DE2811849A1 - 2,6-methano-3-benzazocine, verfahren zu deren herstellung und arzneimittel - Google Patents
2,6-methano-3-benzazocine, verfahren zu deren herstellung und arzneimittelInfo
- Publication number
- DE2811849A1 DE2811849A1 DE19782811849 DE2811849A DE2811849A1 DE 2811849 A1 DE2811849 A1 DE 2811849A1 DE 19782811849 DE19782811849 DE 19782811849 DE 2811849 A DE2811849 A DE 2811849A DE 2811849 A1 DE2811849 A1 DE 2811849A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydroxy
- methano
- alkoxy
- benzazocine
- 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
- 239000003887 narcotic antagonist Substances 0.000 title description 8
- 229940035676 analgesics Drugs 0.000 title description 5
- 239000000730 antalgic agent Substances 0.000 title description 5
- ZJFPQVBARDXZPX-UHFFFAOYSA-N 2,6-methano-3-benzazocine Chemical compound C1=CC=C2C(C3)=CC=NC3=CC2=C1 ZJFPQVBARDXZPX-UHFFFAOYSA-N 0.000 title description 3
- -1 2-phenylethyl 2-cyclopropylethyl Chemical group 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 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 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 11
- 239000005557 antagonist Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 241000894007 species Species 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 230000003042 antagnostic effect Effects 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 239000012458 free base Substances 0.000 description 8
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 8
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 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 7
- 230000008484 agonism Effects 0.000 description 7
- 230000008485 antagonism Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000003533 narcotic effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UIQMVEYFGZJHCZ-SSTWWWIQSA-N Nalorphine Chemical compound C([C@@H](N(CC1)CC=C)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 UIQMVEYFGZJHCZ-SSTWWWIQSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 6
- 229960004373 acetylcholine Drugs 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229960000938 nalorphine Drugs 0.000 description 6
- XVSFHIIADLZQJP-UHFFFAOYSA-M sodium;propane-1-thiolate Chemical compound [Na+].CCC[S-] XVSFHIIADLZQJP-UHFFFAOYSA-M 0.000 description 6
- 238000007920 subcutaneous administration Methods 0.000 description 6
- 230000001270 agonistic effect Effects 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229960005181 morphine Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 241000906446 Theraps Species 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229960000482 pethidine Drugs 0.000 description 4
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003187 abdominal effect Effects 0.000 description 3
- NSLKFRGZLUIUKO-UHFFFAOYSA-N ac1l4avw Chemical class C1C2=CC=CC=C2C2CCNC1C2 NSLKFRGZLUIUKO-UHFFFAOYSA-N 0.000 description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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- ZUDKWPUJKABMPR-UHFFFAOYSA-N 10-methyl-10-azatricyclo[7.3.1.02,7]trideca-1,3,5,7,11-pentaene Chemical class CN1C2C=C3C(=C(C=C1)C2)C=CC=C3 ZUDKWPUJKABMPR-UHFFFAOYSA-N 0.000 description 1
