OA10704A - Thiol derivatives with metallopeptidase inhibitoryactivity. - Google Patents
Thiol derivatives with metallopeptidase inhibitoryactivity. Download PDFInfo
- Publication number
- OA10704A OA10704A OA9800094A OA9800094A OA10704A OA 10704 A OA10704 A OA 10704A OA 9800094 A OA9800094 A OA 9800094A OA 9800094 A OA9800094 A OA 9800094A OA 10704 A OA10704 A OA 10704A
- Authority
- OA
- OAPI
- Prior art keywords
- phenylalanine
- mercapto
- phenylmethylpropionyl
- group
- thiazolyl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
-
- 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
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Treatment Of Fiber Materials (AREA)
- Preliminary Treatment Of Fibers (AREA)
- Medicines Containing Plant Substances (AREA)
Claims (1)
- -27- 010704 Claims 1) A compound of formula Ri * R-CH2-CH-CONH-CH-COOR2 (I) * ch2-r3 wherein R is a mercapto group or a R4COS group convertible in the organism to mercapto group; R j is a straight or branched C2-C4 alkyl group or an aryl or arylalkyl group having from 1 to 6 carbon atoms in the alkyl moiety wherein the aryl is a phenyl or a 5 or 6 memberedaromatic heterocvcle with one or two heteroatoms selected from the group consising ofnitrogen, oxygen and sulphur, optionally substituted with one or more substituents, thesame or different, selected from the group consisting of halogen atoms, hydroxy groups,alkoxy, alkyl, alkylthio, alkylsulphonyl or alkoxycarbonyl groups having from 1 to 6 car-bon atoms in the alkyl moiety, C}-C3 alkyl groups containing one or more fluorine atoms,carboxy groups, nitro groups, amino or aminocarbonyl groups, acylamino groups, amino-sulphonyl groups, mono- or di-alkylamino or mono- or di-alkylaminocarbonyl groupshaving from 1 to 6 carbon atoms in the alkyl moiety; R2 is a hydrogen atom, a straight or branched C {-€4 alkyl or a berrzyl group; R3 is a phenyl group substituted by a 5 or 6 membered aromatic heterocycle with one or twoheteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, beingthephenyl and the heterocyclic groups optionally substituted with one or more substituents,the same or different, as indicated for R ; R4 is a straight or branched C1-C4 alkyl group or a phenyl group; the carbon atoms marked with an asterisk are stereogenic centers; and pharmaceutically acceptable salts thereof. 2) A compound of formula I according to claim 1 wherein R3 is a phenyl group substituted inposition 4 with a heterocyclic group. 3) A compound of formula I according to claim 2 wherein R] represents an arylalkyl groupoptionally substituted with one or more substituents, the same or different, selected from thegroups consisting of halogen atoms, hydroxy, alkyl or alkoxy groups. 010704 -28- 4) A compound of formula I according to claim 3 wherein Rj represents a phenylalkyl groupoptionally substituted with one or more substitueras, the same or different, selected amonghalogen atoms, hydroxy, alkyl or alkoxy groups. 5) A compound of formula I according to claim 1 in the form of a sait with an alkali métal se-lected from the group consisting of sodium, lithium and potassium. 6) A process for the préparation of a compound of formula I according to claim 1 comprising the reaction between a compound of formula R1 I R-CH2-CH-COOH (Π) * wherein R and Rj hâve the above reported meanings; and a phenylalanine dérivative of formula* H9N-CH-COOR9 (ΠΙ) I CH2-R3 wherein R2 and R3 hâve the above reported meanings. 7) A pharmaceutical composition containing a therapeutically effective amount of a compoundof formula I according to claim 1 in admixture with a carrier for pharmaceutical use. 8) A pharmaceutical composition according to claim 6 for the treatment of cardiovascular dis- eases. 9) A method for the treatment of cardiovascular diseases comprising the administration of atherapeutically effective amount of a compound according to claim 1. 10) A compound selected from the group consisting of: N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(2-thiazolyl)-L-phenylalanine methylester; N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(2-pyridyl)-L-phenylalanine methyl ester; N-(3-phenylcarbonylthio“2-phenylmethylpropionyl)-4-(3-pyridyl)-L-phenylalanine benzyl ester; 010704 -29- N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(2-furyl)-L-phenylalanine methyl ester;N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(5-pyrimidinyl)-L-phenylalanine ethylester; N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(2-pyrazinyl)-L-phenylalanine methylester; N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(2-thienyl)-L-phenylalanine methyl ester; N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(3-thienyl)-L-phenylalanine methyl ester; N-(3-phenylcarbonylthio-2-phenylmethylpropionyl)-4-(3-furyl)-L-phenylalanine methyl ester;N-[3-phenylcarbonylthio-2-(3~pyridylmethyl)propionyl]-4-(2-thiazolyl)-L-phenylalaninemethyl ester; N-(3-mercapto-2-phenylmethylpropionyl)-4-(2-thiazolyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(2-pyridyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(3-pyridyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(2-furyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(5-pyrimidinyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(2-pyrazinyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(2-thienyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(3-thienyl)-L-phenylalanine; N-(3-mercapto-2-phenylmethylpropionyl)-4-(3-furyl)-L-phenylalanine; N-[3-mercapto-2-(3-pyridylmethyl)propionyl]-4-(2-thiazolyl)-L-phenylalanine; N-[3-acetylthio-2-(3-methoxyphenyl)methyl-propionyl]-4-(2-thiazolyl)-L-phenylalaninemethyl ester; N-[3-acetylthio-2-(2-fluorophenyl)methyl-propionyl]-4-(2-thiazolyl)-L-phenylalanine methylester; N-[3-phenylcarbonylthio-2-(2-thienyl)methyl-propionyl]-4-(2-thiazolyl)-L-phenylalanine methyl ester; N-[2-(2-furyl)methyl-3-phenylcarbonylthio-propionyl]-4-(2-thiazolyl)-L-phenylalanine methyl ester; 010704 -30- N-[2-(3-methyl-5-isoxazolyl)methyl-3-phenylcarbonylthio-propionyl]-4-(2-thiazolyl)-L-phenylalanine methyl ester; N-[3-mercapto-2-(3-methoxyphenyl)methyl-propionyl]-4-(2-thiazolyl)-L-phenylalanine; 5 N-[3-mercapto-2-(2-thienyl)methyl-propionyl]-4-(2-thiazolyl)-L-phenylalanine; N-[3-mercapto-2-(3-methyl-5-isoxazolyl)methyl-propionyl]-4-(2-thiazolyl)-L-phenylalanine;N-[2-(2-fluorophenyl)methyl-3-mercapto-propionyl]-4-(2-thiazolyl)-L-phenylalanine;N-[2-(2-furyl)methyl-3-mercapto-propionyi]-4-(2-thiazolyI)-L-phenylalanine;and the stereoisomers (2S) or (2R) thereof.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT95MI002773A IT1277737B1 (it) | 1995-12-28 | 1995-12-28 | Derivati tiolici ad attivita' inibitrice delle metallopeptidasi |
Publications (1)
Publication Number | Publication Date |
---|---|
OA10704A true OA10704A (en) | 2002-11-28 |
Family
ID=11372827
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
OA9800094A OA10704A (en) | 1995-12-28 | 1998-06-26 | Thiol derivatives with metallopeptidase inhibitoryactivity. |
Country Status (31)
Country | Link |
---|---|
EP (1) | EP0877740B1 (fr) |
JP (1) | JP2000502687A (fr) |
KR (1) | KR19990076809A (fr) |
CN (1) | CN1071325C (fr) |
AP (1) | AP1186A (fr) |
AR (1) | AR004413A1 (fr) |
AT (1) | ATE292123T1 (fr) |
AU (1) | AU713156B2 (fr) |
BG (1) | BG63942B1 (fr) |
BR (1) | BR9612373A (fr) |
CA (1) | CA2241414A1 (fr) |
CZ (1) | CZ204698A3 (fr) |
DE (1) | DE69634543D1 (fr) |
EA (1) | EA000991B1 (fr) |
EE (1) | EE03766B1 (fr) |
GE (1) | GEP19991871B (fr) |
HK (1) | HK1018008A1 (fr) |
IL (1) | IL124915A (fr) |
IS (1) | IS1885B (fr) |
IT (1) | IT1277737B1 (fr) |
NO (1) | NO310914B1 (fr) |
NZ (1) | NZ325785A (fr) |
OA (1) | OA10704A (fr) |
PL (1) | PL188151B1 (fr) |
RO (1) | RO119882B1 (fr) |
SK (1) | SK282977B6 (fr) |
TR (1) | TR199801229T2 (fr) |
UA (1) | UA62923C2 (fr) |
UY (1) | UY24425A1 (fr) |
WO (1) | WO1997024342A1 (fr) |
ZA (1) | ZA9610891B (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1289522B1 (it) | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di eteroaril-fenilalanine |
MY153569A (en) | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
US8168616B1 (en) | 2000-11-17 | 2012-05-01 | Novartis Ag | Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension |
GB0203665D0 (en) * | 2002-02-15 | 2002-04-03 | Glaxo Group Ltd | Process |
MY140707A (en) | 2002-02-28 | 2010-01-15 | Mitsubishi Tanabe Pharma Corp | Process for preparing a phenylalanine derivative and intermediates thereof |
DE60336986D1 (de) | 2002-03-05 | 2011-06-16 | Sumitomo Chemical Co | Verfahren zur herstellung von biarylverbindungen |
WO2003104200A1 (fr) * | 2002-06-07 | 2003-12-18 | Glaxo Group Limited | Derives de n-mercaptoacyl phenyalanine, leur procede de preparation et les compositions pharmaceutiques les contenant |
GB0213122D0 (en) * | 2002-06-07 | 2002-07-17 | Glaxo Group Ltd | Compounds |
US7045653B2 (en) | 2002-12-23 | 2006-05-16 | Pfizer, Inc. | Pharmaceuticals |
GB0327839D0 (en) | 2003-12-01 | 2003-12-31 | Novartis Ag | Organic compounds |
BRPI0508880A (pt) | 2004-03-17 | 2007-09-04 | Novartis Ag | uso de compostos orgánicos |
CA2757650C (fr) | 2009-04-03 | 2016-06-07 | Statoil Asa | Equipement et procede pour le renforcement d'un trou de forage d'un puits en cours de forage |
CN102811989A (zh) * | 2010-02-03 | 2012-12-05 | Meh联合公司 | 作为具有选择性和生物活性的等排物的多取代氟甲烷 |
WO2011116115A1 (fr) | 2010-03-16 | 2011-09-22 | Novartis Ag | Composition d'aliskiren comprenant un acide gras à chaîne moyenne et procédé de fabrication correspondant |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4401677A (en) * | 1981-10-09 | 1983-08-30 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
FR2652087B1 (fr) * | 1989-09-15 | 1993-10-15 | Bioprojet Ste Civile | Derives d'amino-acides, leur procede de preparation et leurs applications therapeutiques. |
FR2682952B1 (fr) * | 1991-10-25 | 1993-12-03 | Institut Nal Sante Recherc Medic | Nouveaux n-(mercaptoacyl) amino-acides, leur preparation et les compositions pharmaceutiques qui les contiennent. |
IT1273455B (it) * | 1995-01-27 | 1997-07-08 | Zambon Spa | Derivati tiolici ad attivita' inibitrice delle metallopeptidasi |
-
1995
- 1995-12-28 IT IT95MI002773A patent/IT1277737B1/it active IP Right Grant
-
1996
- 1996-12-17 BR BR9612373A patent/BR9612373A/pt not_active Application Discontinuation
- 1996-12-17 EP EP96944583A patent/EP0877740B1/fr not_active Expired - Lifetime
- 1996-12-17 DE DE69634543T patent/DE69634543D1/de not_active Expired - Lifetime
- 1996-12-17 KR KR1019980704934A patent/KR19990076809A/ko not_active Application Discontinuation
- 1996-12-17 IL IL12491596A patent/IL124915A/en not_active IP Right Cessation
- 1996-12-17 SK SK889-98A patent/SK282977B6/sk unknown
- 1996-12-17 CN CN96199354A patent/CN1071325C/zh not_active Expired - Fee Related
- 1996-12-17 EA EA199800544A patent/EA000991B1/ru not_active IP Right Cessation
- 1996-12-17 CA CA002241414A patent/CA2241414A1/fr not_active Abandoned
- 1996-12-17 CZ CZ982046A patent/CZ204698A3/cs unknown
- 1996-12-17 RO RO98-01109A patent/RO119882B1/ro unknown
- 1996-12-17 GE GEAP19964406A patent/GEP19991871B/en unknown
- 1996-12-17 JP JP09524001A patent/JP2000502687A/ja not_active Ceased
- 1996-12-17 PL PL96327580A patent/PL188151B1/pl not_active IP Right Cessation
- 1996-12-17 EE EE9800192A patent/EE03766B1/xx not_active IP Right Cessation
- 1996-12-17 AP APAP/P/1998/001264A patent/AP1186A/en active
- 1996-12-17 UA UA98074090A patent/UA62923C2/uk unknown
- 1996-12-17 WO PCT/EP1996/005663 patent/WO1997024342A1/fr not_active Application Discontinuation
- 1996-12-17 TR TR1998/01229T patent/TR199801229T2/xx unknown
- 1996-12-17 AT AT96944583T patent/ATE292123T1/de not_active IP Right Cessation
- 1996-12-17 AU AU13018/97A patent/AU713156B2/en not_active Ceased
- 1996-12-17 NZ NZ325785A patent/NZ325785A/en unknown
- 1996-12-23 ZA ZA9610891A patent/ZA9610891B/xx unknown
- 1996-12-27 AR ARP960105957A patent/AR004413A1/es not_active Application Discontinuation
- 1996-12-27 UY UY24425A patent/UY24425A1/es not_active IP Right Cessation
-
1998
- 1998-06-18 BG BG102553A patent/BG63942B1/bg unknown
- 1998-06-22 IS IS4780A patent/IS1885B/is unknown
- 1998-06-26 OA OA9800094A patent/OA10704A/en unknown
- 1998-06-26 NO NO19982977A patent/NO310914B1/no unknown
-
1999
- 1999-07-20 HK HK99103110A patent/HK1018008A1/xx not_active IP Right Cessation
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