CA2194397A1 - (-)-(3r)-3-methyl-4-{4-[4-(4-pyridyl)piperazin-1-yl]phenoxy} butyric acid as cellular adhesion inhibitor - Google Patents

(-)-(3r)-3-methyl-4-{4-[4-(4-pyridyl)piperazin-1-yl]phenoxy} butyric acid as cellular adhesion inhibitor

Info

Publication number: CA2194397A1
Authority: CA; Canada
Prior art keywords: optically active; pharmaceutically; ester; active compound; amide
Prior art date: 1995-06-01
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.): Abandoned

Application number

CA002194397A

Other languages

English (en)

French (fr)

Inventor

Stuart Dennett Mills

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Syngenta Ltd

Original Assignee

Individual

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.)

1995-06-01

Filing date

1996-05-28

Publication date

1996-12-05

1995-06-01 Priority claimed from US08/457,538 external-priority patent/US5652242A/en

1995-09-07 Priority claimed from GBGB9518188.9A external-priority patent/GB9518188D0/en

1996-05-28 Application filed by Individual filed Critical Individual

1996-12-05 Publication of CA2194397A1 publication Critical patent/CA2194397A1/en

Status Abandoned legal-status Critical Current

Links

RVVTUJLHUHZYOD-MRXNPFEDSA-N (3r)-3-methyl-4-[4-(4-pyridin-4-ylpiperazin-1-yl)phenoxy]butanoic acid Chemical compound C1=CC(OC[C@H](C)CC(O)=O)=CC=C1N1CCN(C=2C=CN=CC=2)CC1 RVVTUJLHUHZYOD-MRXNPFEDSA-N 0.000 title claims description 3
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FQRKQAKKPIJXNB-CYBMUJFWSA-N tert-butyl (3r)-3-methyl-4-(4-methylphenyl)sulfonyloxybutanoate Chemical group CC(C)(C)OC(=O)C[C@@H](C)COS(=O)(=O)C1=CC=C(C)C=C1 FQRKQAKKPIJXNB-CYBMUJFWSA-N 0.000 claims description 2
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RVVTUJLHUHZYOD-UHFFFAOYSA-N 3-methyl-4-[4-(4-pyridin-4-ylpiperazin-1-yl)phenoxy]butanoic acid Chemical compound C1=CC(OCC(C)CC(O)=O)=CC=C1N1CCN(C=2C=CN=CC=2)CC1 RVVTUJLHUHZYOD-UHFFFAOYSA-N 0.000 claims 1
JUVAUSMNHDGUEX-UHFFFAOYSA-N 4-(4-pyridin-4-ylpiperazin-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1CCN(C=2C=CN=CC=2)CC1 JUVAUSMNHDGUEX-UHFFFAOYSA-N 0.000 claims 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical class N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
208000001435 Thromboembolism Diseases 0.000 description 1
108090000373 Tissue Plasminogen Activator Proteins 0.000 description 1
102000003978 Tissue Plasminogen Activator Human genes 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
206010047249 Venous thrombosis Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000702 anti-platelet effect Effects 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007887 coronary angioplasty Methods 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000006071 cream Substances 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
210000002889 endothelial cell Anatomy 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000002319 fibrinogen receptor antagonist Substances 0.000 description 1
239000003527 fibrinolytic agent Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
OLKGTKIYKWXMOZ-UHFFFAOYSA-N hydroxymethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCO OLKGTKIYKWXMOZ-UHFFFAOYSA-N 0.000 description 1
YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
108010073863 saruplase Proteins 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
229960005202 streptokinase Drugs 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
231100000378 teratogenic Toxicity 0.000 description 1
230000003390 teratogenic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960003433 thalidomide Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
229960000103 thrombolytic agent Drugs 0.000 description 1
229960000187 tissue plasminogen activator Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
108010047303 von Willebrand Factor Proteins 0.000 description 1
102100036537 von Willebrand factor Human genes 0.000 description 1
229960001134 von willebrand factor Drugs 0.000 description 1

Classifications

- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (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)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002194397A 1995-06-01 1996-05-28 (-)-(3r)-3-methyl-4-{4-[4-(4-pyridyl)piperazin-1-yl]phenoxy} butyric acid as cellular adhesion inhibitor Abandoned CA2194397A1 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US08/457,538 US5652242A (en)	1993-03-29	1995-06-01	Heterocyclic derivatives
US08/457538		1995-06-01
GB9518188.9		1995-09-07
GBGB9518188.9A GB9518188D0 (en)	1995-09-07	1995-09-07	Optically active derivative

Publications (1)

Publication Number	Publication Date
CA2194397A1 true CA2194397A1 (en)	1996-12-05

Family

ID=26307696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002194397A Abandoned CA2194397A1 (en)	1995-06-01	1996-05-28	(-)-(3r)-3-methyl-4-{4-[4-(4-pyridyl)piperazin-1-yl]phenoxy} butyric acid as cellular adhesion inhibitor

Country Status (31)

