JPS5970686A - 新規ジアザビシクロ−（３，３，１）−ノナンその製法およびこれを含有する抗不整脈作用を有する医薬 - Google Patents
新規ジアザビシクロ−（３，３，１）−ノナンその製法およびこれを含有する抗不整脈作用を有する医薬Info
- Publication number
- JPS5970686A JPS5970686A JP58154236A JP15423683A JPS5970686A JP S5970686 A JPS5970686 A JP S5970686A JP 58154236 A JP58154236 A JP 58154236A JP 15423683 A JP15423683 A JP 15423683A JP S5970686 A JPS5970686 A JP S5970686A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- compound represented
- independently represent
- hydrogen
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 31
- 230000003288 anthiarrhythmic effect Effects 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title claims description 6
- KTSZYXNHBVWNNV-UHFFFAOYSA-N 1,2-diazabicyclo[3.3.1]nonane Chemical compound C1CNN2CCCC1C2 KTSZYXNHBVWNNV-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 130
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 239000013543 active substance Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000001603 reducing effect Effects 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims 5
- 101150030723 RIR2 gene Proteins 0.000 claims 1
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- 238000000034 method Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- -1 ethylene, propylene, hexylene Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000036747 functional refractory period Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
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- 239000008187 granular material Substances 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- 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 4
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940039750 aconitine Drugs 0.000 description 4
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 230000000297 inotrophic effect Effects 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 206010047289 Ventricular extrasystoles Diseases 0.000 description 2
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- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
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- 150000007514 bases Chemical class 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
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- 239000004359 castor oil Substances 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
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- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
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- 230000035488 systolic blood pressure Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000010626 work up procedure 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D471/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Compositions Of Oxide Ceramics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823234697 DE3234697A1 (de) | 1982-09-18 | 1982-09-18 | Neue diazabicyclo-(3,3,1)-nonane |
| DE3234697.2 | 1982-09-18 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3308735A Division JPH0670056B2 (ja) | 1982-09-18 | 1991-11-25 | 新規テトラオキソ−ジアザビシクロ−（３，３，１）−ノナンおよびその製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5970686A true JPS5970686A (ja) | 1984-04-21 |
Family
ID=6173602
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58154236A Pending JPS5970686A (ja) | 1982-09-18 | 1983-08-25 | 新規ジアザビシクロ−（３，３，１）−ノナンその製法およびこれを含有する抗不整脈作用を有する医薬 |
| JP3308735A Expired - Lifetime JPH0670056B2 (ja) | 1982-09-18 | 1991-11-25 | 新規テトラオキソ−ジアザビシクロ−（３，３，１）−ノナンおよびその製法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3308735A Expired - Lifetime JPH0670056B2 (ja) | 1982-09-18 | 1991-11-25 | 新規テトラオキソ−ジアザビシクロ−（３，３，１）−ノナンおよびその製法 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4550112A (en, 2012) |
| EP (2) | EP0250903B1 (en, 2012) |
| JP (2) | JPS5970686A (en, 2012) |
| AT (2) | ATE69817T1 (en, 2012) |
