GB1146271A - Novel thebaine derivatives - Google Patents
Novel thebaine derivativesInfo
- Publication number
- GB1146271A GB1146271A GB2193/66A GB219366A GB1146271A GB 1146271 A GB1146271 A GB 1146271A GB 2193/66 A GB2193/66 A GB 2193/66A GB 219366 A GB219366 A GB 219366A GB 1146271 A GB1146271 A GB 1146271A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- carbons
- aryloxy
- aryl
- alicyclic
- Prior art date
- 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
Links
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical class 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 title abstract 3
- 125000004104 aryloxy group Chemical group 0.000 abstract 6
- 125000002723 alicyclic group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- VQJMAIZOEPPELO-KYGIZGOZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-(2-hydroxy-5-methylhexan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol hydrochloride Chemical compound Cl.CO[C@]12CC[C@@]3(C[C@@H]1C(C)(O)CCC(C)C)[C@H]1Cc4ccc(O)c5O[C@@H]2[C@]3(CCN1CC1CC1)c45 VQJMAIZOEPPELO-KYGIZGOZSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 238000010306 acid treatment Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- -1 nicotinoyl Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007920 subcutaneous administration Methods 0.000 abstract 1
- 229930003945 thebaine Natural products 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,146,271. Thebaine derivatives. RECKITT & SONS Ltd. 17 Jan., 1967 [17 Jan., 1966; 22 Aug., 1966], Nos. 2193/66 and 31646/66. Heading C26. Novel thebaine-type compounds (and acid salts thereof) of the general formulae, in which Q is -CN, -COOR<SP>4</SP> or -COR<SP>3</SP>; Y is -CH=CH- or, when Q is -COOR<SP>4</SP> or -COR<SP>3</SP> Y is -CH 2 -CH 2 -; R<SP>1</SP> is H, Me, Et, Pr, the group C n H 2n+1 CO- (n is 1, 2 or 3), benzoyl or nicotinoyl; R<SP>2</SP> is H, acetonyl, phenacyl or an alkyl, alkenyl or alkynyl group which groups may contain up to 8 carbons and may be substituted on carbons numbered 1 to 5 (the carbon atom numbered 1 being adjacent to the nitrogen atom) by alicyclic of 4, 5 or 6 carbons, aryl substituted aryl, alkoxy, aryloxy, substituted aryloxy, heterocyclic or substituted amino groups; provided that when Q is -CN, R<SP>2</SP> is methyl; R<SP>3</SP> is an alicyclic group of 3 to 7 carbons, or an alkyl, alkenyl or alkynyl group which groups contain up to 8 carbons and may be substituted on carbons numbered 1 to 4 (the carbon atom numbered 1 being adjacent to the carbon atom bearing the oxygen atom) by an alicyclic, aryl, substituted aryl, alkoxy, aryloxy, substituted aryloxy or heterocyclic group; R<SP>4</SP> is an alicyclic group of from 5 to 7 carbons or an alkyl, alkenyl or alkynyl group containing up to 8 carbons which may be substituted on one of their carbons by an alicyclic, aryl, substituted aryl, alkoxy, aryloxy, substituted aryloxy, heterocyclic or substituted amino group provided that carbon atom numbered 1 attached to the hydroxylic oxygen does not bear a double or triple bond, are prepared by reacting the appropriate ethano or etheno thebaine (substituted at the 7-position with either -CN, -COR<SP>3</SP> or -COOR<SP>4</SP>) with a basic catalyst (this yields compounds of Formula II above) followed by acidic hydrolysis with or without alkylation or acylation to afford R<SP>1</SP>=alkyl or acyl, or the reaction is also operable using catalysts such as BBr 3 or BF 3 . Certain of the above ketones may also be derived from the above nitriles using Grignard reagents R<SP>3</SP>MgX or lithium alkyls followed by acid treatment. Ethano compounds (Y= -CH 2 -CH 2 -) may also be obtained from the corresponding etheno compounds (Y = -CH= CH-) by reduction. The ketal, 5,14 - (1 - acetylethano) - thebainone dimethylketal is also described. Pharmaceutical compositions having power to affect the central nervous system contain as the active ingredient the above novel compounds in association with a carrier and are administered by the subcutaneous or intravenous routes.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2193/66A GB1146271A (en) | 1966-01-17 | 1966-01-17 | Novel thebaine derivatives |
| LU52825D LU52825A1 (en) | 1966-01-17 | 1967-01-16 | |
| ES0335706A ES335706A1 (en) | 1966-01-17 | 1967-01-16 | Procedure for the preparation of derivatives of the theory (Machine-translation by Google Translate, not legally binding) |
| NL6700660A NL6700660A (en) | 1966-01-17 | 1967-01-16 | |
| BE692663D BE692663A (en) | 1966-01-17 | 1967-01-16 | |
| FR91482A FR7301M (en) | 1966-01-17 | 1967-01-17 | |
| GR670136358A GR36358B (en) | 1966-01-17 | 1967-01-17 | METHOD OF MANUFACTURING NEW PRODUCERS OF THIVAIN. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2193/66A GB1146271A (en) | 1966-01-17 | 1966-01-17 | Novel thebaine derivatives |
| GB3164666 | 1966-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1146271A true GB1146271A (en) | 1969-03-26 |
Family
ID=26237352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2193/66A Expired GB1146271A (en) | 1966-01-17 | 1966-01-17 | Novel thebaine derivatives |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE692663A (en) |
| ES (1) | ES335706A1 (en) |
| FR (1) | FR7301M (en) |
| GB (1) | GB1146271A (en) |
| GR (1) | GR36358B (en) |
| LU (1) | LU52825A1 (en) |
| NL (1) | NL6700660A (en) |
-
1966
- 1966-01-17 GB GB2193/66A patent/GB1146271A/en not_active Expired
-
1967
- 1967-01-16 BE BE692663D patent/BE692663A/xx unknown
- 1967-01-16 NL NL6700660A patent/NL6700660A/xx unknown
- 1967-01-16 ES ES0335706A patent/ES335706A1/en not_active Expired
- 1967-01-16 LU LU52825D patent/LU52825A1/xx unknown
- 1967-01-17 FR FR91482A patent/FR7301M/fr not_active Expired
- 1967-01-17 GR GR670136358A patent/GR36358B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU52825A1 (en) | 1967-03-16 |
| NL6700660A (en) | 1967-07-18 |
| BE692663A (en) | 1967-07-03 |
| GR36358B (en) | 1969-02-03 |
| FR7301M (en) | 1969-09-29 |
| ES335706A1 (en) | 1967-12-16 |
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