FI65245C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2,3,4,6,7-hexahydro-11balfah-benso(a)kinoliziner och salter daerav - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2,3,4,6,7-hexahydro-11balfah-benso(a)kinoliziner och salter daerav Download PDFInfo
- Publication number
- FI65245C FI65245C FI781898A FI781898A FI65245C FI 65245 C FI65245 C FI 65245C FI 781898 A FI781898 A FI 781898A FI 781898 A FI781898 A FI 781898A FI 65245 C FI65245 C FI 65245C
- Authority
- FI
- Finland
- Prior art keywords
- hexahydro
- benzo
- mixture
- therapeutic
- hydroxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 9
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000003250 quinolizines Chemical class 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- GANUIJNXRUUOPR-UHFFFAOYSA-N benzo[a]quinolizin-2-one Chemical class C1=CC=C2C3=CC(=O)C=CN3C=CC2=C1 GANUIJNXRUUOPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 11
- 238000002329 infrared spectrum Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000001819 mass spectrum Methods 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
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 4H- benzo [a] quinolizine hydrochloride Chemical compound 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- WSOLXOBNHSHKFH-UHFFFAOYSA-N 3-(9,10-diethoxy-2-oxo-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl)propanenitrile Chemical compound C1CN2CC(CCC#N)C(=O)CC2C2=C1C=C(OCC)C(OCC)=C2 WSOLXOBNHSHKFH-UHFFFAOYSA-N 0.000 description 2
- QLSCNQCATINUIJ-UHFFFAOYSA-N 3-(9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl)propanenitrile Chemical compound C1CN2CC(CCC#N)C(=O)CC2C2=C1C=C(OC)C(OC)=C2 QLSCNQCATINUIJ-UHFFFAOYSA-N 0.000 description 2
- SSSYOIPHXANRMO-UHFFFAOYSA-N 4h-benzo[a]quinolizine Chemical class C1=CC=C2C3=CC=CCN3C=CC2=C1 SSSYOIPHXANRMO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- ZYPDJSJJXZWZJJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-piperidin-4-yloxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCNCC1 ZYPDJSJJXZWZJJ-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- GOKUDAKBEDVQDR-UHFFFAOYSA-N CCOC1=C(C=C2CCN3CCCC(C3=C2C1)CCC#N)OCC Chemical compound CCOC1=C(C=C2CCN3CCCC(C3=C2C1)CCC#N)OCC GOKUDAKBEDVQDR-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000277284 Salvelinus fontinalis Species 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1751A HU175890B (en) | 1977-06-15 | 1977-06-15 | Process for producing new 1,2,3,4,6,7-hexahydro-11-b-alpha-benzo-square bracket-a-square brecket closed-quinolyzine derivatives |
| HUCI001751 | 1977-06-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI781898A7 FI781898A7 (fi) | 1978-12-16 |
| FI65245B FI65245B (fi) | 1983-12-30 |
| FI65245C true FI65245C (fi) | 1984-04-10 |
Family
ID=10994657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI781898A FI65245C (fi) | 1977-06-15 | 1978-06-14 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2,3,4,6,7-hexahydro-11balfah-benso(a)kinoliziner och salter daerav |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4193998A (de) |
| JP (1) | JPS545999A (de) |
| AT (1) | AT363939B (de) |
| DE (1) | DE2824905A1 (de) |
| ES (1) | ES470787A1 (de) |
| FI (1) | FI65245C (de) |
| FR (1) | FR2394546A1 (de) |
| GB (1) | GB2000135B (de) |
| HU (1) | HU175890B (de) |
| IT (1) | IT1203186B (de) |
| NL (1) | NL7800024A (de) |
| SU (1) | SU719499A3 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4992446A (en) * | 1989-09-05 | 1991-02-12 | G. D. Searle & Co. | Tricyclic quinolizine amides |
| WO1997040046A1 (en) * | 1996-04-19 | 1997-10-30 | Nippon Shinyaku Co., Ltd. | Benzoquinolizine derivatives and medicinal compositions |
| US8008500B2 (en) * | 2007-06-08 | 2011-08-30 | General Electric Company | Intermediates useful for making tetrabenazine compounds |
| US7897769B2 (en) * | 2007-10-25 | 2011-03-01 | General Electric Company | Intermediates for fluorinated dihydrotetrabenazine ether imaging agents and probes |
| EP2214721A2 (de) * | 2007-10-25 | 2010-08-11 | General Electric Company | Fluorierte dihydrotetrabenazin-ether-bildgebungsmittel und sonden |
| US7897770B2 (en) * | 2007-10-25 | 2011-03-01 | General Electric Company | Fluorinated dihydrotetrabenazine ether imaging agents and probes |
| US7910738B2 (en) * | 2007-11-29 | 2011-03-22 | General Electric Company | Intermediates for alpha-fluoroalkyl tetrabenazine and dihydrotetrabenazine imaging agents and probes |
| US7902364B2 (en) * | 2007-11-29 | 2011-03-08 | General Electric Company | Alpha-fluoroalkyl tetrabenazine and dihydrotetrabenazine imaging agents and probes |
| US8053578B2 (en) * | 2007-11-29 | 2011-11-08 | General Electric Company | Alpha-fluoroalkyl dihydrotetrabenazine imaging agents and probes |
| US7919622B2 (en) * | 2007-12-07 | 2011-04-05 | Kande Kankanamalage Dayarathna Amarasinghe | Intermediates for fluorinated tetrabenazine carbinol compounds imaging agents and probes |
| US8013161B1 (en) * | 2007-12-07 | 2011-09-06 | General Electric Company | Fluoroalkyl tetrabenazine carbinol compounds as imaging agents and probes |
| CA2801061A1 (en) * | 2010-06-01 | 2011-12-08 | Auspex Pharmaceuticals, Inc. | Benzoquinolone inhibitors of vmat2 |
| CA2883641C (en) | 2012-09-18 | 2021-09-14 | Auspex Pharmaceuticals, Inc. | Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| US9550780B2 (en) | 2012-09-18 | 2017-01-24 | Auspex Pharmaceuticals, Inc. | Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| CN105873589B (zh) | 2013-12-03 | 2019-11-01 | 奥斯拜客斯制药有限公司 | 制造苯并喹啉化合物的方法 |
| CN114767672A (zh) | 2015-03-06 | 2022-07-22 | 奥斯拜客斯制药有限公司 | 氘代丁苯那嗪或包含氘代丁苯那嗪的组合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053845A (en) * | 1962-09-11 | Benzofykedocolines | ||
| CH341161A (de) * | 1956-02-08 | 1959-09-30 | Hoffmann La Roche | Verfahren zur Herstellung von substituierten 2-Hydroxy-benzo [ a ] chinolizinen |
| FI49422C (fi) * | 1961-08-29 | 1975-06-10 | Pfizer | Menetelmä terapeuttisesti arvokkaiden 2-asemassa substituoitujen bents opyridokoliinien (bentso/a/kinolitsiinien) sekä näiden happoadditiosuo lojen valmistamiseksi. |
| US3634431A (en) * | 1969-12-22 | 1972-01-11 | Miles Lab | Acylated and alkylated derivatives of 2-aminohexahydrobenzo(a)quinolizines |
| YU264675A (en) * | 1974-10-23 | 1982-05-31 | Chinoin Gyogyszer Es Vegyeszet | Process for obtaining benzo (a)-quinolizidine derivatives |
| US4133812A (en) * | 1975-11-21 | 1979-01-09 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Process for producing benzo (a) quinolizine derivatives |
-
1977
- 1977-06-15 HU HU77CI1751A patent/HU175890B/hu unknown
-
1978
- 1978-01-02 NL NL7800024A patent/NL7800024A/xx not_active Application Discontinuation
- 1978-06-07 DE DE19782824905 patent/DE2824905A1/de not_active Ceased
- 1978-06-09 AT AT0419478A patent/AT363939B/de not_active IP Right Cessation
- 1978-06-13 IT IT68372/78A patent/IT1203186B/it active
- 1978-06-13 FR FR7817628A patent/FR2394546A1/fr active Granted
- 1978-06-14 US US05/915,379 patent/US4193998A/en not_active Expired - Lifetime
- 1978-06-14 JP JP7100578A patent/JPS545999A/ja active Pending
- 1978-06-14 GB GB7826848A patent/GB2000135B/en not_active Expired
- 1978-06-14 FI FI781898A patent/FI65245C/fi not_active IP Right Cessation
- 1978-06-14 SU SU782626939A patent/SU719499A3/ru active
- 1978-06-14 ES ES470787A patent/ES470787A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4193998A (en) | 1980-03-18 |
| HU175890B (en) | 1980-11-28 |
| FI65245B (fi) | 1983-12-30 |
| GB2000135A (en) | 1979-01-04 |
| AT363939B (de) | 1981-09-10 |
| IT1203186B (it) | 1989-02-15 |
| ES470787A1 (es) | 1979-02-01 |
| SU719499A3 (ru) | 1980-02-29 |
| JPS545999A (en) | 1979-01-17 |
| ATA419478A (de) | 1981-02-15 |
| FR2394546A1 (fr) | 1979-01-12 |
| FR2394546B1 (de) | 1982-07-16 |
| GB2000135B (en) | 1982-01-20 |
| FI781898A7 (fi) | 1978-12-16 |
| IT7868372A0 (it) | 1978-06-13 |
| NL7800024A (nl) | 1978-12-19 |
| DE2824905A1 (de) | 1979-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |