DE2811849C2 - - Google Patents
Info
- Publication number
- DE2811849C2 DE2811849C2 DE2811849A DE2811849A DE2811849C2 DE 2811849 C2 DE2811849 C2 DE 2811849C2 DE 2811849 A DE2811849 A DE 2811849A DE 2811849 A DE2811849 A DE 2811849A DE 2811849 C2 DE2811849 C2 DE 2811849C2
- Authority
- DE
- Germany
- Prior art keywords
- trimethyl
- methano
- test
- hexahydro
- compounds
- 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
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000002253 acid Chemical group 0.000 claims description 15
- 239000005557 antagonist Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- -1 2-cyclopropylethyl Chemical group 0.000 claims description 10
- 230000003444 anaesthetic effect Effects 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 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 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 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 7
- 239000000556 agonist Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 6
- 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 5
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
- 229960004373 acetylcholine Drugs 0.000 description 5
- 230000008484 agonism Effects 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 5
- 230000008485 antagonism Effects 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- XVSFHIIADLZQJP-UHFFFAOYSA-M sodium;propane-1-thiolate Chemical compound [Na+].CCC[S-] XVSFHIIADLZQJP-UHFFFAOYSA-M 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241000906446 Theraps Species 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229960000938 nalorphine Drugs 0.000 description 4
- 239000004081 narcotic agent Substances 0.000 description 4
- 229960000482 pethidine Drugs 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 group C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000003187 abdominal effect Effects 0.000 description 2
- NSLKFRGZLUIUKO-UHFFFAOYSA-N ac1l4avw Chemical class C1C2=CC=CC=C2C2CCNC1C2 NSLKFRGZLUIUKO-UHFFFAOYSA-N 0.000 description 2
- 230000001270 agonistic effect Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003887 narcotic antagonist Substances 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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
- VLOOSZAKJZLWPW-UHFFFAOYSA-N 8-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene Chemical class N1C2CCCC(C3=C1C=CC=C3)C2 VLOOSZAKJZLWPW-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BKKYHTMPFNILQT-UHFFFAOYSA-N [N].N1=CC=CC=CC2=C1C=CC=C2 Chemical group [N].N1=CC=CC=CC2=C1C=CC=C2 BKKYHTMPFNILQT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960004127 naloxone Drugs 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
- 229960005301 pentazocine Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 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
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 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
- 238000002211 ultraviolet spectrum 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 |
| CA286,972A CA1095905A (en) | 1976-09-22 | 1977-09-19 | 2,5-methanobenzo¬g| quinoline-3-carboxylate esters |
| GB38944/77A GB1551562A (en) | 1976-09-22 | 1977-09-19 | 2,5-methanobenzo (g) quinoline-3-carboxylate esters |
| BE1008388A BE858866A (fr) | 1976-09-22 | 1977-09-20 | 2,5-methanobenzo (g) quinoleine-3-carboxylates (esters) |
| NLAANVRAGE7710325,A NL187630C (nl) | 1976-09-22 | 1977-09-20 | Werkwijze ter bereiding van benzazocinederivaten. |
| 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 |
| LU78162A LU78162A1 (enrdf_load_stackoverflow) | 1976-09-22 | 1977-09-22 | |
| DE19772742715 DE2742715A1 (de) | 1976-09-22 | 1977-09-22 | 2,5-methanobenzo eckige klammer auf g eckige klammer zu chinolin-3-carboxylatester |
| AU29030/77A AU514085B2 (en) | 1976-09-22 | 1977-09-22 | 2, 5-Methanobenzo(g) Quinoline 3-carboxylate esters |
| CH81881A CH626882A5 (enrdf_load_stackoverflow) | 1976-09-22 | 1977-09-22 | |
| 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 | |
| FR7728584A FR2375216A1 (fr) | 1976-09-22 | 1977-09-22 | 2,5-methanobenzo (g) quinoleine-3-carboxylates (esters) |
| 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 |
| 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 |
| 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 |
| 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 DE2811849A1 (de) | 1979-09-27 |
| DE2811849C2 true 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 |
|---|---|---|---|---|
| EP0017074A1 (en) * | 1979-03-26 | 1980-10-15 | Sterling Drug Inc. | Process and intermediates for preparing 11-(alkoxy- and alkylmercapto-3-oxoalkyl)-2,6-methano-3-benzazocines |
Family Cites Families (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 |
| NL132139C (enrdf_load_stackoverflow) * | 1966-05-20 | |||
| US3932422A (en) * | 1974-05-20 | 1976-01-13 | Sterling Drug Inc. | 8-Methylene-3-azabicyclo[3.3.1]non-6-en-4-ones |
| US4119628A (en) * | 1976-09-22 | 1978-10-10 | Sterling Drug Inc. | Process for preparing hexahydro-11 (eq)-CH2 CH2 COR5 -2,6-methano-3-benzazocines |
-
1978
- 1978-03-16 BE BE1008770A patent/BE864950A/xx not_active IP Right Cessation
- 1978-03-17 DE DE19782811849 patent/DE2811849A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2811849A1 (de) | 1979-09-27 |
| BE864950A (fr) | 1978-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1795769C3 (de) | 6,7,8,9-Tetrahydro-2H-pyrido [Ua] pyrimidinderivate, deren Salze mit Säuren und quaternäre Methosalze, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| DE2243961C2 (enrdf_load_stackoverflow) | ||
| CH625223A5 (enrdf_load_stackoverflow) | ||
| CH625787A5 (enrdf_load_stackoverflow) | ||
| DE3026201A1 (de) | Aminoaetheroxide, verfahren zu ihrer herstellung sowie ihre therapeutische verwendung | |
| DE2411382B2 (de) | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung | |
| DE1420015B1 (de) | 2'-Hydroxy-5,9-dimethyl-6,7-benzomorphane | |
| DE2555590A1 (de) | 1-substituierte-4-benzylidenpiperidine und verfahren zu ihrer herstellung | |
| DE1645929A1 (de) | Verfahren zur Herstellung von Spiro-tetralinsuccinimiden | |
| DE2305092A1 (de) | Alpha-aminomethylbenzylalkoholderivate | |
| DE2900644A1 (de) | 8 beta -alkyl-substituierte morphian- 6-on verbindungen, verfahren zu deren herstellung, sowie deren verwendung als pharmazeutisches mittel | |
| DE2811849C2 (enrdf_load_stackoverflow) | ||
| DE1925296A1 (de) | Benzomorphanderivate | |
| DE2833505A1 (de) | Tetrahydro-isochinolin-derivate, verfahren zu deren herstellung und mittel enthaltend die derivate | |
| DE2246307C2 (de) | In 1 Stellung substituierte 3-Hydroxymethyl-6,7-dialkoxy-isochinoline, deren Salze und Verfahren zur ihrer Herstellung | |
| DE2649172C2 (enrdf_load_stackoverflow) | ||
| CH530401A (de) | Verfahren zur Herstellung von Phenanthridinderivaten | |
| DE3320028C2 (enrdf_load_stackoverflow) | ||
| DE1916481A1 (de) | Hydroxylaminderivate,ihre Verwendung und Verfahren zur Herstellung derselben | |
| DE1952206C2 (de) | Neue Derivate des Tropans und deren Salze, Verfahren zur Herstellung und Arzneimittel | |
| DE1914925C3 (de) | 1-Cycioalkyimeihyi-3-aiky(-3-phenylpyrrolidinverbi ndungen | |
| DE743467C (de) | Verfahren zur Herstellung von Nicotinsaeure-alkaminestern | |
| DE2948308A1 (de) | Hexahydro-2,6-methano-3-benzazocine, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzung | |
| DE2857122C2 (enrdf_load_stackoverflow) | ||
| CH662116A5 (de) | Kondensierte as-triazinium-derivate. |
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 |