DE2257715A1 - 6-methylen-6-desoxydihydromorphinund codeinderivate - Google Patents
6-methylen-6-desoxydihydromorphinund codeinderivateInfo
- Publication number
- DE2257715A1 DE2257715A1 DE2257715A DE2257715A DE2257715A1 DE 2257715 A1 DE2257715 A1 DE 2257715A1 DE 2257715 A DE2257715 A DE 2257715A DE 2257715 A DE2257715 A DE 2257715A DE 2257715 A1 DE2257715 A1 DE 2257715A1
- Authority
- DE
- Germany
- Prior art keywords
- methylene
- deoxy
- derivatives
- derivative
- allyl
- 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.)
- Granted
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 claims description 5
- LBCZKDPFDXFDTN-GGNLRSJOSA-N 6-methylenedihydrodesoxymorphine Chemical compound O([C@H]1C(CC[C@H]23)=C)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O LBCZKDPFDXFDTN-GGNLRSJOSA-N 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- HLMSIZPQBSYUNL-IPOQPSJVSA-N Noroxymorphone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4 HLMSIZPQBSYUNL-IPOQPSJVSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- -1 phosphomethylene Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 2
- SWIRXSKBBSJXGY-UHFFFAOYSA-N 9-hydroxy-2,3,4,4a,5,6,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical class O1C2C(=O)CCC3C4CC5=CC=C(O)C1=C5C23CCN4 SWIRXSKBBSJXGY-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000005557 antagonist Substances 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000444674 Narcotica Species 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YQYVFVRQLZMJKJ-JBBXEZCESA-N (+)-cyclazocine Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CC1CC1 YQYVFVRQLZMJKJ-JBBXEZCESA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229950002213 cyclazocine Drugs 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960004127 naloxone Drugs 0.000 description 3
- 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 3
- 239000003887 narcotic antagonist Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound 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 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YHFXJKYHUWPWSJ-UHFFFAOYSA-L [Na+].[Na+].OS([O-])=O.OS([O-])=O Chemical compound [Na+].[Na+].OS([O-])=O.OS([O-])=O YHFXJKYHUWPWSJ-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 235000015201 grapefruit juice Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 235000013997 pineapple juice Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
allgemeinen Formel:
eine Hydroxy- oder Methoxygruppe bedeutet und deren
pharmazeutisch verträgliche Salze. Diese Verbindungen sind sehr xtfirksam und besitzen eine lange Wirkungsdauer, wenn sie oral verabreicht werden, z.B. sind sie in so geringen Mengen, wie 0,1 mg/kg wirksam und können in so hohen Mengen, wie 10 mg/kg Körpergewicht verabreicht werden und sie
besitzen eine Wirkungsdauer von 8 bis 12 Stunden. Diese neuen Verbindungen werden aufgrund ihrer hohen Wirksamkeit in kleinen Dosen vorzugsweise mit pharmazeutisch geeigneten inerten Trägern zusammengegeben (vermischt). Irgend ein Träger, wie er für pharmazeutische Zubereitungen geeignet ist, kann verwendet werden. Geeignete inerte Träger für die orale Verabreichung sind z.B. Wasser, Milch mit und ohne Zucker und/oder Stärke, natürliche und synthetische Fruchtsäfte, wie Orangensaft, Grapefruitsaft, Traubensaft, Ananassaft, Zitronensaft und Pflaumensaft und ge-
(i) G-Methylen-ö-desoxy-K-allyl-i^-hydroxydihydronorcodein.
wurde mit viermal 100 cnr Chloroform extrahiert. Die ketonische Substanz wurde von der organischen Schicht entfernt durch Auswaschen mit Natriumbisulfit-Natriumsulfit-Lösung und das Chloroform über Natriumsulfat getrocknet und eingedampft. Der Rückstand wurde aus Äthanol/ Äther umkristallisiert. Man erhielt 3*9 g 6-Methylen-6-de soxy-14-hydroxydihydronormorphin-3-me thoxy-methyläther.
