BG63538B1 - Стабилна нехигроскопична кристална форма на n-[n-n-(4-пиперидин-4-ил) бутаноил)-n-етилглицил] съединения - Google Patents

Стабилна нехигроскопична кристална форма на n-[n-n-(4-пиперидин-4-ил) бутаноил)-n-етилглицил] съединения Download PDF

Info

Publication number: BG63538B1
Authority: BG; Bulgaria
Prior art keywords: compound; acid; cycloalkyl; alkyl; protecting group
Prior art date: 1996-08-21

Application number

BG103225A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103225A (en

Inventor

Zofia CHRZAN

James Mencel

David Toledo-Velasquez

Vincent Windisch

Rick WOODWARD

Diane SELAZAR

Narasimha VEMURI

Anthony GARDETTO

Matthew Powers

Gregory KUBIAK

Robert Liu

Benoit VANASSE

James SHERBINE

Walter Rodriguez

Adam SLEDESKI

Original Assignee

Aventis Pharmaceuticals Products Inc.

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.)

1996-08-21

Filing date

1999-03-04

Publication date

2002-04-30

1999-03-04 Application filed by Aventis Pharmaceuticals Products Inc. filed Critical Aventis Pharmaceuticals Products Inc.

2000-01-31 Publication of BG103225A publication Critical patent/BG103225A/xx

2002-04-30 Publication of BG63538B1 publication Critical patent/BG63538B1/bg

Links

125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 111
238000000034 method Methods 0.000 claims abstract description 77
238000002360 preparation method Methods 0.000 claims abstract description 38
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
-1 (4-piperidin-4-yl) butanoyl Chemical group 0.000 claims description 79
239000002253 acid Substances 0.000 claims description 55
150000003839 salts Chemical class 0.000 claims description 47
125000000217 alkyl group Chemical group 0.000 claims description 44
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 38
125000000753 cycloalkyl group Chemical group 0.000 claims description 35
125000003710 aryl alkyl group Chemical group 0.000 claims description 32
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 21
125000006239 protecting group Chemical group 0.000 claims description 21
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125000000623 heterocyclic group Chemical group 0.000 claims description 16
238000005984 hydrogenation reaction Methods 0.000 claims description 13
125000004948 alkyl aryl alkyl group Chemical group 0.000 claims description 12
125000002877 alkyl aryl group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims description 10
150000003976 azacycloalkanes Chemical group 0.000 claims description 9
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
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238000010168 coupling process Methods 0.000 claims description 7
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MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
229960002429 proline Drugs 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000013391 scatchard analysis Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
239000003634 thrombocyte concentrate Substances 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
PAFMAHIOSMYVGN-UHFFFAOYSA-N trisodium trinitrate Chemical compound [Na+].[Na+].[Na+].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PAFMAHIOSMYVGN-UHFFFAOYSA-N 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
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
ORQXBVXKBGUSBA-QMMMGPOBSA-N β-cyclohexyl-alanine Chemical compound OC(=O)[C@@H](N)CC1CCCCC1 ORQXBVXKBGUSBA-QMMMGPOBSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
- 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
- A61P9/10—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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon 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
- 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
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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

BG103225A 1996-08-21 1999-03-04 Стабилна нехигроскопична кристална форма на n-[n-n-(4-пиперидин-4-ил) бутаноил)-n-етилглицил] съединения BG63538B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2428496P	1996-08-21	1996-08-21
PCT/US1997/014756 WO1998007696A1 (fr)	1996-08-21	1997-08-21	Forme cristalline stable non hygroscopique de composes n-[n-n-(4-(piperidin-4-yl)butanoyl)-n-ethylglycyl]

Publications (2)

Publication Number	Publication Date
BG103225A BG103225A (en)	2000-01-31
BG63538B1 true BG63538B1 (bg)	2002-04-30

Family

ID=21819807

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103225A BG63538B1 (bg)	1996-08-21	1999-03-04	Стабилна нехигроскопична кристална форма на n-[n-n-(4-пиперидин-4-ил) бутаноил)-n-етилглицил] съединения

Country Status (20)

Country	Link
US (2)	US6153588A (fr)
EP (1)	EP0923553B1 (fr)
JP (1)	JP4008499B2 (fr)
KR (1)	KR20000068229A (fr)
CN (2)	CN1491942A (fr)
AP (1)	AP9901462A0 (fr)
AT (1)	ATE390438T1 (fr)
AU (1)	AU733591B2 (fr)
BG (1)	BG63538B1 (fr)
BR (1)	BR9711340A (fr)
CA (1)	CA2263647C (fr)
DE (1)	DE69738601T2 (fr)
EA (1)	EA001362B1 (fr)
IL (1)	IL128561A0 (fr)
NO (1)	NO990721L (fr)
OA (1)	OA10979A (fr)
PL (1)	PL331772A1 (fr)
SK (1)	SK21999A3 (fr)
WO (1)	WO1998007696A1 (fr)
ZA (1)	ZA977510B (fr)

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AP9901462A0 (en) *	1996-08-21	1999-03-31	Aventis Pharmaceuticals Products Inc	Stable non-hygroscopic crystalline form of N-[N-N-(4-(Piperidin-4-YL)Butanoyl)-N-Ethylglycyl] amide.
WO1999019294A1 (fr) *	1997-05-14	1999-04-22	Aventis Pharmaceuticals Products Inc. Legal/Patents	Preparation des pseudotetrapeptides azacycloalkylalcanoyles
IL135553A0 (en) *	1997-10-10	2001-05-20	Aventis Pharm Prod Inc	Process for the preparation of azacycloalkyalkanoyl pseudotetrapeptides
EP1155033A1 (fr) *	1998-12-30	2001-11-21	Aventis Pharmaceuticals Products Inc.	Procede de preparation d'un amide n- n- n-(4-piperidin- 4-yl)butanoyl)- n-ethylglycyl]- (l)-aspartyl]-(l)- $g(b)-cyclohexylalanine cristallin non hygroscopique stable
US20050238834A1 (en) *	2004-04-21	2005-10-27	Eastman Kodak Company	High modulus label with compliant carrier sheet
US8021679B2 (en)	2005-08-25	2011-09-20	Medtronic Vascular, Inc	Nitric oxide-releasing biodegradable polymers useful as medical devices and coatings therefore
US8241619B2 (en)	2006-05-15	2012-08-14	Medtronic Vascular, Inc.	Hindered amine nitric oxide donating polymers for coating medical devices
US7811600B2 (en) *	2007-03-08	2010-10-12	Medtronic Vascular, Inc.	Nitric oxide donating medical devices and methods of making same
US8273828B2 (en) *	2007-07-24	2012-09-25	Medtronic Vascular, Inc.	Methods for introducing reactive secondary amines pendant to polymers backbones that are useful for diazeniumdiolation
US20090222088A1 (en) *	2008-02-29	2009-09-03	Medtronic Vascular, Inc.	Secondary Amine Containing Nitric Oxide Releasing Polymer Composition
US20090232863A1 (en) *	2008-03-17	2009-09-17	Medtronic Vascular, Inc.	Biodegradable Carbon Diazeniumdiolate Based Nitric Oxide Donating Polymers
US20090232868A1 (en) *	2008-03-17	2009-09-17	Medtronic Vascular, Inc.	Nitric Oxide Releasing Polymer Composition
US8158187B2 (en) *	2008-12-19	2012-04-17	Medtronic Vascular, Inc.	Dry diazeniumdiolation methods for producing nitric oxide releasing medical devices
US8709465B2 (en) *	2009-04-13	2014-04-29	Medtronic Vascular, Inc.	Diazeniumdiolated phosphorylcholine polymers for nitric oxide release
US9704557B2 (en) *	2013-09-25	2017-07-11	Qualcomm Incorporated	Method and apparatus for storing retention time profile information based on retention time and temperature
CN108697770B (zh)	2015-12-21	2023-08-01	得克萨斯技术大学联合体	用于溶液相gap肽合成的系统和方法
WO2019217116A1 (fr) *	2018-05-06	2019-11-14	Gap Peptides Llc	Méthode de synthèse en phase solution de peptides
US12024537B2 (en)	2018-05-31	2024-07-02	Sederma	Compositions and methods for chemical synthesis
WO2020159837A1 (fr)	2019-02-01	2020-08-06	Gap Peptides Llc	Stratégie de synthèse pour groupe de protection gap

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US4857508A (en) *	1987-12-03	1989-08-15	Monsanto Company	Novel platelet-aggregation inhibitor peptide derivatives
US4992463A (en) *	1988-07-20	1991-02-12	Monsanto Company	Thienyl peptide mimetic compounds which are useful in inhibiting platelet aggregation
US4952562A (en) *	1989-09-29	1990-08-28	Rorer Pharmaceutical Corporation	Anti-thrombotic peptides and pseudopeptides
US5332726A (en) *	1989-09-29	1994-07-26	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Antithrombotic peptides and pseudopeptides
US5064814A (en) *	1990-04-05	1991-11-12	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Anti-thrombotic peptide and pseudopeptide derivatives
NZ239876A (en) *	1990-09-27	1993-12-23	Merck & Co Inc	Glycyl-b-alanine derivatives and pharmaceutical compositions thereof.
US5264420A (en)	1990-09-27	1993-11-23	Merck & Co., Inc.	Fibrinogen receptor antagonists
US5218138A (en)	1992-09-02	1993-06-08	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Stereoselective reduction of 3-hydroxyket-1-ones to 1,3-syn-dihydroxylated compounds
US5340798A (en) *	1992-10-14	1994-08-23	Merck & Co., Inc.	Fibrinogen receptor antagonists
WO1995001336A1 (fr) *	1993-06-30	1995-01-12	Sumitomo Pharmaceuticals Co., Ltd.	Nouveau derive de piperidine
US5780590A (en) *	1993-10-15	1998-07-14	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
BR9407839A (pt) *	1993-10-15	1997-05-13	Rhone Poulenc Rorer Pharma	Composto composição farmacêutica e processo para a prevenção ou tratamento de trombose em um mamífero em necessidade desta terapia
AU7862794A (en)	1993-10-19	1995-05-08	Sumitomo Pharmaceuticals Company, Limited	2,3-diaminopropionic acid derivative
AP9901462A0 (en) *	1996-08-21	1999-03-31	Aventis Pharmaceuticals Products Inc	Stable non-hygroscopic crystalline form of N-[N-N-(4-(Piperidin-4-YL)Butanoyl)-N-Ethylglycyl] amide.
IL135553A0 (en) *	1997-10-10	2001-05-20	Aventis Pharm Prod Inc	Process for the preparation of azacycloalkyalkanoyl pseudotetrapeptides

1997
- 1997-08-21 AP APAP/P/1999/001462A patent/AP9901462A0/en unknown
- 1997-08-21 JP JP51098398A patent/JP4008499B2/ja not_active Expired - Fee Related
- 1997-08-21 SK SK219-99A patent/SK21999A3/sk unknown
- 1997-08-21 CN CNA021415722A patent/CN1491942A/zh active Pending
- 1997-08-21 BR BR9711340A patent/BR9711340A/pt unknown
- 1997-08-21 DE DE69738601T patent/DE69738601T2/de not_active Expired - Lifetime
- 1997-08-21 PL PL97331772A patent/PL331772A1/xx unknown
- 1997-08-21 AT AT97939488T patent/ATE390438T1/de not_active IP Right Cessation
- 1997-08-21 AU AU41563/97A patent/AU733591B2/en not_active Ceased
- 1997-08-21 KR KR1019997001362A patent/KR20000068229A/ko not_active Ceased
- 1997-08-21 ZA ZA9707510A patent/ZA977510B/xx unknown
- 1997-08-21 CA CA2263647A patent/CA2263647C/fr not_active Expired - Fee Related
- 1997-08-21 CN CN97198210A patent/CN1231659A/zh active Pending
- 1997-08-21 WO PCT/US1997/014756 patent/WO1998007696A1/fr not_active Application Discontinuation
- 1997-08-21 EP EP97939488A patent/EP0923553B1/fr not_active Expired - Lifetime
- 1997-08-21 IL IL12856197A patent/IL128561A0/xx unknown
- 1997-08-21 EA EA199900217A patent/EA001362B1/ru not_active IP Right Cessation
1999
- 1999-02-16 NO NO990721A patent/NO990721L/no unknown
- 1999-02-18 US US09/251,030 patent/US6153588A/en not_active Expired - Fee Related
- 1999-02-19 OA OA9900037A patent/OA10979A/en unknown
- 1999-03-04 BG BG103225A patent/BG63538B1/bg unknown
2000
- 2000-08-15 US US09/639,634 patent/US6753409B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ATE390438T1 (de)	2008-04-15
CN1491942A (zh)	2004-04-28
BR9711340A (pt)	1999-08-17
EP0923553B1 (fr)	2008-03-26
AU4156397A (en)	1998-03-06
DE69738601D1 (de)	2008-05-08
JP4008499B2 (ja)	2007-11-14
US6753409B1 (en)	2004-06-22
EA199900217A1 (ru)	1999-08-26
EP0923553A1 (fr)	1999-06-23
NO990721D0 (no)	1999-02-16
IL128561A0 (en)	2000-01-31
JP2000517305A (ja)	2000-12-26
KR20000068229A (ko)	2000-11-25
WO1998007696A1 (fr)	1998-02-26
OA10979A (en)	2001-11-01
EP0923553A4 (fr)	1999-12-08
SK21999A3 (en)	2000-02-14
EA001362B1 (ru)	2001-02-26
AU733591B2 (en)	2001-05-17
BG103225A (en)	2000-01-31
CA2263647A1 (fr)	1998-02-26
US6153588A (en)	2000-11-28
AP9901462A0 (en)	1999-03-31
DE69738601T2 (de)	2009-04-30
CN1231659A (zh)	1999-10-13
NO990721L (no)	1999-04-20
PL331772A1 (en)	1999-08-02
CA2263647C (fr)	2011-02-15
ZA977510B (en)	1998-05-21

Publication	Publication Date	Title
BG63538B1 (bg)	2002-04-30	Стабилна нехигроскопична кристална форма на n-[n-n-(4-пиперидин-4-ил) бутаноил)-n-етилглицил] съединения
AP904A (en)	2000-11-24	Antithrombotic Azacycloalkylalkanoyl peptides and pseudopeptides.
US5866685A (en)	1999-02-02	Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
US6274705B1 (en)	2001-08-14	Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
MXPA99001772A (en)	1999-06-01	Stable non-hygroscopic crystalline form of n-[n-n-(4-(piperidin-4-yl)butanoyl)-n-ethylglycyl]compounds
MXPA99001773A (en)	1999-06-01	Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
CZ55099A3 (cs)	2000-06-14	Antitrombotické azacykloalkylalkanoylové peptidy a pseudopeptidy
CZ55199A3 (cs)	2000-06-14	Stabilní, nehygroskopická krystalická forma N- [N-[N(4-piperidin-4-yl)butanoyl]-N-ethylgIycyl]ových derivátů
HK1022318A (en)	2000-08-04	Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
HK1006225B (en)	2001-12-07	Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
NZ299833A (en)	1998-04-27	Treating or preventing thrombosis using azacycloalkanol peptides and pseudopeptides