DE2411382C3 - 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung - Google Patents
2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren VerwendungInfo
- Publication number
- DE2411382C3 DE2411382C3 DE2411382A DE2411382A DE2411382C3 DE 2411382 C3 DE2411382 C3 DE 2411382C3 DE 2411382 A DE2411382 A DE 2411382A DE 2411382 A DE2411382 A DE 2411382A DE 2411382 C3 DE2411382 C3 DE 2411382C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- general formula
- acid
- tetrahydrofurfuryl
- chloroform
- 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
- 238000000034 method Methods 0.000 title claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005521 carbonamide group Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 238000007257 deesterification reaction Methods 0.000 claims description 2
- 238000005661 deetherification reaction Methods 0.000 claims description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 27
- 239000000126 substance Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000012452 mother liquor Substances 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
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- 238000001704 evaporation Methods 0.000 description 15
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- -1 lithium aluminum hydride Chemical compound 0.000 description 12
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- 239000002026 chloroform extract Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
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- 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 8
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
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- 238000003776 cleavage reaction Methods 0.000 description 3
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- 229940050176 methyl chloride Drugs 0.000 description 3
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
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- RAMQAMYGQDRQKW-UHFFFAOYSA-N benzene;butan-1-ol Chemical compound CCCCO.C1=CC=CC=C1 RAMQAMYGQDRQKW-UHFFFAOYSA-N 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
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- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
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- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
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- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NGPGDYLVALNKEG-OLXYHTOASA-N diammonium L-tartrate Chemical compound [NH4+].[NH4+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O NGPGDYLVALNKEG-OLXYHTOASA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 229940069417 doxy Drugs 0.000 description 1
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- 239000003814 drug Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 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
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- FDMKROMOVVBUIJ-UHFFFAOYSA-N oxolan-2-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OCCC1 FDMKROMOVVBUIJ-UHFFFAOYSA-N 0.000 description 1
- DVCFNCQPOANJGU-UHFFFAOYSA-N oxolane-2-carbonyl chloride Chemical compound ClC(=O)C1CCCO1 DVCFNCQPOANJGU-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000012063 pure reaction product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 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
- C07D221/26—Benzomorphans
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (57)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2411382A DE2411382C3 (de) | 1974-03-09 | 1974-03-09 | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung |
| AT153875A AT344332B (de) | 1974-03-09 | 1975-02-28 | Verfahren zur herstellung neuer 2-tetrahydrofurfuryl-6,7-benzomorphane und deren saeureadditionssalzen |
| SU7502110984A SU577982A3 (ru) | 1974-03-09 | 1975-03-05 | Способ получени 2-тетрагидрофурфурил6,7-бензоморфанов или их солей |
| CH280275A CH612425A5 (en) | 1974-03-09 | 1975-03-05 | Process for the preparation of novel 2-tetrahydrofurfuryl-6,7-benzomorphans |
| FI750652A FI63571C (fi) | 1974-03-09 | 1975-03-06 | Foerfarande foer framstaellning av analgetiskt verkande racemiska eller diastereomera och optiskt aktiva 2-tetrahydrofurfuryl-(1r/s 5r/s 9r/s)-2'-hydroxi-5,9-dimetyl-6,7-bensomorfaner och deras syraadditionssalter |
| CA221,554A CA1049511A (en) | 1974-03-09 | 1975-03-07 | 2-tetrahydrofurfuryl-6,7-benzomorphanes, their acid addition salts, their use as pharmaceuticals and processes for their production |
| DD184642A DD119236A5 (enrdf_load_html_response) | 1974-03-09 | 1975-03-07 | |
| BE154138A BE826440A (fr) | 1974-03-09 | 1975-03-07 | Nouveaux 2-tetrahydrofurfuryl-6,7-benzomorphanes, leurs sels d'addition avec des acides, leurs utilisation comme medicament et leur procede de fabrication |
| RO7589653A RO69617A (ro) | 1974-03-09 | 1975-03-07 | Procedeu pentru prepararea unor 2-tetrahidrofurfuril-6,7-benzomorfani |
| NL7502724A NL7502724A (nl) | 1974-03-09 | 1975-03-07 | Werkwijze voor de bereiding van nieuwe 2-tetra- hydrofurfuryl-6,7-benzomorfanen en zuuradditie- zouten daarvan, werkwijze voor de bereiding van farmaceutische preparaten die de genoemde stof- fen als werkzaam bestanddeel bevatten, alsmede gevormde farmaceutische preparaten verkregen volgens de laatstgenoemde werkwijze. |
| BG029183A BG25087A3 (bg) | 1974-03-09 | 1975-03-07 | Метод за получаване на 2-тетрахидрофупфупил-6,7 бензоморфани и техните соли |
| MX535975U MX4747E (es) | 1974-03-09 | 1975-03-07 | Procedimiento para la preparacion de 2-tetra-hidrofurfuril-6,7-benzomorfanos |
| NO750773A NO141800C (no) | 1974-03-09 | 1975-03-07 | Analogifremgangsmaate for fremstilling av terapeutisk aktive benzomorfaner. |
| RO7589654A RO70051A (ro) | 1974-03-09 | 1975-03-07 | Procedeu pentru prepararea unor 2-tetrahidrofurfuril-6,7-benzomorfani |
| ZA751394A ZA751394B (en) | 1974-03-09 | 1975-03-07 | Novel benzomorphanes,possessing analgesic effects |
| IL46760A IL46760A (en) | 1974-03-09 | 1975-03-07 | 2-tetrahydrofurfuryl-6,7-benzomorphane derivatives,their production and pharmaceutical compositions containing them |
| FR7507239A FR2262984B1 (enrdf_load_html_response) | 1974-03-09 | 1975-03-07 | |
| MX535875U MX4689E (es) | 1974-03-09 | 1975-03-07 | Procedimiento para la preparacion de 2-tetrahidro furfuril-6,7-benzomorfanos |
| BG030537A BG24813A4 (bg) | 1974-03-09 | 1975-03-07 | Метод за получаване на 2-тетрахидрофурфурил-6,7- бензоморфани и техните соли |
| JP50027915A JPS5827275B2 (ja) | 1974-03-09 | 1975-03-07 | シンキナ ２− テトラヒドロフルフリル −６ ７− ベンゾモルフアンオヨビソノサンフカエンノセイゾウホウホウ |
| BG030538A BG24814A4 (bg) | 1974-03-09 | 1975-03-07 | Метод за получаване на 2-тетрахидрофурфурил-6,7 бензоморфани и техните соли |
| SE7502592A SE421919B (sv) | 1974-03-09 | 1975-03-07 | Forfarande for framstellning av 2-tetrahydrofurfuryl-6,7-bensomorfaner |
| HU75BO1536A HU177408B (en) | 1974-03-09 | 1975-03-07 | Process for preparing new tetrahydrofurfuryl-6,7-benzomorphans |
| IE505/75A IE40945B1 (en) | 1974-03-09 | 1975-03-07 | Benzomorphanes derivatives |
| DK92975A DK137188C (da) | 1974-03-09 | 1975-03-07 | Analogifremgangsmaade til fremstilling af 2-tetrahydrofurfuryl-6,7-benzomorphaner eller syreadditionssalte heraf |
| GB9633/75A GB1496418A (en) | 1974-03-09 | 1975-03-07 | Benzomorphanes derivatives |
| PL1975178582A PL93499B1 (enrdf_load_html_response) | 1974-03-09 | 1975-03-08 | |
| PL1975191318A PL93699B1 (enrdf_load_html_response) | 1974-03-09 | 1975-03-08 | |
| PL1975191319A PL93700B1 (enrdf_load_html_response) | 1974-03-09 | 1975-03-08 | |
| PH16895A PH14127A (en) | 1974-03-09 | 1975-03-10 | 2-tetrahydrofurfuryl-5-lower alkyl-2'oxy-6,7-benzomorphans,salts thereof and compositions containing them |
| CS751583A CS188221B2 (en) | 1974-03-09 | 1975-03-10 | Method of producing new 2-tetrahydrofurfuryl-6,7-benzomorphanes |
| AU78942/75A AU489862B2 (en) | 1974-03-09 | 1975-03-10 | 2-tetrahydrofurfuryl-6, 7-benzomorphanes |
| ES440349A ES440349A1 (es) | 1974-03-09 | 1975-08-20 | Procedimiento para la preparacion de 2-tetrahidrofurfuril-6,7-benzomorfanos. |
| ES440345A ES440345A1 (es) | 1974-03-09 | 1975-08-20 | Procedimiento para la preparacion de 2-tetrahidrofurfuril-6,7-benzomorfanos. |
| ES440348A ES440348A1 (es) | 1974-03-09 | 1975-08-20 | Procedimiento para la preparacion de 2-tetrahidrofurfuril-6,7-benzomorfanos. |
| ES440346A ES440346A1 (es) | 1974-03-09 | 1975-08-20 | Procedimiento para la preparacion de 2-tetrahidrofurfuril-6,7-benzomorfanos. |
| ES440350A ES440350A1 (es) | 1974-03-09 | 1975-08-20 | Procedimiento para la preparacion de 2-tetrahidrofurfuril-6,7-benzomorfanos. |
| ES440347A ES440347A1 (es) | 1974-03-09 | 1975-08-20 | Procedimiento para la preparacion de 2-tetrahidrofurfuril-6,7-benzomorfanos. |
| SU7502199294A SU577983A3 (ru) | 1974-03-09 | 1975-12-19 | Способ получени 2-тетрагидрофурфурил-6,7-бензоморфанов или их солей, рацематов или оптически активных антиподов |
| SU752199295A SU588916A3 (ru) | 1974-03-09 | 1975-12-19 | Способ получени 2-тетрагидрофурил-6,7-бензоморфанов или их солей |
| US05/673,116 US4087532A (en) | 1974-03-09 | 1976-04-02 | Analgesically useful 2-tetrahydrofurfuryl-5-lower alkyl-2-oxy-6,7-benzomorphans and salts thereof |
| AT829776A AT348144B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren - saeureadditionssalzen |
| AT830176A AT348148B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren saeureadditionssalzen |
| AT829876A AT348145B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren - saeureadditionssalzen |
| AT829976A AT348146B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren saeureadditionssalzen |
| AT830276A AT348149B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren saeureadditionssalzen |
| AT829676A AT348143B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren saeureadditionssalzen |
| AT830076A AT348147B (de) | 1974-03-09 | 1976-11-09 | Verfahren zur herstellung neuer 2-tetrahydro- furfuryl-6,7-benzomorphane und deren saeureadditionssalzen |
| CS775011A CS188250B2 (en) | 1974-03-09 | 1977-07-28 | Method of producing new 2-tetrahydrofurfuryl-6,7-benzomorphanes |
| CS775010A CS188249B2 (en) | 1974-03-09 | 1977-07-28 | Method of producing new 2-tetrahydrofurfuryl-6,7-benzomorphanes |
| CH384679A CH620440A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of 2-tetrahydrofurfuryl-6,7-benzomorphans |
| CH384479A CH622014A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of novel 2-tetrahydrofurfuryl-6,7-benzomorphans |
| CH384779A CH622016A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of novel 2-tetrahydrofurfuryl-6,7-benzomorphans |
| CH384379A CH620439A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of 2-tetrahydrofurfuryl- 6,7-benzomorphans |
