NO763587L - - Google Patents

Info

Publication number: NO763587L
Authority: NO; Norway
Prior art keywords: dihydrothebain; reaction; potassium; liquid ammonia; thebaine
Prior art date: 1975-10-22

Application number

NO763587A

Other languages

English (en)

Norwegian (no)

Inventor

D E Portlock

Original Assignee

Sharps Ass

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.)

1975-10-22

Filing date

1976-10-21

Publication date

1977-04-25

1976-10-21 Application filed by Sharps Ass filed Critical Sharps Ass

1977-04-25 Publication of NO763587L publication Critical patent/NO763587L/no

Links

QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 claims description 31
FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 claims description 26
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 24
229910052700 potassium Inorganic materials 0.000 claims description 24
239000011591 potassium Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 21
229930003945 thebaine Natural products 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 11
QKQQEIVDLRUZRP-UHFFFAOYSA-N northebaine Natural products COC1=CC=C2C(NCC3)CC4=CC=C(OC)C5=C4C23C1O5 QKQQEIVDLRUZRP-UHFFFAOYSA-N 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 21
239000000203 mixture Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
235000018185 Betula X alpestris Nutrition 0.000 description 3
235000018212 Betula X uliginosa Nutrition 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
-1 Lithium aluminum hydride Chemical compound 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
229930013053 morphinan alkaloid Natural products 0.000 description 3
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229940006199 ferric cation Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000007306 turnover Effects 0.000 description 2
XJZOLKDBHJPTAT-ATNYCFDYSA-N (4r,4ar,7ar,12bs)-7,9-dimethoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline Chemical compound C([C@@H](N(CC1)C)[C@@H]2CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 XJZOLKDBHJPTAT-ATNYCFDYSA-N 0.000 description 1
229910000608 Fe(NO3)3.9H2O Inorganic materials 0.000 description 1
OGGKNTCSNQEOIM-UHFFFAOYSA-N Neodihydrothebaine Natural products C1CN(C)CCC2=CC=C(OC)C(O)=C2C2=CC(OC)=CC=C21 OGGKNTCSNQEOIM-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000003517 fume Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000005337 ground glass Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000003887 narcotic antagonist Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/28—Morphinans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)

NO763587A 1975-10-22 1976-10-21 NO763587L (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/624,666 US4025521A (en)	1975-10-22	1975-10-22	Method of preparing β-dihydrothebaine

Publications (1)

Publication Number	Publication Date
NO763587L true NO763587L (ja)	1977-04-25

Family

ID=24502853

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO763587A NO763587L (ja)	1975-10-22	1976-10-21

Country Status (10)

Country	Link
US (2)	US4025521A (ja)
JP (1)	JPS5283376A (ja)
BE (1)	BE847512A (ja)
DE (1)	DE2647642A1 (ja)
DK (1)	DK477076A (ja)
FR (1)	FR2328709A1 (ja)
NL (1)	NL7611165A (ja)
NO (1)	NO763587L (ja)
SE (1)	SE7611722L (ja)
ZA (1)	ZA765917B (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5013759A (en) *	1985-06-10	1991-05-07	The Procter & Gamble Company	Compounds and compositions having anti-inflammatory and analgesic activity

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3085091A (en) *		1963-04-09		Novel pkocess fos elimination of
US3474101A (en) *	1960-09-05	1969-10-21	Reckitt & Sons Ltd	Thebaine and oripavine derivatives

