PH26115A - Lactamimides as calcium antahonists - Google Patents

Lactamimides as calcium antahonists Download PDF

Info

Publication number: PH26115A
Authority: PH; Philippines
Prior art keywords: carbon atoms; group; test compound; imino; integer
Prior art date: 1988-06-28

Application number

PH38861A

Other languages

English (en)

Inventor

Michael G Palfreyman

Hsien C Cheng

Norbert L Wiech

John M Kane

Original Assignee

Merrell Dow Pharma

Priority date (The priority date 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 date listed.)

1988-06-28

Filing date

1989-06-27

Publication date

1992-02-24

1989-06-27 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1992-02-24 Publication of PH26115A publication Critical patent/PH26115A/en

Links

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
238000002474 experimental method Methods 0.000 description 3
239000007943 implant Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000008101 lactose Substances 0.000 description 3
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
241001465754 Metazoa Species 0.000 description 2
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
229940125681 anticonvulsant agent Drugs 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
239000000228 antimanic agent Substances 0.000 description 2
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
239000004305 biphenyl Substances 0.000 description 2
230000008061 calcium-channel-blocking effect Effects 0.000 description 2
229940126543 compound 14 Drugs 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
229940126142 compound 16 Drugs 0.000 description 2
229940125810 compound 20 Drugs 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
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
OZWQWKDLSXMIRT-UHFFFAOYSA-N n-(3,3-diphenylpropyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C1CCCCNC1=NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 OZWQWKDLSXMIRT-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003419 tautomerization reaction Methods 0.000 description 2
229960001722 verapamil Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-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
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
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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
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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
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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)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (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)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

PH38861A 1988-06-28 1989-06-27 Lactamimides as calcium antahonists PH26115A (en)

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 (ko)
EP (1)	EP0348891A3 (ko)
JP (1)	JPH0253725A (ko)
KR (1)	KR900000083A (ko)
AU (1)	AU619310B2 (ko)
DK (1)	DK318689A (ko)
PH (1)	PH26115A (ko)
ZA (1)	ZA894755B (ko)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH412463A (de) *	1962-07-10	1966-04-30	Geigy Ag J R	Fungizides Mittel
US3894002A (en) *	1971-05-13	1975-07-08	Richardson Merrell Inc	Substituted naphthylalkylene lactamimides
US3873520A (en) *	1971-05-13	1975-03-25	Richardson Merrell Inc	9-Fluorenyl lactamimides
BE788767A (fr) *	1971-09-13	1973-01-02	Richardson Merrell Inc	Compositions hypoglycemiques contenant des derives de benzhydryllactamimide
US3900565A (en) *	1971-09-13	1975-08-19	Richardson Merrell Inc	Hypoglycemic compositions containing benzhydryllactamimide derivatives
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
US3890445A (en) *	1973-01-05	1975-06-17	Richardson Merrell Inc	Lactamimide derivatives useful as hypoglycemic agents
US3833559A (en) *	1973-01-05	1974-09-03	Richardson Merrell Inc	Dibenzocycloheptenyl lactamimides
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
US4055561A (en) *	1973-04-25	1977-10-25	Richardson-Merrell Inc.	α-Alkylbenzyl lactamimides
US3840523A (en) *	1973-04-25	1974-10-08	Richardson Merrell Inc	Tricyclic arylalkylene 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 JP JP1162844A patent/JPH0253725A/ja active Pending
- 1989-06-27 KR KR1019890008876A patent/KR900000083A/ko not_active Withdrawn
- 1989-06-27 EP EP19890111674 patent/EP0348891A3/en not_active Withdrawn
- 1989-06-27 PH PH38861A patent/PH26115A/en unknown
- 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
EP0348891A3 (en)	1991-05-15
JPH0253725A (ja)	1990-02-22
AU3712289A (en)	1990-01-04
ZA894755B (en)	1990-03-28
US5010072A (en)	1991-04-23
EP0348891A2 (en)	1990-01-03
DK318689D0 (da)	1989-06-27
KR900000083A (ko)	1990-01-30
AU619310B2 (en)	1992-01-23
DK318689A (da)	1989-12-29

Publication	Publication Date	Title
EP1326832B1 (en)	2004-10-06	Chemical compounds
US6630462B2 (en)	2003-10-07	Delta agonist analgesics
AU2001295723A1 (en)	2002-07-04	Chemical compounds
DE60208568D1 (de)	2006-03-30	Prostaglandinanaloga als ep4-rezeptoragonisten
WO1995014007B1 (en)	1995-06-15	Phenyl-alkyl imidazoles as h3-receptor antagonists
BG64116B1 (bg)	2004-01-30	Използване на алфа 1l-адреноцепторни агонисти за лечение на незадържане на урина
US5589486A (en)	1996-12-31	N-hydroxyalkyl-substituted 1,2,3,6-tetrahydro-pyridine and piperidine derivatives
US5082837A (en)	1992-01-21	Lactamimides as calcium antagonists
US4260626A (en)	1981-04-07	Tetrahydro and imidazoline antisecretory compounds
US4061746A (en)	1977-12-06	Lactamimide inhibitors of gastrointestinal hypersecretion
CA2354213A1 (en)	2002-01-28	N-triazolylmethyl-piperazine compounds with neurokinin-receptor antagonist activity
RU2001121084A (ru)	2003-06-27	Новые производные N-триазолилметилпиперазина в качестве антагонистов рецепторов нейрокинина
EP0435177B1 (en)	1994-11-02	4-Benzyl-5-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
US5010072A (en)	1991-04-23	Lactamimides as calcium antagonists
EP0452926B1 (en)	1996-03-13	5-aryl-4-alkyl-3H-1,2,4-triazole-3-thiones useful as memory enhancers
US4055561A (en)	1977-10-25	α-Alkylbenzyl lactamimides
US5198433A (en)	1993-03-30	Lactamimides as calcium antagonists
US5158945A (en)	1992-10-27	Lactamimides as calcium antagonists
US5128337A (en)	1992-07-07	Lactamimides as calcium antagonists
JP2000516257A5 (ko)	2009-05-07
HUT72078A (en)	1996-03-28	Diarylalkyl piperidines useful as multi-drug resistant tumor agents and pharmaceutical compositions containing the compounds
AU662602B2 (en)	1995-09-07	Reversal of multi-drug resistance by triphenyl-azacycloalkane derivatives
AU679130B2 (en)	1997-06-19	3-aryl-4-alkyl and 4,5-dialkyl-4H-1,2,4-triazoles useful as memory enhancers
Ringdahl	1987	Structural requirements for affinity and efficacy of N-(4-amino-2-butynyl) succinimides at muscarinic receptors in the guinea-pig ileum and urinary bladder
JPH02134320A (ja)	1990-05-23	医薬組成物