- HBRWDCMDBHFEAW-UHFFFAOYSA-N 10-methyl-10-azatricyclo[7.3.1.02,7]trideca-4,6-diene Chemical compound CN1C2CC=3C(C(CC1)C2)CC=CC=3 HBRWDCMDBHFEAW-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- UPVCRZBVVOXMDA-UHFFFAOYSA-N trimethylazanium;formate Chemical compound OC=O.CN(C)C UPVCRZBVVOXMDA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/818,713 US4119628A (en) | 1976-09-22 | 1977-07-25 | Process for preparing hexahydro-11 (eq)-CH2 CH2 COR5 -2,6-methano-3-benzazocines |
| SE7710049A SE443362B (sv) | 1976-09-22 | 1977-09-07 | Forfarande for framstellning av hexahydro-2,6-metano-3-bensazociner |
| GB38944/77A GB1551562A (en) | 1976-09-22 | 1977-09-19 | 2,5-methanobenzo (g) quinoline-3-carboxylate esters |
| CA286,972A CA1095905A (en) | 1976-09-22 | 1977-09-19 | 2,5-methanobenzo¬g| quinoline-3-carboxylate esters |
| NLAANVRAGE7710325,A NL187630C (nl) | 1976-09-22 | 1977-09-20 | Werkwijze ter bereiding van benzazocinederivaten. |
| BE1008388A BE858866A (fr) | 1976-09-22 | 1977-09-20 | 2,5-methanobenzo (g) quinoleine-3-carboxylates (esters) |
| DK418577A DK153945C (da) | 1976-09-22 | 1977-09-21 | Alkyl-3-acyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo(g)quinolin-3-carboxylater til brug som mellemprodukter ved fremstilling af 11(eq)-(2-acylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazociner, samt fremgangsmaade til fremstilling af de naevnte benzazociner |
| CH81881A CH626882A5 (enrdf_load_stackoverflow) | 1976-09-22 | 1977-09-22 | |
| LU78162A LU78162A1 (enrdf_load_stackoverflow) | 1976-09-22 | 1977-09-22 | |
| FR7728584A FR2375216A1 (fr) | 1976-09-22 | 1977-09-22 | 2,5-methanobenzo (g) quinoleine-3-carboxylates (esters) |
| AU29030/77A AU514085B2 (en) | 1976-09-22 | 1977-09-22 | 2, 5-Methanobenzo(g) Quinoline 3-carboxylate esters |
| DE19772742715 DE2742715A1 (de) | 1976-09-22 | 1977-09-22 | 2,5-methanobenzo eckige klammer auf g eckige klammer zu chinolin-3-carboxylatester |
| JP11452077A JPS5340777A (en) | 1976-09-22 | 1977-09-22 | 2*55methnobenzo *g* quinolinee33carboxylic acid ester |
| CH1161877A CH624939A5 (enrdf_load_stackoverflow) | 1976-09-22 | 1977-09-22 | |
| FR7803369A FR2378768A1 (fr) | 1976-09-22 | 1978-02-07 | 2,6-methano-3-benzazocines et leur utilisation comme medicaments |
| US05/877,166 US4180667A (en) | 1974-05-20 | 1978-02-13 | 2-Azabicyclo[2.2.2]oct-5-enes |
| US05/878,308 US4148794A (en) | 1976-09-22 | 1978-02-16 | Lower-alkyl 3-R5 CO-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylates |
| BE1008770A BE864950A (fr) | 1976-09-22 | 1978-03-16 | 2,6-methano-3-benzazocines |
| DE19782811849 DE2811849A1 (de) | 1976-09-22 | 1978-03-17 | 2,6-methano-3-benzazocine, verfahren zu deren herstellung und arzneimittel |
| CA361,860A CA1110243A (en) | 1976-09-22 | 1980-10-08 | 2,5-methanobenzo [5] quinoline-3-carboxylate esters |
| US06/243,031 US4335243A (en) | 1978-02-13 | 1981-03-12 | Oximes of 11-(3-oxooctyl)-hexahydro-2,6-methano-3-benzazocines |
| JP59198392A JPS60142962A (ja) | 1976-09-22 | 1984-09-21 | ２，５−メタノベンゾ〔ｇ〕キノリン−３−カルボン酸エステルおよびその製造方法 |
| JP59198393A JPS60142963A (ja) | 1976-09-22 | 1984-09-21 | ２，６−メタノ−３−ベンゾアゾシン誘導体およびその製造方法 |
| SE8501168A SE463420B (sv) | 1976-09-22 | 1985-03-08 | Alkyl-3-acyl-oktahydro-2,5-metanobenso(g)kinolin-3-karboxylater, till anvaendning som mellanprodukter foer framstaellning av 11(eg)-(2-acyletyl)-hexahydro-2,6-metano-3-bensazociner, samt foerfarande foer deras framstaellning |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72537176A | 1976-09-22 | 1976-09-22 | |
| US78574677A | 1977-04-08 | 1977-04-08 | |
