DD209622A5 - Verfahren zur herstellung von 1,4-dihydropyridinen - Google Patents

Verfahren zur herstellung von 1,4-dihydropyridinen Download PDF

Info

Publication number: DD209622A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; low; alkyl; benzyl
Prior art date: 1982-03-11

Application number

DD83248690A

Other languages

German (de)

English (en)

Inventor

Simon F Campbell

Peter E Cross

John K Stubbs

Original Assignee

Pfizer

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.)

1982-03-11

Filing date

1983-03-10

Publication date

1984-05-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10528947&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD209622(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1983-03-10 Application filed by Pfizer filed Critical Pfizer

1984-05-16 Publication of DD209622A5 publication Critical patent/DD209622A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 43
238000002360 preparation method Methods 0.000 title claims abstract description 29
230000008569 process Effects 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 66
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 9
239000011701 zinc Substances 0.000 claims description 9
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
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 claims description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
150000003141 primary amines Chemical class 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 2
150000001412 amines Chemical class 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims 1
-1 2-METHOXY-ETHYL Chemical class 0.000 abstract description 26
230000000747 cardiac effect Effects 0.000 abstract description 4
238000011282 treatment Methods 0.000 abstract description 4
206010002383 Angina Pectoris Diseases 0.000 abstract description 3
230000002265 prevention Effects 0.000 abstract description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
XSGHLZBESSREDT-UHFFFAOYSA-N methylenecyclopropane Chemical class C=C1CC1 XSGHLZBESSREDT-UHFFFAOYSA-N 0.000 abstract 1
239000008177 pharmaceutical agent Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 21
238000010992 reflux Methods 0.000 description 20
239000007787 solid Substances 0.000 description 20
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000004458 analytical method Methods 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
239000007858 starting material Substances 0.000 description 15
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
239000000543 intermediate Substances 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
239000011575 calcium Substances 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000012458 free base Substances 0.000 description 5
229940050411 fumarate Drugs 0.000 description 5
239000010410 layer Substances 0.000 description 5
XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
BSULWPSUVMOMAN-UHFFFAOYSA-N 2-azidoethanol Chemical compound OCCN=[N+]=[N-] BSULWPSUVMOMAN-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
238000003445 Hantzsch reaction Methods 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
RLKBOGLIOLFMEK-NSCUHMNNSA-N amino (e)-but-2-enoate Chemical compound C\C=C\C(=O)ON RLKBOGLIOLFMEK-NSCUHMNNSA-N 0.000 description 4
235000019257 ammonium acetate Nutrition 0.000 description 4
229940043376 ammonium acetate Drugs 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000005544 phthalimido group Chemical group 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 3
150000004729 acetoacetic acid derivatives Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000010779 crude oil Substances 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RIVUDQMCBGGPRV-UHFFFAOYSA-N 2-azidopropan-1-ol Chemical compound OCC(C)N=[N+]=[N-] RIVUDQMCBGGPRV-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 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
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001540 azides Chemical class 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
238000012512 characterization method Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
KTVPZBURNBMJNW-UHFFFAOYSA-N ethyl 4-(2-azidoethoxy)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCCN=[N+]=[N-] KTVPZBURNBMJNW-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
230000000302 ischemic effect Effects 0.000 description 2
MNMKWCPLHQYQLU-UHFFFAOYSA-N methyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoate Chemical compound COC(=O)C(C(C)=O)=CC1=CC=CC=C1Cl MNMKWCPLHQYQLU-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
PAWSVPVNIXFKOS-IHWYPQMZSA-N (Z)-2-aminobutenoic acid Chemical class C\C=C(/N)C(O)=O PAWSVPVNIXFKOS-IHWYPQMZSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
MWFLUYFYHANMCM-UHFFFAOYSA-N 2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCO)C(=O)C2=C1 MWFLUYFYHANMCM-UHFFFAOYSA-N 0.000 description 1
WOUANPHGFPAJCA-UHFFFAOYSA-N 2-[benzyl(methyl)amino]ethanol Chemical compound OCCN(C)CC1=CC=CC=C1 WOUANPHGFPAJCA-UHFFFAOYSA-N 0.000 description 1
DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-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
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
TVRIJORYAZEFDL-UHFFFAOYSA-N 3-O-ethyl 5-O-methyl 2-(2-azidoethoxy)-4-(2-chlorophenyl)-1,6-dimethyl-4H-pyridine-3,5-dicarboxylate Chemical compound N(=[N+]=[N-])CCOC=1N(C(=C(C(C=1C(=O)OCC)C1=C(C=CC=C1)Cl)C(=O)OC)C)C TVRIJORYAZEFDL-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
AHHPZGUFLGCZCF-UHFFFAOYSA-N 3-o-ethyl 5-o-methyl 4-(2-chlorophenyl)-2-[2-(1,3-dioxoisoindol-2-yl)ethoxymethyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(COCCN2C(C3=CC=CC=C3C2=O)=O)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl AHHPZGUFLGCZCF-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
230000002407 ATP formation Effects 0.000 description 1
206010003225 Arteriospasm coronary Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
206010007572 Cardiac hypertrophy Diseases 0.000 description 1
208000006029 Cardiomegaly Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
208000003890 Coronary Vasospasm Diseases 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
206010062575 Muscle contracture Diseases 0.000 description 1
206010028851 Necrosis Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000002253 anti-ischaemic effect Effects 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
150000001768 cations Chemical group 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
208000006111 contracture Diseases 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
201000011634 coronary artery vasospasm Diseases 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
WKKPVYVBLZOGKJ-UHFFFAOYSA-N ethyl 4-(2-azidopropoxy)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCC(C)N=[N+]=[N-] WKKPVYVBLZOGKJ-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
235000013905 glycine and its sodium salt Nutrition 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
210000005003 heart tissue Anatomy 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000004941 influx Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
210000003470 mitochondria Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
230000008113 positive regulation of fatty acid oxidation Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07D211/86—Oxygen atoms
- 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
- 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
- A61P9/10—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
- C07C247/00—Compounds containing azido 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Liquid Crystal Substances (AREA)
Mechanical Pencils And Projecting And Retracting Systems Therefor, And Multi-System Writing Instruments (AREA)
Saccharide Compounds (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Luminescent Compositions (AREA)
Registering, Tensioning, Guiding Webs, And Rollers Therefor (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

DD83248690A 1982-03-11 1983-03-10 Verfahren zur herstellung von 1,4-dihydropyridinen DD209622A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8207180		1982-03-11

Publications (1)

Publication Number	Publication Date
DD209622A5 true DD209622A5 (de)	1984-05-16

Family

ID=10528947

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD83264890A DD218887A5 (de)	1982-03-11	1983-03-10	Verfahren zur herstellung von 1,4-dihydropyridinen
DD83248690A DD209622A5 (de)	1982-03-11	1983-03-10	Verfahren zur herstellung von 1,4-dihydropyridinen

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
DD83264890A DD218887A5 (de)	1982-03-11	1983-03-10	Verfahren zur herstellung von 1,4-dihydropyridinen

Country Status (37)

Country	Link
US (1)	US4572909A (ja)
EP (1)	EP0089167B1 (ja)
JP (1)	JPS58167569A (ja)
KR (1)	KR870000809B1 (ja)
AT (1)	ATE22884T1 (ja)
AU (1)	AU540769B2 (ja)
BA (2)	BA97147B1 (ja)
BG (1)	BG60658B2 (ja)
CA (1)	CA1253865A (ja)
CS (3)	CS240954B2 (ja)
DD (2)	DD218887A5 (ja)
DE (2)	DE19375111I2 (ja)
DK (1)	DK161312C (ja)
EG (1)	EG16987A (ja)
ES (2)	ES520389A0 (ja)
FI (1)	FI81090C (ja)
GR (1)	GR77429B (ja)
HK (1)	HK16288A (ja)
HR (2)	HRP930369B1 (ja)
HU (1)	HU187868B (ja)
IE (2)	IE54667B1 (ja)
IL (1)	IL68091A (ja)
KE (1)	KE3778A (ja)
LU (1)	LU88332I2 (ja)
LV (2)	LV5236A3 (ja)
MY (1)	MY101985A (ja)
NL (1)	NL930063I2 (ja)
NO (3)	NO162818C (ja)
NZ (1)	NZ203521A (ja)
PL (3)	PL140278B1 (ja)
PT (1)	PT76370B (ja)
SG (1)	SG98687G (ja)
SI (2)	SI8310586A8 (ja)
SU (2)	SU1238730A3 (ja)
UA (2)	UA7083A1 (ja)
YU (2)	YU43541B (ja)
ZA (1)	ZA831651B (ja)

