NO323871B1 - Aminosyreforbindelser og deres anvendelse som NEP-, ACE- og ECE-inhibitorer - Google Patents

Aminosyreforbindelser og deres anvendelse som NEP-, ACE- og ECE-inhibitorer Download PDF

Info

Publication number: NO323871B1
Authority: NO; Norway
Prior art keywords: formula; compound; compounds; pharmaceutically acceptable; diastereoisomers
Prior art date: 2000-02-17

Application number

NO20023893A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023893L (no

NO20023893D0 (no

Inventor

Marie-Claude Fournie-Zaluski

Caroline Bennejean

Pierre Renard

Elizabeth Scalbert

Bernard-Pierre Roques

Nicolas Inguimbert

Herve Poras

Original Assignee

Inst Nat Sante Rech Med

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.)

2000-02-17

Filing date

2002-08-16

Publication date

2007-07-16

2002-08-16 Application filed by Inst Nat Sante Rech Med filed Critical Inst Nat Sante Rech Med

2002-08-16 Publication of NO20023893L publication Critical patent/NO20023893L/no

2002-08-16 Publication of NO20023893D0 publication Critical patent/NO20023893D0/no

2007-07-16 Publication of NO323871B1 publication Critical patent/NO323871B1/no

Links

-1 Amino acid compounds Chemical class 0.000 title claims description 23
239000003112 inhibitor Substances 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 173
238000000034 method Methods 0.000 claims description 53
238000004587 chromatography analysis Methods 0.000 claims description 36
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
239000007858 starting material Substances 0.000 claims description 21
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 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
125000002252 acyl group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 13
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125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 10
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FCDJBUMHEIZGOC-ACBHZAAOSA-N (2s)-2-[[2-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-(1h-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid Chemical compound C1CC2=CC(Br)=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CNC2=NC=CC=C12 FCDJBUMHEIZGOC-ACBHZAAOSA-N 0.000 claims 2
YJSMEONIEBYZRH-AOMIVXANSA-N (2s)-3-(1h-indol-3-yl)-2-[[2-(5-methoxy-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]propanoic acid Chemical compound C1=CC=C2C(C[C@H](NC(=O)C(CS)C3C4=CC=C(C=C4CC3)OC)C(O)=O)=CNC2=C1 YJSMEONIEBYZRH-AOMIVXANSA-N 0.000 claims 1
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XNFNGGQRDXFYMM-PPHPATTJSA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate;hydrochloride Chemical compound Cl.C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 XNFNGGQRDXFYMM-PPHPATTJSA-N 0.000 description 1
JQPVBKDLAQDFFY-QMMMGPOBSA-N methyl (2s)-2-amino-3-pyridin-3-ylpropanoate Chemical compound COC(=O)[C@@H](N)CC1=CC=CN=C1 JQPVBKDLAQDFFY-QMMMGPOBSA-N 0.000 description 1
AVVOOUMEMZMDCZ-UHFFFAOYSA-N methyl 2-[[3-acetylsulfanyl-2-(5-bromo-2,3-dihydro-1h-inden-1-yl)propanoyl]amino]-3-(1-benzothiophen-3-yl)propanoate Chemical compound C1CC2=CC(Br)=CC=C2C1C(CSC(C)=O)C(=O)NC(C(=O)OC)CC1=CSC2=CC=CC=C12 AVVOOUMEMZMDCZ-UHFFFAOYSA-N 0.000 description 1
