NO860471L - Fremgangsmaate for fremstilling av nye heterocykliske derivater. - Google Patents

Fremgangsmaate for fremstilling av nye heterocykliske derivater.

Info

Publication number: NO860471L
Authority: NO; Norway
Prior art keywords: carbon atoms; methyl; formula; dihydro; carboxylate
Prior art date: 1985-02-11

Application number

NO860471A

Other languages

English (en)

Norwegian (no)

Inventor

Rodney Brian Hargreaves

Bernard Joseph Mcloughlin

Stuart Dennett Mills

Original Assignee

Ici Plc

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.)

1985-02-11

Filing date

1986-02-11

Publication date

1986-08-12

1986-02-11 Application filed by Ici Plc filed Critical Ici Plc

1986-08-12 Publication of NO860471L publication Critical patent/NO860471L/no

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims description 12
-1 imino, substituted imino, phenylene, substituted phenylene Chemical group 0.000 claims abstract description 59
150000001875 compounds Chemical class 0.000 claims abstract description 46
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
239000002253 acid Substances 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 17
125000002947 alkylene group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
125000003368 amide group Chemical group 0.000 claims abstract description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 5
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
229910052717 sulfur Chemical group 0.000 claims abstract description 4
239000011593 sulfur Chemical group 0.000 claims abstract description 4
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 3
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
125000005551 pyridylene group Chemical group 0.000 claims abstract description 3
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
150000001412 amines Chemical class 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004956 cyclohexylene group Chemical group 0.000 claims description 4
150000002118 epoxides Chemical class 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
GRTJVRIWXZPUPK-UHFFFAOYSA-N 5-o-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethylamino]-4-oxobutyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCC(=O)NCCNCC(O)COC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 GRTJVRIWXZPUPK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical group C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 2
CLFAXWCIBRBYFG-UHFFFAOYSA-N 5-o-[2-[3-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]phenyl]ethyl] 3-o-methyl 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC=2C=C(CCNCC(O)COC=3C=CC=CC=3)C=CC=2)C1C1=CC=CC=C1Cl CLFAXWCIBRBYFG-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Chemical group 0.000 claims description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
RLKBOGLIOLFMEK-NSCUHMNNSA-N amino (e)-but-2-enoate Chemical compound C\C=C\C(=O)ON RLKBOGLIOLFMEK-NSCUHMNNSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000004723 keto acid derivatives Chemical class 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
FYCSLWYYBPKFOE-UHFFFAOYSA-N 5-o-[5-[5-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]pentylamino]-5-oxopentyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCC(=O)NCCCCCNCC(O)COC=2C(=CC=CC=2)C#N)C1C1=CC=CC([N+]([O-])=O)=C1 FYCSLWYYBPKFOE-UHFFFAOYSA-N 0.000 claims 1
125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
230000000903 blocking effect Effects 0.000 abstract description 8
206010020772 Hypertension Diseases 0.000 abstract description 4
108090000312 Calcium Channels Proteins 0.000 abstract description 3
102000003922 Calcium Channels Human genes 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000003921 oil Substances 0.000 description 19
239000000243 solution Substances 0.000 description 19
239000007858 starting material Substances 0.000 description 18
238000004611 spectroscopical analysis Methods 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000003480 eluent Substances 0.000 description 11
230000003276 anti-hypertensive effect Effects 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 9
238000003818 flash chromatography Methods 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
JQQXAMIFWQJQEA-UHFFFAOYSA-N 1-(2-aminoethylamino)-3-phenoxypropan-2-ol Chemical compound NCCNCC(O)COC1=CC=CC=C1 JQQXAMIFWQJQEA-UHFFFAOYSA-N 0.000 description 3
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 3
WMVGJZRQNYHLDN-UHFFFAOYSA-N 4-[5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carbonyl]oxybutanoic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCC(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 WMVGJZRQNYHLDN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 description 2
JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 description 2
FHSNGVSMFOWGPP-UHFFFAOYSA-N 5-o-(6-chlorohexyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCCCCl)C1C1=CC=CC([N+]([O-])=O)=C1 FHSNGVSMFOWGPP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
206010002383 Angina Pectoris Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000005484 gravity Effects 0.000 description 2
208000019622 heart disease Diseases 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical group COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 2
239000000047 product Substances 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BBJUSJOGHYQDQX-WODDMCJRSA-N (2S)-4-[(E)-2-[(2S)-2-carboxy-5,6-dihydroxy-2,3-dihydroindol-1-yl]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid Chemical compound OC(=O)[C@@H]1Cc2cc(O)c(O)cc2N1\C=C\C1=CC(=N[C@@H](C1)C(O)=O)C(O)=O BBJUSJOGHYQDQX-WODDMCJRSA-N 0.000 description 1
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
KTCNGKASVZVXHT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CNC1 KTCNGKASVZVXHT-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical compound NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
JFUBFTVIDOXELL-UHFFFAOYSA-N 2-(3-amino-2-hydroxypropoxy)benzonitrile Chemical compound NCC(O)COC1=CC=CC=C1C#N JFUBFTVIDOXELL-UHFFFAOYSA-N 0.000 description 1
GIUTUZDGHNZVIA-UHFFFAOYSA-N 2-(ethylamino)acetic acid;hydrochloride Chemical compound Cl.CCNCC(O)=O GIUTUZDGHNZVIA-UHFFFAOYSA-N 0.000 description 1
YQNSTSVPCJTWSA-UHFFFAOYSA-N 2-[2-[2-(1,3-dioxoisoindol-2-yl)ethylamino]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCNCCN1C(=O)C2=CC=CC=C2C1=O YQNSTSVPCJTWSA-UHFFFAOYSA-N 0.000 description 1
JZODHWBGGYPWLC-UHFFFAOYSA-N 2-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]isoindole-1,3-dione Chemical compound C1CN(CCO)CCN1CCN1C(=O)C2=CC=CC=C2C1=O JZODHWBGGYPWLC-UHFFFAOYSA-N 0.000 description 1
PLLNVXHAJVXNKA-UHFFFAOYSA-N 2-[2-[benzyl-[2-(1,3-dioxoisoindol-2-yl)ethyl]amino]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCN(CCN1C(C2=CC=CC=C2C1=O)=O)CC1=CC=CC=C1 PLLNVXHAJVXNKA-UHFFFAOYSA-N 0.000 description 1
QCYAJCGCGWQKJT-UHFFFAOYSA-N 2-[3-(2-hydroxyethyl)phenyl]ethanol Chemical compound OCCC1=CC=CC(CCO)=C1 QCYAJCGCGWQKJT-UHFFFAOYSA-N 0.000 description 1
OCOBOYAOMMPHEU-UHFFFAOYSA-N 2-[3-(5-aminopentylamino)-2-hydroxypropoxy]benzonitrile Chemical compound NCCCCCNCC(O)COC1=CC=CC=C1C#N OCOBOYAOMMPHEU-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- A61P9/10—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Hospice & Palliative Care (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO860471A 1985-02-11 1986-02-11 Fremgangsmaate for fremstilling av nye heterocykliske derivater. NO860471L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858503424A GB8503424D0 (en)	1985-02-11	1985-02-11	Heterocyclic derivatives

Publications (1)

Publication Number	Publication Date
NO860471L true NO860471L (no)	1986-08-12

Family

ID=10574269

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO860471A NO860471L (no)	1985-02-11	1986-02-11	Fremgangsmaate for fremstilling av nye heterocykliske derivater.

Country Status (14)

Country	Link
EP (1)	EP0194750A1 (da)
JP (1)	JPS61246162A (da)
AU (2)	AU5397486A (da)
DK (1)	DK66086A (da)
ES (1)	ES8802026A1 (da)
FI (1)	FI860622A7 (da)
GB (1)	GB8503424D0 (da)
GR (1)	GR860382B (da)
HU (1)	HUT40416A (da)
IL (1)	IL77849A0 (da)
NO (1)	NO860471L (da)
PT (1)	PT82021B (da)
WO (1)	WO1986004581A1 (da)
ZA (1)	ZA86997B (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8403866D0 (en) *	1984-02-14	1984-03-21	Recordati Chem Pharm	Diphenylalkylaminoalkyl esters
US4994476A (en) *	1984-10-31	1991-02-19	Bristol-Myers Company	Dihydropyridin-3,5-dicarboxylates incorporating aryloxypropanolamine moieties
EP0254682A1 (de) *	1986-07-22	1988-01-27	Ciba-Geigy Ag	Neue Phenoxyaliphatylphenylenoxyalkylester und -amide
EP0276552A1 (en) *	1986-12-08	1988-08-03	Yamanouchi Pharmaceutical Co. Ltd.	1,4-dihydropyridine derivatives and their production
EP0352863A3 (en) *	1988-07-29	1990-08-22	ZAMBON GROUP S.p.A.	1,4-dihydropyridine dicarboxylic acid derivatives
US5468746A (en) *	1988-07-29	1995-11-21	Zambon Group S.P.A.	Compounds active on the cardiovascular system
IT1229118B (it) *	1988-07-29	1991-07-22	Simes	Composti attivi sul sistema cardiovascolare che presentano sia la struttura dei beta-bloccanti sia una porzione calcio-antagonista
DE69131444T2 (de) *	1990-11-30	1999-12-23	Fujirebio Inc., Tokio/Tokyo	Optisch aktive 1,4-Dihydropyridinderivate sowie Verfahren zu ihrer Herstellung
DE4131346A1 (de) *	1991-09-20	1993-03-25	Bayer Ag	Indolsulfonamid substituierte dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
JPH08502038A (ja) *	1992-07-28	1996-03-05	藤沢薬品工業株式会社	抗高血圧作用を有する１，４−ジヒドロピリジン誘導体およびその製造方法
NL1012886C1 (nl)	1999-08-23	2001-02-26	Rephartox	1,4-Dihydropyridine-5-carbonzuuresterderivaten en werkwijze voor de bereiding ervan.
JP2008521805A (ja) *	2004-11-30	2008-06-26	アーテシアンセラピューティクス，インコーポレイテッド	β−アドレナリン作用性受容体およびホスホジエステラーゼに対する阻害活性を有する強心性化合物
CN101215258A (zh) *	2008-01-21	2008-07-09	中国药科大学	二氢吡啶类钙拮抗剂化合物及其制备方法与医药用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1409865A (en) *	1973-02-13	1975-10-15	Science Union & Cie	Dihydropyridines derivatives their preparation and pharmaceu tical compositions containing them
JPS60156671A (ja) *	1984-01-25	1985-08-16	Yamanouchi Pharmaceut Co Ltd	ジヒドロピリジン誘導体およびその製造法

1985
- 1985-02-11 GB GB858503424A patent/GB8503424D0/en active Pending
1986
- 1986-02-10 IL IL77849A patent/IL77849A0/xx unknown
- 1986-02-10 AU AU53974/86A patent/AU5397486A/en not_active Abandoned
- 1986-02-10 EP EP86300883A patent/EP0194750A1/en not_active Withdrawn
- 1986-02-10 WO PCT/GB1986/000072 patent/WO1986004581A1/en not_active Ceased
- 1986-02-10 GR GR860382A patent/GR860382B/el unknown
- 1986-02-11 AU AU53393/86A patent/AU5339386A/en not_active Abandoned
- 1986-02-11 DK DK66086A patent/DK66086A/da not_active Application Discontinuation
- 1986-02-11 ES ES551843A patent/ES8802026A1/es not_active Expired
- 1986-02-11 NO NO860471A patent/NO860471L/no unknown
- 1986-02-11 HU HU86584A patent/HUT40416A/hu unknown
- 1986-02-11 ZA ZA86997A patent/ZA86997B/xx unknown
- 1986-02-11 FI FI860622A patent/FI860622A7/fi not_active Application Discontinuation
- 1986-02-12 PT PT82021A patent/PT82021B/pt unknown
- 1986-02-12 JP JP61028761A patent/JPS61246162A/ja active Pending

Also Published As

Publication number	Publication date
FI860622A7 (fi)	1986-08-12
PT82021A (en)	1986-03-01
HUT40416A (en)	1986-12-28
AU5397486A (en)	1986-08-26
IL77849A0 (en)	1986-08-31
GB8503424D0 (en)	1985-03-13
WO1986004581A1 (en)	1986-08-14
DK66086D0 (da)	1986-02-11
PT82021B (en)	1987-12-16
ES551843A0 (es)	1988-03-16
FI860622A0 (fi)	1986-02-11
DK66086A (da)	1986-08-12
EP0194750A1 (en)	1986-09-17
ES8802026A1 (es)	1988-03-16
ZA86997B (en)	1986-12-30
GR860382B (en)	1986-05-29
AU5339386A (en)	1986-08-14
JPS61246162A (ja)	1986-11-01

Publication	Publication Date	Title
US4892875A (en)	1990-01-09	Substituted heterocyclylalkyl esters of 1,4-dihydropyridine-3,5-dicarboxylic acids
US4707486A (en)	1987-11-17	Diaryl piperidine containing esters of 1,4-dihydropyridines and coronary therapeutic use
KR920005742B1 (ko)	1992-07-18	약제학상 유용한 디하이드로피리디닐디카르복실레이트 아마이드 및 에스테르의 제조방법
KR880000180B1 (ko)	1988-03-12	디하이드로 피리딘의 제조방법
GB2036722A (en)	1980-07-02	2-Methyl-dihydropyridines
US5591757A (en)	1997-01-07	Dihydropyridine composition
EP0194750A1 (en)	1986-09-17	Dihydropyridine alkanol amines, process for their preparation and pharmaceutical compositions containing them
JPS61257983A (ja)	1986-11-15	１，４−ジヒドロピリジン及びこれを有効成分とする医薬組成物
US5017586A (en)	1991-05-21	5-dialkylaminomethyl-2-furanomethanol derivatives having anti-hypertensive properties
US4895846A (en)	1990-01-23	Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moieties
US4873254A (en)	1989-10-10	1,4-Dihydropyridines substituted by 3-aryloxy-2-hydroxypropyl amino moiety in the 4-phenyl group
US4994476A (en)	1991-02-19	Dihydropyridin-3,5-dicarboxylates incorporating aryloxypropanolamine moieties
NO860462L (no)	1986-08-12	Fremgangsmaate for fremstilling av et dihydropyridin.
US4757071A (en)	1988-07-12	1,4-dihydropyridine derivatives, and pharmaceutical compositions containing same, useful for treating cardiovascular diseases
NO860464L (no)	1986-08-12	Fremgangsmaate for fremstilling av farmasoeytisk aktive dihydropyridinderivater.
JPS62281860A (ja)	1987-12-07	アルキレンアミノアルキレン　ヘテロ原子基を有するジヒドロ−３，５−ジカルボキシレ−ト
JPH0314020B2 (da)	1991-02-25
US4491582A (en)	1985-01-01	N-(substituted piperazino)-1,4-dihydropyridine-3,5-carboxylic acid
JP2866277B2 (ja)	1999-03-08	アルキレンジアミン誘導体
US4547502A (en)	1985-10-15	Dihydropyridines and their use in treating cardiac conditions and hypertension
JPH0710846B2 (ja)	1995-02-08	４−置換オキシ−３−ピリジンカルボキサミド化合物
JP2664941B2 (ja)	1997-10-22	１，４―ジヒドロピリジン化合物
US4818766A (en)	1989-04-04	Novel phenoxyaliphatylphenyleneoxyalkyl esters and amides
US5286869A (en)	1994-02-15	1,4-dihydropyridine derivatives
NO860461L (no)	1986-08-12	Fremgangsmaate for fremstilling av dihydropyridin-derivater