CS235302B2 - Method of bicyclic compounds production - Google Patents
Method of bicyclic compounds production Download PDFInfo
- Publication number
- CS235302B2 CS235302B2 CS825520A CS552082A CS235302B2 CS 235302 B2 CS235302 B2 CS 235302B2 CS 825520 A CS825520 A CS 825520A CS 552082 A CS552082 A CS 552082A CS 235302 B2 CS235302 B2 CS 235302B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- optionally
- substituent
- diazabicyclo
- Prior art date
Links
- 125000002619 bicyclic group Chemical group 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- -1 benzhydryl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims description 17
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 claims 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 2
- SKKZAEPNJBCQLZ-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C1NCC2CNCC1C2O SKKZAEPNJBCQLZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 230000033764 rhythmic process Effects 0.000 abstract description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000000203 mixture Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical group C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 description 4
- RLFKNWNVBRSKKR-UHFFFAOYSA-N 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C1N(C)CC2CN(C)CC1C2O RLFKNWNVBRSKKR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-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
- 239000000155 melt Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 231100001274 therapeutic index Toxicity 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- KYLAMRRELINBMS-CHHVJCJISA-N (E)-2-[9-(4-chlorophenoxy)-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-1-yl]but-2-enedioic acid Chemical compound CN1CC2CN(CC(C1)(C2OC3=CC=C(C=C3)Cl)/C(=C\C(=O)O)/C(=O)O)C KYLAMRRELINBMS-CHHVJCJISA-N 0.000 description 1
- 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
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DXBFAQDHEPLJJC-UHFFFAOYSA-N 3,7-dimethyl-9-[3-(trifluoromethyl)phenoxy]-3,7-diazabicyclo[3.3.1]nonane;dihydrochloride Chemical compound Cl.Cl.C1N(C)CC2CN(C)CC1C2OC1=CC=CC(C(F)(F)F)=C1 DXBFAQDHEPLJJC-UHFFFAOYSA-N 0.000 description 1
- QNHPBEUPUGMRRE-UHFFFAOYSA-N 3,7-dimethyl-9-phenylmethoxy-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1N(C)CC2CN(C)CC1C2OCC1=CC=CC=C1 QNHPBEUPUGMRRE-UHFFFAOYSA-N 0.000 description 1
- UFXLGVBYUIDHFW-WLHGVMLRSA-N 9-benzhydryloxy-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1N(C)CC2CN(C)CC1C2OC(C=1C=CC=CC=1)C1=CC=CC=C1 UFXLGVBYUIDHFW-WLHGVMLRSA-N 0.000 description 1
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000033988 Device pacing issue Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000166550 Strophanthus gratus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 150000001501 aryl fluorides Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 230000002213 calciumantagonistic effect Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003576 central nervous system agent Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000541 pulsatile effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000011287 therapeutic dose 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
- 125000006004 trihaloethyl group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS831747A CS235316B2 (cs) | 1981-07-20 | 1983-03-14 | Způsob výroby bicyklických sloučenin |
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 (1)
| Publication Number | Publication Date |
|---|---|
| CS235302B2 true CS235302B2 (en) | 1985-05-15 |
Family
ID=10957812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS825520A CS235302B2 (en) | 1981-07-20 | 1982-07-19 | Method of bicyclic compounds production |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4451473A (en]) |
| JP (1) | JPS5849383A (en]) |
| AR (1) | AR230447A1 (en]) |
| AT (1) | AT379809B (en]) |
| AU (1) | AU552770B2 (en]) |
| BE (1) | BE893891A (en]) |
| CA (1) | CA1254208A (en]) |
| CH (1) | CH653032A5 (en]) |
| CS (1) | CS235302B2 (en]) |
| DD (1) | DD202575A5 (en]) |
| DE (1) | DE3226921C2 (en]) |
| DK (1) | DK160875C (en]) |
| ES (2) | ES514126A0 (en]) |
| FI (1) | FI71320C (en]) |
| FR (1) | FR2510575B1 (en]) |
| GB (1) | GB2102801B (en]) |
| GR (1) | GR76874B (en]) |
| HU (1) | HU184960B (en]) |
| IL (1) | IL66277A (en]) |
| IN (1) | IN155994B (en]) |
| IT (1) | IT1190920B (en]) |
| MX (1) | MX159288A (en]) |
| NL (1) | NL8202908A (en]) |
| NO (1) | NO157421C (en]) |
| PH (1) | PH18502A (en]) |
| PL (2) | PL135814B1 (en]) |
| PT (1) | PT75265B (en]) |
| SE (1) | SE450704B (en]) |
| SU (2) | SU1222197A3 (en]) |
| YU (1) | YU45867B (en]) |
| ZA (1) | ZA824809B (en]) |
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 |
| AU699465B2 (en) * | 1993-12-29 | 1998-12-03 | Pfizer Inc. | Diazabicyclic neurokinin antagonists |
| GB9726630D0 (en) * | 1997-12-18 | 1998-02-18 | Glaxo Group Ltd | Kv2.1 Antagonists |
| AU1996301A (en) | 1999-12-14 | 2001-06-25 | Neurosearch A/S | Novel heteroaryl-diazabicycloalkanes |
| PT1731518E (pt) | 2004-03-31 | 2014-09-18 | Nippon Soda Co | Composto amina cíclico e agente de controlo de pragas |
| UA86328C2 (uk) * | 2005-10-06 | 2009-04-10 | Ниппон Сода Ко., Лтд. | Циклічні амінові сполуки, засіб для боротьби зі шкідниками |
| PL1932844T3 (pl) | 2005-10-06 | 2015-12-31 | Nippon Soda Co | Usieciowane cykliczne związki aminowe i środki do zwalczania szkodników |
| WO2008132679A1 (en) * | 2007-04-27 | 2008-11-06 | Actelion Pharmaceuticals Ltd | Bridged six-membered ring compounds |
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 FI FI822526A patent/FI71320C/fi not_active IP Right Cessation
- 1982-07-15 GR GR68779A patent/GR76874B/el unknown
- 1982-07-15 CH CH4315/82A patent/CH653032A5/de not_active IP Right Cessation
- 1982-07-16 US US06/398,801 patent/US4451473A/en not_active Expired - Lifetime
- 1982-07-16 PT PT75265A patent/PT75265B/pt not_active IP Right Cessation
- 1982-07-16 DD DD82241725A patent/DD202575A5/de not_active IP Right Cessation
- 1982-07-16 DK DK319982A patent/DK160875C/da active
- 1982-07-19 PH PH27586A patent/PH18502A/en unknown
- 1982-07-19 SE SE8204393A patent/SE450704B/sv not_active IP Right Cessation
- 1982-07-19 MX MX193658A patent/MX159288A/es unknown
- 1982-07-19 SU SU823465423A patent/SU1222197A3/ru active
- 1982-07-19 YU YU157182A patent/YU45867B/sh 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 CS CS825520A patent/CS235302B2/cs unknown
- 1982-07-19 NL NL8202908A patent/NL8202908A/nl not_active Application Discontinuation
- 1982-07-19 NO NO822485A patent/NO157421C/no unknown
- 1982-07-19 GB GB08220818A patent/GB2102801B/en not_active Expired
- 1982-07-19 IT IT22448/82A patent/IT1190920B/it active
- 1982-07-19 JP JP57125600A patent/JPS5849383A/ja active Granted
- 1982-07-19 ES ES514126A patent/ES514126A0/es active Granted
- 1982-07-19 AU AU86176/82A patent/AU552770B2/en not_active Ceased
- 1982-07-19 FR FR8212572A patent/FR2510575B1/fr not_active Expired
- 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
- 1982-07-20 IN IN832/CAL/82A patent/IN155994B/en unknown
-
1983
- 1983-03-14 ES ES520567A patent/ES520567A0/es active Granted
- 1983-09-22 SU SU833646755A patent/SU1272990A3/ru active
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