| CH384879A CH620681A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of novel 2-tetrahydrofurfuryl-6,7-benzomorphans |
| CH384979A CH622017A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of novel 2-tetrahydrofurfuryl-6,7-benzomorphans |
| CH384579A CH622015A5 (en) | 1974-03-09 | 1979-04-24 | Process for the preparation of novel 2-tetrahydrofurfuryl-6,7-benzomorphans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2411382A DE2411382C3 (de) | 1974-03-09 | 1974-03-09 | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2411382A1 DE2411382A1 (de) | 1975-09-18 |
| DE2411382B2 DE2411382B2 (de) | 1979-01-18 |
| DE2411382C3 true DE2411382C3 (de) | 1979-09-06 |
Family
ID=5909593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2411382A Expired DE2411382C3 (de) | 1974-03-09 | 1974-03-09 | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung |
Country Status (25)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716687A1 (de) * | 1977-04-15 | 1978-10-19 | Boehringer Sohn Ingelheim | 2'-hydroxy-2-(5-isoxazolylmethyl)-6,7benzomorphane, deren saeureadditionssalze und diese enthaltende arzneimittel |
| DE2828039A1 (de) * | 1978-06-26 | 1980-01-10 | Boehringer Sohn Ingelheim | 2-(2-alkoxyethyl)-2'-hydroxy-6,7-benzomorphane deren saeureadditionssalze diese enthaltende arzneimittel und verfahren zu deren herstellung |
| US6492420B2 (en) | 1995-03-10 | 2002-12-10 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| US7530461B2 (en) | 1995-03-10 | 2009-05-12 | Photocure Asa | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| KR100444007B1 (ko) * | 1995-03-10 | 2004-12-03 | 포토큐레 에이에스에이 | 광화학치료또는진단에사용하기위한5-아미노레불린산의에스테르 |
| US6992107B1 (en) | 1995-03-10 | 2006-01-31 | Photocure Asa | Esters of 5-aminolevulinic acid and their use as photosensitizing compounds in photochemotherapy |
| GB0018528D0 (en) | 2000-07-27 | 2000-09-13 | Photocure Asa | Compounds |
| US6723750B2 (en) | 2002-03-15 | 2004-04-20 | Allergan, Inc. | Photodynamic therapy for pre-melanomas |
| TW200911796A (en) | 2007-07-26 | 2009-03-16 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| EP2220048B1 (en) | 2007-11-16 | 2017-01-25 | Boehringer Ingelheim International GmbH | Aryl- and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| CA2708303A1 (en) | 2007-12-11 | 2009-06-18 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| WO2009094169A1 (en) | 2008-01-24 | 2009-07-30 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2254872A2 (en) | 2008-02-15 | 2010-12-01 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| CA2723034A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CL2009001059A1 (es) | 2008-05-01 | 2010-11-12 | Boehringer Ingelheim Int | Compuestos derivados de 1,3-oxazin-2-ona-3,6 sustituidos, inhibidores de la actividad de la 11-beta-hidroxiesteroide deshidrogenasa i; composicion farmaceutica que los comprende; utiles en el tratamiento de enfermedades tales como diabetes mellitus, entre otras. |
| US8569292B2 (en) | 2008-05-01 | 2013-10-29 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| JP5711115B2 (ja) | 2008-05-13 | 2015-04-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンゾモルファン及び関連骨格のアリサイクリックカルボン酸誘導体、そのような化合物を含有する医薬及びその使用 |
| US8846668B2 (en) | 2008-07-25 | 2014-09-30 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| ES2432150T3 (es) | 2008-07-25 | 2013-12-02 | Boehringer Ingelheim International Gmbh | Inhibidores cíclicos de la 11 beta-hidroxiesteroide deshidrogenasa 1 |
