CA2248809A1 - N-[(r)-1-{3-(4-piperidyl)propionyl-3-piperidylcarbonyl]-2(s)-acetylamino-beta-alanine utilisee comme antagoniste du recepteur du fibrinogene - Google Patents
N-[(r)-1-{3-(4-piperidyl)propionyl-3-piperidylcarbonyl]-2(s)-acetylamino-beta-alanine utilisee comme antagoniste du recepteur du fibrinogene Download PDFInfo
- Publication number
- CA2248809A1 CA2248809A1 CA002248809A CA2248809A CA2248809A1 CA 2248809 A1 CA2248809 A1 CA 2248809A1 CA 002248809 A CA002248809 A CA 002248809A CA 2248809 A CA2248809 A CA 2248809A CA 2248809 A1 CA2248809 A1 CA 2248809A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- salt
- formula
- acid
- alanine
- 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.)
- Abandoned
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- 239000002319 fibrinogen receptor antagonist Substances 0.000 title description 2
- XPPNPKIUPLMABF-CVEARBPZSA-N (2s)-2-acetamido-3-[[(3r)-1-(3-piperidin-4-ylpropanoyl)piperidine-3-carbonyl]amino]propanoic acid Chemical compound C1[C@H](C(=O)NC[C@H](NC(=O)C)C(O)=O)CCCN1C(=O)CCC1CCNCC1 XPPNPKIUPLMABF-CVEARBPZSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 10
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 abstract 1
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- 229960000187 tissue plasminogen activator Drugs 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 1
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 125000001419 myristoyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical class C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
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- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
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- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 238000001226 reprecipitation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 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
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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
- 125000000297 undecanoyl group Chemical group O=C([*])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])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D211/36—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 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Dérivé de .beta.-alanine représenté par la formule (I). Ce dérivé est un antagoniste de la glycoprotéine IIB/IIIa, un inhibiteur de l'agrégation des plaquettes sanguines et un inhibiteur de la liaison du fibrinogène aux plaquettes sanguines. L'invention porte également sur des procédés d'élaboration de ce dérivé, sur une composition pharmaceutique le renfermant et sur une méthode de prévention et/ou de traitement de maladies indiquées dans la description de l'invention, chez l'être humain et l'animal.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA96/2033 | 1996-03-13 | ||
| ZA962033A ZA962033B (en) | 1995-03-17 | 1996-03-13 | New compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2248809A1 true CA2248809A1 (fr) | 1997-09-18 |
Family
ID=65952245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002248809A Abandoned CA2248809A1 (fr) | 1996-03-13 | 1997-03-12 | N-[(r)-1-{3-(4-piperidyl)propionyl-3-piperidylcarbonyl]-2(s)-acetylamino-beta-alanine utilisee comme antagoniste du recepteur du fibrinogene |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0888302A1 (fr) |
| JP (1) | JP2000506524A (fr) |
| KR (1) | KR19990087694A (fr) |
| CA (1) | CA2248809A1 (fr) |
| WO (1) | WO1997033869A1 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6066651A (en) * | 1997-10-29 | 2000-05-23 | Ortho-Mcneil Pharmaceutical, Inc. | Orally-active nipecotamide glycolamide esters for the treatment of thrombosis disorders |
| AU769718B2 (en) * | 1998-10-12 | 2004-02-05 | Fujisawa Pharmaceutical Co., Ltd. | New processes for producing beta-alanine derivative |
| AUPP646598A0 (en) * | 1998-10-12 | 1998-11-05 | Fujisawa Pharmaceutical Co., Ltd. | New processes for producing alpha-alanine derivative |
| BR0010652A (pt) * | 1999-03-22 | 2002-07-16 | Ortho Mcneil Pharm Inc | Processo de preparação de ácido [s-(r*,s*)]-beta-[[[1-[1-oxo-3-(4-piperidinil)propil]-3-piperi dinil]carbonil]amino]-3-piridinapropanóico e derivados |
| JP2001131078A (ja) * | 1999-11-09 | 2001-05-15 | Iatron Lab Inc | 新規活性固定化血小板及びその製造方法 |
| AUPQ570100A0 (en) * | 2000-02-17 | 2000-03-09 | Fujisawa Pharmaceutical Co., Ltd. | Beta-alanine derivatives and their use as receptor antagonists |
| WO2005079863A1 (fr) * | 2004-02-25 | 2005-09-01 | Astellas Pharma Inc. | Produit de contraste pour la formation d'un thrombus |
| JP6243335B2 (ja) | 2011-08-17 | 2017-12-06 | ピラマル イメージング ソシエテ アノニム | 血小板固有の糖タンパク質ＩＩｂ／ＩＩＩａに結合する化合物と血栓造影のためのその使用 |
| CA2900595A1 (fr) | 2013-02-12 | 2014-08-21 | Bayer Pharma Aktiengesellschaft | