SE450704B - 3,7-diazabicyklo /3,3,1/ nonaner, forfarande for framstellning och farmaceutisk beredning derav - Google Patents
3,7-diazabicyklo /3,3,1/ nonaner, forfarande for framstellning och farmaceutisk beredning deravInfo
- Publication number
- SE450704B SE450704B SE8204393A SE8204393A SE450704B SE 450704 B SE450704 B SE 450704B SE 8204393 A SE8204393 A SE 8204393A SE 8204393 A SE8204393 A SE 8204393A SE 450704 B SE450704 B SE 450704B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- diazabicyclo
- general formula
- dimethyl
- substituents
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 51
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 11
- -1 xanthene-9-carbonyl Chemical group 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- KTSZYXNHBVWNNV-UHFFFAOYSA-N 1,2-diazabicyclo[3.3.1]nonane Chemical compound C1CNN2CCCC1C2 KTSZYXNHBVWNNV-UHFFFAOYSA-N 0.000 claims 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 description 45
- 238000002844 melting Methods 0.000 description 43
- 230000008018 melting Effects 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229960004194 lidocaine Drugs 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 230000033764 rhythmic process Effects 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- DLNXXRCPFQRALD-UHFFFAOYSA-N O.Cl.Cl.CCCCCCCCC Chemical compound O.Cl.Cl.CCCCCCCCC DLNXXRCPFQRALD-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
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- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- ABOWRJQOEJPPFS-UHFFFAOYSA-N nonane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCCC ABOWRJQOEJPPFS-UHFFFAOYSA-N 0.000 description 2
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- 229920002866 paraformaldehyde Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 231100001274 therapeutic index Toxicity 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
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- ZFOVCSTVYYYRSU-ZZXKWVIFSA-N (e)-3-(4-chlorophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=C(Cl)C=C1 ZFOVCSTVYYYRSU-ZZXKWVIFSA-N 0.000 description 1
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- KSAZTFOYZXHOOR-WLHGVMLRSA-N (e)-but-2-enedioic acid;3,7-dimethyl-9-phenoxy-3,7-diazabicyclo[3.3.1]nonane Chemical compound OC(=O)\C=C\C(O)=O.C1N(C)CC2CN(C)CC1C2OC1=CC=CC=C1 KSAZTFOYZXHOOR-WLHGVMLRSA-N 0.000 description 1
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- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical class O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RRIFVBLGSXFWSL-UHFFFAOYSA-N methane;sulfuric acid Chemical compound C.C.OS(O)(=O)=O RRIFVBLGSXFWSL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229960003343 ouabain Drugs 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU812112A HU184960B (en) | 1981-07-20 | 1981-07-20 | Process for preparing new derivatives of 3,7-diazabicyclo/3.3.1/ nonane |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8204393D0 SE8204393D0 (sv) | 1982-07-19 |
| SE8204393L SE8204393L (sv) | 1983-01-21 |
| SE450704B true SE450704B (sv) | 1987-07-20 |
Family
ID=10957812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8204393A SE450704B (sv) | 1981-07-20 | 1982-07-19 | 3,7-diazabicyklo /3,3,1/ nonaner, forfarande for framstellning och farmaceutisk beredning derav |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4451473A (en, 2012) |
| JP (1) | JPS5849383A (en, 2012) |
| AR (1) | AR230447A1 (en, 2012) |
| AT (1) | AT379809B (en, 2012) |
| AU (1) | AU552770B2 (en, 2012) |
| BE (1) | BE893891A (en, 2012) |
| CA (1) | CA1254208A (en, 2012) |
| CH (1) | CH653032A5 (en, 2012) |
| CS (1) | CS235302B2 (en, 2012) |
| DD (1) | DD202575A5 (en, 2012) |
| DE (1) | DE3226921C2 (en, 2012) |
| DK (1) | DK160875C (en, 2012) |
| ES (2) | ES8401972A1 (en, 2012) |
| FI (1) | FI71320C (en, 2012) |
| FR (1) | FR2510575B1 (en, 2012) |
| GB (1) | GB2102801B (en, 2012) |
| GR (1) | GR76874B (en, 2012) |
| HU (1) | HU184960B (en, 2012) |
| IL (1) | IL66277A (en, 2012) |
| IN (1) | IN155994B (en, 2012) |
| IT (1) | IT1190920B (en, 2012) |
| MX (1) | MX159288A (en, 2012) |
| NL (1) | NL8202908A (en, 2012) |
| NO (1) | NO157421C (en, 2012) |
| PH (1) | PH18502A (en, 2012) |
| PL (2) | PL135814B1 (en, 2012) |
| PT (1) | PT75265B (en, 2012) |
| SE (1) | SE450704B (en, 2012) |
| SU (2) | SU1222197A3 (en, 2012) |
| YU (1) | YU45867B (en, 2012) |
| ZA (1) | ZA824809B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5036153A (en) * | 1989-05-11 | 1991-07-30 | Braish Tamim F | Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates |
| HUT74682A (en) * | 1993-12-29 | 1997-01-28 | Pfizer | Diazabicyclic neurokinin antagonists and pharmaceutical compositions containing them |
| GB9726630D0 (en) * | 1997-12-18 | 1998-02-18 | Glaxo Group Ltd | Kv2.1 Antagonists |
| MXPA02005884A (es) * | 1999-12-14 | 2002-10-23 | Neurosearch As | Heteroaril-diazabicicloalcanos novedosos. |
| AU2005228289B2 (en) | 2004-03-31 | 2008-01-10 | Nippon Soda Co., Ltd. | Cyclic amine compound and pest control agent |
| WO2007040280A1 (ja) | 2005-10-06 | 2007-04-12 | Nippon Soda Co., Ltd. | 環状アミン化合物および有害生物防除剤 |
| UA86328C2 (uk) * | 2005-10-06 | 2009-04-10 | Ниппон Сода Ко., Лтд. | Циклічні амінові сполуки, засіб для боротьби зі шкідниками |
| RU2503663C2 (ru) * | 2007-04-27 | 2014-01-10 | Актелион Фармасьютиклз Лтд | Мостиковые шестичленные циклические соединения |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078272A (en) * | 1963-02-19 | N-aza-bicyclo-alkylene-imino | ||
| DE2428792A1 (de) * | 1974-06-14 | 1976-01-02 | Knoll Ag | Neue antiarrhythmika |
| DE2726571A1 (de) * | 1977-06-13 | 1978-12-21 | Basf Ag | Neue bispidinderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
-
1981
- 1981-07-20 HU HU812112A patent/HU184960B/hu not_active IP Right Cessation
-
1982
- 1982-07-06 ZA ZA824809A patent/ZA824809B/xx unknown
- 1982-07-08 IL IL66277A patent/IL66277A/xx not_active IP Right Cessation
- 1982-07-13 AT AT0272382A patent/AT379809B/de not_active IP Right Cessation
- 1982-07-13 CA CA000407149A patent/CA1254208A/en not_active Expired
- 1982-07-15 GR GR68779A patent/GR76874B/el unknown
- 1982-07-15 FI FI822526A patent/FI71320C/fi not_active IP Right Cessation
- 1982-07-15 CH CH4315/82A patent/CH653032A5/de not_active IP Right Cessation
- 1982-07-16 PT PT75265A patent/PT75265B/pt not_active IP Right Cessation
- 1982-07-16 DK DK319982A patent/DK160875C/da active
- 1982-07-16 DD DD82241725A patent/DD202575A5/de not_active IP Right Cessation
- 1982-07-16 US US06/398,801 patent/US4451473A/en not_active Expired - Lifetime
- 1982-07-19 GB GB08220818A patent/GB2102801B/en not_active Expired
- 1982-07-19 SU SU823465423A patent/SU1222197A3/ru active
- 1982-07-19 NO NO822485A patent/NO157421C/no unknown
- 1982-07-19 DE DE3226921A patent/DE3226921C2/de not_active Expired - Fee Related
- 1982-07-19 AR AR290016A patent/AR230447A1/es active
- 1982-07-19 ES ES514126A patent/ES8401972A1/es not_active Expired
- 1982-07-19 CS CS825520A patent/CS235302B2/cs unknown
- 1982-07-19 FR FR8212572A patent/FR2510575B1/fr not_active Expired
- 1982-07-19 IT IT22448/82A patent/IT1190920B/it active
- 1982-07-19 YU YU157182A patent/YU45867B/sh unknown
- 1982-07-19 PH PH27586A patent/PH18502A/en unknown
- 1982-07-19 AU AU86176/82A patent/AU552770B2/en not_active Ceased
- 1982-07-19 SE SE8204393A patent/SE450704B/sv not_active IP Right Cessation
- 1982-07-19 JP JP57125600A patent/JPS5849383A/ja active Granted
- 1982-07-19 NL NL8202908A patent/NL8202908A/nl not_active Application Discontinuation
- 1982-07-19 MX MX193658A patent/MX159288A/es unknown
- 1982-07-20 IN IN832/CAL/82A patent/IN155994B/en unknown
- 1982-07-20 PL PL1982244329A patent/PL135814B1/pl unknown
- 1982-07-20 PL PL1982237566A patent/PL135878B1/pl unknown
- 1982-07-20 BE BE0/208636A patent/BE893891A/fr not_active IP Right Cessation
-
1983
- 1983-03-14 ES ES520567A patent/ES520567A0/es active Granted
- 1983-09-22 SU SU833646755A patent/SU1272990A3/ru active
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