Families Citing this family (186)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4572908A (en) *	1982-12-21	1986-02-25	Pfizer Inc.	Dihydropyridines
GB8306666D0 (en) *	1983-03-10	1983-04-13	Pfizer Ltd	Therapeutic agents
EP0125803A3 (en) *	1983-04-27	1987-01-21	FISONS plc	Pharmaceutically active dihydropyridines
EP0168841B1 (en) *	1983-12-19	1988-09-28	Pfizer Limited	Dihydropyridine intermediate
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
GB8414518D0 (en) *	1984-06-07	1984-07-11	Pfizer Ltd	Therapeutic agents
GB8421039D0 (en) *	1984-08-17	1984-09-19	Wyeth John & Brother Ltd	Heterocyclic compounds
GR851819B (ja) *	1984-08-17	1985-11-26	Wyeth John & Brother Ltd
IL77843A (en) *	1985-02-11	1989-07-31	Syntex Inc	Dihydropyridine derivatives,process and novel intermediates for their preparation and pharmaceutical compositions containing them
IL78642A0 (en) *	1985-05-03	1986-08-31	Pfizer	Dihydropyridines and pharmaceutical compositions containing them
DE3531498A1 (de) *	1985-09-04	1987-03-05	Bayer Ag	Dihydropyridin-2-hydroxyamine, verfahren zur herstellung und ihre verwendung in arzneimitteln
EP0225175A3 (en) *	1985-11-28	1988-12-28	FISONS plc	Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof
DE3544211A1 (de) *	1985-12-13	1987-06-19	Bayer Ag	Neue, fluorhaltige 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
IT1204460B (it) *	1986-02-20	1989-03-01	Glaxo Spa	Derivati eterociclici
GB8608335D0 (en) *	1986-04-04	1986-05-08	Pfizer Ltd	Pharmaceutically acceptable salts
US4983740A (en) *	1986-08-04	1991-01-08	Adir Et Compagnie	Process for 1,4-dihydropyridine compounds
FR2649395B1 (fr) *	1989-07-04	1992-11-06	Adir	Nouveau derive de la dihydro-1,4 pyridine denomme (-) i1(((amino-2 ethoxy)-2 ethoxy) methyli1) -2 (dichloro-2,3 phenyl)-4 ethoxycarbonyl-3 methoxycarbonyl-5 methyl-6 dihydro-1,4 pyridine, son procede de preparation et les compositions qui le contiennent
FR2602231B1 (fr) *	1986-08-04	1988-10-28	Adir	Nouveaux derives de la dihydro-1,4 pyridine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
US5196410A (en) *	1986-10-31	1993-03-23	Pfizer Inc.	Transdermal flux enhancing compositions
IT1213555B (it) *	1986-12-11	1989-12-20	Boehringer Biochemia Srl	2 metiltiometildiidropiridine, un processo per laloro preparazione e composizioni farmaceutiche che le contengono.
JPS63196564A (ja) *	1987-02-10	1988-08-15	Agency Of Ind Science & Technol	イミドオリゴマ−の製造方法
IT1215381B (it) *	1987-03-12	1990-02-08	Boehringer Biochemia Srl	Farmaceutiche che le contengono. carbonil- e solfonil- derivati di 2-(aminoalchiltio)metil-1,4-diidropiridine, un metodo per la loro preparazione e composizioni
GB8709447D0 (en) *	1987-04-21	1987-05-28	Pfizer Ltd	Dihydropyridines
GB8710493D0 (en) *	1987-05-02	1987-06-03	Pfizer Ltd	Dihydropyridines
DE3906406C1 (ja) *	1989-03-01	1990-10-25	Goedecke Ag, 1000 Berlin, De
US5234943A (en) *	1989-04-13	1993-08-10	Bayer Aktiengesellschaft	Fungicidal 3-(2-chloro-3-trifluoromethylphenyl)-4-cyanopyrrole
DE4128132A1 (de) *	1991-08-24	1993-02-25	Bayer Ag	3-(2-chlor-3-trifluormethylphenyl)-4-cyanopyrrol, dessen herstellung und verwendung und neue zwischenprodukte
FR2652083B1 (fr) *	1989-09-20	1992-01-24	Ador Cie	Nouveau procede de separation d'isomeres optiques des derives de la dihydro-1,4 pyridine.
US5270323A (en) *	1990-05-31	1993-12-14	Pfizer Inc.	Method of treating impotence
US6057344A (en)	1991-11-26	2000-05-02	Sepracor, Inc.	Methods for treating hypertension, and angina using optically pure (-) amlodipine
JPH07501547A (ja) *	1991-11-26	1995-02-16	セプラコア，インコーポレーテッド	光学的に純粋な（−）アムロジピンを用いる，高血圧，狭心症および他の疾患を治療するための方法および組成物
US6162802A (en) *	1992-03-10	2000-12-19	Papa; Joseph	Synergistic combination therapy using benazepril and amlodipine for the treatment of cardiovascular disorders and compositions therefor
EP1614420A3 (en) *	1992-11-25	2006-04-19	Sepracor Inc.	Treatment of hypertension, angina and other disorders using (-) amlodipine
SI9200344B (sl) *	1992-11-26	1998-06-30	Lek,	Postopek za pripravo amlodipin benzensulfonata
US5389654A (en) *	1992-11-26	1995-02-14	Lek, Tovarna, Farmacevtskih In Kemicnih . . .	3-ethyl 5-methyl(±)2-[2-(N-tritylamino)ethoxymethyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-6-methyl-3,5-pyridinedicarboxylate
US6221335B1 (en) *	1994-03-25	2001-04-24	Isotechnika, Inc.	Method of using deuterated calcium channel blockers
ATE235251T1 (de)	1995-03-16	2003-04-15	Pfizer	Verwendung von amlodipin, eines seiner salze oder felodipin in kombination mit einem ace-hemmer zur herstellung eines arzneimittels zur behandlung von nicht ischämischer kongestiver herzinsuffizienz
NZ280378A (en) *	1995-11-01	1998-04-27	Apotex Inc	4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid compounds, preparation, intermediate compounds
HU221810B1 (hu) *	1997-08-12	2003-01-28	EGIS Gyógyszergyár Rt.	Eljárás amlodipin-bezilát előállítására és az eljárás intermedierjei
GT199800127A (es) *	1997-08-29	2000-02-01		Combinaciones terapeuticas.
ZA9810319B (en) *	1997-11-14	2000-05-11	Gea Farmaceutisk Fabrik As	Process for the preparation of acetal derivatives of 1,4-dihydropyridines, novel acetal derivatives and the use of the acetal derivatives for the preparation of other 1,4-dihydropyridines.
ZA9810320B (en) *	1997-11-14	2000-05-11	Gea Farmaceutisk Fabrik As	Process for the preparation of 1,4-dihydropyridines and novel compounds of use for such purpose.
ES2151850B1 (es) *	1998-10-26	2001-08-16	Esteve Quimica Sa	Intermedio para la sintesis de amlodipino para su obtencion y utilizacion correspondiente.
RU2142942C1 (ru) *	1999-04-28	1999-12-20	Дж. Б.Кемикалс энд Фармасьютикалс Лтд.	Способ получения монобензолсульфоната 3-этил-5-метилового эфира 2-[(2-аминоэтокси)метил]-4-(2-хлорфенил)-1,4-дигидро-6-метил-3,5-пиридинди карбоновой кислоты