XGZQUCOSKASFJV-UHFFFAOYSA-N methyl 2-[[3-acetylsulfanyl-2-(5-bromo-2,3-dihydro-1h-inden-1-yl)propanoyl]amino]-3-pyridin-3-ylpropanoate Chemical compound C1CC2=CC(Br)=CC=C2C1C(CSC(C)=O)C(=O)NC(C(=O)OC)CC1=CC=CN=C1 XGZQUCOSKASFJV-UHFFFAOYSA-N 0.000 description 1
YICCZSAAKWYLMA-UHFFFAOYSA-N methyl 2-[[3-acetylsulfanyl-2-(5-bromo-2,3-dihydro-1h-inden-1-yl)propanoyl]amino]-3-quinolin-2-ylpropanoate Chemical compound C1CC2=CC(Br)=CC=C2C1C(CSC(C)=O)C(=O)NC(C(=O)OC)CC1=CC=C(C=CC=C2)C2=N1 YICCZSAAKWYLMA-UHFFFAOYSA-N 0.000 description 1
FGLIVUIACOOOGS-UHFFFAOYSA-N methyl 2-amino-3-(1h-pyrrolo[2,3-b]pyridin-3-yl)propanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OC)=CNC2=N1 FGLIVUIACOOOGS-UHFFFAOYSA-N 0.000 description 1
MXYPFBOKALCISX-UHFFFAOYSA-N methyl 2-amino-3-(1h-pyrrolo[2,3-c]pyridin-3-yl)propanoate Chemical compound N1=CC=C2C(CC(N)C(=O)OC)=CNC2=C1 MXYPFBOKALCISX-UHFFFAOYSA-N 0.000 description 1
LGFNUHUUIUKCIV-UHFFFAOYSA-N methyl 2-amino-3-(1h-pyrrolo[3,2-h]quinolin-3-yl)propanoate Chemical compound C1=CC2=CC=CN=C2C2=C1C(CC(N)C(=O)OC)=CN2 LGFNUHUUIUKCIV-UHFFFAOYSA-N 0.000 description 1
GMBFOJYRVSBVCC-UHFFFAOYSA-N methyl 2-amino-3-(2h-indazol-3-yl)propanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OC)=NNC2=C1 GMBFOJYRVSBVCC-UHFFFAOYSA-N 0.000 description 1
WLAQXNVMSYAGLF-UHFFFAOYSA-N methyl 2-amino-3-(5-bromo-1h-indol-3-yl)propanoate Chemical compound C1=C(Br)C=C2C(CC(N)C(=O)OC)=CNC2=C1 WLAQXNVMSYAGLF-UHFFFAOYSA-N 0.000 description 1
QOBUNYVBTXFCEZ-UHFFFAOYSA-N methyl 2-amino-3-(5-hydroxy-1h-indol-3-yl)propanoate Chemical compound C1=C(O)C=C2C(CC(N)C(=O)OC)=CNC2=C1 QOBUNYVBTXFCEZ-UHFFFAOYSA-N 0.000 description 1
ZLVRWEGIPKKGJL-UHFFFAOYSA-N methyl 2-amino-3-(5-methoxy-1h-indol-3-yl)propanoate Chemical compound C1=C(OC)C=C2C(CC(N)C(=O)OC)=CNC2=C1 ZLVRWEGIPKKGJL-UHFFFAOYSA-N 0.000 description 1
MNJWYOVJMKMIFA-UHFFFAOYSA-N methyl 2-amino-3-(5-methyl-1h-indol-3-yl)propanoate Chemical compound C1=C(C)C=C2C(CC(N)C(=O)OC)=CNC2=C1 MNJWYOVJMKMIFA-UHFFFAOYSA-N 0.000 description 1
ZALWIXKRHZLOLN-UHFFFAOYSA-N methyl 2-amino-3-(6-fluoro-1h-indol-3-yl)propanoate Chemical compound FC1=CC=C2C(CC(N)C(=O)OC)=CNC2=C1 ZALWIXKRHZLOLN-UHFFFAOYSA-N 0.000 description 1
PDGMDZRZEWHXQJ-UHFFFAOYSA-N methyl 2-amino-3-(7-methoxy-1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OC)=CNC2=C1OC PDGMDZRZEWHXQJ-UHFFFAOYSA-N 0.000 description 1
VONDDLRINFBWKK-UHFFFAOYSA-N methyl 3-acridin-9-yl-2-aminopropanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OC)=C(C=CC=C3)C3=NC2=C1 VONDDLRINFBWKK-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000006289 propionylation Effects 0.000 description 1
238000010515 propionylation reaction Methods 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000007634 remodeling Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
238000011894 semi-preparative HPLC Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
POSZUTFLHGNLHX-KSBRXOFISA-N tris maleate Chemical compound OCC(N)(CO)CO.OCC(N)(CO)CO.OC(=O)\C=C/C(O)=O POSZUTFLHGNLHX-KSBRXOFISA-N 0.000 description 1
230000006442 vascular tone Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Toxicology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
Quinoline Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

