DD250533A5 - Verfahren zur herstellung eines dihydropyridinderivates - Google Patents

Verfahren zur herstellung eines dihydropyridinderivates Download PDF

Info

Publication number: DD250533A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; hydroxy; formula; group; dicarboxylate
Prior art date: 1985-02-11

Application number

DD86286947A

Other languages

German (de)

English (en)

Inventor

Rodney B Hargreaves

Bernard J Mcloughlin

Stuart D Mills

Original Assignee

��@��@��@��k��

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

1986-02-10

Publication date

1987-10-14

1986-02-10 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1987-10-14 Publication of DD250533A5 publication Critical patent/DD250533A5/de

Links

YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims description 28
238000004519 manufacturing process Methods 0.000 title description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 47
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
150000001875 compounds Chemical class 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
125000002947 alkylene group Chemical group 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
125000004450 alkenylene group Chemical group 0.000 claims abstract description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 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
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
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 3
229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
-1 hydroxy, amino, nitro, carbamoyl Chemical group 0.000 claims description 114
238000006243 chemical reaction Methods 0.000 claims description 20
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
125000001589 carboacyl group Chemical group 0.000 claims description 6
125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
125000003302 alkenyloxy group Chemical group 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000005336 allyloxy group Chemical group 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
150000002118 epoxides Chemical class 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
150000004723 keto acid derivatives Chemical class 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000004414 alkyl thio 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
125000005605 benzo group Chemical group 0.000 claims description 2
125000002993 cycloalkylene group Chemical group 0.000 claims description 2
IYFXDOXPZVAABR-UHFFFAOYSA-N diethyl 4-[2-[4-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC([N+]([O-])=O)=CC=C1OCCCCNCC(O)COC1=CC=CC=C1C#N IYFXDOXPZVAABR-UHFFFAOYSA-N 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000005283 haloketone group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 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 class [H]* 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
125000005551 pyridylene group Chemical group 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
XYZSXBPRDUWIJX-UHFFFAOYSA-N dimethyl 4-[2-[3-[(2-hydroxy-3-phenoxypropyl)amino]-3-methylbutoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC([N+]([O-])=O)=CC=C1OCCC(C)(C)NCC(O)COC1=CC=CC=C1 XYZSXBPRDUWIJX-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
230000003276 anti-hypertensive effect Effects 0.000 abstract description 13
125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
239000003921 oil Substances 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
239000000203 mixture Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 17
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
239000000543 intermediate Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 8
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 8
239000005695 Ammonium acetate Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 8
229940043376 ammonium acetate Drugs 0.000 description 8
235000019257 ammonium acetate Nutrition 0.000 description 8
230000000903 blocking effect Effects 0.000 description 8
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 7
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 7
101150065749 Churc1 gene Proteins 0.000 description 7
102100038239 Protein Churchill Human genes 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-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
239000000047 product Substances 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000004480 active ingredient Substances 0.000 description 4
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 3
KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 3
JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical compound NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VFVHWCKUHAEDMY-UHFFFAOYSA-N 2-chloro-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=O)=C1 VFVHWCKUHAEDMY-UHFFFAOYSA-N 0.000 description 2
206010002383 Angina Pectoris Diseases 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
229910001424 calcium ion Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
OOZCFDZVXLWKOS-UHFFFAOYSA-N dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC([N+]([O-])=O)=CC=C1OCCCCN OOZCFDZVXLWKOS-UHFFFAOYSA-N 0.000 description 2
GQJFGCIETONRNJ-UHFFFAOYSA-N dimethyl 4-[2-[4-[(2-hydroxy-3-phenoxypropyl)amino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC([N+]([O-])=O)=CC=C1OCCCCNCC(O)COC1=CC=CC=C1 GQJFGCIETONRNJ-UHFFFAOYSA-N 0.000 description 2
HDTNLHHNQYBOHJ-UHFFFAOYSA-N dimethyl pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=CN=CC(C(=O)OC)=C1 HDTNLHHNQYBOHJ-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
208000019622 heart disease Diseases 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000008194 pharmaceutical composition 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
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
238000001953 recrystallisation Methods 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
229940125723 sedative agent Drugs 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
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 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
FQDIANVAWVHZIR-UPHRSURJSA-N (z)-1,4-dichlorobut-2-ene Chemical compound ClC\C=C/CCl FQDIANVAWVHZIR-UPHRSURJSA-N 0.000 description 1
UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 1
YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
JQQXAMIFWQJQEA-UHFFFAOYSA-N 1-(2-aminoethylamino)-3-phenoxypropan-2-ol Chemical compound NCCNCC(O)COC1=CC=CC=C1 JQQXAMIFWQJQEA-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
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 1
RXXQPDFZOJJHOL-UHFFFAOYSA-N 2-(4-chlorobutoxy)-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(OCCCCCl)C(C=O)=C1 RXXQPDFZOJJHOL-UHFFFAOYSA-N 0.000 description 1
BGCVCJBIFBISFN-UHFFFAOYSA-N 2-(cyanomethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCC#N BGCVCJBIFBISFN-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
CELWRHKCSFXXTC-UHFFFAOYSA-N 2-[2-[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridin-4-yl]-5-nitrophenoxy]acetic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=C([N+]([O-])=O)C=C1OCC(O)=O CELWRHKCSFXXTC-UHFFFAOYSA-N 0.000 description 1
PHWNKGQVWPYLJT-UHFFFAOYSA-N 2-[3-(1,3-dioxoisoindol-2-yl)propylsulfanyl]-5-nitrobenzaldehyde Chemical compound O=CC1=CC([N+](=O)[O-])=CC=C1SCCCN1C(=O)C2=CC=CC=C2C1=O PHWNKGQVWPYLJT-UHFFFAOYSA-N 0.000 description 1
SRKBYWLOUWUYLB-UHFFFAOYSA-N 2-[3-(2-aminoethylamino)-2-hydroxypropoxy]benzonitrile Chemical compound NCCNCC(O)COC1=CC=CC=C1C#N SRKBYWLOUWUYLB-UHFFFAOYSA-N 0.000 description 1
LLHDFGLDPWLUOT-UHFFFAOYSA-N 2-[4-(1,3-dioxoisoindol-2-yl)butoxy]-5-nitrobenzaldehyde Chemical compound O=CC1=CC([N+](=O)[O-])=CC=C1OCCCCN1C(=O)C2=CC=CC=C2C1=O LLHDFGLDPWLUOT-UHFFFAOYSA-N 0.000 description 1
JVUCZNZTOCBCED-UHFFFAOYSA-N 2-[[2-[2-[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridin-4-yl]-4-nitrophenoxy]acetyl]amino]acetic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC([N+]([O-])=O)=CC=C1OCC(=O)NCC(O)=O JVUCZNZTOCBCED-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
PHRHXTTZZWUGNN-UHFFFAOYSA-N 3-amino-3-methylbutan-1-ol Chemical compound CC(C)(N)CCO PHRHXTTZZWUGNN-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
LJHOQCDTDVDTIG-UHFFFAOYSA-N 5-o-ethyl 3-o-methyl 4-[2-(4-chlorobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC([N+]([O-])=O)=CC=C1OCCCCCl LJHOQCDTDVDTIG-UHFFFAOYSA-N 0.000 description 1
240000006409 Acacia auriculiformis Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
ISIRDOOSEVVUFF-UHFFFAOYSA-N COC(=O)C1(CNC(=C(C1C1=C(C=CC=C1)[N+](=O)[O-])C(=O)OC)C)C Chemical group COC(=O)C1(CNC(=C(C1C1=C(C=CC=C1)[N+](=O)[O-])C(=O)OC)C)C ISIRDOOSEVVUFF-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
240000001879 Digitalis lutea Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
239000000026 Pentaerythritol tetranitrate Substances 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical compound C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
BBBQNAXNSQHGLQ-UHFFFAOYSA-N [3-(2-aminoethyl)phenyl]methanol Chemical compound NCCC1=CC=CC(CO)=C1 BBBQNAXNSQHGLQ-UHFFFAOYSA-N 0.000 description 1
HREPEKPEKJXBGT-UHFFFAOYSA-N [3-(chloromethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(CCl)=C1 HREPEKPEKJXBGT-UHFFFAOYSA-N 0.000 description 1
MRJUPJKYBZVMCR-UHFFFAOYSA-N [4-(2-aminoethyl)phenyl]methanol Chemical compound NCCC1=CC=C(CO)C=C1 MRJUPJKYBZVMCR-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000013543 active substance Substances 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229960002274 atenolol Drugs 0.000 description 1
101150113720 aunc gene Proteins 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
229960004980 betanidine Drugs 0.000 description 1
NIVZHWNOUVJHKV-UHFFFAOYSA-N bethanidine Chemical compound CN\C(=N/C)NCC1=CC=CC=C1 NIVZHWNOUVJHKV-UHFFFAOYSA-N 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229940003871 calcium ion Drugs 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
229960002155 chlorothiazide Drugs 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
229960001523 chlortalidone Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
230000008602 contraction Effects 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
229960004486 desoxycorticosterone acetate Drugs 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
VETCBVIZEFYHDG-UHFFFAOYSA-N dimethyl 4-[2-(3-chloropropoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC([N+]([O-])=O)=CC=C1OCCCCl VETCBVIZEFYHDG-UHFFFAOYSA-N 0.000 description 1
VZIROQUAOLVLBP-UHFFFAOYSA-N dimethyl 4-[2-[(3-hydroxyphenyl)methoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC([N+]([O-])=O)=CC=C1OCC1=CC=CC(O)=C1 VZIROQUAOLVLBP-UHFFFAOYSA-N 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229940079593 drug Drugs 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
UJHPAPSCNKCIRR-UHFFFAOYSA-N ethyl 4-(2-formyl-4-nitrophenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=CC=C([N+]([O-])=O)C=C1C=O UJHPAPSCNKCIRR-UHFFFAOYSA-N 0.000 description 1
XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229960003711 glyceryl trinitrate Drugs 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
230000005484 gravity Effects 0.000 description 1
229960003602 guanethidine Drugs 0.000 description 1
ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229960002003 hydrochlorothiazide Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005555 hypertensive agent Substances 0.000 description 1
UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000006207 intravenous dosage form Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
229960000201 isosorbide dinitrate Drugs 0.000 description 1
238000005304 joining Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000000936 membranestabilizing effect Effects 0.000 description 1
229960004815 meprobamate Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
CMADSXVGXNLKHA-UHFFFAOYSA-N methyl 2-(cyanomethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CC#N CMADSXVGXNLKHA-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000013059 nephrectomy Methods 0.000 description 1
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 1
229960001597 nifedipine Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229960002695 phenobarbital Drugs 0.000 description 1
MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
210000003240 portal vein Anatomy 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
GJAWHXHKYYXBSV-UHFFFAOYSA-L quinolinate(2-) Chemical compound [O-]C(=O)C1=CC=CN=C1C([O-])=O GJAWHXHKYYXBSV-UHFFFAOYSA-L 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229960001032 trihexyphenidyl Drugs 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- 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
- 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
- A61P9/06—Antiarrhythmics
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
- 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
- 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
- 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
- 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

Landscapes

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

DD86286947A 1985-02-11 1986-02-10 Verfahren zur herstellung eines dihydropyridinderivates DD250533A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858503425A GB8503425D0 (en)	1985-02-11	1985-02-11	Alkanolamine derivatives

Publications (1)

Publication Number	Publication Date
DD250533A5 true DD250533A5 (de)	1987-10-14

Family

ID=10574270

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86286947A DD250533A5 (de)	1985-02-11	1986-02-10	Verfahren zur herstellung eines dihydropyridinderivates

Country Status (21)

Country	Link
US (1)	US4873254A (cs)
EP (1)	EP0194751B1 (cs)
JP (1)	JPH0819100B2 (cs)
KR (1)	KR860006443A (cs)
AU (1)	AU5339486A (cs)
CS (1)	CS273172B2 (cs)
DD (1)	DD250533A5 (cs)
DE (1)	DE3684803D1 (cs)
DK (1)	DK66186A (cs)
ES (2)	ES8802139A1 (cs)
FI (1)	FI860621A7 (cs)
GB (2)	GB8503425D0 (cs)
GR (1)	GR860369B (cs)
HU (1)	HU196179B (cs)
NO (1)	NO860465L (cs)
NZ (1)	NZ215083A (cs)
PH (1)	PH22683A (cs)
PL (2)	PL153857B1 (cs)
PT (1)	PT82008B (cs)
SU (1)	SU1590041A3 (cs)
ZA (1)	ZA86967B (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6112662A (ja) *	1984-06-28	1986-01-21	Yamanouchi Pharmaceut Co Ltd	ジヒドロピリジン誘導体及びその製法
EP0276552A1 (en) *	1986-12-08	1988-08-03	Yamanouchi Pharmaceutical Co. Ltd.	1,4-dihydropyridine derivatives and their production
GB9102031D0 (en) *	1991-01-30	1991-03-13	Fujisawa Pharmaceutical Co	Dihydropyridine compounds,and process for their preparation
WO2000005209A1 (fr) *	1998-07-23	2000-02-03	Lin, Tong-Ho	GUAIACOXYPROPANOLAMINES A ACTIVITE α/β-ADRENOLYTIQUE
AR070950A1 (es) *	2007-11-01	2010-05-19	Acucela Inc	Compuestos derivados de amina, composiciones farmaceuticas de ellos, compuestos inhibidores de produccion de 11-cis-retinol y metodos para tratar enfermedades y trastornos oftalmicos

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2228363A1 (de) *	1972-06-10	1974-01-03	Bayer Ag	1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
GB1409865A (en) *	1973-02-13	1975-10-15	Science Union & Cie	Dihydropyridines derivatives their preparation and pharmaceu tical compositions containing them
US4500527A (en) *	1983-06-22	1985-02-19	Usv Pharmaceutical Corporation	Antihypertensive 4[(3-alkylamino-2-hydroxypropyl)-oxyiminomethyl phenyl]-1,4-dihydropyridines
JPS6112662A (ja) *	1984-06-28	1986-01-21	Yamanouchi Pharmaceut Co Ltd	ジヒドロピリジン誘導体及びその製法

1985
- 1985-02-11 GB GB858503425A patent/GB8503425D0/en active Pending
1986
- 1986-02-04 GB GB868602704A patent/GB8602704D0/en active Pending
- 1986-02-07 GR GR860369A patent/GR860369B/el unknown
- 1986-02-10 EP EP86300884A patent/EP0194751B1/en not_active Expired - Lifetime
- 1986-02-10 PT PT82008A patent/PT82008B/pt not_active IP Right Cessation
- 1986-02-10 ZA ZA86967A patent/ZA86967B/xx unknown
- 1986-02-10 NZ NZ215083A patent/NZ215083A/xx unknown
- 1986-02-10 DD DD86286947A patent/DD250533A5/de unknown
- 1986-02-10 NO NO860465A patent/NO860465L/no unknown
- 1986-02-10 HU HU86535A patent/HU196179B/hu not_active IP Right Cessation
- 1986-02-10 CS CS91186A patent/CS273172B2/cs unknown
- 1986-02-10 DE DE8686300884T patent/DE3684803D1/de not_active Expired - Lifetime
- 1986-02-10 SU SU864027023A patent/SU1590041A3/ru active
- 1986-02-11 PH PH33404A patent/PH22683A/en unknown
- 1986-02-11 PL PL1986265252A patent/PL153857B1/pl unknown
- 1986-02-11 US US07/828,363 patent/US4873254A/en not_active Expired - Lifetime
- 1986-02-11 PL PL1986257902A patent/PL149828B1/pl unknown
- 1986-02-11 ES ES551844A patent/ES8802139A1/es not_active Expired
- 1986-02-11 DK DK66186A patent/DK66186A/da not_active Application Discontinuation
- 1986-02-11 FI FI860621A patent/FI860621A7/fi not_active Application Discontinuation
- 1986-02-11 AU AU53394/86A patent/AU5339486A/en not_active Abandoned
- 1986-02-11 KR KR1019860000921A patent/KR860006443A/ko not_active Ceased
- 1986-02-12 JP JP61028760A patent/JPH0819100B2/ja not_active Expired - Lifetime
1987
- 1987-07-16 ES ES557630A patent/ES8802496A1/es not_active Expired

Also Published As

Publication number	Publication date
PL153857B1 (en)	1991-06-28
SU1590041A3 (ru)	1990-08-30
ES8802139A1 (es)	1988-04-01
JPS61233669A (ja)	1986-10-17
CS273172B2 (en)	1991-03-12
ZA86967B (en)	1986-11-26
GB8602704D0 (en)	1986-03-12
AU5339486A (en)	1986-08-14
GR860369B (en)	1986-06-02
EP0194751B1 (en)	1992-04-15
KR860006443A (ko)	1986-09-11
DK66186A (da)	1986-08-12
ES551844A0 (es)	1988-04-01
EP0194751A1 (en)	1986-09-17
HUT40415A (en)	1986-12-28
FI860621A0 (fi)	1986-02-11
NZ215083A (en)	1989-10-27
US4873254A (en)	1989-10-10
FI860621A7 (fi)	1986-08-12
PT82008B (pt)	1988-07-01
PL257902A1 (en)	1988-03-03
NO860465L (no)	1986-08-12
GB8503425D0 (en)	1985-03-13
DE3684803D1 (de)	1992-05-21
PL265252A1 (en)	1988-06-09
ES8802496A1 (es)	1988-07-01
ES557630A0 (es)	1988-07-01
DK66186D0 (da)	1986-02-11
HU196179B (en)	1988-10-28
PT82008A (en)	1986-03-01
CS91186A2 (en)	1990-07-12
PH22683A (en)	1988-11-14
PL149828B1 (en)	1990-03-31
JPH0819100B2 (ja)	1996-02-28