HN2000000050A (es)	1999-05-27	2001-02-02	Pfizer Prod Inc	Sal mutua de amlodipino y atorvastatina
BR0011006A (pt)	1999-05-27	2002-02-19	Pfizer Prod Inc	Prõ-drogas mútuas de amlodipina e atorvastatina
UA72768C2 (en)	1999-07-05	2005-04-15	Richter Gedeon Vegyeszet	A method for obtaining amilodipine benzenesulphonate
RU2146672C1 (ru) *	1999-10-13	2000-03-20	Др.Редди'С Лабораторис Лтд.	Способ получения 3-этил-5-метил(±)2[2-аминоэтокси)-метил]-4-(2-хлорфенил)-1,4-дигидро- 6-метил-3,5-пиридиндикарбоксилат монобензолсульфоната
CN1091441C (zh) *	1999-12-04	2002-09-25	昆明赛诺制药有限公司	甲磺酸氨氯地平及其制法和应用
US6521647B2 (en)	2000-04-04	2003-02-18	Pfizer Inc.	Treatment of renal disorders
NZ521853A (en) *	2000-04-11	2003-11-28	Sankyo Co	Stabilized pharmaceutical compositions containing a calcium blocker
AU2001284413A1 (en) *	2000-08-30	2002-03-13	Sankyo Company Limited	Medicinal compositions for preventing or treating heart failure
GB0027410D0 (en) *	2000-11-09	2000-12-27	Pfizer Ltd	Mutual prodrug of amlodipine and atorvastatin
US6737430B2 (en)	2000-11-09	2004-05-18	Pfizer, Inc.	Mutual prodrug of amlodipine and atorvastatin
MXPA03005882A (es)	2000-12-29	2005-04-19	Pfizer Ltd	Derivado amida de amlodipina.
WO2002053535A2 (en) *	2000-12-29	2002-07-11	Bioorganics B.V.	Process for making amlodipine, derivatives thereof, and precursors therefor
KR20030066782A (ko) *	2000-12-29	2003-08-09	화이자 리미티드	암로디핀 말레에이트를 제조하는 방법
AT5874U1 (de)	2000-12-29	2003-01-27	Bioorg Bv	Pharmazeutische zubereitungen enthaltend amlodipinmaleat
CA2433284A1 (en)	2000-12-29	2002-07-11	Pfizer Limited	Reference standards and processes for determining the purity or stability of amlodipine maleate
CA2433181C (en) *	2000-12-29	2005-11-22	Pfizer Limited	Amlodipine hemifumarate
BR0116553A (pt) *	2000-12-29	2004-02-03	Pfizer Ltd	Composto, composição farmacêutica para tratamento de angina ou hipertensão, processo, processo para tratamento ou prevenção de angina ou hipertensão, composição de ingredientes farmaceuticamente ativos, composição farmacêutica para tratamento ou prevenção de angina ou hipertensão e processo para tratar ou prevenir angina ou hipertensão
WO2002053541A1 (en)	2000-12-29	2002-07-11	Pfizer Limited	Amide derivative of amlodipine
BR0116552A (pt) *	2000-12-29	2004-02-03	Pfizer Ltd	Hemi-maleato de amlodipina, processo, método para o tratamento ou prevenção de angina ou hipertensão, composição farmacêutica, para uso no tratamento e/ou de angina ou da hipertensão
US6653481B2 (en)	2000-12-29	2003-11-25	Synthon Bv	Process for making amlodipine
RS53403A (sr) *	2000-12-29	2006-10-27	Pfizer Limited	Postupak za dobijanje amlodipin maleata
US7335380B2 (en)	2000-12-29	2008-02-26	Synthon Ip Inc.	Amlodipine free base
KR100374767B1 (ko) *	2001-03-13	2003-03-03	한미약품공업 주식회사	개선된 암로디핀의 제조 방법
KR100452491B1 (ko) *	2001-03-29	2004-10-12	한미약품 주식회사	신규한 결정형 암로디핀 캠실레이트 염 및 그의 제조방법
ATE454890T1 (de)	2001-07-06	2010-01-15	Lek Pharmaceuticals	Verfahren zur herstellung hochreines amlodipinbenzolsulfonat
GB0120808D0 (en) *	2001-08-28	2001-10-17	Pfizer Ltd	Crystalline material
US6680334B2 (en)	2001-08-28	2004-01-20	Pfizer Inc	Crystalline material
US20030180354A1 (en) *	2001-10-17	2003-09-25	Dr. Reddy's Laboratories Limited	Amlodipine maleate formulations
US20040001886A1 (en) *	2001-10-17	2004-01-01	Dr. Reddy's Laboratories Limited	Stabilized pharmaceutical formulations containing amlodipine maleate
IL163666A0 (en)	2002-02-22	2005-12-18	New River Pharmaceuticals Inc	Active agent delivery systems and methods for protecting and administering active agents
US6562983B1 (en) *	2002-03-18	2003-05-13	Council Of Scientific And Industrial Research	Process for the preparation of alkyl 4[2-(phthalimido)ethoxy]-acetoacetate
AU2003225370A1 (en) *	2002-04-13	2003-11-03	Hanlim Pharmaceutical Co., Ltd.	Amlodipine nicotinate and process for the preparation thereof
US6699892B2 (en)	2002-06-04	2004-03-02	Yung Shin Pharmaceutical Industrial Co., Ltd.	Pharmaceutically acceptable salt of amlodipine and method of preparing the same
KR20040011751A (ko) *	2002-07-30	2004-02-11	씨제이 주식회사	암로디핀의 유기산염
KR100496436B1 (ko) *	2002-07-30	2005-06-20	씨제이 주식회사	암로디핀의 유기산염
KR100538641B1 (ko) *	2002-07-30	2005-12-22	씨제이 주식회사	암로디핀의 유기산염
KR100462304B1 (ko)	2002-07-30	2004-12-17	씨제이 주식회사	암로디핀의 유기산염
EP1545519B1 (en)	2002-08-19	2011-03-23	Pfizer Inc.	Combination therapy for hyperproliferative diseases
KR100467669B1 (ko) *	2002-08-21	2005-01-24	씨제이 주식회사	암로디핀의 유기산염
US6784297B2 (en) *	2002-09-04	2004-08-31	Kopran Limited	Process for the preparation of anti-ischemic and anti-hypertensive drug amlodipine besylate
CA2525700C (en)	2002-09-11	2009-11-24	Hanlim Pharmaceutical Co., Ltd.	S-(-)-amlodipine nicotinate and process for the preparation thereof
AU2003253460A1 (en)	2002-09-19	2004-04-08	Cj Corporation	Crystalline organic acid salt of amlodipine
KR100596369B1 (ko)	2002-09-19	2006-07-03	씨제이 주식회사	결정형의 암로디핀 유기산염
US20040072879A1 (en) *	2002-10-10	2004-04-15	Dr. Reddy's Laboratories Limited	Crystalline 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine maleate salt (Amlodipine)
AU2002368531A1 (en) *	2002-12-30	2004-07-22	Eos Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ticaret A.S.	Isolation of dihydropyridine derivative and preparation salts thereof
DE10335027A1 (de) *	2003-07-31	2005-02-17	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verwendung von Angiotensin II Rezeptor Antagonisten
RS20050590A (sr) *	2003-01-31	2007-09-21	Sankyo Company Limited,	Lek za profilaksu i tretman arterioskleroze i hipertenzije
US20050019395A1 (en) *	2003-04-14	2005-01-27	Gabor Pragai	Formulations of amlodipine maleate
US20050159403A1 (en) *	2003-04-22	2005-07-21	Pharmacia Corporation	Compositions of a cyclooxygenase-2 selective inhibitor and a calcium modulating agent for the treatment of central nervous system damage
US20060135506A1 (en) *	2003-04-22	2006-06-22	Pharmacia Corporation	Compositions of a cyclooxygenase-2 selective inhibitor and a calcium modulating agent for the treatment of pain, inflammation or inflammation mediated disorders
GB2415696B (en) *	2003-04-25	2007-06-20	Cipla Ltd	Process for preparing amlodipine mesylate monohydrate
WO2004110998A1 (en) *	2003-05-16	2004-12-23	Ambit Biosciences Corporation	Pyrrole compounds and uses thereof
US20050182125A1 (en) *	2003-05-16	2005-08-18	Ambit Biosciences Corporation	Pyrrole compounds and uses thereof
CN1812983A (zh) *	2003-05-30	2006-08-02	兰贝克赛实验室有限公司	取代的吡咯衍生物及其作为hmg－co抑制剂的用途
CA2532807A1 (en) *	2003-07-17	2005-02-03	Cotherix, Inc.	Combination therapies for treatment of hypertension and complications in patients with diabetes or metabolic syndrome
US20050037063A1 (en) *	2003-07-21	2005-02-17	Bolton Anthony E.	Combined therapies
CH697952B1 (de) *	2003-07-25	2009-03-31	Siegfried Generics Int Ag	Verfahren zur Reinigung der freien Amlodipinbase.
WO2005023769A1 (en) *	2003-09-04	2005-03-17	Cipla Limited	Process for the preparation of amlodipine salts
AU2004272078A1 (en) *	2003-09-10	2005-03-24	Synta Pharmaceuticals Corp.	Dihydropyridine compounds for treating or preventing metabolic disorders
KR100841409B1 (ko) *	2003-12-16	2008-06-25	에스케이케미칼주식회사	암로디핀 겐티세이트 염과 이의 제조방법
US7262318B2 (en) *	2004-03-10	2007-08-28	Pfizer, Inc.	Substituted heteroaryl- and phenylsulfamoyl compounds
US20060030602A1 (en) *	2004-03-16	2006-02-09	Sepracor Inc.	(S)-amlodipine malate
US7244765B2 (en) *	2004-06-25	2007-07-17	Cytokine Pharmasciences, Inc	Guanylhydrazone salts, compositions, processes of making and methods of using
US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
WO2006003672A1 (en) *	2004-07-02	2006-01-12	Matrix Laboratories Ltd	Process for the preparation of pure amlodipine
EP1796653A2 (en) *	2004-07-26	2007-06-20	Actelion Pharmaceuticals Ltd.	Treatment of pulmonary hypertension by inhaled iloprost with a microparticle formulation
RS53141B (sr) *	2004-11-05	2014-06-30	Boehringer Ingelheim International Gmbh	Dvoslojna tableta koja sadrži telmisartan i amlodipin
AU2005308575A1 (en) *	2004-11-23	2006-06-01	Warner-Lambert Company Llc	7-(2h-pyrazol-3-yl)-3, 5-dihyroxy-heptanoic acid derivatives as HMG Co-A reductase inhibitors for the treatment of lipidemia
EP1833466A1 (en) *	2004-12-28	2007-09-19	Ranbaxy Laboratories Limited	Methods for the preparation of stable pharmaceutical solid dosage forms of atorvastatin and amlodipine
US20080268049A1 (en) *	2005-02-11	2008-10-30	Dhaliwal Mona	Stable Solid Dosage Forms of Amlodipine and Benazepril
CN101247832B (zh) *	2005-06-27	2011-12-28	第一三共株式会社	含有血管紧张素ⅱ受体拮抗剂和钙通道阻断剂的药物制剂
AU2006264407B2 (en) *	2005-07-04	2012-08-30	Ramu Krishnan	Improved drug or pharmaceutical compounds and a preparation thereof
ES2265781B1 (es) *	2005-08-04	2007-12-01	Ercros Industrial, S.A.	Procedimiento para la obtencion de besilato de amlodipina.
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7893050B2 (en) *	2005-10-26	2011-02-22	Asahi Kasei Pharma Corporation	Fasudil in combination therapies for the treatment of pulmonary arterial hypertension
EP2351569B1 (en)	2005-10-26	2012-08-22	Asahi Kasei Pharma Corporation	Fasudil in combination therapies for the treatment of pulmonary arterial hypertension
SG166829A1 (en) *	2005-11-08	2010-12-29	Ranbaxy Lab Ltd	Process for (3r, 5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4- [(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3, 5-dihydroxy-heptanoic acid hemi calcium salt
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
TW200806648A (en) *	2005-11-29	2008-02-01	Sankyo Co	Acid addition salts of dihydropyridine derivatives
TW200736245A (en) *	2005-11-29	2007-10-01	Sankyo Co	Acid addition salts of optically active dihydropyridine derivatives
US7919506B2 (en)	2006-03-10	2011-04-05	Pfizer Inc.	Dibenzyl amine compounds and derivatives
WO2008020314A2 (en) *	2006-03-14	2008-02-21	Ranbaxy Laboratories Limited	Statin stabilizing dosage formulations
US20070260065A1 (en) *	2006-05-03	2007-11-08	Vijayabhaskar Bolugoddu	Process for preparing amlodipine
WO2008010087A2 (en) *	2006-07-14	2008-01-24	Ranbaxy Laboratories Limited	Polymorphic forms of an hmg-coa reductase inhibitor and uses thereof
WO2008023869A1 (en) *	2006-08-24	2008-02-28	Hanall Pharmaceutical Co., Ltd.	Combined pharmeceutical formulation with controlled-release comprising dihydropyridine calcium channel blockers and hmg-coa reductase inhibitors
TWI399223B (zh) *	2006-09-15	2013-06-21	Daiichi Sankyo Co Ltd	奧美沙坦酯及氨氯地平之固體劑型
US20080096863A1 (en) *	2006-10-19	2008-04-24	Torrent Pharmaceuticals Limited	Stable pharmaceutical compositions of calcium channel blocker and an ACE inhibitor
CN101167724B (zh) *	2006-10-25	2012-08-22	北京华安佛医药研究中心有限公司	含有氨氯地平的药物组合物在制备治疗下尿路疾病药物中的用途
KR100830003B1 (ko)	2006-10-31	2008-05-15	씨제이제일제당 (주)	결정성 ｓ-(-)-암로디핀 아디핀산 염 무수물 및 이의 제조방법
JP5498168B2 (ja)	2006-12-01	2014-05-21	ブリストル−マイヤーズスクイブカンパニー	アテローム性動脈硬化および循環器疾患の治療のためのｃｅｔｐ阻害剤としてのｎ−（（３−ベンジル）−２，２−（ビス−フェニル）−プロパン−１−アミン誘導体
GB0624084D0 (en) *	2006-12-01	2007-01-10	Selamine Ltd	Ramipril amino acid salts
GB0624087D0 (en) *	2006-12-01	2007-01-10	Selamine Ltd	Ramipril combination salt
GB0624090D0 (en) *	2006-12-01	2007-01-10	Selamine Ltd	Ramipril amine salts
TWI384986B (zh) *	2007-01-17	2013-02-11	Lg Life Sciences Ltd	抗病毒劑之順丁烯二酸單鹽以及含有該單鹽之醫藥組成物
CN101230035B (zh) *	2007-03-23	2010-11-03	浙江尖峰药业有限公司	门冬氨酸氨氯地平系列盐及其制备方法和其组合物、制剂以及片剂
EP1975167A1 (en) *	2007-03-30	2008-10-01	Esteve Quimica, S.A.	Acetone solvate of phthaloyl amlodipine
WO2008124121A1 (en) *	2007-04-06	2008-10-16	Scidose, Llc	Co-therapy with and combinations of statins and 1,4-dihydropyridine-3,5-dicarboxydiesters
US20090062352A1 (en) *	2007-08-29	2009-03-05	Protia, Llc	Deuterium-enriched amlodipine
WO2009032286A2 (en)	2007-09-06	2009-03-12	Nektar Therapeutics Al, Corporation	Oligomer-calcium channel blocker conjugates
PE20091156A1 (es) *	2007-12-17	2009-09-03	Astrazeneca Ab	Sales de (3-{[[3-(6-amino-2-butoxi-8-oxo-7,8-dihidro-9h-purin-9-il)propil](3-morfolin-4-ilpropil)amino]metil}fenil)acetato de metilo
WO2009084003A1 (en) *	2007-12-31	2009-07-09	Lupin Limited	Pharmaceutical compositions of amlodipine and valsartan
ES2510866T3 (es)	2008-03-13	2014-10-21	Daiichi Sankyo Company, Limited	Mejora de la solubilidad de una preparación que contiene olmesartán medoxomilo
CN101560181B (zh) *	2008-04-16	2013-02-27	北京万全阳光医学技术有限公司	一种氨氯地平游离碱的制备方法
CN101367759B (zh) *	2008-10-06	2011-03-16	北京赛科药业有限责任公司	一种高纯度苯磺酸氨氯地平的合成方法
JP2010100562A (ja) *	2008-10-23	2010-05-06	Daito Kk	アムロジピン製造中間体の精製方法
JP2012528799A (ja)	2009-06-02	2012-11-15	ダウグローバルテクノロジーズエルエルシー	徐放製剤
EP2509596B1 (en)	2009-12-08	2019-08-28	Case Western Reserve University	Gamma aminoacids for treating ocular disorders
WO2011117876A1 (en)	2010-03-26	2011-09-29	Fdc Limited	An improved process for the preparation of amlodipine free base and acid addition salts thereof
IT1400309B1 (it)	2010-05-10	2013-05-24	Menarini Int Operations Lu Sa	Associazione di inibitori della xantina ossidasi e calcio antagonisti e loro uso.
EP2575808A1 (en)	2010-05-28	2013-04-10	Mahmut Bilgic	Combination of antihypertensive agents
EP2575757A1 (en)	2010-06-03	2013-04-10	Mahmut Bilgic	Water soluble formulation comprising a combination of amlodipine and a statin
US8883844B2 (en)	2010-09-24	2014-11-11	Nitrogenix Inc.	Nitric oxide releasing amino acid ester for treatment of pulmonary hypertension and other respiratory conditions
WO2012055941A1 (en)	2010-10-27	2012-05-03	Krka,Tovarna Zdravil, D. D., Novo Mesto	Multilayer pharmaceutical composition comprising telmisartan and amlodipine
TR201100152A2 (tr)	2011-01-06	2012-07-23	Bi̇lgi̇ç Mahmut	Amlodipin içeren efervesan bileşimler.
CN102070516A (zh) *	2011-02-22	2011-05-25	广东东阳光药业有限公司	一种制备氨氯地平的方法
WO2012123966A1 (en)	2011-03-04	2012-09-20	Arch Pharmalabs Limited	Process for the preparation of 4 -substituted -1, 4-dihydropyridines
UA110244C2 (en)	2011-04-12	2015-12-10	Boryung Pharm	Antihypertensive pharmaceutical composition
US9446032B2 (en)	2011-08-26	2016-09-20	Wockhardt Limited	Methods for treating cardiovascular disorders
CN102382041B (zh) *	2011-12-02	2016-01-20	东北制药集团股份有限公司	一种马来酸氨氯地平的制备方法
PL236001B1 (pl)	2012-12-21	2020-11-30	Adamed Spolka Z Ograniczona Odpowiedzialnoscia	Złożona kompozycja farmaceutyczna zawierająca kandesartan cyleksetylu oraz amlodypinę, sposób jej wytwarzania oraz jednostkowa postać dawkowania zawierająca tę kompozycję
CN103044314A (zh) *	2013-01-06	2013-04-17	先声药业有限公司	马来酸氨氯地平的制备方法
JP5952748B2 (ja) *	2013-01-25	2016-07-13	東和薬品株式会社	フタロイルアムロジピンの新規結晶形態およびそれを用いる高純度なアムロジピンベシル酸塩の製造方法
US20150374713A1 (en)	2013-02-08	2015-12-31	Wockhardt Limited	Stable pharmeceutical composition of amlodipine and benazepril or salts thereof
SG11201507496UA (en)	2013-04-17	2015-11-27	Pfizer	N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
EP3025711B1 (en)	2013-07-23	2020-11-18	Daiichi Sankyo Company, Limited	Medicine for preventing or treating hypertension
CN104262237A (zh) *	2014-09-28	2015-01-07	常州瑞明药业有限公司	氨氯地平自由碱的合成方法
WO2016055901A1 (en)	2014-10-08	2016-04-14	Pfizer Inc.	Substituted amide compounds
CN104529877A (zh) *	2015-01-22	2015-04-22	华东理工常熟研究院有限公司	氨氯地平-癸酸离子液体及其制备方法和用途
CZ2015687A3 (cs)	2015-10-02	2017-04-12	Zentiva, K.S.	Farmaceutická kompozice obsahující kombinaci kandesartanu, amlodipinu a hydrochlorthiazidu
WO2017068532A1 (en)	2015-10-23	2017-04-27	Ftf Pharma Private Limited	Oral solution of dihydropyridine derivatives
EP3434284A4 (en)	2016-03-24	2019-11-13	Daiichi Sankyo Company, Limited	MEDICINE FOR THE TREATMENT OF KIDNEY DISEASE
JP6411662B2 (ja)	2016-05-30	2018-10-24	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	固定容量配合剤
EP3960158B1 (en)	2016-10-07	2025-05-21	Silvergate Pharmaceuticals, Inc.	Amlodipine formulations
US10350171B2 (en)	2017-07-06	2019-07-16	Dexcel Ltd.	Celecoxib and amlodipine formulation and method of making the same
CN112334134A (zh)	2018-04-11	2021-02-05	希沃盖特制药公司	氨氯地平制剂
US11417416B2 (en)	2018-06-14	2022-08-16	Astrazeneca Uk Limited	Methods for lowering blood pressure with a dihydropyridine-type calcium channel blocker pharmaceutical composition
JP7470646B2 (ja)	2018-06-14	2024-04-18	アストラゼネカ・ユーケイ・リミテッド	コルチコステロイド医薬組成物を用いて喘息の症状を治療および予防するための方法
US11248001B2 (en)	2019-01-18	2022-02-15	Astrazeneca Ab	PCSK9 inhibitors and methods of use thereof
CN113840538B (zh)	2019-05-21	2025-03-07	雀巢产品有限公司	膳食丁酸酯
GB2595203A (en)	2020-03-03	2021-11-24	Alkaloid Ad Skopje	Formulation
GB202102575D0 (en)	2021-02-23	2021-04-07	Teva Pharmaceutical Industries Ltd	Fixed-dose pharmaceutical compositions
GB2636158A (en)	2023-12-01	2025-06-11	Novumgen Ltd	An orally disintegrating tablet containing amlodipine or pharmaceutically acceptable salts thereof and the process of preparing the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1552911A (en) *	1975-07-02	1979-09-19	Fujisawa Pharmaceutical Co	1,4 dihydropyridine derivatives and the preparation thereof
JPS5547656A (en) *	1978-09-29	1980-04-04	Dainippon Pharmaceut Co Ltd	2-(2-substituted aminoethyl)-1,4-dihydropyridine derivative and its derivative
SE7910521L (sv) *	1979-12-20	1981-06-21	Haessle Ab	Nya 2-metyl-6-substituerade-4-(2,3-disubstituerad fenyl)-1,4-dihydropyridin-3,5-diestrar med hypotesiva egenskaper, samt forfarande for deras framstellning, och farmaceutiska beredningar innehallande desamma
CS228917B2 (en) *	1981-03-14	1984-05-14	Pfizer	Method of preparing substituted derivatives of 1,4-dihydropyridine
DE3739854A1 (de) *	1987-11-25	1989-06-08	Philips Patentverwaltung	Verfahren zur herstellung von titandioxid-pulver

1983
- 1983-02-23 DK DK081383A patent/DK161312C/da not_active IP Right Cessation
- 1983-03-03 PL PL1983240854A patent/PL140278B1/pl unknown
- 1983-03-03 PL PL1983250767A patent/PL140575B1/pl unknown
- 1983-03-03 PL PL1983255811A patent/PL141830B1/pl unknown
- 1983-03-03 CS CS831499A patent/CS240954B2/cs unknown
- 1983-03-04 UA UA3571949A patent/UA7083A1/uk unknown
- 1983-03-04 SU SU833571949A patent/SU1238730A3/ru active
- 1983-03-04 UA UA3675004A patent/UA7082A1/uk unknown
- 1983-03-04 HU HU83759A patent/HU187868B/hu unknown
- 1983-03-08 EP EP83301227A patent/EP0089167B1/en not_active Expired
- 1983-03-08 AT AT83301227T patent/ATE22884T1/de active
- 1983-03-08 GR GR70728A patent/GR77429B/el unknown
- 1983-03-08 DE DE1993175111 patent/DE19375111I2/de active Active
- 1983-03-08 ES ES520389A patent/ES520389A0/es active Granted
- 1983-03-08 DE DE8383301227T patent/DE3366920D1/de not_active Expired
- 1983-03-08 KR KR1019830000935A patent/KR870000809B1/ko not_active Expired
- 1983-03-09 IL IL68091A patent/IL68091A/xx not_active IP Right Cessation
- 1983-03-09 CA CA000423148A patent/CA1253865A/en not_active Expired
- 1983-03-09 NZ NZ203521A patent/NZ203521A/en unknown
- 1983-03-09 FI FI830789A patent/FI81090C/fi not_active IP Right Cessation
- 1983-03-09 EG EG163/83A patent/EG16987A/xx active
- 1983-03-10 YU YU586/83A patent/YU43541B/xx unknown
- 1983-03-10 DD DD83264890A patent/DD218887A5/de unknown
- 1983-03-10 AU AU12351/83A patent/AU540769B2/en not_active Expired
- 1983-03-10 IE IE520/83A patent/IE54667B1/en not_active IP Right Cessation
- 1983-03-10 IE IE3092/86A patent/IE54765B1/en not_active IP Right Cessation
- 1983-03-10 ZA ZA831651A patent/ZA831651B/xx unknown
- 1983-03-10 PT PT76370A patent/PT76370B/pt unknown
- 1983-03-10 DD DD83248690A patent/DD209622A5/de unknown
- 1983-03-10 NO NO830847A patent/NO162818C/no not_active IP Right Cessation
- 1983-03-10 SI SI8310586A patent/SI8310586A8/sl unknown
- 1983-03-11 JP JP58040534A patent/JPS58167569A/ja active Granted
- 1983-10-14 ES ES526459A patent/ES8505201A1/es not_active Expired
- 1983-12-14 SU SU833675004A patent/SU1227110A3/ru active
1984
- 1984-02-03 US US06/576,982 patent/US4572909A/en not_active Expired - Lifetime
- 1984-04-06 CS CS841592A patent/CS240998B2/cs unknown
1985
- 1985-09-10 YU YU1419/85A patent/YU43417B/xx unknown
- 1985-09-10 SI SI8511419A patent/SI8511419A8/sl unknown
1986
- 1986-11-06 NO NO864435A patent/NO170275C/no not_active IP Right Cessation
1987
- 1987-08-14 MY MYPI87001340A patent/MY101985A/en unknown
- 1987-10-08 KE KE3778A patent/KE3778A/xx unknown
- 1987-11-05 SG SG986/87A patent/SG98687G/en unknown
1988
- 1988-03-03 HK HK162/88A patent/HK16288A/en not_active IP Right Cessation
1991
- 1991-12-31 CS CS914188A patent/CS418891A3/cs unknown
1992
- 1992-03-17 BG BG96079A patent/BG60658B2/xx unknown
1993
- 1993-03-16 HR HR930369A patent/HRP930369B1/xx not_active IP Right Cessation
- 1993-03-16 HR HR930370A patent/HRP930370B1/xx not_active IP Right Cessation
- 1993-06-11 NL NL930063C patent/NL930063I2/nl unknown
- 1993-06-24 LU LU88332C patent/LU88332I2/fr unknown
- 1993-06-28 LV LV930666A patent/LV5236A3/xx unknown
- 1993-06-28 LV LV930667A patent/LV5235A3/xx unknown
1994
- 1994-11-02 NO NO1994020C patent/NO1994020I1/no unknown
1997
- 1997-03-28 BA BA970147A patent/BA97147B1/bs active
1998
- 1998-03-04 BA BA980207A patent/BA98207B1/bs active

Also Published As

Publication number	Publication date
IE863092L (en)	1983-09-11
LV5236A3 (lv)	1993-10-10
LV5235A3 (lv)	1993-10-10
JPS58167569A (ja)	1983-10-03
NO830847L (no)	1983-09-12
IL68091A (en)	1986-11-30
ATE22884T1 (de)	1986-11-15
ES8503654A1 (es)	1985-03-16
DK81383A (da)	1983-09-12
YU43417B (en)	1989-06-30
PL250767A1 (en)	1985-12-17
IE830520L (en)	1983-09-11
PT76370A (en)	1983-04-01
EP0089167A2 (en)	1983-09-21
YU58683A (en)	1986-06-30
HRP930370B1 (en)	1996-02-29
NO162818B (no)	1989-11-13
NO864435L (no)	1983-09-12
PL141830B1 (en)	1987-08-31
PL140575B1 (en)	1987-05-30
ES520389A0 (es)	1985-03-16
KR840004073A (ko)	1984-10-06
SG98687G (en)	1988-09-23
NO1994020I1 (no)	1994-11-02
ES526459A0 (es)	1985-05-16
CS240998B2 (en)	1986-03-13
FI81090B (fi)	1990-05-31
CS149983A2 (en)	1985-06-13
NL930063I2 (nl)	1993-10-01
SI8511419A8 (sl)	1996-10-31
SI8310586A8 (sl)	1996-02-29
FI830789L (fi)	1983-09-12
IE54667B1 (en)	1990-01-03
US4572909A (en)	1986-02-25
EP0089167B1 (en)	1986-10-15
LU88332I2 (fr)	1994-05-04
PL140278B1 (en)	1987-04-30
NO162818C (no)	1990-02-21
EP0089167A3 (en)	1984-07-11
DE3366920D1 (en)	1986-11-20
DD218887A5 (de)	1985-02-20
GR77429B (ja)	1984-09-14
BA97147B1 (bs)	1998-12-28
AU1235183A (en)	1983-09-22
CS159284A2 (en)	1985-06-13
HRP930369B1 (en)	1996-02-29
UA7082A1 (uk)	1995-06-30
YU43541B (en)	1989-08-31
NZ203521A (en)	1985-09-13
IE54765B1 (en)	1990-01-31
DK81383D0 (da)	1983-02-23
PT76370B (en)	1986-03-27
MY101985A (en)	1992-02-29
NO170275B (no)	1992-06-22
CA1253865A (en)	1989-05-09
DE19375111I2 (de)	2001-06-13
ES8505201A1 (es)	1985-05-16
HK16288A (en)	1988-03-11
KR870000809B1 (ko)	1987-04-20
NO864435D0 (no)	1986-11-06
DK161312C (da)	1991-12-09
SU1227110A3 (ru)	1986-04-23
NL930063I1 (nl)	1993-09-01
YU141985A (en)	1986-06-30
CS240954B2 (en)	1986-03-13
ZA831651B (en)	1983-12-28
FI81090C (fi)	1990-09-10
SU1238730A3 (ru)	1986-06-15
PL240854A1 (en)	1985-04-09
JPS626703B2 (ja)	1987-02-13
IL68091A0 (en)	1983-06-15
EG16987A (en)	1991-03-30
NO170275C (no)	1992-09-30
FI830789A0 (fi)	1983-03-09
UA7083A1 (uk)	1995-06-30
BA98207B1 (bs)	1999-08-02
DK161312B (da)	1991-06-24
CS418891A3 (en)	1992-09-16
AU540769B2 (en)	1984-12-06
BG60658B2 (en)	1995-11-30
HU187868B (en)	1986-02-28
KE3778A (en)	1987-11-27

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)

Publication	Publication Date	Title
DD218887A5 (de)	1985-02-20	Verfahren zur herstellung von 1,4-dihydropyridinen
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
AT389875B (de)	1990-02-12	Verfahren zur herstellung von 4h-1-benzopyran-4-on-derivaten, neue 4h-1-benzopyran-4-on-derivate und ihre verwendung als arzneimittel
DD202430A5 (de)	1983-09-14	Verfahren zur herstellung von dihydropyridinen
DE29724281U1 (de)	2000-08-10	4-Phenylpiperidin-Verbindungen
CH637938A5 (de)	1983-08-31	Verfahren zur herstellung neuer 1,4-dihydropyridinderivate.
DE2824064A1 (de)	1978-12-14	Phthalazin-derivate, ihre herstellung und solche derivate enthaltende arzneimittel
AT7109U2 (de)	2004-10-25	Verfahren zur herstellung von amlodipinmaleat
DE69621469T2 (de)	2002-12-12	Phenylpiperidin-derivate
DE3787657T2 (de)	1994-02-03	Aminosäure-Derivate.
DE3002367A1 (de)	1980-07-24	2-substituierte trans-5-aryl-2,3,4,4a,5, 9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
CH642353A5 (de)	1984-04-13	2-methyl-dihydropyridin-verbindung, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel.
DE2461802C2 (de)	1985-01-03	Pyrazincarboxamidderivate
DE2816884A1 (de)	1978-11-02	Anilinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
CH647519A5 (de)	1985-01-31	Bluthochdruck senkende amine.
DD207712A5 (de)	1984-03-14	Verfahren zur herstellung von diestern
DE2919800A1 (de)	1979-11-22	4-amino-2-piperidinochinazolin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DE2806909C2 (ja)	1988-04-07
CH645368A5 (de)	1984-09-28	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung.
DE3423003A1 (de)	1986-01-02	Benzo(c)(1,8)naphthyridine, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen
DD297813A5 (de)	1992-01-23	Verfahren zur herstellung von dihydropyridinamiden
DE3628215C2 (de)	1996-09-19	1,4-Dihydro-2-alkylenamino-3,5-dicarbonester-4-(2-propenyl)-phenyl-pyridine, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitung
EP0657432B1 (de)	2003-03-12	Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität
DE831696C (de)	1952-02-18	Verfahren zur Herstellung von Antihistaminen
DE3785963T2 (de)	1993-09-02	Dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.