Claims (8)
- PATENTANSPHÜCHE/\y e-Methylen-ö-desoxy-dlhydromorphin und codeinderivate der allgemeinen Formel:in der H, ein Wasserstoff atom, eine Allyl- oder Cyclopropylmethylgruppe, Bo ein Vaseerstoffatom oder eine Hydroxygruppe und H, eine Hydroxy- oder Methoxygruppe bedeutet und deren pharmazeutisch geeignete Salze·
- 2) Verfahren zur Herstellung von 6-Methylen-6-deeoj^- dihydrononnorphinderivaten nach Anspruch 1, dadurch gekennzeichnet , daß man ein Dihydronormorphinonderivat mit einem Überschuß an einem Phospho-
- -309822/1181
- methylenylü in, einen flüchtigen organischen Lösungsfflittel unter Rückfluß erhitzt.
- 5) Verfahren nach Anspruch 2, dadurch gekennzeichnet , daß man ein Dihydronormorphinon-3-methoxy-methylätherderivat mit einem Überschuß an einem Phosphomethylenylid in einem flüchtigen organischen Lösungsmittel unter Eückfluß erhitzt und den Äther des 6-Methylen-6-desoxydihydronormorρhin-3-IQethoxyJaethylderivats anschließend mit verdünnter Säure und einem. verdünnten Hydroxid umsetzt. :Verfahren nach Anspruch 3? dadurch gekennzeichnet , daß man als Mhydronormorphinonderivat 14-Hydroxydihydronormorphinon oder H-Allyldihydronormorphinon verwendet.5) Verfahren nach Anspruch 3 oder 4, dadurch gekennzeichnet , daß man als Phosphomethylenylifl Iriphenylphosphomethylen verwendet.
- 6) Verwendung der Verbindungen nach Anspruch 1, gegebenenfalls zusammen mit einem pharmazeutisch geeigneten Träger in Arzneimitteln·
- 7) Verwendung nach Anspruch 6, dadurch gekennzeichnet , daß der Anteil der Verbindung 0,5 bis 2. Gew.-% beträgt.
- 8) Verwendung nach Anspruch 6 oder 7, dadurch gekennzeichnet , daß der Träger Wasser ist.309822/1
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00202575A US3814768A (en) | 1971-11-26 | 1971-11-26 | 6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2257715A1 true DE2257715A1 (de) | 1973-05-30 |
DE2257715C2 DE2257715C2 (de) | 1985-06-05 |
Family
ID=22750450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2257715A Expired DE2257715C2 (de) | 1971-11-26 | 1972-11-24 | N-substituierte 6-Methylen-6-desoxy-14-hydroxydihydronormorphinderivate |
Country Status (7)
Country | Link |
---|---|
US (1) | US3814768A (de) |
JP (1) | JPS5653556B2 (de) |
CA (1) | CA974235A (de) |
CH (1) | CH578568A5 (de) |
DE (1) | DE2257715C2 (de) |
FR (1) | FR2160957B1 (de) |
GB (1) | GB1411129A (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0140367A2 (de) * | 1983-11-01 | 1985-05-08 | Ivax Laboratories, Inc. | Verfahren zur Herstellung von 6-Desoxy-6-methylennaloxon und 6-Desoxy-6-methylennaltrexon |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4322426A (en) * | 1980-04-28 | 1982-03-30 | E. I. Du Pont De Nemours And Company | 17-Substituted-6-desoxy-7,8-dihydro-6α-methylnoroxymorphone narcotic antagonists |
JPS5855258A (ja) * | 1981-09-30 | 1983-04-01 | Ricoh Co Ltd | 熱転写型カラープリンタ |
JPS5889377A (ja) * | 1981-11-20 | 1983-05-27 | Canon Inc | ドツトプリンタ |
US4477457A (en) * | 1982-10-28 | 1984-10-16 | E. I. Du Pont De Nemours And Company | Method for inducing anorexia using nalmetrene |
US4478840A (en) * | 1983-10-11 | 1984-10-23 | E. I. Du Pont De Nemours And Company | Appetite suppressing compositions and methods |
US4639455A (en) * | 1984-10-02 | 1987-01-27 | Key Pharmaceuticals, Inc. | Means of aiding in the prevention of sudden infant death syndrome |
US4751307A (en) * | 1985-01-17 | 1988-06-14 | Mallinckrodt, Inc. | Wittig-reaction processes |
DE3690457T1 (de) * | 1985-09-06 | 1987-08-06 | ||
US5028612A (en) * | 1990-03-22 | 1991-07-02 | Hillel Glover | Method for treating emotional numbness |
US7736665B2 (en) * | 2002-05-31 | 2010-06-15 | Titan Pharmaceuticals, Inc. | Implantable polymeric device for sustained release of buprenorphine |
KR101152183B1 (ko) | 2003-03-31 | 2012-06-15 | 타이탄 파머슈티컬즈 인코퍼레이티드 | 도파민 아고니스트의 지속 방출을 위한 이식가능한 폴리머디바이스 |
CA2614289A1 (en) * | 2005-07-08 | 2007-01-18 | Braincells, Inc. | Methods for identifying agents and conditions that modulate neurogenesis |
CN103012416B (zh) * | 2011-09-28 | 2015-07-01 | 辽宁海思科制药有限公司 | 一种盐酸纳美芬的制备方法 |
TWI560170B (en) * | 2011-12-06 | 2016-12-01 | Lundbeck & Co As H | Process for recovery of nalmefene hydrochloride |
CN102584840A (zh) * | 2011-12-28 | 2012-07-18 | 南京优科生物医药有限公司 | 一种制备纳美芬化合物的方法 |
US20140005216A1 (en) | 2012-06-27 | 2014-01-02 | H. Lundbeck A/S | Nalmefene for reduction of alcohol consumption in specific target populations |
HU231191B1 (hu) | 2013-04-15 | 2021-08-30 | Szegedi Tudományegyetem | Izotóp tartalmú morfin molekulák |
CN103204859B (zh) * | 2013-04-25 | 2015-12-02 | 四川海思科制药有限公司 | 一种盐酸纳美芬化合物及其制备方法 |
RU2016145411A (ru) | 2014-04-22 | 2018-05-23 | Оцука Фармасьютикал Ко., Лтд. | Комбинация брекспипразола и налмефена, и ее применение для лечения синдрома химической зависимости |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3162639A (en) * | 1964-12-22 | G-desoxy-ix-hydroxy-dihydromorphine |
-
1971
- 1971-11-26 US US00202575A patent/US3814768A/en not_active Expired - Lifetime
-
1972
- 1972-11-22 FR FR7241464A patent/FR2160957B1/fr not_active Expired
- 1972-11-23 GB GB5421372A patent/GB1411129A/en not_active Expired
- 1972-11-23 CA CA157,312A patent/CA974235A/en not_active Expired
- 1972-11-24 CH CH1715072A patent/CH578568A5/xx not_active IP Right Cessation
- 1972-11-24 DE DE2257715A patent/DE2257715C2/de not_active Expired
- 1972-11-24 JP JP11849472A patent/JPS5653556B2/ja not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3162639A (en) * | 1964-12-22 | G-desoxy-ix-hydroxy-dihydromorphine |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0140367A2 (de) * | 1983-11-01 | 1985-05-08 | Ivax Laboratories, Inc. | Verfahren zur Herstellung von 6-Desoxy-6-methylennaloxon und 6-Desoxy-6-methylennaltrexon |
EP0140367A3 (de) * | 1983-11-01 | 1988-07-20 | Ivax Laboratories, Inc. | Verfahren zur Herstellung von 6-Desoxy-6-methylennaloxon und 6-Desoxy-6-methylennaltrexon |
Also Published As
Publication number | Publication date |
---|---|
DE2257715C2 (de) | 1985-06-05 |
FR2160957B1 (de) | 1975-11-28 |
FR2160957A1 (de) | 1973-07-06 |
JPS5653556B2 (de) | 1981-12-19 |
CA974235A (en) | 1975-09-09 |
CH578568A5 (de) | 1976-08-13 |
US3814768A (en) | 1974-06-04 |
JPS4858000A (de) | 1973-08-14 |
GB1411129A (en) | 1975-10-22 |
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