Country	Link
EP (1)	EP0796247A1 (ko)
JP (1)	JP2885941B2 (ko)
KR (1)	KR100245957B1 (ko)
AT (1)	AT406675B (ko)
AU (1)	AU710105B2 (ko)
BE (1)	BE1009520A5 (ko)
BR (1)	BR9606409A (ko)
CA (1)	CA2194397A1 (ko)
CH (1)	CH691808A5 (ko)
CZ (1)	CZ26997A3 (ko)
DE (1)	DE19680509T1 (ko)
DK (1)	DK10697A (ko)
ES (1)	ES2137886B1 (ko)
FI (1)	FI970393L (ko)
GB (1)	GB2304340B (ko)
GR (1)	GR1002702B (ko)
HU (1)	HUP9700274A3 (ko)
IE (1)	IE960405A1 (ko)
IL (1)	IL118477A0 (ko)
IT (1)	IT1290839B1 (ko)
LU (1)	LU90008B1 (ko)
MC (1)	MC2418A1 (ko)
MX (1)	MX9700379A (ko)
NL (1)	NL1003243C2 (ko)
NO (1)	NO307460B1 (ko)
NZ (1)	NZ308597A (ko)
PL (1)	PL318440A1 (ko)
SE (1)	SE510812C2 (ko)
SK (1)	SK13097A3 (ko)
TR (1)	TR199700020T1 (ko)
WO (1)	WO1996038416A1 (ko)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0100158A3 (en) *	1982-07-28	1985-03-27	The Upjohn Company	(3-pyridinyl)heteroalkarylalkanols, alkanoic acids and esters
GB8609630D0 (en) *	1986-04-19	1986-05-21	Pfizer Ltd	Anti-arrhythmia agents
ZW4194A1 (en) *	1993-03-29	1994-12-21	Zeneca Ltd	Heterocyclic compounds
DK0825184T3 (da) *	1993-03-29	2001-09-10	Astrazeneca Ab	Heterocykliske derivater som blodpladeaggregeringsinhibitorer

1996
- 1996-05-28 MX MX9700379A patent/MX9700379A/es unknown
- 1996-05-28 BR BR9606409A patent/BR9606409A/pt not_active Application Discontinuation
- 1996-05-28 CA CA002194397A patent/CA2194397A1/en not_active Abandoned
- 1996-05-28 GB GB9627127A patent/GB2304340B/en not_active Expired - Fee Related
- 1996-05-28 KR KR1019970700532A patent/KR100245957B1/ko not_active IP Right Cessation
- 1996-05-28 AU AU58272/96A patent/AU710105B2/en not_active Ceased
- 1996-05-28 JP JP8536281A patent/JP2885941B2/ja not_active Expired - Fee Related
- 1996-05-28 ES ES009750006A patent/ES2137886B1/es not_active Expired - Fee Related
- 1996-05-28 CH CH00224/97A patent/CH691808A5/de not_active IP Right Cessation
- 1996-05-28 AT AT0900596A patent/AT406675B/de active
- 1996-05-28 DE DE19680509T patent/DE19680509T1/de not_active Withdrawn
- 1996-05-28 GR GR960100176A patent/GR1002702B/el not_active IP Right Cessation
- 1996-05-28 SK SK130-97A patent/SK13097A3/sk unknown
- 1996-05-28 PL PL96318440A patent/PL318440A1/xx unknown
- 1996-05-28 CZ CZ97269A patent/CZ26997A3/cs unknown
- 1996-05-28 TR TR97/00020T patent/TR199700020T1/xx unknown
- 1996-05-28 HU HU9700274A patent/HUP9700274A3/hu unknown
- 1996-05-28 NZ NZ308597A patent/NZ308597A/en unknown
- 1996-05-28 EP EP96919906A patent/EP0796247A1/en not_active Withdrawn
- 1996-05-28 WO PCT/GB1996/001260 patent/WO1996038416A1/en not_active IP Right Cessation
- 1996-05-29 MC MC2347A patent/MC2418A1/xx unknown
- 1996-05-30 IL IL11847796A patent/IL118477A0/xx unknown
- 1996-05-31 IE IE960405A patent/IE960405A1/en not_active IP Right Cessation
- 1996-05-31 IT IT96MI001113A patent/IT1290839B1/it active IP Right Grant
- 1996-05-31 BE BE9600491A patent/BE1009520A5/fr not_active IP Right Cessation
- 1996-05-31 NL NL1003243A patent/NL1003243C2/xx not_active IP Right Cessation
1997
- 1997-01-22 LU LU90008A patent/LU90008B1/fr active
- 1997-01-24 SE SE9700203A patent/SE510812C2/sv not_active IP Right Cessation
- 1997-01-30 DK DK010697A patent/DK10697A/da not_active Application Discontinuation
- 1997-01-30 FI FI970393A patent/FI970393L/fi unknown
- 1997-01-31 NO NO970437A patent/NO307460B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES2137886B1 (es)	2000-08-16
FI970393A0 (fi)	1997-01-30
IL118477A0 (en)	1996-09-12
ATA900596A (de)	1999-12-15
HUP9700274A2 (hu)	1999-06-28
TR199700020T1 (tr)	1997-04-22
SK13097A3 (en)	1997-08-06
EP0796247A1 (en)	1997-09-24
AU5827296A (en)	1996-12-18
NZ308597A (en)	1998-11-25
NO970437D0 (no)	1997-01-31
ES2137886A1 (es)	1999-12-16
HU9700274D0 (en)	1997-04-28
NO970437L (no)	1997-02-20
GR1002702B (el)	1997-05-22
NL1003243C2 (nl)	1996-12-04
JPH09512836A (ja)	1997-12-22
GB2304340A (en)	1997-03-19
FI970393L (fi)	1997-01-30
WO1996038416A1 (en)	1996-12-05
BE1009520A5 (fr)	1997-04-01
DK10697A (da)	1997-04-01
AT406675B (de)	2000-07-25
AU710105B2 (en)	1999-09-16
BR9606409A (pt)	1997-09-30
DE19680509T1 (de)	1997-12-04
HUP9700274A3 (en)	2000-02-28
ITMI961113A0 (it)	1996-05-31
SE9700203D0 (sv)	1997-01-24
NO307460B1 (no)	2000-04-10
CH691808A5 (de)	2001-10-31
SE510812C2 (sv)	1999-06-28
GB2304340B (en)	1998-07-29
CZ26997A3 (en)	1997-08-13
IT1290839B1 (it)	1998-12-14
MC2418A1 (fr)	1997-05-23
MX9700379A (es)	1997-04-30
LU90008B1 (fr)	1997-04-16
IE960405A1 (en)	1996-12-11
PL318440A1 (en)	1997-06-09
KR970704689A (ko)	1997-09-06
KR100245957B1 (ko)	2000-04-01
GB9627127D0 (en)	1997-02-19
SE9700203L (sv)	1997-01-24
JP2885941B2 (ja)	1999-04-26
ITMI961113A1 (it)	1997-12-01

Publication	Publication Date	Title
EP0478328B1 (en)	1996-01-10	Novel fibrinogen receptor antagonists
ES2219894T3 (es)	2004-12-01	Derivados heterociclicos que inhiben el factor xa.
CA2390231A1 (en)	2001-05-17	Dipeptidyl peptidase iv inhibitors and methods of making and using dipeptidyl peptidase iv inhibitors
SK63194A3 (en)	1994-12-07	Peptide derivatives
WO1992016549A1 (de)	1992-10-01	Para-substituierte phenylalanin-derivate
CA2268621A1 (en)	1999-10-13	2-pipirazinone-1-acetic acid derivative, production and use thereof
JPH01503063A (ja)	1989-10-19	抗炎症組成物
JP2021531310A (ja)	2021-11-18	ボロン酸誘導体
JPH072820A (ja)	1995-01-06	不可逆ヒト免疫不全ウイルス（ｈｉｖ）プロテアーゼ阻害剤、その中間体、組成物およびその製法
CA2252086A1 (en)	1997-10-16	6-substituted amino-4-oxa-1-azabicyclo¬3,2,0\|heptan-7-one derivatives as cysteine protease inhibitors
US11434198B2 (en)	2022-09-06	Compounds and methods for the treatment of neurodegenerative diseases
CA2022112A1 (en)	1991-02-01	Certain imidazole compounds as transglutaminase inhibitors
DE69420345T2 (de)	1999-12-30	Benzothiazolsulfonamid-derivate, verfahren zu deren herstellung und anwendungen
CN101790528A (zh)	2010-07-28	氨基酰基前药
CA2070983A1 (en)	1992-12-12	Cyclic renin inhibitors
CA2194397A1 (en)	1996-12-05	(-)-(3r)-3-methyl-4-{4-[4-(4-pyridyl)piperazin-1-yl]phenoxy} butyric acid as cellular adhesion inhibitor
SK281025B6 (sk)	2000-11-07	(1-fenyl-1-heterocyklyl)alkánové deriváty, spôsoby ich prípravy, medziprodukty na ich prípravu, farmaceutické prostriedky s ich obsahom a ich použitie
JPH10175967A (ja)	1998-06-30	新規なｎ−ベンジルピペラジン化合物、その製造法及びそれを含有する医薬組成物
HU205951B (en)	1992-07-28	Process for producing amino-acid derivatives and pharmaceutical compositions containing them
CA2887420A1 (en)	2014-04-24	Matrix metalloproteinase inhibitors and methods for the treatment of pain and other diseases
CA2022110A1 (en)	1991-02-01	Azole compounds and their use as transglutaminase inhibitors
CA2022115A1 (en)	1991-02-01	Imidazole compounds and their use as transglutaminase inhibitors
CA2230445C (en)	2002-12-10	Fibrinogen receptor antagonists and medicinal preparations containing the same as the active ingredient
US5817680A (en)	1998-10-06	Hemoregulatory compounds
CH677610A5 (ko)	1991-06-14

Legal Events

Date	Code	Title	Description
2003-05-28	FZDE	Discontinued