NO20023893A 2000-02-17 2002-08-16 Aminosyreforbindelser og deres anvendelse som NEP-, ACE- og ECE-inhibitorer NO323871B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0001937A FR2805259B1 (fr)	2000-02-17	2000-02-17	Nouveaux derives d'aminoacides n-mercaptoacyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
PCT/FR2001/000463 WO2001060822A1 (fr)	2000-02-17	2001-02-16	Derives d'aminoacides et leur utilisation en tant qu'inhibiteurs de la nep, l'ace et l'ece

Publications (3)

Publication Number	Publication Date
NO20023893L NO20023893L (no)	2002-08-16
NO20023893D0 NO20023893D0 (no)	2002-08-16
NO323871B1 true NO323871B1 (no)	2007-07-16

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NO20023893A NO323871B1 (no)	2000-02-17	2002-08-16	Aminosyreforbindelser og deres anvendelse som NEP-, ACE- og ECE-inhibitorer

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Country	Link
US (1)	US6716852B2 (de)
EP (1)	EP1255757B1 (de)
JP (1)	JP2003523343A (de)
KR (1)	KR100491605B1 (de)
CN (1)	CN1186344C (de)
AR (1)	AR029468A1 (de)
AT (1)	ATE243210T1 (de)
AU (2)	AU3569801A (de)
BR (1)	BR0108409A (de)
CA (1)	CA2400537A1 (de)
CZ (1)	CZ20022811A3 (de)
DE (1)	DE60100388T2 (de)
DK (1)	DK1255757T3 (de)
EA (1)	EA005004B1 (de)
ES (1)	ES2202279T3 (de)
FR (1)	FR2805259B1 (de)
HU (1)	HUP0300248A3 (de)
MX (1)	MXPA02007973A (de)
NO (1)	NO323871B1 (de)
PL (1)	PL357243A1 (de)
PT (1)	PT1255757E (de)
SK (1)	SK11822002A3 (de)
WO (1)	WO2001060822A1 (de)
ZA (1)	ZA200206221B (de)

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WO2001080441A2 (en)	2000-04-14	2001-10-25	Current Technologies, Llc	Digital communications utilizing medium voltage power distribution lines
FR2823212B1 (fr) *	2001-04-10	2005-12-02	Inst Nat Sante Rech Med	Inhibiteurs de la toxine botulique de type b
JP5138938B2 (ja)	2003-12-19	2013-02-06	プレキシコンインコーポレーテッド	Ｒｅｔ調節剤の開発のための化合物および方法
WO2008063888A2 (en)	2006-11-22	2008-05-29	Plexxikon, Inc.	Compounds modulating c-fms and/or c-kit activity and uses therefor
JP2010533729A (ja)	2007-07-17	2010-10-28	プレキシコン，インコーポレーテッド	キナーゼ調節のための化合物と方法、及びそのための適応
FR2931151A1 (fr) *	2008-05-13	2009-11-20	Pharmaleads Soc Par Actions Si	Nouveaux derives d'amino-acides, leur procede de preparation et leur utilisation therapeutique
CA2738573C (en)	2009-04-03	2013-02-19	F. Hoffmann-La Roche Ag	Compositions of propane-1 sulfonic acid {3-[5-(4-chloro-phenyl)-1h-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide and uses thereof
JP2013510166A (ja)	2009-11-06	2013-03-21	プレキシコンインコーポレーテッド	キナーゼ調節のための化合物、方法およびその適用
PE20141360A1 (es)	2011-02-07	2014-10-13	Plexxikon Inc	Compuestos y metodos para la modulacion de quinasas e indicaciones para los mismos.
TWI558702B (zh)	2011-02-21	2016-11-21	普雷辛肯公司	醫藥活性物質的固態形式
US9150570B2 (en)	2012-05-31	2015-10-06	Plexxikon Inc.	Synthesis of heterocyclic compounds

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CA2038379C (en) *	1990-03-22	2002-11-05	Norma G. Delaney	Trifluoromethyl mercaptan and mercaptoacyl derivatives and method of using same
IT1277736B1 (it) *	1995-12-28	1997-11-12	Zambon Spa	Derivati tiolici ad attivita' inibitrice delle metallopeptidasi
FR2745571B1 (fr) *	1996-03-04	1998-06-19	Inst Nat Sante Rech Med	Nouveaux derives soufres comportant une liaison amide, leur procede de preparation, leur application a titre de medicaments, et les compositions pharmaceutiques les renfermant

2000
- 2000-02-17 FR FR0001937A patent/FR2805259B1/fr not_active Expired - Fee Related
2001
- 2001-02-15 AR ARP010100675A patent/AR029468A1/es unknown
- 2001-02-16 CZ CZ20022811A patent/CZ20022811A3/cs unknown
- 2001-02-16 HU HU0300248A patent/HUP0300248A3/hu unknown
- 2001-02-16 AU AU3569801A patent/AU3569801A/xx active Pending
- 2001-02-16 PL PL01357243A patent/PL357243A1/xx not_active Application Discontinuation
- 2001-02-16 KR KR10-2002-7010552A patent/KR100491605B1/ko not_active Expired - Fee Related
- 2001-02-16 AU AU2001235698A patent/AU2001235698B2/en not_active Ceased
- 2001-02-16 US US10/203,704 patent/US6716852B2/en not_active Expired - Fee Related
- 2001-02-16 PT PT01907822T patent/PT1255757E/pt unknown
- 2001-02-16 DK DK01907822T patent/DK1255757T3/da active
- 2001-02-16 SK SK1182-2002A patent/SK11822002A3/sk unknown
- 2001-02-16 CN CNB018050921A patent/CN1186344C/zh not_active Expired - Fee Related
- 2001-02-16 AT AT01907822T patent/ATE243210T1/de not_active IP Right Cessation
- 2001-02-16 MX MXPA02007973A patent/MXPA02007973A/es active IP Right Grant
- 2001-02-16 WO PCT/FR2001/000463 patent/WO2001060822A1/fr not_active Ceased
- 2001-02-16 BR BR0108409-7A patent/BR0108409A/pt not_active IP Right Cessation
- 2001-02-16 EA EA200200807A patent/EA005004B1/ru not_active IP Right Cessation
- 2001-02-16 ES ES01907822T patent/ES2202279T3/es not_active Expired - Lifetime
- 2001-02-16 EP EP01907822A patent/EP1255757B1/de not_active Expired - Lifetime
- 2001-02-16 CA CA002400537A patent/CA2400537A1/fr not_active Abandoned
- 2001-02-16 JP JP2001560206A patent/JP2003523343A/ja active Pending
- 2001-02-16 DE DE60100388T patent/DE60100388T2/de not_active Expired - Fee Related
2002
- 2002-08-05 ZA ZA200206221A patent/ZA200206221B/en unknown
- 2002-08-16 NO NO20023893A patent/NO323871B1/no unknown

Also Published As

Publication number	Publication date
ES2202279T3 (es)	2004-04-01
HUP0300248A3 (en)	2005-07-28
EP1255757A1 (de)	2002-11-13
NO20023893L (no)	2002-08-16
KR20020072581A (ko)	2002-09-16
PT1255757E (pt)	2003-10-31
PL357243A1 (en)	2004-07-26
EA005004B1 (ru)	2004-10-28
ZA200206221B (en)	2003-08-20
CN1400974A (zh)	2003-03-05
FR2805259B1 (fr)	2002-03-29
CN1186344C (zh)	2005-01-26
MXPA02007973A (es)	2005-10-05
DK1255757T3 (da)	2003-10-13
KR100491605B1 (ko)	2005-05-27
AU2001235698B2 (en)	2005-02-17
EP1255757B1 (de)	2003-06-18
WO2001060822A8 (fr)	2001-09-27
WO2001060822A1 (fr)	2001-08-23
HUP0300248A2 (hu)	2003-06-28
SK11822002A3 (sk)	2003-03-04
BR0108409A (pt)	2003-03-11
EA200200807A1 (ru)	2002-12-26
AU3569801A (en)	2001-08-27
CA2400537A1 (fr)	2001-08-23
CZ20022811A3 (cs)	2003-01-15
US20030055086A1 (en)	2003-03-20
NO20023893D0 (no)	2002-08-16
JP2003523343A (ja)	2003-08-05
US6716852B2 (en)	2004-04-06
FR2805259A1 (fr)	2001-08-24
HK1050896A1 (en)	2003-07-11
DE60100388T2 (de)	2004-05-19
ATE243210T1 (de)	2003-07-15
DE60100388D1 (de)	2003-07-24
AR029468A1 (es)	2003-07-02

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