DE2441533C2 - 6-Desoxy-6-azido-14-hydroxy-7,8-dihydro-isomorphin, dessen Herstellung und diese Verbindung enthaltende Arzneimittel - Google Patents
6-Desoxy-6-azido-14-hydroxy-7,8-dihydro-isomorphin, dessen Herstellung und diese Verbindung enthaltende ArzneimittelInfo
- Publication number
- DE2441533C2 DE2441533C2 DE2441533A DE2441533A DE2441533C2 DE 2441533 C2 DE2441533 C2 DE 2441533C2 DE 2441533 A DE2441533 A DE 2441533A DE 2441533 A DE2441533 A DE 2441533A DE 2441533 C2 DE2441533 C2 DE 2441533C2
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- azido
- isomorphine
- deoxy
- dihydro
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims 4
- 239000003814 drug Substances 0.000 title claims 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 claims description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 230000000202 analgesic effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- AABLHGPVOULICI-BRJGLHKUSA-N hydromorphinol Chemical compound O([C@H]1[C@H](CC[C@]23O)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O AABLHGPVOULICI-BRJGLHKUSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 231100001274 therapeutic index Toxicity 0.000 claims description 3
- 229940035676 analgesics Drugs 0.000 claims description 2
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 239000002585 base Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- BQJCRHHNABKAKU-NOSXKOESSA-N (4r,4ar,7r,7ar,12bs)-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol 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-NOSXKOESSA-N 0.000 claims 1
- 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 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000021736 acetylation Effects 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- -1 alkyl sulfonic acid Chemical compound 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000004675 formic acid derivatives Chemical class 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 230000003533 narcotic effect Effects 0.000 claims 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003873 salicylate salts Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 4
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 3
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229960001797 methadone Drugs 0.000 description 3
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 3
- 229960005301 pentazocine Drugs 0.000 description 3
- 229960000482 pethidine Drugs 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 230000009191 jumping Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 2
- 229960004127 naloxone Drugs 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010010219 Compulsions Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241001416488 Dipodidae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 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
-
- 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:
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUAA750A HU169430B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-09-04 | 1973-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2441533A1 DE2441533A1 (de) | 1975-03-20 |
| DE2441533C2 true DE2441533C2 (de) | 1984-02-09 |
Family
ID=10992987
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2462592A Expired DE2462592C2 (de) | 1973-09-04 | 1974-08-30 | 3-(0-Äthyl)-6-desoxy-6-azido-7,8-dihydro-isomorphin, dessen Herstellung und diese Verbindung enthaltende Arzneimittel |
| DE2441533A Expired DE2441533C2 (de) | 1973-09-04 | 1974-08-30 | 6-Desoxy-6-azido-14-hydroxy-7,8-dihydro-isomorphin, dessen Herstellung und diese Verbindung enthaltende Arzneimittel |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2462592A Expired DE2462592C2 (de) | 1973-09-04 | 1974-08-30 | 3-(0-Äthyl)-6-desoxy-6-azido-7,8-dihydro-isomorphin, dessen Herstellung und diese Verbindung enthaltende Arzneimittel |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5549600Y2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-12-25 | 1980-11-18 | ||
| CA2143864C (en) * | 1993-07-23 | 2006-01-24 | Hiroshi Nagase | Morphinan derivatives and pharmaceutical use thereof |
-
1973
- 1973-09-04 HU HUAA750A patent/HU169430B/hu not_active IP Right Cessation
-
1974
- 1974-08-29 AR AR255368A patent/AR219471A1/es active
- 1974-08-30 DE DE2462592A patent/DE2462592C2/de not_active Expired
- 1974-08-30 DE DE2441533A patent/DE2441533C2/de not_active Expired
- 1974-08-30 SE SE7411053A patent/SE418501B/xx unknown
- 1974-08-31 ES ES429708A patent/ES429708A1/es not_active Expired
- 1974-09-02 FR FR7429824A patent/FR2242102B1/fr not_active Expired
- 1974-09-02 NL NL7411614A patent/NL7411614A/xx not_active Application Discontinuation
- 1974-09-03 SU SU742058446A patent/SU615859A3/ru active
- 1974-09-03 CH CH1196174A patent/CH605957A5/xx not_active IP Right Cessation
- 1974-09-03 DK DK465974A patent/DK143851C/da not_active IP Right Cessation
- 1974-09-03 CA CA208,380A patent/CA1021776A/en not_active Expired
- 1974-09-04 BE BE148210A patent/BE819545A/xx not_active IP Right Cessation
- 1974-09-04 JP JP49101007A patent/JPS5050400A/ja active Pending
- 1974-09-04 GB GB38681/74A patent/GB1484988A/en not_active Expired
- 1974-09-04 FI FI2582/74A patent/FI56838C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| SE418501B (sv) | 1981-06-09 |
| DK143851B (da) | 1981-10-19 |
| SU615859A3 (ru) | 1978-07-15 |
| SE7411053L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-05 |
| GB1484988A (en) | 1977-09-08 |
| FR2242102B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-11-04 |
| FI56838C (fi) | 1980-04-10 |
| DK465974A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-05 |
| CH605957A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-13 |
| HU169430B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-28 |
| FI258274A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-05 |
| CA1021776A (en) | 1977-11-29 |
| NL7411614A (nl) | 1975-03-06 |
| DK143851C (da) | 1982-04-05 |
| FR2242102A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-28 |
| ES429708A1 (es) | 1977-06-16 |
| BE819545A (fr) | 1974-12-31 |
| DE2462592C2 (de) | 1984-03-01 |
| JPS5050400A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-06 |
| AR219471A1 (es) | 1980-08-29 |
| DE2441533A1 (de) | 1975-03-20 |
| FI56838B (fi) | 1979-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| D2 | Grant after examination | ||
| AH | Division in |
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