CA1129885A - Methode de preparation de la verbenone, du myrtenal et du pinocarbeol et utilisation therapeutique - Google Patents

Methode de preparation de la verbenone, du myrtenal et du pinocarbeol et utilisation therapeutique

Info

Publication number: CA1129885A
Authority: CA; Canada
Prior art keywords: verbenone; myrtenal; compounds; fraction; pinocarveol
Prior art date: 1976-06-03
Legal status (The legal status 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 status listed.): Expired

Application number

CA369,574A

Other languages

English (en)

Inventor

Davide Vegezzi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

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

1981-01-28

Publication date

1982-08-17

1976-06-03 Priority claimed from CH704276A external-priority patent/CH625197A5/it

1981-01-28 Application filed by Individual filed Critical Individual

1981-01-28 Priority to CA369,574A priority Critical patent/CA1129885A/fr

1982-08-17 Application granted granted Critical

1982-08-17 Publication of CA1129885A publication Critical patent/CA1129885A/fr

Status Expired legal-status Critical Current

Links

DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-N 0.000 title claims abstract description 30
DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 title claims abstract description 28
DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 title claims abstract description 26
KMRMUZKLFIEVAO-RKDXNWHRSA-N Myrtenal Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2C=O KMRMUZKLFIEVAO-RKDXNWHRSA-N 0.000 title claims abstract description 25
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 abstract description 24
238000000034 method Methods 0.000 title claims description 15
229930006721 pinocarveol Natural products 0.000 title abstract description 18
LCYXQUJDODZYIJ-UHFFFAOYSA-N pinocarveol Chemical compound C1C2C(C)(C)C1CC(O)C2=C LCYXQUJDODZYIJ-UHFFFAOYSA-N 0.000 title abstract description 17
238000002360 preparation method Methods 0.000 title description 9
230000001225 therapeutic effect Effects 0.000 title description 7
239000000203 mixture Substances 0.000 claims abstract description 23
150000003505 terpenes Chemical class 0.000 claims abstract description 15
235000007586 terpenes Nutrition 0.000 claims abstract description 14
230000003647 oxidation Effects 0.000 claims abstract description 8
238000007254 oxidation reaction Methods 0.000 claims abstract description 8
230000001590 oxidative effect Effects 0.000 claims abstract description 6
150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 3
238000004508 fractional distillation Methods 0.000 claims abstract description 3
238000000926 separation method Methods 0.000 claims abstract 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 6
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 5
229910052753 mercury Inorganic materials 0.000 claims description 5
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 4
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 3
150000001298 alcohols Chemical class 0.000 claims description 3
MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 3
229940117975 chromium trioxide Drugs 0.000 claims description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 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
LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 28
201000010099 disease Diseases 0.000 abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
239000011369 resultant mixture Substances 0.000 abstract 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 40
229960000230 sobrerol Drugs 0.000 description 23
OMDMTHRBGUBUCO-UHFFFAOYSA-N trans-sobrerol Natural products CC1=CCC(C(C)(C)O)CC1O OMDMTHRBGUBUCO-UHFFFAOYSA-N 0.000 description 22
238000000338 in vitro Methods 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
206010030113 Oedema Diseases 0.000 description 7
241000283973 Oryctolagus cuniculus Species 0.000 description 7
241000700159 Rattus Species 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
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 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000002776 aggregation Effects 0.000 description 6
238000004220 aggregation Methods 0.000 description 6
230000003182 bronchodilatating effect Effects 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000000243 solution Substances 0.000 description 6
210000003437 trachea Anatomy 0.000 description 6
WONIGEXYPVIKFS-UHFFFAOYSA-N Verbenol Chemical class CC1=CC(O)C2C(C)(C)C1C2 WONIGEXYPVIKFS-UHFFFAOYSA-N 0.000 description 5
210000001772 blood platelet Anatomy 0.000 description 5
239000000126 substance Substances 0.000 description 5
OMDMTHRBGUBUCO-BDAKNGLRSA-N (1s,5r)-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-BDAKNGLRSA-N 0.000 description 4
241000700199 Cavia porcellus Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
230000002744 anti-aggregatory effect Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000011651 chromium Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
210000003205 muscle Anatomy 0.000 description 4
238000010992 reflux Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
RXBQNMWIQKOSCS-RKDXNWHRSA-N Myrtenol Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2CO RXBQNMWIQKOSCS-RKDXNWHRSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
235000010418 carrageenan Nutrition 0.000 description 3
229920001525 carrageenan Polymers 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000012071 phase Substances 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
IRZWAJHUWGZMMT-UHFFFAOYSA-N Chrysanthenol Natural products CC1=CCC2C(C)(C)C1C2O IRZWAJHUWGZMMT-UHFFFAOYSA-N 0.000 description 2
241000588722 Escherichia Species 0.000 description 2
206010018910 Haemolysis Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
208000005392 Spasm Diseases 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000001476 alcoholic effect Effects 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
239000008346 aqueous phase Substances 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000008588 hemolysis Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 2
230000010412 perfusion Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
208000008423 pleurisy Diseases 0.000 description 2
239000000047 product Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QJVOZXGJOGJKPT-IGHBBLSQSA-N (1r,2r,5s,11ar)-2-(prop-2-en-1-yl)-1,2,3,4,5,6,11,11a-octahydro-10h-1,5-methanopyrido[1,2-a][1,5]diazocin-10-one Chemical compound C([C@@H]12)C(=O)C=CN1C[C@@H]1CN[C@H](CC=C)[C@H]2C1 QJVOZXGJOGJKPT-IGHBBLSQSA-N 0.000 description 1
AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-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
XSFWDHONRBZVEJ-UHFFFAOYSA-N 7-[3-[[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino]propyl]-1,3-dimethylpurine-2,6-dione;hydron;chloride Chemical compound Cl.C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 XSFWDHONRBZVEJ-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
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
241000588724 Escherichia coli Species 0.000 description 1
241000766653 Macrocephalon maleo Species 0.000 description 1
244000062730 Melissa officinalis Species 0.000 description 1
235000010654 Melissa officinalis Nutrition 0.000 description 1
101100490488 Mus musculus Add3 gene Proteins 0.000 description 1
240000005125 Myrtus communis Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
244000042295 Vigna mungo Species 0.000 description 1
235000010716 Vigna mungo Nutrition 0.000 description 1
229940022682 acetone Drugs 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000013543 active substance Substances 0.000 description 1
QJVOZXGJOGJKPT-UHFFFAOYSA-N albine Natural products C12CC(=O)C=CN2CC2CNC(CC=C)C1C2 QJVOZXGJOGJKPT-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
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 1
229930006723 alpha-pinene oxide Natural products 0.000 description 1
125000003425 alpha-pinene oxide group Chemical group 0.000 description 1
150000007854 aminals Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 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
229960004544 cortisone Drugs 0.000 description 1
229910003460 diamond Inorganic materials 0.000 description 1
239000010432 diamond Substances 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000727 fraction Substances 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
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000865 liniment Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
108700025647 major vault Proteins 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
210000005090 tracheal smooth muscle Anatomy 0.000 description 1
230000017105 transposition Effects 0.000 description 1
CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA369,574A 1976-06-03 1981-01-28 Methode de preparation de la verbenone, du myrtenal et du pinocarbeol et utilisation therapeutique Expired CA1129885A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA369,574A CA1129885A (fr)	1976-06-03	1981-01-28	Methode de preparation de la verbenone, du myrtenal et du pinocarbeol et utilisation therapeutique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH7042/76		1976-06-03
CH704276A CH625197A5 (en)	1976-06-03	1976-06-03	Process for preparing verbenone, myrtenal and pinocarveol
CA279,610A CA1099214A (fr)	1976-06-03	1977-06-01	Methode de preparation de la verbenone, du myrtenal et du pinocarveol et usages therapeutiques
CA369,574A CA1129885A (fr)	1976-06-03	1981-01-28	Methode de preparation de la verbenone, du myrtenal et du pinocarbeol et utilisation therapeutique

