GB1330581A - Production of codeine and intermediate compounds therein - Google Patents
Production of codeine and intermediate compounds thereinInfo
- Publication number
- GB1330581A GB1330581A GB1925571A GB1925571A GB1330581A GB 1330581 A GB1330581 A GB 1330581A GB 1925571 A GB1925571 A GB 1925571A GB 1925571 A GB1925571 A GB 1925571A GB 1330581 A GB1330581 A GB 1330581A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- vii
- benzenesulphonyl
- mesyl
- tosyl
- 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
- 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 title abstract 9
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 229960004126 codeine Drugs 0.000 title abstract 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 title abstract 4
- -1 aralkoxycarbonyl Chemical group 0.000 abstract 10
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical group N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 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
- C07D221/28—Morphinans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- 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:
- C07D489/02—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 oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE90137 | 1970-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1330581A true GB1330581A (en) | 1973-09-19 |
Family
ID=3841365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1925571A Expired GB1330581A (en) | 1970-06-09 | 1971-06-07 | Production of codeine and intermediate compounds therein |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA939665A (enrdf_load_stackoverflow) |
| CH (1) | CH560218A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2128467A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2096107A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1330581A (enrdf_load_stackoverflow) |
| NL (1) | NL7107921A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982000144A1 (en) * | 1980-07-03 | 1982-01-21 | Us Commerce | A short total synthesis of dihydrothebainone,dihydrocodeinone,and nordihydrocodeinone |
| US4368326A (en) | 1980-07-03 | 1983-01-11 | Rice Kenner C | Short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydroccodeinone |
| US4521601A (en) * | 1981-05-20 | 1985-06-04 | The United States Of America As Represented By The Department Of Health & Human Services | Practical total synthesis unnatural enantiomers of opium-derived morphinans |
-
1971
- 1971-06-07 GB GB1925571A patent/GB1330581A/en not_active Expired
- 1971-06-08 DE DE19712128467 patent/DE2128467A1/de active Pending
- 1971-06-08 CA CA115,150A patent/CA939665A/en not_active Expired
- 1971-06-09 FR FR7120860A patent/FR2096107A5/fr not_active Expired
- 1971-06-09 NL NL7107921A patent/NL7107921A/xx unknown
- 1971-06-09 CH CH837571A patent/CH560218A5/de not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982000144A1 (en) * | 1980-07-03 | 1982-01-21 | Us Commerce | A short total synthesis of dihydrothebainone,dihydrocodeinone,and nordihydrocodeinone |
| EP0043706A3 (en) * | 1980-07-03 | 1982-03-24 | THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce | A short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydrocodeinone |
| US4368326A (en) | 1980-07-03 | 1983-01-11 | Rice Kenner C | Short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydroccodeinone |
| US4521601A (en) * | 1981-05-20 | 1985-06-04 | The United States Of America As Represented By The Department Of Health & Human Services | Practical total synthesis unnatural enantiomers of opium-derived morphinans |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2096107A5 (enrdf_load_stackoverflow) | 1972-02-11 |
| NL7107921A (enrdf_load_stackoverflow) | 1971-12-13 |
| CA939665A (en) | 1974-01-08 |
| DE2128467A1 (de) | 1971-12-30 |
| CH560218A5 (enrdf_load_stackoverflow) | 1975-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |