US3896226A - 6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts thereof, and use of the same as a narcotic antagonist - Google Patents
6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts thereof, and use of the same as a narcotic antagonist Download PDFInfo
- Publication number
- US3896226A US3896226A US446498A US44649874A US3896226A US 3896226 A US3896226 A US 3896226A US 446498 A US446498 A US 446498A US 44649874 A US44649874 A US 44649874A US 3896226 A US3896226 A US 3896226A
- Authority
- US
- United States
- Prior art keywords
- methylene
- desoxy
- set forth
- compound
- narcotic antagonist
- 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 - Lifetime
Links
- 239000003887 narcotic antagonist Substances 0.000 title claims abstract description 48
- 150000003839 salts Chemical class 0.000 title abstract description 15
- RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical class C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 title abstract description 7
- NRZXMZPWLHNERF-GGNLRSJOSA-N (4R,4aR,7aS,12bS)-3-methyl-7-methylidene-1,2,4,4a,7a,10,11,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol Chemical compound C=C([C@@H]1OC2=C(O)CC3)C=C[C@H]4[C@]5([H])N(C)CC[C@@]41C2=C3C5 NRZXMZPWLHNERF-GGNLRSJOSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 230000037396 body weight Effects 0.000 claims description 10
- 230000003042 antagnostic effect Effects 0.000 claims description 4
- 239000004081 narcotic agent Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical group 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 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229960004127 naloxone Drugs 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YQYVFVRQLZMJKJ-JBBXEZCESA-N (+)-cyclazocine Chemical group C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CC1CC1 YQYVFVRQLZMJKJ-JBBXEZCESA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229950002213 cyclazocine Drugs 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000969 carrier 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
- 230000000694 effects Effects 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 229920002472 Starch Polymers 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound 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 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 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
- 235000015203 fruit juice Nutrition 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000002045 lasting effect Effects 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
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 230000003533 narcotic effect Effects 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
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 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
- 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
- 208000018526 Narcotic-Related disease Diseases 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
- 239000004264 Petrolatum Substances 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
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- -1 alkaline earth metal salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 235000015201 grapefruit juice Nutrition 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 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
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 201000005040 opiate dependence Diseases 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
- 230000000737 periodic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019527 sweetened beverage Nutrition 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:
-
- 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
Definitions
- novel compounds can be combined to form metal salts thereof as, for example, combined with alkali metal and alkaline earth metal salts, sodium salts being the preferred form.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (19)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US446498A US3896226A (en) | 1971-11-26 | 1974-02-27 | 6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts thereof, and use of the same as a narcotic antagonist |
Applications Claiming Priority (2)
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 |
US446498A US3896226A (en) | 1971-11-26 | 1974-02-27 | 6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts thereof, and use of the same as a narcotic antagonist |
Publications (1)
Publication Number | Publication Date |
---|---|
US3896226A true US3896226A (en) | 1975-07-22 |
Family
ID=26897815
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US446498A Expired - Lifetime US3896226A (en) | 1971-11-26 | 1974-02-27 | 6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts thereof, and use of the same as a narcotic antagonist |
Country Status (1)
Country | Link |
---|---|
US (1) | US3896226A (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1983003197A1 (en) | 1982-03-16 | 1983-09-29 | Univ Rockefeller | Method for controlling gastrointestinal dysmotility |
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 |
US4751307A (en) * | 1985-01-17 | 1988-06-14 | Mallinckrodt, Inc. | Wittig-reaction processes |
US4785000A (en) * | 1986-06-18 | 1988-11-15 | The Rockefeller University | Method of treating patients suffering from chronic pain or chronic cough |
WO1989010125A1 (en) * | 1988-04-27 | 1989-11-02 | Baker Cummins Pharmaceuticals, Inc | Method of reversing the side effects of epidural analgesics |
US4946848A (en) * | 1985-10-29 | 1990-08-07 | Baker Cumins Dermatologicals, Inc. | Method of treating pruritus with nalmefene and clonidine |
US4972308A (en) * | 1990-01-16 | 1990-11-20 | Chen I Ming | Innovated lamp fitting set without welding |
US4987136A (en) * | 1982-03-16 | 1991-01-22 | The Rockefeller University | Method for controlling gastrointestinal dysmotility |
US5028612A (en) * | 1990-03-22 | 1991-07-02 | Hillel Glover | Method for treating emotional numbness |
US5668285A (en) * | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
US5783583A (en) * | 1996-04-12 | 1998-07-21 | Simon; David Lew | 17-(cyclopropylmethyl)-4,5alpha-epoxy-6-methylenemorphinan-3,14-diol, hydrochloride salt for the purpose of rapid narcotic detoxification |
US5919760A (en) * | 1996-04-12 | 1999-07-06 | Intensive Narcotic Detoxification Centers Of America, Llc | Method for treating acute and severe diarrhea |
US5922705A (en) * | 1996-04-12 | 1999-07-13 | Intensive Narcotic Detoxification Centers Of America, Llc | Rapid narcotic detoxification |
US6271240B1 (en) | 1996-05-06 | 2001-08-07 | David Lew Simon | Methods for improved regulation of endogenous dopamine in prolonged treatment of opioid addicted individuals |
US20030026838A1 (en) * | 2001-06-26 | 2003-02-06 | Farrell John J. | Tamper-proof narcotic delivery system |
US20070015138A1 (en) * | 2005-07-08 | 2007-01-18 | Braincells, Inc. | Methods for identifying agents and conditions that modulate neurogenesis |
US20090076052A1 (en) * | 2007-09-15 | 2009-03-19 | Protia, Llc | Deuterium-enriched nalmefene |
WO2013083685A1 (en) * | 2011-12-06 | 2013-06-13 | H. Lundbeck A/S | Process for recovery of nalmefene hydrochloride |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3153042A (en) * | 1964-10-13 | Morphinone and codeinone derivatives | ||
US3162639A (en) * | 1964-12-22 | G-desoxy-ix-hydroxy-dihydromorphine | ||
US3322771A (en) * | 1967-05-30 | Intermediates for preparing thebaine derivatives | ||
US3332950A (en) * | 1963-03-23 | 1967-07-25 | Endo Lab | 14-hydroxydihydronormorphinone derivatives |
US3773955A (en) * | 1970-08-03 | 1973-11-20 | Bristol Myers Co | Analgetic compositions |
-
1974
- 1974-02-27 US US446498A patent/US3896226A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3153042A (en) * | 1964-10-13 | Morphinone and codeinone derivatives | ||
US3162639A (en) * | 1964-12-22 | G-desoxy-ix-hydroxy-dihydromorphine | ||
US3322771A (en) * | 1967-05-30 | Intermediates for preparing thebaine derivatives | ||
US3332950A (en) * | 1963-03-23 | 1967-07-25 | Endo Lab | 14-hydroxydihydronormorphinone derivatives |
US3773955A (en) * | 1970-08-03 | 1973-11-20 | Bristol Myers Co | Analgetic compositions |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1983003197A1 (en) | 1982-03-16 | 1983-09-29 | Univ Rockefeller | Method for controlling gastrointestinal dysmotility |
US4987136A (en) * | 1982-03-16 | 1991-01-22 | The Rockefeller University | Method for controlling gastrointestinal dysmotility |
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 |
US4751307A (en) * | 1985-01-17 | 1988-06-14 | Mallinckrodt, Inc. | Wittig-reaction processes |
US4946848A (en) * | 1985-10-29 | 1990-08-07 | Baker Cumins Dermatologicals, Inc. | Method of treating pruritus with nalmefene and clonidine |
US4785000A (en) * | 1986-06-18 | 1988-11-15 | The Rockefeller University | Method of treating patients suffering from chronic pain or chronic cough |
US5668285A (en) * | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
WO1989010125A1 (en) * | 1988-04-27 | 1989-11-02 | Baker Cummins Pharmaceuticals, Inc | Method of reversing the side effects of epidural analgesics |
US4972308A (en) * | 1990-01-16 | 1990-11-20 | Chen I Ming | Innovated lamp fitting set without welding |
US5028612A (en) * | 1990-03-22 | 1991-07-02 | Hillel Glover | Method for treating emotional numbness |
US5919760A (en) * | 1996-04-12 | 1999-07-06 | Intensive Narcotic Detoxification Centers Of America, Llc | Method for treating acute and severe diarrhea |
US5922705A (en) * | 1996-04-12 | 1999-07-13 | Intensive Narcotic Detoxification Centers Of America, Llc | Rapid narcotic detoxification |
US6087356A (en) * | 1996-04-12 | 2000-07-11 | Simon; David Lew | Rapid narcotic detoxification |
US5783583A (en) * | 1996-04-12 | 1998-07-21 | Simon; David Lew | 17-(cyclopropylmethyl)-4,5alpha-epoxy-6-methylenemorphinan-3,14-diol, hydrochloride salt for the purpose of rapid narcotic detoxification |
US6271240B1 (en) | 1996-05-06 | 2001-08-07 | David Lew Simon | Methods for improved regulation of endogenous dopamine in prolonged treatment of opioid addicted individuals |
US7968119B2 (en) | 2001-06-26 | 2011-06-28 | Farrell John J | Tamper-proof narcotic delivery system |
US20030026838A1 (en) * | 2001-06-26 | 2003-02-06 | Farrell John J. | Tamper-proof narcotic delivery system |
US20070015138A1 (en) * | 2005-07-08 | 2007-01-18 | Braincells, Inc. | Methods for identifying agents and conditions that modulate neurogenesis |
US20090076052A1 (en) * | 2007-09-15 | 2009-03-19 | Protia, Llc | Deuterium-enriched nalmefene |
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