Publications (1)

Publication Number	Publication Date
CA1129885A true CA1129885A (fr)	1982-08-17

Family

ID=27165101

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA369,574A Expired CA1129885A (fr)	1976-06-03	1981-01-28	Methode de preparation de la verbenone, du myrtenal et du pinocarbeol et utilisation therapeutique

Country Status (1)

Country	Link
CA (1)	CA1129885A (fr)

1981
- 1981-01-28 CA CA369,574A patent/CA1129885A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-08-17	MKEX	Expiry

Publication	Publication Date	Title
US4400394A (en)	1983-08-23	Benzylidene derivatives
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US4584321A (en)	1986-04-22	3-(3-Hydroxybutoxy)-1-butanol in pharmaceutical compositions
CA1302417C (fr)	1992-06-02	1-naphtols substitues en 2 utilises comme inhibiteurs de la 5-lipogenase
US4375479A (en)	1983-03-01	Indanyl derivatives and use
CA1121269A (fr)	1982-04-06	5-methoxy-psoralen, nouveau medicament et procede de synthese
EP0378456B1 (fr)	1993-09-15	Dérivés de tétraline
Work et al.	1963	Acylations of Dilithio β-Diketones with Aliphatic Esters [ILL] Form 1, 3, 5-Triketones. Cyclizations to 4-Pyrones and 4-Pyridones
KR860000320B1 (ko)	1986-04-09	N-치환 아지리딘-2-카르복실산 유도체의 제조방법
FI59250C (fi)	1981-07-10	Foerfarande foer framstaellning av cancerostatiskt och immunstimulerande verkande 4-imino-1,3-diazabicyklo-(3,1,0)-hexan-2-on
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
GB1585831A (en)	1981-03-11	Process for the preparation of verbenone and myrtenal and therapeutical uses thereof
Bender et al.	1975	Synthesis and biological properties of some novel heterocyclic homoprostanoids
US4285935A (en)	1981-08-25	Dehydropeptide compounds, their production and their medical use
CH643838A5 (de)	1984-06-29	15-epi-prostacyclinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate.
ES2214270T3 (es)	2004-09-16	Derivados de (-)-verbenona.
Ngo et al.	1999	Autoxidation of 4-amorphen-11-ol and the biogenesis of nor-and seco-amorphane sesquiterpenes from Fabiana imbricata
JPS5935387B2 (ja)	1984-08-28	３−アミノ−２−ヒドロキシプロパンのジ−置換フエノ−ルエ−テル類、その製法ならびに医薬用途
US5405868A (en)	1995-04-11	5-methoxy-psoralen as new medicament and process for the synthesis thereof
US4075336A (en)	1978-02-21	Thiazines and method
KR940009791B1 (ko)	1994-10-17	퀴누클리딘 유도체의 제조방법
US4092350A (en)	1978-05-30	Alkanoic acid, process for its production and method of use thereof
US3826839A (en)	1974-07-30	Anti-arthritic compositions comprising ester derivatives of pulvinic acid and methods of producing anti-arthritic activity
US3682963A (en)	1972-08-08	Dimethylbenzodithian-2-oxide