| AU (1) | AU564910B2 (en, 2012) |
| CA (1) | CA1254209A (en, 2012) |
| CS (1) | CS389891A3 (en, 2012) |
| DD (1) | DD213923A5 (en, 2012) |
| DE (3) | DE3234697A1 (en, 2012) |
| DK (1) | DK165833C (en, 2012) |
| ES (1) | ES525653A0 (en, 2012) |
| FI (1) | FI76338C (en, 2012) |
| GE (1) | GEP19960316B (en, 2012) |
| GR (1) | GR78722B (en, 2012) |
| HU (1) | HU191096B (en, 2012) |
| IE (1) | IE57580B1 (en, 2012) |
| IL (1) | IL69751A (en, 2012) |
| MX (1) | MX9202996A (en, 2012) |
| NO (1) | NO160516C (en, 2012) |
| NZ (1) | NZ205627A (en, 2012) |
| PH (1) | PH20768A (en, 2012) |
| PT (1) | PT77344B (en, 2012) |
| SU (1) | SU1272989A3 (en, 2012) |
| UA (1) | UA817A1 (en, 2012) |
| ZA (1) | ZA836185B (en, 2012) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3529872A1 (de) * | 1985-08-21 | 1987-02-26 | Kali Chemie Pharma Gmbh | Neue tetraoxoverbindungen |
| WO1989000158A1 (en) * | 1987-07-02 | 1989-01-12 | Pfizer Inc. | Bridged-diazabicycloalkyl quinolone carboxylic acids and esters |
| DE3722134A1 (de) * | 1987-07-04 | 1989-01-19 | Kali Chemie Pharma Gmbh | 3-sulfonyl-3,7-diazabicyclo(3,3,1)nonan- verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| PT88381B (pt) * | 1987-09-09 | 1995-07-06 | Kali Chemie Pharma Gmbh | Processo para a preparacao de novos compostos 3,7-diazabiciclo{3,3,1} nonano, e de composicoes farmaceuticas que contem estes compostos |
| DE4019080A1 (de) * | 1990-06-15 | 1991-12-19 | Kali Chemie Pharma Gmbh | Neue 3,7-diazabicycolo (3,3,1)nonan-verbindungen enthaltende arzneimittel |
| DE4139763A1 (de) * | 1991-12-03 | 1993-06-09 | Kali-Chemie Pharma Gmbh, 3000 Hannover, De | Kristalline fumarsaure salze von 9,9-alkylen-3,7-diazabicyclononan-verbindungen und diese verbindungen enthaltende arzneimittel |
| DE4402933A1 (de) * | 1994-02-01 | 1995-08-03 | Kali Chemie Pharma Gmbh | Neue 3-Benzoyl-3,7-diazabicyclo[3,3,1] nonan-Verbindungen enthaltende Arzneimittel |
| DE4421324A1 (de) | 1994-06-17 | 1995-12-21 | Kali Chemie Pharma Gmbh | Neue 3,7-Diazabicyclo [3,3,1] nonan-Verbindungen enthaltende Arzneimittel |
| SE9704709D0 (sv) | 1997-12-17 | 1997-12-17 | Astra Ab | Pharmaceutically active compounds |
| US20050004113A1 (en) * | 1999-06-16 | 2005-01-06 | Astrazeneca Ab | New bispidine compounds useful in the treatment of cardiac arrhythmias |
| US20040229900A1 (en) * | 1999-06-16 | 2004-11-18 | Astrazeneca Ab | Bispidine compounds useful in the treatment of cardiac arrythmias |
| SE9902270D0 (sv) | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| SE9904765D0 (sv) | 1999-12-23 | 1999-12-23 | Astra Ab | Pharmaceutically-useful compounds |
| SE0002603D0 (sv) * | 2000-07-07 | 2000-07-07 | Astrazeneca Ab | New compounds |
| US6808924B1 (en) | 2000-07-11 | 2004-10-26 | Claudia Lanari | Mouse mammary tumor lines expressing estrogen and progesterone receptors |
| AR030756A1 (es) * | 2000-10-02 | 2003-09-03 | Astrazeneca Ab | Compuesto de oxabispidina util en el tratamiento de arritmias cardiacas |
| SE0003795D0 (sv) * | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Pharmaceutically useful compounds |
| SE0100326D0 (sv) * | 2001-02-02 | 2001-02-02 | Astrazeneca Ab | New compounds |
| DE10131217A1 (de) | 2001-06-28 | 2003-01-09 | Solvay Pharm Gmbh | 3-Phenyl-3,7-diazabicyclo 3,3,1 nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| TW200418468A (en) | 2002-11-18 | 2004-10-01 | Solvay Pharm Gmbh | Liquid pharmaceutical formulations containing 3,7-diazabicyclo[3,3,1]nonane compounds and method of treatments relating to anti-arrhytmic events |
| RU2228934C1 (ru) * | 2003-05-20 | 2004-05-20 | ООО "Исследовательский институт химического разнообразия" | Замещенные 3,7-диазобицикло[3.3.1]нонаны, фокусированная библиотека и комбинаторная библиотека |
| US20050054667A1 (en) * | 2003-07-21 | 2005-03-10 | Solvay Pharmaceuticals Gmbh | Method of treating or inhibiting anti-arrhythmic events in male human patients |
