CA1166158A - Agents for treating diseases in circulatory organs - Google Patents
Agents for treating diseases in circulatory organsInfo
- Publication number
- CA1166158A CA1166158A CA000379686A CA379686A CA1166158A CA 1166158 A CA1166158 A CA 1166158A CA 000379686 A CA000379686 A CA 000379686A CA 379686 A CA379686 A CA 379686A CA 1166158 A CA1166158 A CA 1166158A
- Authority
- CA
- Canada
- Prior art keywords
- agent according
- piperazine
- piperazine compound
- salt
- compound
- 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 9
- 201000010099 disease Diseases 0.000 title claims abstract description 8
- 210000000056 organ Anatomy 0.000 title claims abstract description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- -1 piperazine compound Chemical class 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 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 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 239000008101 lactose Substances 0.000 claims description 6
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 208000019622 heart disease Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 210000005259 peripheral blood Anatomy 0.000 claims description 2
- 239000011886 peripheral blood Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229940124549 vasodilator Drugs 0.000 claims description 2
- 239000003071 vasodilator agent Substances 0.000 claims description 2
- 208000020446 Cardiac disease Diseases 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 230000036772 blood pressure Effects 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000017531 blood circulation Effects 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 230000009885 systemic effect Effects 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000002490 cerebral effect Effects 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- IMAWRJZYXYLGBL-UHFFFAOYSA-N 2-methoxy-1-phenylpiperazine Chemical compound COC1CNCCN1C1=CC=CC=C1 IMAWRJZYXYLGBL-UHFFFAOYSA-N 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000011872 intimate mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000001168 carotid artery common Anatomy 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QQSDCUORXOXRSZ-UHFFFAOYSA-N ethyl 6-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]hexanoate Chemical compound C1CN(CCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC(C)C QQSDCUORXOXRSZ-UHFFFAOYSA-N 0.000 description 3
- ICBAZWPFWUMUGZ-UHFFFAOYSA-N ethyl 7-[4-(2-methoxyphenyl)piperazin-1-yl]heptanoate Chemical compound C1CN(CCCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC ICBAZWPFWUMUGZ-UHFFFAOYSA-N 0.000 description 3
- UUMVQLKOADOZPL-UHFFFAOYSA-N ethyl 7-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]heptanoate Chemical compound C1CN(CCCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC(C)C UUMVQLKOADOZPL-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 3
- MBQCUNZRKORVBQ-UHFFFAOYSA-N methyl 7-[4-(2-methoxyphenyl)piperazin-1-yl]heptanoate Chemical compound C1CN(CCCCCCC(=O)OC)CCN1C1=CC=CC=C1OC MBQCUNZRKORVBQ-UHFFFAOYSA-N 0.000 description 3
- 210000002254 renal artery Anatomy 0.000 description 3
- HCZZEIJLVGYBEP-WLHGVMLRSA-N (e)-but-2-enedioic acid;ethyl 7-[4-(2-methoxyphenyl)piperazin-1-yl]heptanoate Chemical compound OC(=O)\C=C\C(O)=O.C1CN(CCCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC HCZZEIJLVGYBEP-WLHGVMLRSA-N 0.000 description 2
- NHGMVOCUWYRDNW-UHFFFAOYSA-N 1-phenyl-2-propan-2-yloxypiperazine Chemical compound CC(C)OC1CNCCN1C1=CC=CC=C1 NHGMVOCUWYRDNW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
- MPOYRJLESXRKKR-UHFFFAOYSA-N ethyl 5-[4-(2-methoxyphenyl)piperazin-1-yl]pentanoate Chemical compound C1CN(CCCCC(=O)OCC)CCN1C1=CC=CC=C1OC MPOYRJLESXRKKR-UHFFFAOYSA-N 0.000 description 2
- AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 2
- OOBFNDGMAGSNKA-UHFFFAOYSA-N ethyl 7-bromoheptanoate Chemical compound CCOC(=O)CCCCCCBr OOBFNDGMAGSNKA-UHFFFAOYSA-N 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- 239000007902 hard capsule Substances 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- QJULELIONYLITF-UHFFFAOYSA-N 1-(2-propan-2-yloxyphenyl)piperazine Chemical compound CC(C)OC1=CC=CC=C1N1CCNCC1 QJULELIONYLITF-UHFFFAOYSA-N 0.000 description 1
- CWINYJBSPMHNFC-UHFFFAOYSA-N 2-bromo-3-methylhexanoic acid Chemical compound CCCC(C)C(Br)C(O)=O CWINYJBSPMHNFC-UHFFFAOYSA-N 0.000 description 1
- ZTTWQKYKGNLCCA-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine Chemical compound N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 ZTTWQKYKGNLCCA-UHFFFAOYSA-N 0.000 description 1
- YBNRTIKUBPWTDQ-UHFFFAOYSA-N 7-[4-(2-methoxyphenyl)piperazin-1-yl]heptanoic acid Chemical compound COC1=CC=CC=C1N1CCN(CCCCCCC(O)=O)CC1 YBNRTIKUBPWTDQ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- QMTOOSGIZUKEOB-UHFFFAOYSA-N ethyl 5-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]pentanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCC(=O)OCC)CCN1C1=CC=CC=C1OC(C)C QMTOOSGIZUKEOB-UHFFFAOYSA-N 0.000 description 1
- GALHAPHTUOWASU-UHFFFAOYSA-N ethyl 6-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]hexanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC(C)C GALHAPHTUOWASU-UHFFFAOYSA-N 0.000 description 1
- DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 1
- AVYGFGAIGWSFJB-UHFFFAOYSA-N ethyl 7-[4-(2-methoxyphenyl)piperazin-1-yl]-3-methylheptanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCC(C)CC(=O)OCC)CCN1C1=CC=CC=C1OC AVYGFGAIGWSFJB-UHFFFAOYSA-N 0.000 description 1
- MJURRVGRIQWKFL-UHFFFAOYSA-N ethyl 7-[4-(2-methoxyphenyl)piperazin-1-yl]heptanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC MJURRVGRIQWKFL-UHFFFAOYSA-N 0.000 description 1
- DQVNRBKBVWDRPF-UHFFFAOYSA-N ethyl 7-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]heptanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCCCC(=O)OCC)CCN1C1=CC=CC=C1OC(C)C DQVNRBKBVWDRPF-UHFFFAOYSA-N 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960005384 hydralazine hydrochloride Drugs 0.000 description 1
- ZUXNZUWOTSUBMN-UHFFFAOYSA-N hydralazine hydrochloride Chemical compound Cl.C1=CC=C2C(NN)=NN=CC2=C1 ZUXNZUWOTSUBMN-UHFFFAOYSA-N 0.000 description 1
- ZGWQDMTYAQEMHA-UHFFFAOYSA-N hydron;1-(2-methoxyphenyl)piperazine;dichloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCNCC1 ZGWQDMTYAQEMHA-UHFFFAOYSA-N 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- SFAWEJDGDGMPBW-UHFFFAOYSA-N methyl 7-[4-(2-methoxyphenyl)piperazin-1-yl]heptanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCCCC(=O)OC)CCN1C1=CC=CC=C1OC SFAWEJDGDGMPBW-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 210000002385 vertebral artery Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- 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
- C07D295/15—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 to an acyclic saturated chain
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
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- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP79043/1980 | 1980-06-13 | ||
| JP7904380A JPS574921A (en) | 1980-06-13 | 1980-06-13 | Remedy for cardiovascular disorder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1166158A true CA1166158A (en) | 1984-04-24 |
Family
ID=13678875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000379686A Expired CA1166158A (en) | 1980-06-13 | 1981-06-12 | Agents for treating diseases in circulatory organs |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4438115A (en, 2012) |
| EP (1) | EP0042162B1 (en, 2012) |
| JP (1) | JPS574921A (en, 2012) |
| KR (1) | KR850000215B1 (en, 2012) |
| AR (1) | AR229471A1 (en, 2012) |
| AT (1) | ATE5372T1 (en, 2012) |
| CA (1) | CA1166158A (en, 2012) |
| DE (1) | DE3161490D1 (en, 2012) |
| ZA (1) | ZA813937B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4397855A (en) * | 1981-06-26 | 1983-08-09 | Warner-Lambert Company | 4-(Substituted)-α, α-dimethyl-1-piperazine pentanoic acids and derivatives as anti-arteriosclerotic agents and method |
| US4772475A (en) * | 1985-03-08 | 1988-09-20 | Yamanouchi Pharmaceutical Co., Ltd. | Controlled-release multiple units pharmaceutical formulation |
| JPH048416Y2 (en, 2012) * | 1985-10-15 | 1992-03-03 | ||
| GB2271930B (en) * | 1992-11-03 | 1996-07-24 | Wyeth John & Brother Ltd | Pharmaceutical piperazine derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH354084A (fr) * | 1955-06-29 | 1961-05-15 | Parke Davis & Co | Procédé de préparation de pipérazines |
| US2922788A (en) | 1958-05-26 | 1960-01-26 | Parke Davis & Co | Phenylpiperazine compounds and process for producing the same |
| BE662455A (en, 2012) * | 1964-04-14 | |||
| FR2326923A1 (fr) * | 1975-10-08 | 1977-05-06 | Bouchara Emile | Derives du bis(piperazinyl-1)-1,2 ethane |
| DE2555290A1 (de) * | 1975-12-09 | 1977-06-16 | Boehringer Mannheim Gmbh | Neue benzopyron-derivate und verfahren zu ihrer herstellung |
-
1980
- 1980-06-13 JP JP7904380A patent/JPS574921A/ja active Granted
-
1981
- 1981-06-10 US US06/272,077 patent/US4438115A/en not_active Expired - Fee Related
- 1981-06-11 ZA ZA813937A patent/ZA813937B/xx unknown
- 1981-06-12 AR AR285707A patent/AR229471A1/es active
- 1981-06-12 AT AT81104560T patent/ATE5372T1/de not_active IP Right Cessation
- 1981-06-12 CA CA000379686A patent/CA1166158A/en not_active Expired
- 1981-06-12 EP EP81104560A patent/EP0042162B1/en not_active Expired
- 1981-06-12 KR KR1019810002129A patent/KR850000215B1/ko not_active Expired
- 1981-06-12 DE DE8181104560T patent/DE3161490D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS574921A (en) | 1982-01-11 |
| DE3161490D1 (en) | 1983-12-29 |
| EP0042162A3 (en) | 1982-03-10 |
| EP0042162A2 (en) | 1981-12-23 |
| AR229471A1 (es) | 1983-08-31 |
| US4438115A (en) | 1984-03-20 |
| ATE5372T1 (de) | 1983-12-15 |
| EP0042162B1 (en) | 1983-11-23 |
| KR830006257A (ko) | 1983-09-20 |
| ZA813937B (en) | 1982-07-28 |
| KR850000215B1 (ko) | 1985-03-06 |
| JPH0138089B2 (en, 2012) | 1989-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |