CA2089972A1 - Sulfonamidocarboxamides - Google Patents

Sulfonamidocarboxamides

Info

Publication number
CA2089972A1
CA2089972A1 CA2089972A CA2089972A CA2089972A1 CA 2089972 A1 CA2089972 A1 CA 2089972A1 CA 2089972 A CA2089972 A CA 2089972A CA 2089972 A CA2089972 A CA 2089972A CA 2089972 A1 CA2089972 A1 CA 2089972A1
Authority
CA
Canada
Prior art keywords
sulfonamidocarboxamides
sulphonamidocarboxamides
amidination
fibrinogen
clotting
Prior art date
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.)
Granted
Application number
CA2089972A
Other languages
French (fr)
Other versions
CA2089972C (en
Inventor
Jean Ackermann
David Banner
Klaus Gubernator
Kurt Hilpert
Gerard Schmid
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of CA2089972A1 publication Critical patent/CA2089972A1/en
Application granted granted Critical
Publication of CA2089972C publication Critical patent/CA2089972C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • 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
    • 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
    • C07D211/26—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 nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • 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
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • 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
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • 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
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

The novel sulphonamidocarboxamides of the formula (see fig. I) wherein A, M, Q, X and Y have the significance given in the description, as well as hydrates or solvates thereof inhibit thrombin-induced blood platelet aggregation and clotting of fibrinogen in plasma. They are manufactured by amidination of a cyclic amino group standing for grouping X or by C(O)N(Q) amide formation.
CA002089972A 1992-03-06 1993-02-19 Sulfonamidocarboxamides Expired - Fee Related CA2089972C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH728/92 1992-03-06
CH72892 1992-03-06
CH180/93 1993-01-21
CH18093 1993-01-21

Publications (2)

Publication Number Publication Date
CA2089972A1 true CA2089972A1 (en) 1993-09-07
CA2089972C CA2089972C (en) 1999-06-08

Family

ID=25683792

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002089972A Expired - Fee Related CA2089972C (en) 1992-03-06 1993-02-19 Sulfonamidocarboxamides

Country Status (24)

Country Link
US (4) US5405854A (en)
EP (1) EP0559046B1 (en)
JP (1) JPH0780848B2 (en)
CN (1) CN1076690A (en)
AT (1) ATE203013T1 (en)
AU (1) AU665230B2 (en)
BG (1) BG61506B1 (en)
CA (1) CA2089972C (en)
CZ (1) CZ286926B6 (en)
DE (1) DE59310186D1 (en)
DK (1) DK0559046T3 (en)
ES (1) ES2161217T3 (en)
FI (1) FI103880B (en)
GR (1) GR3036870T3 (en)
HU (2) HUT70156A (en)
IL (3) IL120727A (en)
IS (1) IS3983A (en)
MY (1) MY131303A (en)
NO (1) NO302818B1 (en)
NZ (1) NZ247014A (en)
PT (1) PT559046E (en)
RO (1) RO112863B1 (en)
RU (1) RU2133739C1 (en)
TW (1) TW223629B (en)

Families Citing this family (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201303B (en) * 1990-07-05 1993-03-01 Hoffmann La Roche
TW223629B (en) * 1992-03-06 1994-05-11 Hoffmann La Roche
US6534536B1 (en) * 1994-03-16 2003-03-18 Bristol-Myers Squibb Company Alkylsulfonamido heterocyclic thrombin inhibitors
JPH06340619A (en) * 1993-05-03 1994-12-13 Bristol Myers Squibb Co Guanidyl- or amidinyl-substituted methylamino heterocyclic thrombin inhibitor
US6984627B1 (en) 1993-06-03 2006-01-10 Astrazeneca Ab Peptide derivatives
TW394760B (en) * 1993-09-07 2000-06-21 Hoffmann La Roche Novel Carboxamides, process for their preparation and pharmaceutical composition containing the same
US5536867A (en) * 1994-04-27 1996-07-16 Hoffmann-La Roche Inc. Process for the manufacture of dicarboxamides
EP0684238A3 (en) * 1994-04-27 1997-01-15 Hoffmann La Roche Process for the manufacture of dicarboxamides.
US5731439A (en) * 1995-03-24 1998-03-24 The Dupont Merck Pharmaceutical Company Piperidine containing aminobornic acids
US5610308A (en) * 1995-05-18 1997-03-11 Bristol-Myers Squibb Company Process for preparing intermediates for thrombin inhibitors
JPH11508558A (en) * 1995-06-27 1999-07-27 メルク エンド カンパニー インコーポレーテッド Pyridinone thrombin inhibitor
SA96170106A (en) 1995-07-06 2005-12-03 أسترا أكتيبولاج New amino acid derivatives
CA2227607C (en) 1995-07-26 2008-06-10 Mitsubishi Chemical Corporation Penicillaminamide derivatives
US5792769A (en) * 1995-09-29 1998-08-11 3-Dimensional Pharmaceuticals, Inc. Guanidino protease inhibitors
ES2293651T3 (en) * 1995-11-28 2008-03-16 Cephalon, Inc. INHIBITORS OF CYSTEINE AND SERINE PROTEASES DERIVED FROM AMINO ACIDS D.
TWI238827B (en) 1995-12-21 2005-09-01 Astrazeneca Ab Prodrugs of thrombin inhibitors
EP0883405B1 (en) * 1995-12-29 2004-02-25 3-Dimensional Pharmaceuticals, Inc. Amidino protease inhibitors
ZA9756B (en) * 1996-01-16 1997-07-17 Warner Lambert Co Process for preparing 4,6-disubstituted pyrido[3,4-d]-pyrimidines
US5780480A (en) * 1996-02-28 1998-07-14 Merck & Co., Inc. Fibrinogen receptor antagonists
SE9602263D0 (en) 1996-06-07 1996-06-07 Astra Ab New amino acid derivatives
US5668289A (en) * 1996-06-24 1997-09-16 Merck & Co., Inc. Pyridinone thrombin inhibitors
US5840733A (en) * 1996-07-01 1998-11-24 Redcell, Canada, Inc. Methods and compositions for producing novel conjugates of thrombin inhibitors and endogenous carriers resulting in anti-thrombins with extended lifetimes
SE9602646D0 (en) 1996-07-04 1996-07-04 Astra Ab Pharmaceutically useful compounds
US6756389B2 (en) * 1996-08-09 2004-06-29 Cambridge Neuroscience, Inc. Pharmaceutically active compounds and methods of use
AU3970697A (en) * 1996-08-15 1998-03-06 Du Pont Pharmaceuticals Company Cyclic carbamates and isoxazolidines as iib/iiia antagonists
US5872138A (en) * 1996-09-13 1999-02-16 Merck & Co., Inc. Thrombin inhibitors
US5869487A (en) * 1996-10-24 1999-02-09 Merck & Co., Inc. Pyrido 3,4-B!pyrazines for use as thrombin inhibitors
US6017934A (en) * 1997-01-22 2000-01-25 Merck & Co., Inc. Thrombin inhibitors
US5792779A (en) * 1997-02-19 1998-08-11 Merck & Co., Inc. Pyridinone thrombin inhibitors
US5932606A (en) * 1997-03-24 1999-08-03 Merck & Co., Inc. Pyrazinone, pyridinone, piperidine and pyrrolidine thrombin inhibitors
US6291511B1 (en) 1997-05-29 2001-09-18 Merck & Co., Inc. Biarylalkanoic acids as cell adhesion inhibitors
DE69833654T2 (en) * 1997-05-29 2006-12-14 Merck & Co., Inc. (A New Jersey Corp.) BIARYL ALKANIC ACIDS IN USE AS CELL ADHESION INHIBITORS
AR013084A1 (en) 1997-06-19 2000-12-13 Astrazeneca Ab USEFUL AMIDINE DERIVATIVES AS THROMBIN INHIBITORS, PHARMACEUTICAL COMPOSITION, USE OF SUCH COMPOUNDS FOR THE PREPARATION OF MEDICINES AND THE PROCESS FOR THE PREPARATION OF THE MENTIONED COMPOUNDS
US6011038A (en) * 1997-09-05 2000-01-04 Merck & Co., Inc. Pyrazinone thrombin inhibitors
US6087373A (en) * 1997-09-23 2000-07-11 Merck & Co., Inc. Thrombin inhibitors
US6133297A (en) * 1997-09-30 2000-10-17 Merck & Co., Inc. Thrombin inhibitors
SE9704543D0 (en) 1997-12-05 1997-12-05 Astra Ab New compounds
US6623981B2 (en) * 1998-01-27 2003-09-23 Bristol-Myers Squibb Company Detection of patients at risk for developing integrin antagonist/agonist mediated disease states
US6147078A (en) * 1998-05-19 2000-11-14 Merck & Co., Inc. Pyrazinone thrombin inhibitors
CA2333040A1 (en) * 1998-05-26 1999-12-02 Merck & Co., Inc. Imidazopyridine thrombin inhibitors
CA2343109A1 (en) * 1998-09-28 2000-04-06 Merck & Co., Inc. Thrombin inhibitors
CA2348734A1 (en) 1998-10-30 2000-05-11 Merck & Co., Inc. Thrombin inhibitors
AU752186B2 (en) 1998-10-30 2002-09-12 Merck & Co., Inc. Thrombin inhibitors
SE9804313D0 (en) 1998-12-14 1998-12-14 Astra Ab New compounds
IL143987A (en) 1999-01-13 2005-12-18 Astrazeneca Ab Amidinobenzylamine derivatives, processes for their preparation, pharmaceutical compositions containing them and use of such compositions in the preparation of a medicament for the inhibition of thrombin
US6239132B1 (en) 1999-04-23 2001-05-29 Merck & Co., Inc. Thrombin inhibitors
EP1189618A4 (en) 1999-06-04 2002-06-19 Merck & Co Inc Thrombin inhibitors
UA58636C2 (en) 1999-06-04 2003-08-15 Мерк Енд Ко., Інк. Pyrazinone thrombin inhibitors, pharmaceutical composition, method for treatment conditions caused by thrombus formation
AU2044401A (en) 1999-11-23 2001-06-04 Merck & Co., Inc. Pyrazinone thrombin inhibitors
SE0000382D0 (en) 2000-02-07 2000-02-07 Astrazeneca Ab New process
CA2403558A1 (en) 2000-03-23 2001-09-27 Merck & Co., Inc. Thrombin inhibitors
SE0001803D0 (en) 2000-05-16 2000-05-16 Astrazeneca Ab New compounds i
US6433186B1 (en) 2000-08-16 2002-08-13 Astrazeneca Ab Amidino derivatives and their use as thormbin inhibitors
US7129233B2 (en) 2000-12-01 2006-10-31 Astrazeneca Ab Mandelic acid derivatives and their use as thrombin inhibitors
AR035216A1 (en) 2000-12-01 2004-05-05 Astrazeneca Ab MANDELIC ACID DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE DERIVATIVES, USE OF THESE DERIVATIVES FOR THE MANUFACTURE OF MEDICINES, TREATMENT METHODS, PROCESSES FOR THE PREPARATION OF THESE DERIVATIVES, AND INTERMEDIARY COMPOUNDS
AR034517A1 (en) 2001-06-21 2004-02-25 Astrazeneca Ab PHARMACEUTICAL FORMULATION
GB0207449D0 (en) * 2002-03-28 2002-05-08 Glaxo Group Ltd Novel compounds
SE0201661D0 (en) 2002-05-31 2002-05-31 Astrazeneca Ab New salts
SE0201659D0 (en) 2002-05-31 2002-05-31 Astrazeneca Ab Modified release pharmaceutical formulation
US7781424B2 (en) 2003-05-27 2010-08-24 Astrazeneca Ab Modified release pharmaceutical formulation
US7250415B2 (en) * 2003-06-04 2007-07-31 Bristol-Myers Squibb Company 1,1-Disubstitutedcycloalkyl-, glycinamidyl-, sulfonyl-amidino-, and tetrahydropyrimidinyl-containing diaminoalkyl, β-aminoacids, α-aminoacids and derivatives thereof as factor Xa inhibitors
US7795205B2 (en) 2004-04-12 2010-09-14 Canyon Pharmaceuticals, Inc. Methods for effecting regression of tumor mass and size in a metastasized pancreatic tumor
GB0507577D0 (en) 2005-04-14 2005-05-18 Novartis Ag Organic compounds
JP2006298785A (en) * 2005-04-18 2006-11-02 Mitsui Chemicals Inc Diamine derivative, its manufacturing method and bactericide having the same as active ingredient
TW200827336A (en) 2006-12-06 2008-07-01 Astrazeneca Ab New crystalline forms
ES2824098T3 (en) 2013-08-16 2021-05-11 Triad Nat Security Llc Compounds and methods to improve plant performance
KR102116107B1 (en) 2013-12-30 2020-05-28 삼성디스플레이 주식회사 Display device
WO2015106200A2 (en) 2014-01-10 2015-07-16 Cornell University Dipeptides as inhibitors of human immunoproteasomes
EP3193904A4 (en) * 2014-08-18 2018-04-11 Cornell University Dipeptidomimetics as inhibitors of human immunoproteasomes
CN108351169B (en) 2015-10-15 2022-01-28 康奈尔大学 Proteasome inhibitors and uses thereof
WO2019075252A1 (en) 2017-10-11 2019-04-18 Cornell University Peptidomimetic proteasome inhibitors

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE420919B (en) * 1973-08-13 1981-11-09 Mitsubishi Chem Ind PROCEDURE FOR THE PREPARATION OF N? 722-DANSYL-L-ARGIN INGREDIENTS AND PHARMACEUTICAL ACCEPTABLE ACID ADDITION SALTS THEREOF
US4258192A (en) * 1977-12-16 1981-03-24 Mitsubishi Chemical Industries Limited N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US4433152A (en) * 1981-05-25 1984-02-21 Nippon Chemiphar Co., Ltd. Amidinopiperidine derivatives
SE8203887D0 (en) * 1982-06-23 1982-06-23 Kabivitrum Ab NEW TROMBIN INHIBITIVE ASSOCIATIONS
US5037808A (en) * 1988-07-20 1991-08-06 Monsanto Co. Indolyl platelet-aggregation inhibitors
US4879313A (en) * 1988-07-20 1989-11-07 Mosanto Company Novel platelet-aggregation inhibitors
US5053393A (en) * 1988-07-20 1991-10-01 Monsanto Company Novel platelet-aggregation inhibitor
US5084466A (en) * 1989-01-31 1992-01-28 Hoffmann-La Roche Inc. Novel carboxamide pyridine compounds which have useful pharmaceutical utility
TW201303B (en) * 1990-07-05 1993-03-01 Hoffmann La Roche
JP3258659B2 (en) * 1991-03-06 2002-02-18 ジー．デイー．サール アンド カンパニー Phenylamidine derivatives useful as platelet aggregation inhibitors
TW223629B (en) * 1992-03-06 1994-05-11 Hoffmann La Roche

Also Published As

Publication number Publication date
US5405854A (en) 1995-04-11
NO930819D0 (en) 1993-03-05
FI930990A (en) 1993-09-07
JPH0625195A (en) 1994-02-01
BG61506B1 (en) 1997-10-31
CZ34693A3 (en) 1993-12-15
US5763604A (en) 1998-06-09
CA2089972C (en) 1999-06-08
AU3391693A (en) 1993-09-09
IS3983A (en) 1993-09-07
IL120727A0 (en) 1997-08-14
AU665230B2 (en) 1995-12-21
BG97493A (en) 1994-03-24
PT559046E (en) 2002-01-30
EP0559046A1 (en) 1993-09-08
CZ286926B6 (en) 2000-08-16
CN1076690A (en) 1993-09-29
HU211252A9 (en) 1995-11-28
US5677448A (en) 1997-10-14
NO930819L (en) 1993-09-07
HUT70156A (en) 1995-09-28
ATE203013T1 (en) 2001-07-15
EP0559046B1 (en) 2001-07-11
IL120727A (en) 1998-08-16
JPH0780848B2 (en) 1995-08-30
DK0559046T3 (en) 2001-11-05
RU2133739C1 (en) 1999-07-27
NZ247014A (en) 1995-11-27
TW223629B (en) 1994-05-11
FI103880B1 (en) 1999-10-15
DE59310186D1 (en) 2001-08-16
FI930990A0 (en) 1993-03-05
ES2161217T3 (en) 2001-12-01
IL104893A0 (en) 1993-07-08
NO302818B1 (en) 1998-04-27
US5578594A (en) 1996-11-26
MY131303A (en) 2007-08-30
RO112863B1 (en) 1998-01-30
FI103880B (en) 1999-10-15
HU9300572D0 (en) 1993-05-28
GR3036870T3 (en) 2002-01-31

Similar Documents

Publication Publication Date Title
CA2089972A1 (en) Sulfonamidocarboxamides
IL98690A0 (en) Guanidines,their manufacture and pharmaceutical compositions containing them
AU1268797A (en) Cyclic adhesion inhibitors
RU93004666A (en) SULPHONAMIDOKARBOXIMIDES
EP0775487A4 (en) Triazine derivative and medicine
AP9701010A0 (en) Piperidineacetic acid derivatives useful as fibrinogen.
CA2048212A1 (en) Sulfonamide derivatives
GR3021769T3 (en) N-(isoquinolein-5-yl)-sulfonyl azacycloalkanes, their process of preparation and pharmaceutical compositions containing them
CA2056005A1 (en) Thrombin-binding substance and process for preparing the same

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed