PH26115A - Lactamimides as calcium antahonists - Google Patents
Lactamimides as calcium antahonists Download PDFInfo
- Publication number
- PH26115A PH26115A PH38861A PH38861A PH26115A PH 26115 A PH26115 A PH 26115A PH 38861 A PH38861 A PH 38861A PH 38861 A PH38861 A PH 38861A PH 26115 A PH26115 A PH 26115A
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- PH
- Philippines
- Prior art keywords
- carbon atoms
- group
- test compound
- imino
- integer
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- 239000011575 calcium Substances 0.000 title claims description 25
- 229910052791 calcium Inorganic materials 0.000 title claims description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- -1 2,2- diphenylpentyl Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000008485 antagonism Effects 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 3
- CKXZJIAJKYYQLR-UHFFFAOYSA-N n-(2-phenylphenyl)-1-azacyclotridecen-2-amine Chemical compound C1CCCCCCCCCCNC1=NC1=CC=CC=C1C1=CC=CC=C1 CKXZJIAJKYYQLR-UHFFFAOYSA-N 0.000 claims description 3
- WWPISVNKRIXADH-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-1-azacyclotridecen-2-amine Chemical compound C1CC2CC1CC2N=C1CCCCCCCCCCCN1 WWPISVNKRIXADH-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- QSIYTPCKNAPAJY-UHFFFAOYSA-N aluminum;ethoxy-oxido-oxophosphanium;2-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O.C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 QSIYTPCKNAPAJY-UHFFFAOYSA-N 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 38
- 229960004166 diltiazem Drugs 0.000 description 35
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 25
- 230000027455 binding Effects 0.000 description 13
- 229940127291 Calcium channel antagonist Drugs 0.000 description 12
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 12
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 231100000673 dose–response relationship Toxicity 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 9
- 241000700199 Cavia porcellus Species 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- UFADJPZTTUWZMP-UHFFFAOYSA-N azacyclotridecane Chemical compound C1CCCCCCNCCCCC1 UFADJPZTTUWZMP-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- 210000003405 ileum Anatomy 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 description 7
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 7
- 239000000480 calcium channel blocker Substances 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- 230000008602 contraction Effects 0.000 description 7
- 229960005425 nitrendipine Drugs 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000012528 membrane Substances 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- NRHDCQLCSOWVTF-UHFFFAOYSA-N azonane Chemical compound C1CCCCNCCC1 NRHDCQLCSOWVTF-UHFFFAOYSA-N 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 229940099112 cornstarch Drugs 0.000 description 5
- 230000001186 cumulative effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 5
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 241000244155 Taenia Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000011533 pre-incubation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 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 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- KFAUAWMNLGGWLP-UHFFFAOYSA-N azacyclododecane Chemical compound C1CCCCCNCCCCC1 KFAUAWMNLGGWLP-UHFFFAOYSA-N 0.000 description 3
- UOIGOLSKSFDTHJ-UHFFFAOYSA-N azacycloundecane Chemical compound C1CCCCCNCCCC1 UOIGOLSKSFDTHJ-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
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- 230000005764 inhibitory process Effects 0.000 description 3
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- 239000003446 ligand Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 238000000159 protein binding assay Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- HWGJWYNMDPTGTD-UHFFFAOYSA-N 1h-azonine Chemical compound C=1C=CC=CNC=CC=1 HWGJWYNMDPTGTD-UHFFFAOYSA-N 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical class CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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- 229920002873 Polyethylenimine Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000003561 anti-manic effect Effects 0.000 description 2
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- 229940030600 antihypertensive agent Drugs 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- VJEIIJANCJRLFJ-UHFFFAOYSA-N azecane Chemical compound C1CCCCNCCCC1 VJEIIJANCJRLFJ-UHFFFAOYSA-N 0.000 description 2
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- 230000008061 calcium-channel-blocking effect Effects 0.000 description 2
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- FPXDAAIHWNWNGJ-UHFFFAOYSA-N n-(2,2-diphenylethyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CN=C1CCCCCN1 FPXDAAIHWNWNGJ-UHFFFAOYSA-N 0.000 description 2
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- IIYYUPIEAXUAPB-UHFFFAOYSA-N n-(9h-fluoren-9-yl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C1CCNC1=NC1C2=CC=CC=C2C2=CC=CC=C21 IIYYUPIEAXUAPB-UHFFFAOYSA-N 0.000 description 1
- XSVGRBMQRVCJBY-HZPDHXFCSA-N n-[(1r,2r)-2-cyclohexylcyclopentyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound N([C@@H]1CCC[C@@H]1C1CCCCC1)=C1CCCCCN1 XSVGRBMQRVCJBY-HZPDHXFCSA-N 0.000 description 1
- RTRIXVOSRYRSBP-FGZHOGPDSA-N n-[(1r,2r)-2-phenylcyclopentyl]-1-azacyclotridecen-2-amine Chemical compound N([C@@H]1CCC[C@@H]1C=1C=CC=CC=1)C1=NCCCCCCCCCCC1 RTRIXVOSRYRSBP-FGZHOGPDSA-N 0.000 description 1
- ZOLIZNDWBAVXHU-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1=CC(Cl)=CC=C1CN=C1NCCCC1 ZOLIZNDWBAVXHU-UHFFFAOYSA-N 0.000 description 1
- YBOWESQHCLCEKI-UHFFFAOYSA-N n-[(4-dodecoxy-2-methylphenyl)methyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound CC1=CC(OCCCCCCCCCCCC)=CC=C1CN=C1NCCCCC1 YBOWESQHCLCEKI-UHFFFAOYSA-N 0.000 description 1
- WBFSWZAYAYOMBG-UHFFFAOYSA-N n-[1-(2,3-dihydro-1h-inden-4-yl)ethyl]-1-methyl-azacyclododecan-2-imine Chemical compound C=1C=CC=2CCCC=2C=1C(C)N=C1CCCCCCCCCCN1C WBFSWZAYAYOMBG-UHFFFAOYSA-N 0.000 description 1
- SXRRVVHLNCCYMN-UHFFFAOYSA-N n-[1-(2,3-dihydro-1h-inden-4-yl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC=2CCCC=2C=1C(C)N=C1CCCCCN1 SXRRVVHLNCCYMN-UHFFFAOYSA-N 0.000 description 1
- TZBNQWINMZRPLS-UHFFFAOYSA-N n-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C=1C=C2CCCCC2=CC=1C(C)N=C1CCCCN1 TZBNQWINMZRPLS-UHFFFAOYSA-N 0.000 description 1
- BOHHXUQZCBSKLJ-UHFFFAOYSA-N n-[1-(6-dodecylnaphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC2=CC(CCCCCCCCCCCC)=CC=C2C=1C(C)N=C1CCCCCN1 BOHHXUQZCBSKLJ-UHFFFAOYSA-N 0.000 description 1
- ICRWYJLRZKTTSZ-UHFFFAOYSA-N n-[1-(9h-fluoren-2-yl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=C(C2=CC=CC=C2C2)C2=CC=1C(C)N=C1CCCCCN1 ICRWYJLRZKTTSZ-UHFFFAOYSA-N 0.000 description 1
- UIUMZAZFFRVYKV-UHFFFAOYSA-N n-[1-(furan-2-yl)hex-4-enyl]-1-azacyclotridecen-2-amine Chemical compound C=1C=COC=1C(CCC=CC)N=C1CCCCCCCCCCCN1 UIUMZAZFFRVYKV-UHFFFAOYSA-N 0.000 description 1
- ZGYUMAWMRQYHKF-UHFFFAOYSA-N n-[1-[4-(3,7-dimethyloctoxy)phenyl]ethyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1=CC(OCCC(C)CCCC(C)C)=CC=C1C(C)N=C1NCCCC1 ZGYUMAWMRQYHKF-UHFFFAOYSA-N 0.000 description 1
- JSLKVKNOYUOFHD-UHFFFAOYSA-N n-[2-(2-propylphenyl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound CCCC1=CC=CC=C1CCN=C1NCCCCC1 JSLKVKNOYUOFHD-UHFFFAOYSA-N 0.000 description 1
- IHJZUFLRTVQYLQ-UHFFFAOYSA-N n-benzhydryl-1-azacyclotridecen-2-amine Chemical compound C1CCCCCCCCCCNC1=NC(C=1C=CC=CC=1)C1=CC=CC=C1 IHJZUFLRTVQYLQ-UHFFFAOYSA-N 0.000 description 1
- JOFGGEPLKVPQSC-UHFFFAOYSA-N n-benzhydryl-1-methylpiperidin-2-imine Chemical compound CN1CCCCC1=NC(C=1C=CC=CC=1)C1=CC=CC=C1 JOFGGEPLKVPQSC-UHFFFAOYSA-N 0.000 description 1
- DKKOGBSTGPXBRI-UHFFFAOYSA-N n-benzyl-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC=CC=1CNC1=NCCCCC1 DKKOGBSTGPXBRI-UHFFFAOYSA-N 0.000 description 1
- QVFOMDGJICIQEA-UHFFFAOYSA-N n-benzyl-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C=1C=CC=CC=1CNC1=NCCC1 QVFOMDGJICIQEA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 229920000260 silastic Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/212,544 US5010072A (en) | 1988-06-28 | 1988-06-28 | Lactamimides as calcium antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26115A true PH26115A (en) | 1992-02-24 |
Family
ID=22791465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38861A PH26115A (en) | 1988-06-28 | 1989-06-27 | Lactamimides as calcium antahonists |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5010072A (de) |
| EP (1) | EP0348891A3 (de) |
| JP (1) | JPH0253725A (de) |
| KR (1) | KR900000083A (de) |
| AU (1) | AU619310B2 (de) |
| DK (1) | DK318689A (de) |
| PH (1) | PH26115A (de) |
| ZA (1) | ZA894755B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19990048801A (ko) * | 1997-12-10 | 1999-07-05 | 차동천 | 유기성 폐기물의 발효 처리장치 및 그 처리방법 |
| KR102648928B1 (ko) * | 2020-07-20 | 2024-03-18 | 임주연 | 가축분뇨의 퇴비화 방법 및 장치 |
| KR102318901B1 (ko) * | 2021-04-29 | 2021-10-28 | 정종균 | 퇴비 발효 종균 분배기 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH412463A (de) * | 1962-07-10 | 1966-04-30 | Geigy Ag J R | Fungizides Mittel |
| US3873520A (en) * | 1971-05-13 | 1975-03-25 | Richardson Merrell Inc | 9-Fluorenyl lactamimides |
| US3894002A (en) * | 1971-05-13 | 1975-07-08 | Richardson Merrell Inc | Substituted naphthylalkylene lactamimides |
| US3900565A (en) * | 1971-09-13 | 1975-08-19 | Richardson Merrell Inc | Hypoglycemic compositions containing benzhydryllactamimide derivatives |
| BE788767A (fr) * | 1971-09-13 | 1973-01-02 | Richardson Merrell Inc | Compositions hypoglycemiques contenant des derives de benzhydryllactamimide |
| US3881006A (en) * | 1971-09-13 | 1975-04-29 | Richardson Merrell Inc | Hypoglycemic compositions containing benzhydryllactamimide derivatives |
| US3838851A (en) * | 1972-02-22 | 1974-10-01 | Addressograph Multigraph | Bottom sheet feeder |
| US3852269A (en) * | 1972-04-18 | 1974-12-03 | Richardson Merrell Inc | Diphenylalkyllactamimide derivatives |
| US3803170A (en) * | 1972-08-11 | 1974-04-09 | Richardson Merrell Inc | 2-((1-benzylcyclopentyl)imino)pyrrolidine |
| US3838151A (en) * | 1972-08-11 | 1974-09-24 | Richardson Merrell Inc | Cycloalkyllactamimides |
| US3833559A (en) * | 1973-01-05 | 1974-09-03 | Richardson Merrell Inc | Dibenzocycloheptenyl lactamimides |
| US3890445A (en) * | 1973-01-05 | 1975-06-17 | Richardson Merrell Inc | Lactamimide derivatives useful as hypoglycemic agents |
| US3816457A (en) * | 1973-01-05 | 1974-06-11 | Richardson Merrell Inc | Lactamimide derivatives |
| US3845071A (en) * | 1973-03-12 | 1974-10-29 | Richardson Merrell Inc | Imidazo(1,2-a)azacycloalkanes |
| US3931155A (en) * | 1973-04-25 | 1976-01-06 | Richardson-Merrell Inc. | Process for preparing 2-azacycloalkylmethyl ketones |
| US4055561A (en) * | 1973-04-25 | 1977-10-25 | Richardson-Merrell Inc. | α-Alkylbenzyl lactamimides |
| US3840524A (en) * | 1973-04-25 | 1974-10-08 | Richardson Merrell Inc | Alpha-cycloalkylbenzyl lactamimides |
-
1988
- 1988-06-28 US US07/212,544 patent/US5010072A/en not_active Expired - Fee Related
-
1989
- 1989-06-22 ZA ZA894755A patent/ZA894755B/xx unknown
- 1989-06-27 EP EP19890111674 patent/EP0348891A3/de not_active Withdrawn
- 1989-06-27 KR KR1019890008876A patent/KR900000083A/ko not_active Withdrawn
- 1989-06-27 PH PH38861A patent/PH26115A/en unknown
- 1989-06-27 JP JP1162844A patent/JPH0253725A/ja active Pending
- 1989-06-27 DK DK318689A patent/DK318689A/da not_active Application Discontinuation
- 1989-06-28 AU AU37122/89A patent/AU619310B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US5010072A (en) | 1991-04-23 |
| DK318689A (da) | 1989-12-29 |
| ZA894755B (en) | 1990-03-28 |
| AU619310B2 (en) | 1992-01-23 |
| EP0348891A2 (de) | 1990-01-03 |
| JPH0253725A (ja) | 1990-02-22 |
| DK318689D0 (da) | 1989-06-27 |
| EP0348891A3 (de) | 1991-05-15 |
| AU3712289A (en) | 1990-01-04 |
| KR900000083A (ko) | 1990-01-30 |
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