NO792901L - Alfa-aryl-alfa,alfa-bis(omega-(disubstituert amino)alkyl)-ag cetamidforbindelser og fremgangsmaate til deres fremstillin - Google Patents
Alfa-aryl-alfa,alfa-bis(omega-(disubstituert amino)alkyl)-ag cetamidforbindelser og fremgangsmaate til deres fremstillinInfo
- Publication number
- NO792901L NO792901L NO792901A NO792901A NO792901L NO 792901 L NO792901 L NO 792901L NO 792901 A NO792901 A NO 792901A NO 792901 A NO792901 A NO 792901A NO 792901 L NO792901 L NO 792901L
- Authority
- NO
- Norway
- Prior art keywords
- alpha
- carbon atoms
- lower alkyl
- alk
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 77
- -1 AMINO Chemical class 0.000 title claims description 54
- 238000002360 preparation method Methods 0.000 title abstract description 4
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 title 1
- 229940047583 cetamide Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 64
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 231100000252 nontoxic Toxicity 0.000 claims description 25
- 230000003000 nontoxic effect Effects 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 14
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 14
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 2
- IXOVQCURABUBQE-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]acetamide Chemical compound CC(C)N(C(C)C)CCNC(C)=O IXOVQCURABUBQE-UHFFFAOYSA-N 0.000 claims description 2
- SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 134
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000006467 substitution reaction Methods 0.000 description 24
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- DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- 238000002425 crystallisation Methods 0.000 description 8
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- 235000011132 calcium sulphate Nutrition 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- WNAGNSRMNMQWRI-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-naphthalen-1-ylbutanenitrile Chemical compound C1=CC=C2C(C(C#N)CCN(C(C)C)C(C)C)=CC=CC2=C1 WNAGNSRMNMQWRI-UHFFFAOYSA-N 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 4
- HFZWZBJJPJQAEZ-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-(4-phenylphenyl)butanenitrile Chemical compound C1=CC(C(C#N)CCN(C(C)C)C(C)C)=CC=C1C1=CC=CC=C1 HFZWZBJJPJQAEZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- ZAETYTPFTJNPQR-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-phenylbutanenitrile Chemical compound CC(C)N(C(C)C)CCC(C#N)C1=CC=CC=C1 ZAETYTPFTJNPQR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 244000166550 Strophanthus gratus Species 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 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 3
- 229960003343 ouabain Drugs 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- QNINGUUJGUIPOJ-UHFFFAOYSA-N 1-(2-chloroethyl)-4-phenylpiperidine Chemical compound C1CN(CCCl)CCC1C1=CC=CC=C1 QNINGUUJGUIPOJ-UHFFFAOYSA-N 0.000 description 2
- DQTOCXIHYIQHCK-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=C(Br)C(CBr)=CC=C21 DQTOCXIHYIQHCK-UHFFFAOYSA-N 0.000 description 2
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- LEHUXYKZQGAKGG-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-(2-fluorophenyl)butanenitrile Chemical compound CC(C)N(C(C)C)CCC(C#N)C1=CC=CC=C1F LEHUXYKZQGAKGG-UHFFFAOYSA-N 0.000 description 2
- SWVUWKUFMMUEDC-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]butanenitrile Chemical compound CC(C)N(C(C)C)CCCC#N SWVUWKUFMMUEDC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 2
- 150000007960 acetonitrile Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001624 naphthyl group Chemical class 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
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- VLVZLKYJLMZLOO-UHFFFAOYSA-N 2-(1-bromonaphthalen-2-yl)-2-[2-[di(propan-2-yl)amino]ethyl]-4-piperidin-1-ylbutanenitrile Chemical compound C=1C=C2C=CC=CC2=C(Br)C=1C(CCN(C(C)C)C(C)C)(C#N)CCN1CCCCC1 VLVZLKYJLMZLOO-UHFFFAOYSA-N 0.000 description 1
- HDWQTJPZSOKPOX-UHFFFAOYSA-N 2-[2-(2,6-dimethylpiperidin-1-yl)ethyl]-4-[di(propan-2-yl)amino]-2-(2-fluorophenyl)butanenitrile Chemical compound C=1C=CC=C(F)C=1C(CCN(C(C)C)C(C)C)(C#N)CCN1C(C)CCCC1C HDWQTJPZSOKPOX-UHFFFAOYSA-N 0.000 description 1
- NYBGFANHLQXKCP-UHFFFAOYSA-N 2-[2-[cyclohexyl(methyl)amino]ethyl]-4-[di(propan-2-yl)amino]-2-(4-phenylphenyl)butanenitrile Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CCN(C(C)C)C(C)C)(C#N)CCN(C)C1CCCCC1 NYBGFANHLQXKCP-UHFFFAOYSA-N 0.000 description 1
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- PHHQMXOWHQUKJR-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-[2-[di(propan-2-yl)amino]ethyl]-3-methyl-2-naphthalen-1-ylbutanamide Chemical compound C1=CC=C2C(C(C(C)CN(C(C)C)C(C)C)(C(N)=O)CCN(C(C)C)C(C)C)=CC=CC2=C1 PHHQMXOWHQUKJR-UHFFFAOYSA-N 0.000 description 1
- HHTRXBLDKUYFRT-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-[2-[di(propan-2-yl)amino]ethyl]-3-methyl-2-naphthalen-1-ylbutanenitrile Chemical compound C1=CC=C2C(C(C#N)(C(C)CN(C(C)C)C(C)C)CCN(C(C)C)C(C)C)=CC=CC2=C1 HHTRXBLDKUYFRT-UHFFFAOYSA-N 0.000 description 1
- STHPVHWYIVPVDY-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-[2-[di(propan-2-yl)amino]ethyl]-3-methyl-2-phenylbutanenitrile Chemical compound CC(C)N(C(C)C)CCC(C#N)(C(C)CN(C(C)C)C(C)C)C1=CC=CC=C1 STHPVHWYIVPVDY-UHFFFAOYSA-N 0.000 description 1
- KNFCDGOYLDBMDI-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-naphthalen-2-ylbutanenitrile Chemical compound C1=CC=CC2=CC(C(C#N)CCN(C(C)C)C(C)C)=CC=C21 KNFCDGOYLDBMDI-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 206010015856 Extrasystoles Diseases 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- MCVHNCIHXMQWGY-UHFFFAOYSA-N n-(2-chloroethyl)-n-methylcyclohexanamine Chemical compound ClCCN(C)C1CCCCC1 MCVHNCIHXMQWGY-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance 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
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/940,527 US4217306A (en) | 1978-05-01 | 1978-09-08 | α-Aryl-α,α-bis[ω-(disubstituted amino)alkyl]-acetamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO792901L true NO792901L (no) | 1980-03-11 |
Family
ID=25474978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO792901A NO792901L (no) | 1978-09-08 | 1979-09-07 | Alfa-aryl-alfa,alfa-bis(omega-(disubstituert amino)alkyl)-ag cetamidforbindelser og fremgangsmaate til deres fremstillin |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4217306A (xx) |
| JP (1) | JPS5592350A (xx) |
| AT (3) | AT364813B (xx) |
| AU (1) | AU5068679A (xx) |
| BE (1) | BE878662A (xx) |
| CA (1) | CA1136622A (xx) |
| DE (1) | DE2936287A1 (xx) |
| DK (1) | DK374879A (xx) |
| ES (1) | ES483985A1 (xx) |
| FI (1) | FI792780A (xx) |
| FR (1) | FR2435462A1 (xx) |
| GB (1) | GB2030984B (xx) |
| GR (1) | GR72494B (xx) |
| IL (1) | IL58200A (xx) |
| IT (1) | IT1120561B (xx) |
| NL (1) | NL7906745A (xx) |
| NO (1) | NO792901L (xx) |
| NZ (1) | NZ191505A (xx) |
| PT (1) | PT70151B (xx) |
| SE (1) | SE7907432L (xx) |
| ZA (1) | ZA794764B (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5097035A (en) * | 1984-07-09 | 1992-03-17 | G. D. Searle & Co. | Monobasic disobutamide derivatives |
| US4639524A (en) * | 1984-07-09 | 1987-01-27 | G. D. Searle & Co. | Monobasic disobutamide derivatives |
| US4791199A (en) * | 1985-09-19 | 1988-12-13 | G. D. Searle & Co. | Process for antiarrhythmic 1,3-diazabicyclo[4.4.0]dec-2-en-4-ones |
| EP0370712A3 (en) * | 1988-11-18 | 1991-10-02 | Ajinomoto Co., Inc. | Ethylamine derivatives and hypotensives containing the same |
| FR2686339B1 (fr) * | 1992-01-22 | 1994-03-11 | Adir Cie | Nouveaux amides et sulfonamides naphtaleniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5432284A (en) * | 1993-09-08 | 1995-07-11 | G. D. Searle & Co. | Process for the preparation of heterocyclic alkylamide derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2884436A (en) * | 1954-08-28 | 1959-04-28 | Nl Combinatie Chem Ind | Parasympathicolytically active alpha, alpha-diphenyl-gamma-dialkylaminobutyramide compounds and manufacture thereof |
| US3022314A (en) * | 1955-06-20 | 1962-02-20 | Upjohn Co | Alpha-phenyl-omega-amino-alkanamides |
| US3022302A (en) * | 1956-03-15 | 1962-02-20 | Pharmacia Ab | Manufacture of nu, nu-disubstituted amides of aryl acetic acids |
| US3078275A (en) * | 1956-05-28 | 1963-02-19 | Upjohn Co | N, n-disubstituted-alpha-(tertiaryaminoalkyl)-alpha, alpha-diphenylacetamides |
| US2894955A (en) * | 1956-11-19 | 1959-07-14 | Upjohn Co | Organic compounds |
| US3225091A (en) * | 1962-02-01 | 1965-12-21 | Lilly Co Eli | Anticholinergic substituted butyramides |
| NL124729C (xx) * | 1963-05-14 | |||
| US4107205A (en) * | 1977-03-11 | 1978-08-15 | G. D. Searle & Co. | α-Aryl-α,α-bis[ω-(disubstituted amino)alkyl]acetamides and related compounds |
-
1978
- 1978-09-08 US US05/940,527 patent/US4217306A/en not_active Expired - Lifetime
-
1979
- 1979-09-07 AU AU50686/79A patent/AU5068679A/en not_active Abandoned
- 1979-09-07 GR GR59993A patent/GR72494B/el unknown
- 1979-09-07 DK DK374879A patent/DK374879A/da not_active Application Discontinuation
- 1979-09-07 GB GB7931218A patent/GB2030984B/en not_active Expired
- 1979-09-07 AT AT0592679A patent/AT364813B/de not_active IP Right Cessation
- 1979-09-07 FI FI792780A patent/FI792780A/fi not_active Application Discontinuation
- 1979-09-07 BE BE0/197051A patent/BE878662A/fr unknown
- 1979-09-07 NO NO792901A patent/NO792901L/no unknown
- 1979-09-07 JP JP11508979A patent/JPS5592350A/ja active Pending
- 1979-09-07 ZA ZA00794764A patent/ZA794764B/xx unknown
- 1979-09-07 FR FR7922468A patent/FR2435462A1/fr active Pending
- 1979-09-07 SE SE7907432A patent/SE7907432L/xx not_active Application Discontinuation
- 1979-09-07 IT IT50202/79A patent/IT1120561B/it active
- 1979-09-07 PT PT70151A patent/PT70151B/pt unknown
- 1979-09-07 CA CA000335200A patent/CA1136622A/en not_active Expired
- 1979-09-07 ES ES483985A patent/ES483985A1/es not_active Expired
- 1979-09-07 NZ NZ191505A patent/NZ191505A/xx unknown
- 1979-09-07 IL IL58200A patent/IL58200A/xx unknown
- 1979-09-07 DE DE19792936287 patent/DE2936287A1/de not_active Withdrawn
- 1979-09-10 NL NL7906745A patent/NL7906745A/nl not_active Application Discontinuation
-
1980
- 1980-12-10 AT AT0600280A patent/AT370088B/de not_active IP Right Cessation
- 1980-12-10 AT AT0600180A patent/AT370087B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA600180A (de) | 1982-07-15 |
| CA1136622A (en) | 1982-11-30 |
| IL58200A0 (en) | 1979-12-30 |
| DE2936287A1 (de) | 1980-03-20 |
| ES483985A1 (es) | 1980-04-16 |
| GB2030984A (en) | 1980-04-16 |
| ZA794764B (en) | 1981-04-29 |
| FR2435462A1 (fr) | 1980-04-04 |
| NZ191505A (en) | 1982-03-30 |
| FI792780A (fi) | 1980-03-09 |
| GB2030984B (en) | 1983-07-27 |
| AT370087B (de) | 1983-02-25 |
| JPS5592350A (en) | 1980-07-12 |
| IT7950202A0 (it) | 1979-09-07 |
| NL7906745A (nl) | 1980-03-11 |
| ATA600280A (de) | 1982-07-15 |
| PT70151B (pt) | 1981-12-11 |
| US4217306A (en) | 1980-08-12 |
| AU5068679A (en) | 1980-03-27 |
| IL58200A (en) | 1982-12-31 |
| IT1120561B (it) | 1986-03-26 |
| DK374879A (da) | 1980-03-09 |
| AT370088B (de) | 1983-02-25 |
| BE878662A (fr) | 1980-03-07 |
| SE7907432L (sv) | 1980-03-09 |
| AT364813B (de) | 1981-11-25 |
| PT70151A (en) | 1979-09-01 |
| ATA592679A (de) | 1981-04-15 |
| GR72494B (xx) | 1983-11-15 |
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