| US05/818,713 US4119628A (en) | 1976-09-22 | 1977-07-25 | Process for preparing hexahydro-11 (eq)-CH2 CH2 COR5 -2,6-methano-3-benzazocines |
| US05/877,166 US4180667A (en) | 1974-05-20 | 1978-02-13 | 2-Azabicyclo[2.2.2]oct-5-enes |
| DE19782811849 DE2811849A1 (de) | 1976-09-22 | 1978-03-17 | 2,6-methano-3-benzazocine, verfahren zu deren herstellung und arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2811849A1 true DE2811849A1 (de) | 1979-09-27 |
| DE2811849C2 DE2811849C2 (enrdf_load_stackoverflow) | 1990-05-23 |
Family
ID=27510522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782811849 Granted DE2811849A1 (de) | 1974-05-20 | 1978-03-17 | 2,6-methano-3-benzazocine, verfahren zu deren herstellung und arzneimittel |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE864950A (enrdf_load_stackoverflow) |
| DE (1) | DE2811849A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019056A1 (en) * | 1979-03-26 | 1980-11-26 | Sterling Drug Inc. | Process for preparing 11-lower alkylthio-3-oxo-lower-alkyl-hexahydro-2,6-methano-3-benzazocines |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250678A (en) * | 1963-01-16 | 1966-05-10 | Sterling Drug Inc | Analgesia producing benzazocines |
| US3345373A (en) * | 1964-05-25 | 1967-10-03 | Smith Kline French Lab | 2-polymethylallyl-5, 9-dimethyl-6, 7-benzmorphans and derivatives |
| US3372165A (en) * | 1960-12-01 | 1968-03-05 | Sterling Drug Inc | 1, 2, 3, 4, 5, 6-hexahydro-8-hydroxy-2, 6-methano-3-benzazocine derivatives |
| US3514463A (en) * | 1966-05-20 | 1970-05-26 | Merck & Co Inc | 5,9-diethyl benzomorphan derivatives |
| US3932422A (en) * | 1974-05-20 | 1976-01-13 | Sterling Drug Inc. | 8-Methylene-3-azabicyclo[3.3.1]non-6-en-4-ones |
| DE2742715A1 (de) * | 1976-09-22 | 1978-03-23 | Sterling Drug Inc | 2,5-methanobenzo eckige klammer auf g eckige klammer zu chinolin-3-carboxylatester |
-
1978
- 1978-03-16 BE BE1008770A patent/BE864950A/xx not_active IP Right Cessation
- 1978-03-17 DE DE19782811849 patent/DE2811849A1/de active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3372165A (en) * | 1960-12-01 | 1968-03-05 | Sterling Drug Inc | 1, 2, 3, 4, 5, 6-hexahydro-8-hydroxy-2, 6-methano-3-benzazocine derivatives |
| US3250678A (en) * | 1963-01-16 | 1966-05-10 | Sterling Drug Inc | Analgesia producing benzazocines |
| US3345373A (en) * | 1964-05-25 | 1967-10-03 | Smith Kline French Lab | 2-polymethylallyl-5, 9-dimethyl-6, 7-benzmorphans and derivatives |
| US3514463A (en) * | 1966-05-20 | 1970-05-26 | Merck & Co Inc | 5,9-diethyl benzomorphan derivatives |
| US3932422A (en) * | 1974-05-20 | 1976-01-13 | Sterling Drug Inc. | 8-Methylene-3-azabicyclo[3.3.1]non-6-en-4-ones |
| DE2742715A1 (de) * | 1976-09-22 | 1978-03-23 | Sterling Drug Inc | 2,5-methanobenzo eckige klammer auf g eckige klammer zu chinolin-3-carboxylatester |
Non-Patent Citations (2)
| Title |
|---|
| Journal of Med. Chem. 12, 288, 1969 * |
| Journal of Med. Chem. 20, 682, 1977 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2811849C2 (enrdf_load_stackoverflow) | 1990-05-23 |
| BE864950A (fr) | 1978-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07D221/26 |
|
| 8181 | Inventor (new situation) |
Free format text: MICHNE, WILLIAM FRANCIS, AVERILL PARK, N.Y., US LEWIS, THOMAS RICHARD, DELMAR, N.Y., US |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |