-02-12
ZA773345B (en)	1978-04-26
BE855297A (fr)	1977-10-03
ATA394077A (de)	1979-01-15
CS251755B2 (en)	1987-08-13
AU2573277A (en)	1978-12-07
JPS52151156A (en)	1977-12-15
DE2725247A1 (de)	1977-12-22
AU519521B2 (en)	1981-12-10
PL198600A1 (pl)	1978-06-19
IT1074511B (it)	1985-04-20
NL7705934A (nl)	1977-12-06
PT66619B (fr)	1978-10-27
FI771765A (xx)	1977-12-04
ES459425A1 (es)	1978-04-01
SE424723B (sv)	1982-08-09
HU178205B (en)	1982-03-28
OA05678A (fr)	1981-05-31
FR2416878A1 (fr)	1979-09-07

Publication	Publication Date	Title
Smolinsky	1961	The vapor phase pyrolysis of several subsituted azidobenzenes
US5384121A (en)	1995-01-24	Method for the extraction of sesquiterpene lactones
EP0173186B1 (de)	1988-12-21	Flavanonderivate
EP0025192B1 (de)	1983-05-11	Substituierte Oxirancarbonsäuren, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende Arzneimittel
EP0183169B1 (de)	1989-05-10	Halogen-hydroxy-flavone
NO771926L (no)	1977-12-06	Fremgangsm}te for fremstilling av verbenon, myrtenal og pinokarveol
DE3038966C2 (xx)	1989-12-28
Haller et al.	1942	The Constituents of Derris and Other Rotenone-bearing Plants.
JPS604801B2 (ja)	1985-02-06	抗皮膚真菌剤
US4190675A (en)	1980-02-26	Method for the preparation of verbenone, myrtenal and pinocarveol and their therapeutical use
CH668183A5 (de)	1988-12-15	Therapeutisches mittel zur behandlung von leberversagen.
Silvyana et al.	2022	Azadirachta indica Hexane Extract: Potent Antibacterial Activity Against Propionibacterium acne and Identification of its Chemicals Content
US3833610A (en)	1974-09-03	3,5-dioxo-2,3,5,6-tetrahydro-(4h)-pyrane and thiopyrane-4-carboxanilides
DE2847836C3 (de)	1981-12-17	Verfahren zur Gewinnung eines Terpengemisches mit antipsoriatischer Wirksamkeit
EP0343573B1 (de)	1993-08-04	Neue 1,2-dithiol-3-thion-S-oxid-Verbindungen enthaltende Arzneimittel
US4847246A (en)	1989-07-11	Antiviral compositions derived from fireflies and their methods of use
CA1129885A (en)	1982-08-17	Method for the preparation of verbenone, myrtenal and pinocarveol and their therapeutical use
BRIGGS et al.	1947	The essential oil of Dacrydium kirkii
BRIGGS et al.	1948	The essential oil of Phyllocladus trichomanoides
DE69908367T2 (de)	2004-03-25	Polyhydroxyalkylpyrazine derivate und deren herstellung und diese enthaltende arzneimittel
Barrowcliff	1907	LXXXI.—The constituents of the essential oil of American Pennyroyal. Occurrence of a dextro-menthone
DD144048A5 (de)	1980-09-24	Verfahren zur gewinnung natuerlicher terpene mit antipsoriatischer wirksamkeit
DD272085A5 (de)	1989-09-27	Verfahren zur herstellung des rechtsdrehenden isomeren von alpha-(4,5,6,7-tetrahydro-(3,2-c)-thieno-5-pyridyl)-(2-chlor-phenyl)-essigsaeure--methylester
HANAOKA et al.	1981	Clinical Pharmacological Study of Zomepirac Sodium (McN-2783) Phase I Study
DE3907512A1 (de)	1990-09-20	Neue aryloxy-alkylamine, deren herstellung und diese enthaltende arzneimittel