DE2265255C2 - 2-Aminoäthylhexahydrophenanthren-Derivate und deren Säureadditionssalze - Google Patents
2-Aminoäthylhexahydrophenanthren-Derivate und deren SäureadditionssalzeInfo
- Publication number
- DE2265255C2 DE2265255C2 DE2265255A DE2265255A DE2265255C2 DE 2265255 C2 DE2265255 C2 DE 2265255C2 DE 2265255 A DE2265255 A DE 2265255A DE 2265255 A DE2265255 A DE 2265255A DE 2265255 C2 DE2265255 C2 DE 2265255C2
- Authority
- DE
- Germany
- Prior art keywords
- derivatives
- addition salts
- acid addition
- general formula
- compound
- 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
- 239000002253 acid Substances 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 2-aminoethylhexahydrophenanthrene derivatives Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003533 narcotic effect Effects 0.000 claims description 2
- NPKIPXIGRMJHLC-FGTMMUONSA-N (1S,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-10-ol Chemical compound C1CCC[C@@]2(O)[C@]3([H])N(C)CC[C@@]21C1=CC(OC)=CC=C1C3 NPKIPXIGRMJHLC-FGTMMUONSA-N 0.000 claims 2
- 239000008896 Opium Substances 0.000 claims 2
- 229930013930 alkaloid Natural products 0.000 claims 2
- 229960001027 opium Drugs 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 1
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical class C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 claims 1
- 229940051807 opiod analgesics morphinan derivative Drugs 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003891 oxalate salts Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 150000003809 morphinane derivatives Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010013654 Drug abuse Diseases 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- 238000006257 total synthesis reaction Methods 0.000 description 2
- LJVHJHLTRBXGMH-HNQUOIGGSA-N (e)-1,4-dibromobut-1-ene Chemical compound BrCC\C=C\Br LJVHJHLTRBXGMH-HNQUOIGGSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 239000005457 ice water Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 239000003887 narcotic antagonist Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (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)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17883771A | 1971-09-08 | 1971-09-08 | |
| US00217633A US3819635A (en) | 1971-09-08 | 1972-01-13 | 14-hydroxymorphinan derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2265255A1 DE2265255A1 (de) | 1977-01-27 |
| DE2265255C2 true DE2265255C2 (de) | 1986-06-05 |
Family
ID=26874723
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2243961A Granted DE2243961A1 (de) | 1971-09-08 | 1972-09-07 | Verfahren zur herstellung von analgetischen verbindungen |
| DE2265256A Expired DE2265256C2 (de) | 1971-09-08 | 1972-09-07 | Morphinanderivate und Verfahren zu deren Herstellung |
| DE2265255A Expired DE2265255C2 (de) | 1971-09-08 | 1972-09-07 | 2-Aminoäthylhexahydrophenanthren-Derivate und deren Säureadditionssalze |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2243961A Granted DE2243961A1 (de) | 1971-09-08 | 1972-09-07 | Verfahren zur herstellung von analgetischen verbindungen |
| DE2265256A Expired DE2265256C2 (de) | 1971-09-08 | 1972-09-07 | Morphinanderivate und Verfahren zu deren Herstellung |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3819635A (en:Method) |
| JP (1) | JPS5310596B2 (en:Method) |
| AU (1) | AU470102B2 (en:Method) |
| BE (1) | BE788478A (en:Method) |
| CA (1) | CA999578A (en:Method) |
| CH (1) | CH590845A5 (en:Method) |
| CY (1) | CY980A (en:Method) |
| DD (1) | DD100255A5 (en:Method) |
| DE (3) | DE2243961A1 (en:Method) |
| DK (1) | DK141624B (en:Method) |
| FR (1) | FR2154481B1 (en:Method) |
| GB (2) | GB1412129A (en:Method) |
| HK (1) | HK2679A (en:Method) |
| IE (2) | IE36688B1 (en:Method) |
| KE (1) | KE2911A (en:Method) |
| MY (1) | MY7900027A (en:Method) |
| NL (1) | NL162072C (en:Method) |
| SE (2) | SE398877B (en:Method) |
| YU (1) | YU45099B (en:Method) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910920A (en) * | 1973-11-07 | 1975-10-07 | Bristol Myers Co | 3,14,17-Substituted-6,7-tetramethylenemorphinans |
| US3980641A (en) * | 1975-07-31 | 1976-09-14 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinans |
| US4017497A (en) * | 1975-11-18 | 1977-04-12 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinan derivatives |
| US4139534A (en) * | 1977-02-17 | 1979-02-13 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinan derivatives |
| US4052389A (en) * | 1976-03-23 | 1977-10-04 | Bristol-Myers Company | Derivatives of 9,10-dihydroxy-1-(p-alkoxybenzyl)-perhydroisoquinoline oxazine-3-one |
| US4058531A (en) * | 1976-03-23 | 1977-11-15 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinan derivatives |
| JPS52136176A (en) * | 1976-03-23 | 1977-11-14 | Bristol Myers Co | Method of improving 144hydroxymorphinan derivatives |
| GB1593191A (en) * | 1977-03-23 | 1981-07-15 | Reckitt & Colmann Prod Ltd | Derivatives of morphine |
| GB1587831A (en) * | 1977-03-23 | 1981-04-08 | Reckitt & Colmann Prod Ltd | Morphine derivatives |
| US4115389A (en) * | 1977-05-02 | 1978-09-19 | Bristol-Myers Company | Process of N-demethylating (-)-1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline |
| US4338320A (en) * | 1978-11-15 | 1982-07-06 | The Board Of Regents Of The University Of Nebraska | Esters of 6'-hydroxycinchonine, and a method of treating arrythmia with them |
| US4228285A (en) * | 1979-02-28 | 1980-10-14 | Bristol-Myers Company | 14-Hydroxy-6-oxamorphinans and 14-hydroxy-6-oxaisomorphinans |
| US4272540A (en) * | 1979-04-24 | 1981-06-09 | Sisa, Incorporated | 14-Methoxymorphinan-6-one compounds and therapeutic methods of treating pain and drug dependence with them |
| US4322427A (en) * | 1981-04-16 | 1982-03-30 | Bristol-Myers Company | Analgetic compositions and methods of use |
| JP3948026B2 (ja) * | 1993-07-19 | 2007-07-25 | 東レ株式会社 | 脳細胞保護剤 |
| CA2143864C (en) * | 1993-07-23 | 2006-01-24 | Hiroshi Nagase | Morphinan derivatives and pharmaceutical use thereof |
| CZ281174B6 (cs) * | 1993-08-13 | 1996-07-17 | Galena, A.S. | Způsob přípravy 3,14ß-dihydroxy-17-normorfinanu |
| AU753278B2 (en) | 1998-02-25 | 2002-10-10 | Abbott Laboratories | Butorphanol sustained release formulations |
| US20040167164A1 (en) * | 1998-05-05 | 2004-08-26 | Jose Pozuelo | Compositions and methods for treating particular chemical addictions and mental illnesses |
| CA2486157C (en) | 2002-05-17 | 2013-04-16 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US7501433B2 (en) * | 2002-05-17 | 2009-03-10 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US7923454B2 (en) | 2002-05-17 | 2011-04-12 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US8017622B2 (en) * | 2003-05-16 | 2011-09-13 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| CN103073496B (zh) * | 2013-02-18 | 2015-08-26 | 苏州立新制药有限公司 | 右美沙芬的制备方法 |
| CN106794155B (zh) | 2014-10-14 | 2020-10-30 | 久光制药株式会社 | 贴附剂 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3166559A (en) * | 1965-01-19 | J-lower alkoxy-x-phenyloxy-ix-hydroxy- | ||
| GB1028407A (en) * | 1962-04-06 | 1966-05-04 | Shionogi & Co | Improvements in or relating to morphinan derivatives and their preparation |
| FR1362540A (fr) * | 1963-04-05 | 1964-06-05 | Shionogi & Co | Dérivés n substitués du morphinane et leur production |
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0
- BE BE788478D patent/BE788478A/xx not_active IP Right Cessation
-
1972
- 1972-01-13 US US00217633A patent/US3819635A/en not_active Expired - Lifetime
- 1972-08-23 CA CA150,036A patent/CA999578A/en not_active Expired
- 1972-09-01 AU AU46228/72A patent/AU470102B2/en not_active Expired
- 1972-09-06 IE IE103/76A patent/IE36688B1/xx unknown
- 1972-09-06 IE IE1213/72A patent/IE36687B1/xx unknown
- 1972-09-06 DK DK440172AA patent/DK141624B/da not_active IP Right Cessation
- 1972-09-06 SE SE7211522A patent/SE398877B/xx unknown
- 1972-09-07 GB GB4161972A patent/GB1412129A/en not_active Expired
- 1972-09-07 CH CH1315472A patent/CH590845A5/xx not_active IP Right Cessation
- 1972-09-07 GB GB1057175A patent/GB1412130A/en not_active Expired
- 1972-09-07 DE DE2243961A patent/DE2243961A1/de active Granted
- 1972-09-07 FR FR7231816A patent/FR2154481B1/fr not_active Expired
- 1972-09-07 DE DE2265256A patent/DE2265256C2/de not_active Expired
- 1972-09-07 JP JP8916172A patent/JPS5310596B2/ja not_active Expired
- 1972-09-07 YU YU227772A patent/YU45099B/sh unknown
- 1972-09-07 NL NL7212176.A patent/NL162072C/xx not_active IP Right Cessation
- 1972-09-07 CY CY980A patent/CY980A/xx unknown
- 1972-09-07 DE DE2265255A patent/DE2265255C2/de not_active Expired
- 1972-09-08 DD DD165557A patent/DD100255A5/xx unknown
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1975
- 1975-06-02 SE SE7506292A patent/SE403286B/xx not_active IP Right Cessation
-
1978
- 1978-12-24 KE KE2911A patent/KE2911A/xx unknown
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1979
- 1979-01-11 HK HK26/79A patent/HK2679A/xx unknown
- 1979-12-30 MY MY27/79A patent/MY7900027A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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