JPH08509723A - アミジノおよびグアニジノ置換ボロン酸トリプシン様酵素阻害剤 - Google Patents

アミジノおよびグアニジノ置換ボロン酸トリプシン様酵素阻害剤

Info

Publication number: JPH08509723A
Authority: JP; Japan
Prior art keywords: phe; pro; boro; nhc; alkyl
Prior art date: 1993-04-27
Legal status (The legal status 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 status listed.): Pending

Application number

JP6524316A

Other languages

English (en)

Japanese (ja)

Inventor

フイービツグ，ジヨン・マシユー

ケトナー，チヤールズ・エイドリアン

リー，シヤン−リアン・オー

カリーニ，デイビツド・ジヨン

Original Assignee

ザ・デュポン・メルク・ファーマシュウティカル・カンパニー

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.)

1993-04-27

Filing date

1994-04-21

Publication date

1996-10-15

1994-04-21 Application filed by ザ・デュポン・メルク・ファーマシュウティカル・カンパニー filed Critical ザ・デュポン・メルク・ファーマシュウティカル・カンパニー

1996-10-15 Publication of JPH08509723A publication Critical patent/JPH08509723A/ja

Status Pending legal-status Critical Current

Links

-1 guanidino-substituted boronic acid Chemical class 0.000 title claims description 35
230000001810 trypsinlike Effects 0.000 title description 5
239000002532 enzyme inhibitor Substances 0.000 title description 2
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 47
150000001875 compounds Chemical class 0.000 claims description 31
125000003118 aryl group Chemical group 0.000 claims description 23
125000000539 amino acid group Chemical group 0.000 claims description 12
WEQJQNWXCSUVMA-RYUDHWBXSA-N Phe-Pro Chemical compound C([C@H]([NH3+])C(=O)N1[C@@H](CCC1)C([O-])=O)C1=CC=CC=C1 WEQJQNWXCSUVMA-RYUDHWBXSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
229910052740 iodine Inorganic materials 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
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
230000000903 blocking effect Effects 0.000 claims description 5
229910052796 boron Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
COQOYMRZIFLJII-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].CC(C)(O)C(C)(C)O COQOYMRZIFLJII-UHFFFAOYSA-N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 30
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238000000034 method Methods 0.000 description 27
238000003786 synthesis reaction Methods 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
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239000003112 inhibitor Substances 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
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ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 9
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 9
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BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 6
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239000000706 filtrate Substances 0.000 description 5
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230000002829 reductive effect Effects 0.000 description 5
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ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 4
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229940122388 Thrombin inhibitor Drugs 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
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239000000872 buffer Substances 0.000 description 4
DKRMKJKQCXCUGJ-UHFFFAOYSA-N dichloromethylboronic acid Chemical compound OB(O)C(Cl)Cl DKRMKJKQCXCUGJ-UHFFFAOYSA-N 0.000 description 4
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238000001914 filtration Methods 0.000 description 4
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
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239000000126 substance Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
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MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
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125000002707 L-tryptophyl group Chemical group [H]C1=C([H])C([H])=C2C(C([C@](N([H])[H])(C(=O)[*])[H])([H])[H])=C([H])N([H])C2=C1[H] 0.000 description 3
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
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238000005481 NMR spectroscopy Methods 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

JP6524316A 1993-04-27 1994-04-21 アミジノおよびグアニジノ置換ボロン酸トリプシン様酵素阻害剤 Pending JPH08509723A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US5283593A	1993-04-27	1993-04-27
US08/052,835		1993-04-27
US20405594A	1994-03-02	1994-03-02
US08/204,055		1994-03-02
PCT/US1994/004058 WO1994025049A1 (fr)	1993-04-27	1994-04-21	Acide boronique a substitution amidino et guanidino en tant qu'inhibiteur d'enzymes de type trypsine

Publications (1)

Publication Number	Publication Date
JPH08509723A true JPH08509723A (ja)	1996-10-15

Family

ID=26731141

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6524316A Pending JPH08509723A (ja)	1993-04-27	1994-04-21	アミジノおよびグアニジノ置換ボロン酸トリプシン様酵素阻害剤

Country Status (7)

Country	Link
EP (1)	EP0696199A4 (fr)
JP (1)	JPH08509723A (fr)
AU (1)	AU6703894A (fr)
CA (1)	CA2161216A1 (fr)
IL (1)	IL109319A0 (fr)
TW (1)	TW286318B (fr)
WO (1)	WO1994025049A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010531352A (ja) *	2007-06-28	2010-09-24	オブシェストヴォエスオグラニチェノイオトヴェトストヴェノスチュ “ビオニカ”	新規トロンビン機能性化合物およびそれらに基づいた医薬組成物
JP2010531353A (ja) *	2007-06-28	2010-09-24	オブシェストヴォエスオグラニチェノイオトヴェトストヴェノスチュ “ビオニカ”	新規抗凝血組成物、それらを基にした血栓症疾患治療のための医薬組成品、および血液希釈による凝固亢進障害改善のための血漿代用液

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL111175A0 (en) *	1993-10-07	1994-12-29	Du Pont Merck Pharma	Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them
US5561146A (en) *	1994-06-10	1996-10-01	Bristol-Myers Squibb Company	Modified guanidino and amidino thrombin inhibitors
FR2721611B1 (fr)	1994-06-22	1996-09-27	Adir	Nouveaux dérivés peptidiques de l'acide boronique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent .
CN1121384C (zh)	1995-07-26	2003-09-17	三菱化学株式会社	青霉胺酰胺衍生物
FR2739858B1 (fr) *	1995-10-11	1997-11-14	Synthelabo	Derives de n-sulfonyl- et n-sulfamoylpeptidylprolinamide, leur preparation et leur application en therapeutique
US6649593B1 (en)	1999-10-13	2003-11-18	Tularik Inc.	Modulators of SREBP processing
WO2002096933A1 (fr)	2001-05-30	2002-12-05	Novartis Ag	Derives d'acide 2-{[n-(2-amino-3-(heteroaryl ou aryl)propionyl)-aminoacyl]-amino}-alkylboronique
BR0314450A (pt)	2002-09-09	2005-07-26	Trigen Ltd	Sais de ácido borÈnico com adição de uma base farmaceuticamente aceitável, formulação farmacêutica, e uso dos referidos sais para preparar uma formulação farmacêutica
US20050288253A1 (en)	2002-09-09	2005-12-29	Trigen Limited	Boronic acid salts
US7576206B2 (en)	2003-08-14	2009-08-18	Cephalon, Inc.	Proteasome inhibitors and methods of using the same
US7223745B2 (en)	2003-08-14	2007-05-29	Cephalon, Inc.	Proteasome inhibitors and methods of using the same
US7468383B2 (en)	2005-02-11	2008-12-23	Cephalon, Inc.	Proteasome inhibitors and methods of using the same
AU2010341530B2 (en)	2009-12-22	2016-03-10	Cephalon, Inc.	Proteasome inhibitors and processes for their preparation, purification and use
US10526315B2 (en)	2016-06-21	2020-01-07	Orion Ophthalmology LLC	Carbocyclic prolinamide derivatives
PL3472149T3 (pl)	2016-06-21	2024-02-12	Orion Ophthalmology LLC	Heterocykliczne pochodne prolinamidu

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4537773A (en) *	1983-12-05	1985-08-27	E. I. Du Pont De Nemours And Company	α-Aminoboronic acid derivatives
US4499082A (en) *	1983-12-05	1985-02-12	E. I. Du Pont De Nemours And Company	α-Aminoboronic acid peptides
GB9024129D0 (en) *	1990-11-06	1990-12-19	Thrombosis Research Trust	Inhibitors and substrates of thrombin
IL111175A0 (en) *	1993-10-07	1994-12-29	Du Pont Merck Pharma	Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them

1994
- 1994-04-13 IL IL10931994A patent/IL109319A0/xx unknown
- 1994-04-21 WO PCT/US1994/004058 patent/WO1994025049A1/fr not_active Ceased
- 1994-04-21 AU AU67038/94A patent/AU6703894A/en not_active Abandoned
- 1994-04-21 CA CA002161216A patent/CA2161216A1/fr not_active Abandoned
- 1994-04-21 JP JP6524316A patent/JPH08509723A/ja active Pending
- 1994-04-21 EP EP94914776A patent/EP0696199A4/fr not_active Withdrawn
- 1994-05-07 TW TW083104198A patent/TW286318B/zh active

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010531352A (ja) *	2007-06-28	2010-09-24	オブシェストヴォエスオグラニチェノイオトヴェトストヴェノスチュ “ビオニカ”	新規トロンビン機能性化合物およびそれらに基づいた医薬組成物
JP2010531353A (ja) *	2007-06-28	2010-09-24	オブシェストヴォエスオグラニチェノイオトヴェトストヴェノスチュ “ビオニカ”	新規抗凝血組成物、それらを基にした血栓症疾患治療のための医薬組成品、および血液希釈による凝固亢進障害改善のための血漿代用液

Also Published As

Publication number	Publication date
IL109319A0 (en)	1994-07-31
EP0696199A4 (fr)	1997-06-25
EP0696199A1 (fr)	1996-02-14
WO1994025049A1 (fr)	1994-11-10
CA2161216A1 (fr)	1994-11-10
AU6703894A (en)	1994-11-21
TW286318B (fr)	1996-09-21

Publication	Publication Date	Title
EP1050540B1 (fr)	2006-12-27	Inhibiteurs de dipeptidyl-aminopeptidase de type IV
US6825169B1 (en)	2004-11-30	Inhibitors of dipeptidyl-aminopeptidase type IV
JPH08509723A (ja)	1996-10-15	アミジノおよびグアニジノ置換ボロン酸トリプシン様酵素阻害剤
US5462928A (en)	1995-10-31	Inhibitors of dipeptidyl-aminopeptidase type IV
AU623592B2 (en)	1992-05-21	Peptide boronic acid inhibitors of trypsin-like proteases
CA2200192C (fr)	2001-01-16	Inhibiteurs amidino et guanidino substitues d'enzymes semblables a la trypsine
EP0528858B1 (fr)	1997-01-22	Inhibiteurs de dipeptidyl-aminopeptidase de type iv
US5242904A (en)	1993-09-07	Peptide boronic acid inhibitors of trypsin-like proteases
EP1658255B1 (fr)	2009-02-18	Inhibiteurs de proteasome et methodes les utilisant
US5250720A (en)	1993-10-05	Intermediates for preparing peptide boronic acid inhibitors of trypsin-like proteases
US5639739A (en)	1997-06-17	Imidazole containing aminoboronic acids
WO1995011689A1 (fr)	1995-05-04	Utilisation d'inhibiteurs de la dipeptidylaminopeptidase pour bloquer l'entree du vih dans des cellules
CA2853272A1 (fr)	2005-10-20	Synthese d'ester borique et de composes acides
CA2116181A1 (fr)	1994-08-25	Nouveaux derives peptidiques de l'acide boronique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US6127340A (en)	2000-10-03	Serine protease inhibitors
US6482797B1 (en)	2002-11-19	N-terminal site selective inhibitors of human angiotensin conversion enzyme (ACE)
CA1333208C (fr)	1994-11-22	Peptides contenant de l'acide boronique inhibant les proteases apparentees a la trypsine
HK1015611B (en)	2001-12-14	Inhibitors of dipeptidyl-aminopeptidase type iv

JPH08509723A - アミジノおよびグアニジノ置換ボロン酸トリプシン様酵素阻害剤 - Google Patents

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Applications Claiming Priority (5)

Publications (1)

Family

ID=26731141

Family Applications (1)

Country Status (7)

Cited By (2)

Families Citing this family (15)

Family Cites Families (4)

Cited By (2)

Also Published As

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