CS277644B6 - Pharmaceutical preparation for treating cardial and vascular hypertrophy and hyperplasia - Google Patents

Pharmaceutical preparation for treating cardial and vascular hypertrophy and hyperplasia Download PDF

Info

Publication number: CS277644B6
Authority: CS; Czechoslovakia
Prior art keywords: alkyl; carbon atoms; carboxylic acid; aryl; optionally substituted
Prior art date: 1989-08-11

Application number

CS903958A

Other languages

Czech (cs)

English (en)

Other versions

CS395890A3 (en

Inventor

Wolfgang Dr Linz

Bernward Prof Dr Scholkens

Wolfgang Dr Scholz

Gabriele Dr Wiemer

Hansjorg Dr Urbach

Rainer Dr Henning

Volker Dr Teetz

Original Assignee

Hoechst Ag

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.)

1989-08-11

Filing date

1990-08-10

Publication date

1993-03-17

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6386970&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS277644(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-08-10 Application filed by Hoechst Ag filed Critical Hoechst Ag

1992-08-12 Publication of CS395890A3 publication Critical patent/CS395890A3/cs

1993-03-17 Publication of CS277644B6 publication Critical patent/CS277644B6/cs

Links

206010020718 hyperplasia Diseases 0.000 title claims description 12
206010072810 Vascular wall hypertrophy Diseases 0.000 title claims description 10
239000000825 pharmaceutical preparation Substances 0.000 title description 2
-1 aliphatic radical Chemical class 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000003118 aryl group Chemical group 0.000 claims description 36
229910052717 sulfur Inorganic materials 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 20
239000005541 ACE inhibitor Substances 0.000 claims description 18
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
125000006413 ring segment Chemical group 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 13
208000006029 Cardiomegaly Diseases 0.000 claims description 11
206010007572 Cardiac hypertrophy Diseases 0.000 claims description 10
230000000747 cardiac effect Effects 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
235000008206 alpha-amino acids Nutrition 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000003003 spiro group Chemical group 0.000 claims description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
125000002723 alicyclic group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004344 phenylpropyl group Chemical group 0.000 claims description 3
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 3
UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 claims description 2
SBUWIPJHZAJVSM-UHFFFAOYSA-N 1,2,3,3a,4,5,6,7,8,8a-decahydrocyclohepta[b]pyrrole Chemical compound C1CCCCC2NCCC21 SBUWIPJHZAJVSM-UHFFFAOYSA-N 0.000 claims description 2
NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical class C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 claims description 2
PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical class C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 claims description 2
ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical compound C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 claims description 2
MFOUWLGLIHXCOZ-UHFFFAOYSA-N 2,3,3a,4,5,7a-hexahydro-1h-indole Chemical compound C1CC=CC2NCCC21 MFOUWLGLIHXCOZ-UHFFFAOYSA-N 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
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101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
FLLUHHKAVNMUKU-OFQXOLIOSA-N (3s,4as)-2-[(2s)-2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl]-3,4,4a,5-tetrahydro-1h-isoquinoline-3-carboxylic acid Chemical compound N([C@@H](C)C(=O)N1[C@@H](C[C@@H]2CC=CC=C2C1)C(O)=O)C(C(=O)OCC)CCC1=CC=CC=C1 FLLUHHKAVNMUKU-OFQXOLIOSA-N 0.000 claims 1
NSENYWQRQUNUGD-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-ium-3-carboxylate Chemical compound C1CCCC2CNC(C(=O)O)CC21 NSENYWQRQUNUGD-UHFFFAOYSA-N 0.000 claims 1
WSSDGZWSPMAECX-UHFFFAOYSA-N 2-azabicyclo[3.1.0]hexane Chemical compound C1CNC2CC21 WSSDGZWSPMAECX-UHFFFAOYSA-N 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
125000000304 alkynyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
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229940125532 enzyme inhibitor Drugs 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000003039 tetrahydroisoquinolinyl group Chemical class C1(NCCC2=CC=CC=C12)* 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 description 8
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 7
CUKWUWBLQQDQAC-VEQWQPCFSA-N (3s)-3-amino-4-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s,3s)-1-[[(2s)-1-[(2s)-2-[[(1s)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-ox Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 CUKWUWBLQQDQAC-VEQWQPCFSA-N 0.000 description 6
102000005862 Angiotensin II Human genes 0.000 description 6
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229950006323 angiotensin ii Drugs 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000243 solution Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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239000003102 growth factor Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
102100030988 Angiotensin-converting enzyme Human genes 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
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KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
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KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
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LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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ADKDJHASTPQGEO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[b]pyrrole Chemical compound C1CNC2CCCC21 ADKDJHASTPQGEO-UHFFFAOYSA-N 0.000 description 1
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235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229960002490 fosinopril Drugs 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
125000005553 heteroaryloxy group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960002394 lisinopril Drugs 0.000 description 1
RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
150000002668 lysine derivatives Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
108020004999 messenger RNA Proteins 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
210000000663 muscle cell Anatomy 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
BSIZUMJRKYHEBR-QGZVFWFLSA-N n-hydroxy-2(r)-[[(4-methoxyphenyl)sulfonyl](3-picolyl)amino]-3-methylbutanamide hydrochloride Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N([C@H](C(C)C)C(=O)NO)CC1=CC=CN=C1 BSIZUMJRKYHEBR-QGZVFWFLSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
229960002582 perindopril Drugs 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000007505 plaque formation Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
229960003401 ramipril Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000014616 translation Effects 0.000 description 1
230000001228 trophic effect Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
229960002769 zofenopril Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
- A61K38/556—Angiotensin converting enzyme inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Gastroenterology & Hepatology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Immunology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Epidemiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Medicinal Preparation (AREA)
Medicines Containing Plant Substances (AREA)
Crucibles And Fluidized-Bed Furnaces (AREA)
Preliminary Treatment Of Fibers (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Enzymes And Modification Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Element Separation (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

CS903958A 1989-08-11 1990-08-10 Pharmaceutical preparation for treating cardial and vascular hypertrophy and hyperplasia CS277644B6 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3926606A DE3926606A1 (de)	1989-08-11	1989-08-11	Verfahren zur behandlung der cardialen sowie der vasculaeren hypertrophie und hyperplasie

Publications (2)

Publication Number	Publication Date
CS395890A3 CS395890A3 (en)	1992-08-12
CS277644B6 true CS277644B6 (en)	1993-03-17

Family

ID=6386970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS903958A CS277644B6 (en)	1989-08-11	1990-08-10	Pharmaceutical preparation for treating cardial and vascular hypertrophy and hyperplasia

Country Status (22)

Country	Link
US (1)	US5231083A (no)
EP (1)	EP0417473B1 (no)
JP (1)	JP3452199B2 (no)
KR (1)	KR0185969B1 (no)
AT (1)	ATE94409T1 (no)
AU (1)	AU631914B2 (no)
CA (1)	CA2023089C (no)
CS (1)	CS277644B6 (no)
DD (1)	DD297063A5 (no)
DE (2)	DE3926606A1 (no)
DK (1)	DK0417473T3 (no)
ES (1)	ES2059931T3 (no)
FI (1)	FI903936A7 (no)
HU (1)	HU205008B (no)
IE (1)	IE64604B1 (no)
IL (1)	IL95327A (no)
NO (1)	NO306979B1 (no)
NZ (1)	NZ234836A (no)
PH (1)	PH30831A (no)
PL (1)	PL286442A1 (no)
PT (1)	PT94957B (no)
ZA (1)	ZA906327B (no)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE157871T1 (de)	1994-05-19	1997-09-15	Mitsubishi Chem Corp	Arzneimittel zur therapeutischen und prophylaktischen behandlung von krankheiten, die durch hyperplasie der glatten muskelzellen bedingt sind
SG68529A1 (en) *	1995-05-25	1999-11-16	Univ Singapore	The use of des-aspartate-angiotensin i (agr-val-tyr-ile-his-pro-phe-his-leu) as an anti-cardiac hypertrophic agent
SE9903028D0 (sv) *	1999-08-27	1999-08-27	Astra Ab	New use
DK1216038T3 (da) *	1999-08-30	2005-12-27	Sanofi Aventis Deutschland	Anvendelse af inhibitorer af reninangiotensinsystemet ved forebyggelsen af cardiovaskulære hændelser
US6395767B2 (en) *	2000-03-10	2002-05-28	Bristol-Myers Squibb Company	Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method
KR20070085754A (ko) *	2004-11-05	2007-08-27	킹 파머슈티칼스 리서치 앤드 디벨로프먼트 아이엔씨	안정화된 라미프릴 조성물 및 제조 방법
JP5951625B2 (ja)	2010-11-24	2016-07-13	ザ・トラスティーズ・オブ・コランビア・ユニバーシティー・イン・ザ・シティー・オブ・ニューヨークＴｈｅＴｒｕｓｔｅｅｓＯｆＣｏｌｕｍｂｉａＵｎｉｖｅｒｓｉｔｙＩｎＴｈｅＣｉｔｙＯｆＮｅｗＹｏｒｋ	加齢性黄斑変性症およびシュタルガルト病の処置のための非レチノイドｒｂｐ４アンタゴニスト
US9333202B2 (en)	2012-05-01	2016-05-10	The Trustees Of Columbia University In The City Of New York	Non-retinoid antagonists for treatment of age-related macular degeneration and stargardt disease
WO2014152018A1 (en) *	2013-03-14	2014-09-25	The Trustees Of Columbia University In The City Of New York	Octahydrocyclopentapyrroles, their preparation and use
US9938291B2 (en)	2013-03-14	2018-04-10	The Trustess Of Columbia University In The City Of New York	N-alkyl-2-phenoxyethanamines, their preparation and use
EP3495357B1 (en)	2013-03-14	2021-05-05	The Trustees of Columbia University in the City of New York	4-phenylpiperidines, their preparation and use
US9944644B2 (en)	2013-03-14	2018-04-17	The Trustees Of Columbia University In The City Of New York	Octahydropyrrolopyrroles their preparation and use
SG11201608943VA (en)	2014-04-30	2016-11-29	Univ Columbia	Substituted 4-phenylpiperidines, their preparaiton and use

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL58849A (en) *	1978-12-11	1983-03-31	Merck & Co Inc	Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them
US4311705A (en) *	1980-10-06	1982-01-19	E. R. Squibb & Sons, Inc.	Carboxyalkanoyl and hydroxycarbamoylalkanoyl derivatives of substituted prolines
US4337201A (en) *	1980-12-04	1982-06-29	E. R. Squibb & Sons, Inc.	Phosphinylalkanoyl substituted prolines
US4381297A (en) *	1981-05-04	1983-04-26	E. R. Squibb & Sons, Inc.	Substituted carbonyl phosphinyl-alkanoyl compounds
US4602002A (en) *	1983-02-07	1986-07-22	Merck & Co., Inc.	N-carboxymethyl substituted lysyl and α-(ε-aminoalkyl) glycyl amino acid antihypertensive agents
US4587253A (en) *	1984-07-30	1986-05-06	Merck & Co., Inc.	Bridged pyridine compounds useful as calcium channel blockers and analgesics
US4548941A (en) *	1984-07-30	1985-10-22	Merck & Co., Inc.	1,5-Methano-1H-4-benzazonine dicarboxylates, process for preparing and use as calcium blockers
US4599341A (en) *	1984-10-01	1986-07-08	Merck & Co., Inc.	Substituted and bridged pyridines useful as calcium channel blockers
US4656188A (en) *	1985-10-09	1987-04-07	Merck & Co., Inc.	Ace inhibitors in macular degeneration
DE3705220A1 (de) *	1987-02-19	1988-09-01	Boehringer Ingelheim Kg	Mittel zur behandlung von coronarerkrankungen oder organischem hirnsyndrom
ZA896851B (en) *	1988-09-14	1990-06-27	Hoffmann La Roche	Use of ace-inhibitors

1989
- 1989-08-11 DE DE3926606A patent/DE3926606A1/de not_active Withdrawn
1990
- 1990-08-08 DK DK90115230.6T patent/DK0417473T3/da active
- 1990-08-08 ES ES90115230T patent/ES2059931T3/es not_active Expired - Lifetime
- 1990-08-08 AT AT90115230T patent/ATE94409T1/de not_active IP Right Cessation
- 1990-08-08 DE DE90115230T patent/DE59002721D1/de not_active Expired - Lifetime
- 1990-08-08 EP EP90115230A patent/EP0417473B1/de not_active Expired - Lifetime
- 1990-08-09 PT PT94957A patent/PT94957B/pt not_active IP Right Cessation
- 1990-08-09 NZ NZ234836A patent/NZ234836A/en unknown
- 1990-08-09 IL IL9532790A patent/IL95327A/en unknown
- 1990-08-09 US US07/564,618 patent/US5231083A/en not_active Expired - Lifetime
- 1990-08-09 DD DD90343366A patent/DD297063A5/de unknown
- 1990-08-09 PH PH41000A patent/PH30831A/en unknown
- 1990-08-09 FI FI903936A patent/FI903936A7/fi not_active Application Discontinuation
- 1990-08-10 PL PL28644290A patent/PL286442A1/xx unknown
- 1990-08-10 JP JP21056490A patent/JP3452199B2/ja not_active Expired - Lifetime
- 1990-08-10 KR KR1019900012267A patent/KR0185969B1/ko not_active Expired - Lifetime
- 1990-08-10 AU AU60920/90A patent/AU631914B2/en not_active Expired
- 1990-08-10 CA CA002023089A patent/CA2023089C/en not_active Expired - Lifetime
- 1990-08-10 CS CS903958A patent/CS277644B6/cs not_active IP Right Cessation
- 1990-08-10 IE IE291090A patent/IE64604B1/en not_active IP Right Cessation
- 1990-08-10 ZA ZA906327A patent/ZA906327B/xx unknown
- 1990-08-10 HU HU904966A patent/HU205008B/hu unknown
- 1990-08-10 NO NO903532A patent/NO306979B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH0383957A (ja)	1991-04-09
EP0417473B1 (de)	1993-09-15
IE64604B1 (en)	1995-08-23
CA2023089C (en)	2003-01-14
PT94957B (pt)	1997-05-28
NZ234836A (en)	1997-05-26
HUT54504A (en)	1991-03-28
NO903532D0 (no)	1990-08-10
NO306979B1 (no)	2000-01-24
JP3452199B2 (ja)	2003-09-29
PL286442A1 (en)	1992-03-09
ZA906327B (en)	1991-05-29
AU631914B2 (en)	1992-12-10
IE902910A1 (en)	1991-02-27
HU904966D0 (en)	1991-01-28
FI903936A7 (fi)	1991-02-12
KR910004189A (ko)	1991-03-28
DE3926606A1 (de)	1991-02-14
IL95327A0 (en)	1991-06-30
ES2059931T3 (es)	1994-11-16
HU205008B (en)	1992-03-30
ATE94409T1 (de)	1993-10-15
IL95327A (en)	1995-10-31
AU6092090A (en)	1991-02-14
CA2023089A1 (en)	1991-02-12
FI903936A0 (fi)	1990-08-09
NO903532L (no)	1991-02-12
US5231083A (en)	1993-07-27
DE59002721D1 (de)	1993-10-21
DK0417473T3 (da)	1993-12-13
EP0417473A1 (de)	1991-03-20
PT94957A (pt)	1991-05-22
DD297063A5 (de)	1992-01-02
PH30831A (en)	1997-10-17
CS395890A3 (en)	1992-08-12
KR0185969B1 (ko)	1999-05-01

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2010-08-18	MK4A	Patent expired	Effective date: 20100810

Publication	Publication Date	Title
US5721244A (en)	1998-02-24	Combination of angiotensin-converting enzyme inhibitors with calcium antagonists as well as their use in drugs
US5256687A (en)	1993-10-26	Pharmaceutical composition for the treatment of high blood pressure
KR930008094B1 (ko)	1993-08-25	안기오텐신 전환효소 억제제의 제조방법
CS277644B6 (en)	1993-03-17	Pharmaceutical preparation for treating cardial and vascular hypertrophy and hyperplasia
US5403856A (en)	1995-04-04	Method of treating cardiac insufficiency using angiotensin-converting enzyme inhibitors
US5231080A (en)	1993-07-27	Method for the treatment of atherosclerosis, thrombosis, and peripheral vessel disease
US5684016A (en)	1997-11-04	Method of treating cardiac insufficiency
US4975453A (en)	1990-12-04	Combination of angiotensin converting enzyme inhibitors with potassium channel modulators and use thereof in pharmaceuticals
DE3610391A1 (de)	1987-10-08	Verbindungen mit nootroper wirkung, diese enthaltende mittel und deren verwendung bei der behandlung und prophylaxe cognitiver dysfunktionen
EP0488059B1 (de)	1995-09-06	Verwendung einer Kombination aus Angiotensin-Converting-Enzyme-Hemmer und Calciumantagonist zur Behandlung einer Proteinurie
HK1006148B (en)	1999-02-12	Use of a combination of an ace inhibitor with a calcium antagonist in the treatment of proteinuria
KR940010032B1 (ko)	1994-10-21	고혈압 치료용 약제학적 조성물의 제조방법
JPH01128997A (ja)	1989-05-22	アミノ酸エステル及びその製造方法