| US8680093B2 (en) | 2009-04-30 | 2014-03-25 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| AR078887A1 (es) | 2009-11-06 | 2011-12-07 | Boehringer Ingelheim Int | Derivados arilo y heteroarilcarbonilo de hexahidroindenopiridina y octahidrobenzoquinolina y composiciones farmaceuticas que los contienen. |
| WO2011159760A1 (en) | 2010-06-16 | 2011-12-22 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| TWI537258B (zh) | 2010-11-05 | 2016-06-11 | 百靈佳殷格翰國際股份有限公司 | 六氫茚并吡啶及八氫苯并喹啉之芳基－及雜環芳基羰基衍生物 |
| JP2014524438A (ja) | 2011-08-17 | 2014-09-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | インデノピリジン誘導体 |
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1974
- 1974-03-09 DE DE2411382A patent/DE2411382C3/de not_active Expired
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1975
- 1975-02-28 AT AT153875A patent/AT344332B/de not_active IP Right Cessation
- 1975-03-05 SU SU7502110984A patent/SU577982A3/ru active
- 1975-03-05 CH CH280275A patent/CH612425A5/xx not_active IP Right Cessation
- 1975-03-06 FI FI750652A patent/FI63571C/fi not_active IP Right Cessation
- 1975-03-07 ZA ZA751394A patent/ZA751394B/xx unknown
- 1975-03-07 IL IL46760A patent/IL46760A/xx unknown
- 1975-03-07 DD DD184642A patent/DD119236A5/xx unknown
- 1975-03-07 NO NO750773A patent/NO141800C/no unknown
- 1975-03-07 GB GB9633/75A patent/GB1496418A/en not_active Expired
- 1975-03-07 BG BG030538A patent/BG24814A4/xx unknown
- 1975-03-07 JP JP50027915A patent/JPS5827275B2/ja not_active Expired
- 1975-03-07 RO RO7589654A patent/RO70051A/ro unknown
- 1975-03-07 RO RO7589653A patent/RO69617A/ro unknown
- 1975-03-07 FR FR7507239A patent/FR2262984B1/fr not_active Expired
- 1975-03-07 SE SE7502592A patent/SE421919B/xx not_active IP Right Cessation
- 1975-03-07 HU HU75BO1536A patent/HU177408B/hu unknown
- 1975-03-07 CA CA221,554A patent/CA1049511A/en not_active Expired
- 1975-03-07 BG BG030537A patent/BG24813A4/xx unknown
- 1975-03-07 NL NL7502724A patent/NL7502724A/xx not_active Application Discontinuation
- 1975-03-07 DK DK92975A patent/DK137188C/da active
- 1975-03-07 BG BG029183A patent/BG25087A3/xx unknown
- 1975-03-07 IE IE505/75A patent/IE40945B1/xx unknown
- 1975-03-07 BE BE154138A patent/BE826440A/xx not_active IP Right Cessation
- 1975-03-08 PL PL1975178582A patent/PL93499B1/pl unknown
- 1975-03-08 PL PL1975191319A patent/PL93700B1/pl unknown
- 1975-03-08 PL PL1975191318A patent/PL93699B1/pl unknown
- 1975-03-10 CS CS751583A patent/CS188221B2/cs unknown
- 1975-03-10 PH PH16895A patent/PH14127A/en unknown
- 1975-08-20 ES ES440348A patent/ES440348A1/es not_active Expired
- 1975-08-20 ES ES440346A patent/ES440346A1/es not_active Expired
- 1975-08-20 ES ES440347A patent/ES440347A1/es not_active Expired
- 1975-08-20 ES ES440350A patent/ES440350A1/es not_active Expired
- 1975-08-20 ES ES440349A patent/ES440349A1/es not_active Expired
- 1975-08-20 ES ES440345A patent/ES440345A1/es not_active Expired
- 1975-12-19 SU SU752199295A patent/SU588916A3/ru active
- 1975-12-19 SU SU7502199294A patent/SU577983A3/ru active
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1979
- 1979-04-24 CH CH384579A patent/CH622015A5/de not_active IP Right Cessation
- 1979-04-24 CH CH384479A patent/CH622014A5/de not_active IP Right Cessation
- 1979-04-24 CH CH384979A patent/CH622017A5/de not_active IP Right Cessation
- 1979-04-24 CH CH384779A patent/CH622016A5/de not_active IP Right Cessation
- 1979-04-24 CH CH384879A patent/CH620681A5/de not_active IP Right Cessation
- 1979-04-24 CH CH384679A patent/CH620440A5/de not_active IP Right Cessation
- 1979-04-24 CH CH384379A patent/CH620439A5/de not_active IP Right Cessation
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