1975
- 1975-10-22 US US05/624,666 patent/US4025521A/en not_active Expired - Lifetime
1976
- 1976-10-01 ZA ZA765917A patent/ZA765917B/xx unknown
- 1976-10-08 NL NL7611165A patent/NL7611165A/xx not_active Application Discontinuation
- 1976-10-20 FR FR7631577A patent/FR2328709A1/fr not_active Withdrawn
- 1976-10-21 JP JP12558476A patent/JPS5283376A/ja active Pending
- 1976-10-21 DE DE19762647642 patent/DE2647642A1/de active Pending
- 1976-10-21 SE SE7611722A patent/SE7611722L/xx unknown
- 1976-10-21 DK DK477076A patent/DK477076A/da unknown
- 1976-10-21 BE BE171694A patent/BE847512A/xx unknown
- 1976-10-21 NO NO763587A patent/NO763587L/no unknown
- 1976-12-23 US US05/757,460 patent/US4075132A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NL7611165A (nl)	1977-04-26
ZA765917B (en)	1977-09-28
JPS5283376A (en)	1977-07-12
SE7611722L (sv)	1977-04-23
FR2328709A1 (fr)	1977-05-20
US4075132A (en)	1978-02-21
DE2647642A1 (de)	1977-05-12
BE847512A (fr)	1977-02-14
DK477076A (da)	1977-04-23
US4025521A (en)	1977-05-24

Publication	Publication Date	Title
Russell et al.	1966	Methylation of Aromatic Hydrocarbons by Dimethyl Sulfoxide in the Presence of Base1
Cava et al.	1959	Condensed cyclobutane aromatic compounds. VIII. The mechanism of formation of 1, 2-dibromobenzocyclobutene; a new Diels-Alder synthesis
Kabalka et al.	1975	New mild conversion of ketones to the corresponding methylene derivatives
Paquette et al.	1978	Domino Diels-Alder reactions. 6. Domino Diels-Alder cycloadditions to 9, 10-dihydrofulvalene and 11, 12-dihydrosesquifulvalene. A synthetic tool for the elaboration of polycondensed alicyclic systems
Paquette et al.	1988	Dodecahedrane. Improved synthetic access to, and monofunctionalization of, the spherical hydrocarbon. Spectral properties of the derivatives
Muratake et al.	2002	Synthesis of a compound having the essential structural unit for the hetisine-type of aconite alkaloids
Corey et al.	1987	Two-step synthesis of furans by Mn (III)-promoted annulation of enol ethers
Wong et al.	1968	Synthesis of optically active deacetyl anisomycin
NO763587L (ja)	1977-04-25
Katritzky et al.	1971	1, 3-Dipolar character of six-membered aromatic rings. Part I. 1-Methyl-3-oxidopyridinium
Wada et al.	1977	SYNTHESIS OF α, β-UNSATURATED ALDEHYDES BY MEANS OF 3-METHOXY-1-PHENYLTHIO-1-PROPENE
DePuy et al.	1964	Cyclopentadienone Ethylene Ketal1
Heaney et al.	1968	Aryne chemistry. Part XII. Some cycloaddition reactions of tetrachlorobenzyne
Greenwood et al.	1968	A cyclisation of humulene
Byers et al.	1985	Improved preparation and new reactions of β-(1-phenylthio) cyclopropyl enones
Lassak et al.	1973	The two C 8 epimers of 3β-Acetoxylanost-9 (11)-en-7-one
Gream et al.	1974	The camphenehydro (methylcamphenilyl) and isobornyl (bornyl) cations. III. Oxidative decarboxylation of carboxylic acids with lead tetraacetate
Eisch et al.	1971	Nonpyridinoid aza-aromatic systems. II. Reactions of the anions of benzo [b][1] pyrindine and its 1, 2-dihydro derivative
Kametani et al.	1974	A simple route to spiro [indene-2, 1′-isoquinoline] s, a spiro [indene-2, 1′-β-carboline], and hexadehydroyohimbane
Karim et al.	1974	Bridgehead reactivity in protoadamantane. Ionic bromination
CN114751814B (zh)	2023-07-04	一种倍半萜类化合物的制备方法
Woźaniak et al.	1978	On the synthesis and animation of 5‐chloro‐and 5‐bromo‐1, 7‐naphthyridine
Jawdosiuk et al.	1983	Synthesis of 3-Noradamantamine
Dehmlow et al.	1992	Dioxa-cage and bridged compounds as possible precursors for tricyclo [5.5. 0.04, 10] dodeca-2, 5, 8, 11-tetraene
Allan et al.	1970	The decomposition of Bicyclo [3, 3, 1] nonan-9-ylidene