Publication	Publication Date	Title
DE3787346T2 (de)	1994-04-21	Dihydropyridin-Derivate, ihre Herstellung und ihre Verwendung.
CH664757A5 (de)	1988-03-31	Pharmazeutisch nuetzliche dihydropyridinylcarbonsaeureamide und ester.
CH642353A5 (de)	1984-04-13	2-methyl-dihydropyridin-verbindung, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel.
DD219770A5 (de)	1985-03-13	Verfahren zur herstellung von piperidindion-derivaten
DE2651083A1 (de)	1978-05-18	Neue o-alkylierte hydroxylamine, verfahren zu ihrer herstellung und ihre verwendung
DE3042769A1 (de)	1982-06-09	C-3 verknuepfte 1,4-dihydropyridine, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung
EP0008645B1 (de)	1984-09-05	Alkoxyphenylpyrrolidone, Verfahren zu ihrer Herstellung und Arzneimittel auf Basis dieser Verbindungen
DE69720021T2 (de)	2004-02-05	1,4-disubstituierte piperazine
EP0194750A1 (en)	1986-09-17	Dihydropyridine alkanol amines, process for their preparation and pharmaceutical compositions containing them
DE69102477T2 (de)	1995-02-09	3-Aminochroman-Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen.
DE60013225T2 (de)	2005-09-01	4-Hydroxy-4-Phenylpiperidin-Derivate mit opioid-agonistischer Aktivität und di ese enthaltende Pharmazeutika
US4873254A (en)	1989-10-10	1,4-Dihydropyridines substituted by 3-aryloxy-2-hydroxypropyl amino moiety in the 4-phenyl group
DE2650013C3 (de)	1981-04-02	1.4-Dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsäureisopropyl-(2-propoxy-äthyl)-ester, Verfahren zu seiner Herstellung sowie ihn enthaltende Arzneimittel
DE4117750A1 (de)	1992-12-24	Neue 2-amino-5-cyano-1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
WO1979000426A1 (fr)	1979-07-12	Diamine cyclique n, n'-disubstituee et procede pour sa preparation
DE68912252T2 (de)	1994-07-07	Imidazolantiarrythmische Mittel.
DE2412520A1 (de)	1974-10-10	Tricyclische verbindungen
EP0072961A1 (de)	1983-03-02	1-Phenylindazol-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE69007045T2 (de)	1994-08-04	Piperidinderivate, Verfahren zur Herstellung sowie diese enthaltende pharmazeutische Präparate.
EP0657432B1 (de)	2003-03-12	Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität
DE2437883C3 (de)	1977-03-10	N-Substltuierte Glycinester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0194047A1 (en)	1986-09-10	Dihydropyridine alkanol amines, process for their preparation and pharmaceutical compositions containing them
AT345291B (de)	1978-09-11	Verfahren zur herstellung von neuen cyclisch substituierten derivaten des 1-amino-2-propanols und deren salzen
DE10129119B4 (de)	2007-10-04	Kristalline Salze von Benzoylbenzofuran-Derivaten, insbesondere von[2-(4-{1-[2-((S)-sec.-Butoxycarbonylmethyl)-benzofuran-3-carbonyl]-methanoyl}-2,6-diiod-phenoxy)-ethyl]-diethylamino und [2-(4-{1-[(3-Methyl-2-(S)-Butoxycarbonylmethyl)-benzofuran-3-carbonyl]- methanoyl}-2,6-diiodphenoxy)-ethyl]-diethylamino, deren Verwendung und Herstellung sowie diese Salze enthaltende Arzneimittel
EP0322396A1 (de)	1989-06-28	Neue Derivate von Benzimidazol, ihre Herstellung und Verwendung