| WO2005011690A1 (en) * | 2003-07-21 | 2005-02-10 | Solvay Pharmaceuticals Gmbh | Use of 3,7-diazabicyclo`3, 3,1 !nonane compounds for the treatment and/or prophylaxis of anti-arrhythmic events in male human patients |
| WO2005030207A1 (en) * | 2003-09-26 | 2005-04-07 | Solvay Pharmaceuticals Gmbh | Use of 3, 7-diazabicyclo (3.3.1) nonane compounds for the treatment of brugada syndrome |
| SE0302775D0 (sv) * | 2003-10-20 | 2003-10-20 | Astrazeneca Ab | Chemical compound and assay |
| SE0401540D0 (sv) * | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
| SE0401539D0 (sv) | 2004-06-15 | 2004-06-15 | Astrazeneca Ab | New compounds |
| CA2609938A1 (en) * | 2005-06-13 | 2006-12-21 | Astrazeneca Ab | New oxabispidine compounds for the treatment of cardiac arrhythmias |
| US10399926B1 (en) | 2018-08-01 | 2019-09-03 | Divi's Laboratories Ltd. | Process for the preparation of gabapentin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111791A (en, 2012) * | 1974-06-14 | 1976-01-30 | Knoll Ag | |
| JPS5379896A (en) * | 1976-12-23 | 1978-07-14 | Bayer Ag | Novel nonane compound process for preparing same and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU76173A1 (en, 2012) * | 1976-11-11 | 1978-07-10 | ||
| DE2726571A1 (de) * | 1977-06-13 | 1978-12-21 | Basf Ag | Neue bispidinderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
-
1982
- 1982-09-18 DE DE19823234697 patent/DE3234697A1/de not_active Withdrawn
-
1983
- 1983-08-22 ZA ZA836185A patent/ZA836185B/xx unknown
- 1983-08-25 JP JP58154236A patent/JPS5970686A/ja active Pending
- 1983-09-09 DD DD83254711A patent/DD213923A5/de unknown
- 1983-09-12 AT AT87108007T patent/ATE69817T1/de not_active IP Right Cessation
- 1983-09-12 DE DE8383108990T patent/DE3380409D1/de not_active Expired
- 1983-09-12 EP EP87108007A patent/EP0250903B1/de not_active Expired - Lifetime
- 1983-09-12 EP EP83108990A patent/EP0103833B1/de not_active Expired
- 1983-09-12 DE DE8787108007T patent/DE3382466D1/de not_active Expired - Lifetime
- 1983-09-12 AT AT83108990T patent/ATE45579T1/de not_active IP Right Cessation
- 1983-09-14 HU HU833182A patent/HU191096B/hu unknown
- 1983-09-16 AU AU19206/83A patent/AU564910B2/en not_active Expired
- 1983-09-16 CA CA000436831A patent/CA1254209A/en not_active Expired
- 1983-09-16 PT PT77344A patent/PT77344B/pt unknown
- 1983-09-16 DK DK422583A patent/DK165833C/da not_active IP Right Cessation
- 1983-09-16 SU SU833646751A patent/SU1272989A3/ru active
- 1983-09-16 NO NO833346A patent/NO160516C/no not_active IP Right Cessation
- 1983-09-16 IL IL69751A patent/IL69751A/xx not_active IP Right Cessation
- 1983-09-16 GR GR72462A patent/GR78722B/el unknown
- 1983-09-16 ES ES525653A patent/ES525653A0/es active Granted
- 1983-09-16 UA UA3646751A patent/UA817A1/uk unknown
- 1983-09-16 NZ NZ205627A patent/NZ205627A/en unknown
- 1983-09-16 PH PH29556A patent/PH20768A/en unknown
- 1983-09-16 US US06/532,762 patent/US4550112A/en not_active Expired - Lifetime
- 1983-09-16 IE IE2186/83A patent/IE57580B1/en not_active IP Right Cessation
- 1983-09-19 FI FI833339A patent/FI76338C/fi not_active IP Right Cessation
-
1987
- 1987-05-27 US US07/054,868 patent/US4742172A/en not_active Expired - Lifetime
-
1991
- 1991-11-25 JP JP3308735A patent/JPH0670056B2/ja not_active Expired - Lifetime
- 1991-12-19 CS CS913898A patent/CS389891A3/cs unknown
-
1992
- 1992-06-18 MX MX9202996A patent/MX9202996A/es unknown
-
1993
- 1993-05-19 GE GEAP1993774A patent/GEP19960316B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111791A (en, 2012) * | 1974-06-14 | 1976-01-30 | Knoll Ag | |
| JPS5379896A (en) * | 1976-12-23 | 1978-07-14 | Bayer Ag | Novel nonane compound process for preparing same and application thereof |
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