CA1084057A - 3-substituted-5-phenyl-5-pyridyl hydantoins - Google Patents
3-substituted-5-phenyl-5-pyridyl hydantoinsInfo
- Publication number
- CA1084057A CA1084057A CA263,467A CA263467A CA1084057A CA 1084057 A CA1084057 A CA 1084057A CA 263467 A CA263467 A CA 263467A CA 1084057 A CA1084057 A CA 1084057A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- pyridyl
- compound
- hydantoin
- piperidyl
- 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.)
- Expired
Links
- -1 3-substituted-5-phenyl-5-pyridyl hydantoins Chemical class 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 11
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 11
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 102
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 238000010992 reflux Methods 0.000 claims description 14
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- MOPNUALPUUGSHV-UHFFFAOYSA-N 5-phenyl-3-[3-(4-phenylpiperidin-1-yl)propyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2N=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN(CC1)CCC1C1=CC=CC=C1 MOPNUALPUUGSHV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- RCYLZMNKASDGTJ-UHFFFAOYSA-N 5-phenyl-3-[3-(4-phenylpiperidin-1-yl)propyl]-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2C=CN=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN(CC1)CCC1C1=CC=CC=C1 RCYLZMNKASDGTJ-UHFFFAOYSA-N 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- GPLZLLHJTRBCBY-UHFFFAOYSA-N 5-phenyl-3-[3-(4-phenylpiperidin-1-yl)propyl]-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2C=NC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN(CC1)CCC1C1=CC=CC=C1 GPLZLLHJTRBCBY-UHFFFAOYSA-N 0.000 claims description 4
- VRQDOVYCRPSXLU-UHFFFAOYSA-N 3-[3-(4-hydroxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 VRQDOVYCRPSXLU-UHFFFAOYSA-N 0.000 claims description 3
- RRQKNNRRIBWQOO-UHFFFAOYSA-N 5-phenyl-3-[2-(4-phenylpiperidin-1-yl)ethyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2N=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCN(CC1)CCC1C1=CC=CC=C1 RRQKNNRRIBWQOO-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- BFZYGDREJMDJDY-UHFFFAOYSA-N 3-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 BFZYGDREJMDJDY-UHFFFAOYSA-N 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 3
- OUSCZLDZHTXERY-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-[3-(4-hydroxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound OC(=O)\C=C/C(O)=O.C1CC(O)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 OUSCZLDZHTXERY-BTJKTKAUSA-N 0.000 claims 2
- WJTXQGSHHKYDCS-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-phenyl-3-[3-(4-phenylpiperidin-1-yl)propyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound OC(=O)\C=C/C(O)=O.O=C1NC(C=2N=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN(CC1)CCC1C1=CC=CC=C1 WJTXQGSHHKYDCS-BTJKTKAUSA-N 0.000 claims 2
- OGWICGFMYNMQID-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-phenyl-3-[3-(4-phenylpiperidin-1-yl)propyl]-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound OC(=O)\C=C/C(O)=O.O=C1NC(C=2C=NC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN(CC1)CCC1C1=CC=CC=C1 OGWICGFMYNMQID-BTJKTKAUSA-N 0.000 claims 2
- KYEQBVHBWVYCMH-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-phenyl-3-[3-(4-phenylpiperidin-1-yl)propyl]-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound OC(=O)\C=C/C(O)=O.O=C1NC(C=2C=CN=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCN(CC1)CCC1C1=CC=CC=C1 KYEQBVHBWVYCMH-BTJKTKAUSA-N 0.000 claims 2
- LWJYZYZSGHPCIH-UHFFFAOYSA-N 3-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 LWJYZYZSGHPCIH-UHFFFAOYSA-N 0.000 claims 2
- IJJWDUJWOVOXRW-UHFFFAOYSA-N 3-[(4-methoxy-4-phenylpiperidin-1-yl)methyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 IJJWDUJWOVOXRW-UHFFFAOYSA-N 0.000 claims 2
- WZLDAMIQNFMRAP-UHFFFAOYSA-N 3-[2-(4-hydroxy-4-phenylpiperidin-1-yl)ethyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 WZLDAMIQNFMRAP-UHFFFAOYSA-N 0.000 claims 2
- CYFQSHLRLARQQK-UHFFFAOYSA-N 3-[2-(4-hydroxy-4-phenylpiperidin-1-yl)ethyl]-5-phenyl-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1C=NC=CC=1)C1=CC=CC=C1 CYFQSHLRLARQQK-UHFFFAOYSA-N 0.000 claims 2
- WENGAKPUMVROJX-UHFFFAOYSA-N 3-[2-(4-hydroxy-4-phenylpiperidin-1-yl)ethyl]-5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 WENGAKPUMVROJX-UHFFFAOYSA-N 0.000 claims 2
- RGHPZFMGWSGMPE-UHFFFAOYSA-N 3-[2-(4-methoxy-4-phenylpiperidin-1-yl)ethyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 RGHPZFMGWSGMPE-UHFFFAOYSA-N 0.000 claims 2
- OYWKKFKIYDPYPL-UHFFFAOYSA-N 3-[2-(4-methoxy-4-phenylpiperidin-1-yl)ethyl]-5-phenyl-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1C=NC=CC=1)C1=CC=CC=C1 OYWKKFKIYDPYPL-UHFFFAOYSA-N 0.000 claims 2
- FRINHHRJUVRUTD-UHFFFAOYSA-N 3-[2-(4-methoxy-4-phenylpiperidin-1-yl)ethyl]-5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 FRINHHRJUVRUTD-UHFFFAOYSA-N 0.000 claims 2
- JUIRIEMYBTXZHE-UHFFFAOYSA-N 3-[3-(4-hydroxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1C=NC=CC=1)C1=CC=CC=C1 JUIRIEMYBTXZHE-UHFFFAOYSA-N 0.000 claims 2
- LRMRIEGYVRHDDI-UHFFFAOYSA-N 3-[3-(4-hydroxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 LRMRIEGYVRHDDI-UHFFFAOYSA-N 0.000 claims 2
- PDZMIKHCTXHGLD-UHFFFAOYSA-N 3-[3-(4-methoxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 PDZMIKHCTXHGLD-UHFFFAOYSA-N 0.000 claims 2
- MVOBHWANVCSWRC-UHFFFAOYSA-N 3-[3-(4-methoxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1C=NC=CC=1)C1=CC=CC=C1 MVOBHWANVCSWRC-UHFFFAOYSA-N 0.000 claims 2
- KJQAGBCYZDAJGB-UHFFFAOYSA-N 3-[3-(4-methoxy-4-phenylpiperidin-1-yl)propyl]-5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(OC)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 KJQAGBCYZDAJGB-UHFFFAOYSA-N 0.000 claims 2
- IVGXNGVOWWRZGN-UHFFFAOYSA-N 5-phenyl-3-[(4-phenyl-4-propoxypiperidin-1-yl)methyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 IVGXNGVOWWRZGN-UHFFFAOYSA-N 0.000 claims 2
- VFWOKDDVWZYSFW-UHFFFAOYSA-N 5-phenyl-3-[(4-phenylpiperidin-1-yl)methyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2N=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CN(CC1)CCC1C1=CC=CC=C1 VFWOKDDVWZYSFW-UHFFFAOYSA-N 0.000 claims 2
- CZIJVYNLHGCFSR-UHFFFAOYSA-N 5-phenyl-3-[(4-phenylpiperidin-1-yl)methyl]-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2C=CN=CC=2)(C=2C=CC=CC=2)C(=O)N1CN(CC1)CCC1C1=CC=CC=C1 CZIJVYNLHGCFSR-UHFFFAOYSA-N 0.000 claims 2
- FEEPWYMVDNBPSP-UHFFFAOYSA-N 5-phenyl-3-[2-(4-phenyl-4-propoxypiperidin-1-yl)ethyl]-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1C=NC=CC=1)C1=CC=CC=C1 FEEPWYMVDNBPSP-UHFFFAOYSA-N 0.000 claims 2
- WVQIZYFHBHAVQP-UHFFFAOYSA-N 5-phenyl-3-[2-(4-phenyl-4-propoxypiperidin-1-yl)ethyl]-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 WVQIZYFHBHAVQP-UHFFFAOYSA-N 0.000 claims 2
- RTHHLQQNEQIKNH-UHFFFAOYSA-N 5-phenyl-3-[2-(4-phenylpiperidin-1-yl)ethyl]-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2C=NC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCN(CC1)CCC1C1=CC=CC=C1 RTHHLQQNEQIKNH-UHFFFAOYSA-N 0.000 claims 2
- WHQNSQAMDZVJAB-UHFFFAOYSA-N 5-phenyl-3-[2-(4-phenylpiperidin-1-yl)ethyl]-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound O=C1NC(C=2C=CN=CC=2)(C=2C=CC=CC=2)C(=O)N1CCN(CC1)CCC1C1=CC=CC=C1 WHQNSQAMDZVJAB-UHFFFAOYSA-N 0.000 claims 2
- FGNQVTGSSVGRHL-UHFFFAOYSA-N 5-phenyl-3-[3-(4-phenyl-4-propoxypiperidin-1-yl)propyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 FGNQVTGSSVGRHL-UHFFFAOYSA-N 0.000 claims 2
- MMBJUCAHXPRSTA-UHFFFAOYSA-N 5-phenyl-3-[3-(4-phenyl-4-propoxypiperidin-1-yl)propyl]-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1C=NC=CC=1)C1=CC=CC=C1 MMBJUCAHXPRSTA-UHFFFAOYSA-N 0.000 claims 2
- DNWDGWIFFAFFBF-UHFFFAOYSA-N 5-phenyl-3-[3-(4-phenyl-4-propoxypiperidin-1-yl)propyl]-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CCCN(C1=O)C(=O)NC1(C=1C=CN=CC=1)C1=CC=CC=C1 DNWDGWIFFAFFBF-UHFFFAOYSA-N 0.000 claims 2
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 claims 2
- SWTXBMYIAUISDS-UHFFFAOYSA-N 5-phenyl-3-[2-(4-phenyl-4-propoxypiperidin-1-yl)ethyl]-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound C1CC(OCCC)(C=2C=CC=CC=2)CCN1CCN(C1=O)C(=O)NC1(C=1N=CC=CC=1)C1=CC=CC=C1 SWTXBMYIAUISDS-UHFFFAOYSA-N 0.000 claims 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 abstract description 8
- 230000006793 arrhythmia Effects 0.000 abstract description 7
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 238000002512 chemotherapy Methods 0.000 abstract description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 16
- 230000003288 anthiarrhythmic effect Effects 0.000 description 10
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 9
- 239000003416 antiarrhythmic agent Substances 0.000 description 8
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 8
- 229960001404 quinidine Drugs 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- PINMPUBSZMXYMA-UHFFFAOYSA-N 5-phenyl-5-pyridin-3-ylimidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)C1(C=1C=NC=CC=1)C1=CC=CC=C1 PINMPUBSZMXYMA-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- FMDLEALHAOALOD-UHFFFAOYSA-N 5-phenyl-5-pyridin-2-ylimidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)C1(C=1N=CC=CC=1)C1=CC=CC=C1 FMDLEALHAOALOD-UHFFFAOYSA-N 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- VYUUHZBFLMZUHW-UHFFFAOYSA-N 5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)C1(C=1C=CN=CC=1)C1=CC=CC=C1 VYUUHZBFLMZUHW-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
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- 230000001225 therapeutic effect Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- PEXVQAFFEHJDBW-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperidine Chemical compound C1CN(CCCCl)CCC1C1=CC=CC=C1 PEXVQAFFEHJDBW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
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- 229960002036 phenytoin Drugs 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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- CVSAHWJKZJHWRK-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCN(CCCCl)CC1 CVSAHWJKZJHWRK-UHFFFAOYSA-N 0.000 description 2
- KPZNLTOEEUQWOP-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperidine;hydrochloride Chemical compound Cl.C1CN(CCCCl)CCC1C1=CC=CC=C1 KPZNLTOEEUQWOP-UHFFFAOYSA-N 0.000 description 2
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- OLKRUXJTEOUXJJ-UHFFFAOYSA-N 1-(2-chloroethyl)-4-methoxy-4-phenylpiperidine Chemical compound C=1C=CC=CC=1C1(OC)CCN(CCCl)CC1 OLKRUXJTEOUXJJ-UHFFFAOYSA-N 0.000 description 1
- RGNYDSWVHDVUNX-UHFFFAOYSA-N 1-(2-chloroethyl)-4-phenyl-4-propoxypiperidine Chemical compound C=1C=CC=CC=1C1(OCCC)CCN(CCCl)CC1 RGNYDSWVHDVUNX-UHFFFAOYSA-N 0.000 description 1
- MWUNJGWOIOLNPF-UHFFFAOYSA-N 1-(2-chloroethyl)-4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCN(CCCl)CC1 MWUNJGWOIOLNPF-UHFFFAOYSA-N 0.000 description 1
- RSOCHTLBPFYQLS-UHFFFAOYSA-N 1-(3-chloropropyl)-4-methoxy-4-phenylpiperidine Chemical compound C=1C=CC=CC=1C1(OC)CCN(CCCCl)CC1 RSOCHTLBPFYQLS-UHFFFAOYSA-N 0.000 description 1
- JPICBPJRTPGTRJ-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenyl-4-propoxypiperidine Chemical compound C=1C=CC=CC=1C1(OCCC)CCN(CCCCl)CC1 JPICBPJRTPGTRJ-UHFFFAOYSA-N 0.000 description 1
- MEUVQYDLGMHBHQ-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperidin-4-ol;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(O)CCN(CCCCl)CC1 MEUVQYDLGMHBHQ-UHFFFAOYSA-N 0.000 description 1
- PDZAPWVREPSGDT-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxy-4-phenylpiperidine Chemical compound C=1C=CC=CC=1C1(OC)CCN(CCl)CC1 PDZAPWVREPSGDT-UHFFFAOYSA-N 0.000 description 1
- GKDZIHVEXOCDIT-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylpiperidine Chemical class C1CN(CCl)CCC1C1=CC=CC=C1 GKDZIHVEXOCDIT-UHFFFAOYSA-N 0.000 description 1
- LYJLGWRMOGHUMS-UHFFFAOYSA-N 1-[1-(3-chloropropyl)cyclohexa-2,4-dien-1-yl]piperidine Chemical compound C1CCCCN1C1(CCCCl)CC=CC=C1 LYJLGWRMOGHUMS-UHFFFAOYSA-N 0.000 description 1
- ZKISCCNMDWZDCF-UHFFFAOYSA-N 4-methoxy-4-phenylpiperidine Chemical compound C=1C=CC=CC=1C1(OC)CCNCC1 ZKISCCNMDWZDCF-UHFFFAOYSA-N 0.000 description 1
- ODLGSHHBBCINCC-UHFFFAOYSA-N 4-phenyl-4-propoxypiperidine Chemical compound C=1C=CC=CC=1C1(OCCC)CCNCC1 ODLGSHHBBCINCC-UHFFFAOYSA-N 0.000 description 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 206010003662 Atrial flutter Diseases 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
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- 241000208011 Digitalis Species 0.000 description 1
- 206010015856 Extrasystoles Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000000418 Premature Cardiac Complexes Diseases 0.000 description 1
- 206010038669 Respiratory arrest Diseases 0.000 description 1
- 208000003734 Supraventricular Tachycardia Diseases 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 210000000188 diaphragm Anatomy 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 230000037024 effective refractory period Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- UPZJLQCUYUTZIE-UHFFFAOYSA-N hydron;4-phenylpiperidine;chloride Chemical compound Cl.C1CNCCC1C1=CC=CC=C1 UPZJLQCUYUTZIE-UHFFFAOYSA-N 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical class C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 description 1
- 230000008288 physiological mechanism Effects 0.000 description 1
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- 229960000948 quinine Drugs 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/664,920 US3994904A (en) | 1976-03-08 | 1976-03-08 | 3-Substituted -5-phenyl-5-pyridyl hydantoins |
| US664,920 | 1976-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1084057A true CA1084057A (en) | 1980-08-19 |
Family
ID=24667998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,467A Expired CA1084057A (en) | 1976-03-08 | 1976-10-15 | 3-substituted-5-phenyl-5-pyridyl hydantoins |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3994904A (en, 2012) |
| JP (1) | JPS52108979A (en, 2012) |
| BE (1) | BE848385A (en, 2012) |
| CA (1) | CA1084057A (en, 2012) |
| DE (1) | DE2649707A1 (en, 2012) |
| FR (1) | FR2343477A1 (en, 2012) |
| GB (1) | GB1533642A (en, 2012) |
| NL (1) | NL7612713A (en, 2012) |
| ZA (1) | ZA766199B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6355659B1 (en) | 1994-07-29 | 2002-03-12 | Laboratorios Del Dr. Esteve, S.A. | 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same |
| FR2723091B1 (fr) * | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
| GB2355456A (en) * | 1999-09-30 | 2001-04-25 | Merck & Co Inc | Novel arylhydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
| US7687072B2 (en) * | 2002-10-31 | 2010-03-30 | Auburn University | Biocidal particles of methylated polystyrene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526231A (en) * | 1946-10-21 | 1950-10-17 | Parke Davis & Co | 5-phenyl-5-pyridyl hydantoins |
| US3892748A (en) * | 1973-07-20 | 1975-07-01 | Miles Lab | 5,5-Diphenyl-3-(piperidino, tetrahydropyridyl-1-and piperazino)-hydantoins |
-
1976
- 1976-03-08 US US05/664,920 patent/US3994904A/en not_active Expired - Lifetime
- 1976-10-04 US US05/729,164 patent/US4061760A/en not_active Expired - Lifetime
- 1976-10-15 CA CA263,467A patent/CA1084057A/en not_active Expired
- 1976-10-18 ZA ZA766199A patent/ZA766199B/xx unknown
- 1976-10-22 GB GB44015/76A patent/GB1533642A/en not_active Expired
- 1976-10-29 DE DE19762649707 patent/DE2649707A1/de active Pending
- 1976-11-15 JP JP13643276A patent/JPS52108979A/ja active Granted
- 1976-11-15 FR FR7634363A patent/FR2343477A1/fr not_active Withdrawn
- 1976-11-16 BE BE172399A patent/BE848385A/xx unknown
- 1976-11-16 NL NL7612713A patent/NL7612713A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52108979A (en) | 1977-09-12 |
| US3994904A (en) | 1976-11-30 |
| DE2649707A1 (de) | 1977-09-15 |
| JPS5547638B2 (en, 2012) | 1980-12-01 |
| AU1880876A (en) | 1977-09-01 |
| FR2343477A1 (fr) | 1977-10-07 |
| US4061760A (en) | 1977-12-06 |
| BE848385A (fr) | 1977-05-16 |
| ZA766199B (en) | 1977-09-28 |
| GB1533642A (en) | 1978-11-29 |
| NL7612713A (nl) | 1977-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19970819 |