GB919311A - Derivatives of 14-hydroxycodeine and their preparation - Google Patents
Derivatives of 14-hydroxycodeine and their preparationInfo
- Publication number
- GB919311A GB919311A GB3460458A GB3460458A GB919311A GB 919311 A GB919311 A GB 919311A GB 3460458 A GB3460458 A GB 3460458A GB 3460458 A GB3460458 A GB 3460458A GB 919311 A GB919311 A GB 919311A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acyl
- derivatives
- carboxylic
- preparation
- general formula
- 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
- 238000002360 preparation method Methods 0.000 title abstract 5
- YPZPXTZKBNWUTF-QMVVXIJUSA-N (4r,4as,7s,7ar,12bs)-9-methoxy-3-methyl-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol Chemical class O[C@H]([C@@H]1O2)C=C[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C YPZPXTZKBNWUTF-QMVVXIJUSA-N 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- 125000002252 acyl group Chemical group 0.000 abstract 9
- 125000001589 carboacyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 239000012279 sodium borohydride Substances 0.000 abstract 3
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical class C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- YYCRAERBSFHMPL-XFKAJCMBSA-N (4r,4as,7ar,12bs)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O=C([C@@H]1O2)C=C[C@@]3(O)[C@]4([H])N(C)CC[C@]13C1=C2C(OC)=CC=C1C4 YYCRAERBSFHMPL-XFKAJCMBSA-N 0.000 abstract 1
- YPZPXTZKBNWUTF-UHFFFAOYSA-N 14beta-Hydroxy-codein Natural products O1C2C(O)C=CC3(O)C4CC5=CC=C(OC)C1=C5C23CCN4C YPZPXTZKBNWUTF-UHFFFAOYSA-N 0.000 abstract 1
- YYCRAERBSFHMPL-UHFFFAOYSA-N 14beta-Hydroxycodeinone Natural products O1C2C(=O)C=CC3(O)C4CC5=CC=C(OC)C1=C5C23CCN4C YYCRAERBSFHMPL-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- RBOXVHNMENFORY-UHFFFAOYSA-N 9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol Chemical class C1C(N(CCC234)C)C2CCC(O)C3OC2=C4C1=CC=C2OC RBOXVHNMENFORY-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- OROGSEYTTFOCAN-KEMUOJQUSA-N isocodeine Chemical class C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-KEMUOJQUSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- -1 p-toluenesulphonyl Chemical group 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises: (a) codeine derivatives of the general formula <FORM:0919311/IV (b)/1> wherein R10 and R11 each represent a hydrogen atom or a carboxylic acyl group and may be the same or different), and the preparation thereof by (i) (when R10 = R11 = H) reducing 14-hydroxycodeinone with sodium borohydride, lithium aluminium hydride or aluminium isopropoxide, (ii) when R10 and R11 are identical acyl groups) acylating 14-hydroxycodeine with a carboxylic acid anhydride or halide, (iii) (when R10 = acyl and R11 = H) reducing a 14-acyloxycodeinone with sodium borohydride, (iv) (when R10 and R11 are identical or different carboxylic acyl groups) acylating a 14-acyloxycodeine with a carboxylic acid anhydride or halide and (v) when R10 = H and R11 = acyl) heating a compound in which R10 and R11 are both acyl with methanol; (b) 7,8 - dihydrocodeine derivatives of the general formula <FORM:0919311/IV (b)/2> (wherein R12 represents a carboxylic acyl group), and the preparation thereof by catalytically hydrogenating a p 14-acyloxycodeine in the presence of platinum; (c) codeine derivatives of the general formula <FORM:0919311/IV (b)/3> wherein R13 represents a hydrogen atom or a carboxylic acyl group and R14 a p-toluenesulphonyl group) and their 7,8-dihydro derivatives, and the preparation thereof by (i) reacting the corresponding 6-hydroxy compounds (III, R14 = H) with p-toluenesulphonyl chloride in the presence of pyridine, or (ii) (when R13 = H) heating a compound in which R13 = acyl with methanol; and (d) isocodeine derivatives of the general formula <FORM:0919311/IV (b)/4> (wherein R15 and R16 each represent a hydrogen atom or a carboxylic acyl group and may be the same or different), and their 7,8-dihydro derivatives other than those in which R15 = R16 = H or acetyl, and the preparation thereof by (i) (when R15 and R16 are both acyl) heating a compound in which one or both of R15 and R16 is or are hydrogen with a carboxylic acid anhydride or halide, (ii) (when R15 = H and R16 = acyl) heating a compound in which R15 and R16 are both acyl with methanol, and (iii) (for the 7,8-dihydro compounds in which R15 = acyl and R16 = H) reducing a 14-acyloxydihydrocodeinone with sodium borohydride. The products are useful as analgesic agents, particularly in the form of their water-soluble non-toxic acid addition salts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3460458A GB919311A (en) | 1958-10-29 | 1958-10-29 | Derivatives of 14-hydroxycodeine and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3460458A GB919311A (en) | 1958-10-29 | 1958-10-29 | Derivatives of 14-hydroxycodeine and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB919311A true GB919311A (en) | 1963-02-20 |
Family
ID=10367716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3460458A Expired GB919311A (en) | 1958-10-29 | 1958-10-29 | Derivatives of 14-hydroxycodeine and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB919311A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0577847A4 (en) * | 1992-01-23 | 1994-12-07 | Toray Industries | MORPHINAN DERIVATIVES AND MEDICAL USE. |
| EP0663401A4 (en) * | 1993-07-23 | 1996-06-26 | Toray Industries | Morphinan derivative and medicinal use. |
-
1958
- 1958-10-29 GB GB3460458A patent/GB919311A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0577847A4 (en) * | 1992-01-23 | 1994-12-07 | Toray Industries | MORPHINAN DERIVATIVES AND MEDICAL USE. |
| EP0846694A1 (en) * | 1992-01-23 | 1998-06-10 | Toray Industries, Inc. | Morphinan derivative and its pharmaceutical applications |
| US6277859B1 (en) | 1992-01-23 | 2001-08-21 | Toray Industries, Inc. | Morphinan derivative and its pharmaceutical applications |
| US6323212B1 (en) | 1992-01-23 | 2001-11-27 | Toray Industries, Inc. | Morphinan derivative and its pharmaceutical applications |
| EP0663401A4 (en) * | 1993-07-23 | 1996-06-26 | Toray Industries | Morphinan derivative and medicinal use. |
| US6177438B1 (en) | 1993-07-23 | 2001-01-23 | Toray Industries, Inc. | Morphinan derivatives and pharmaceutical use thereof |
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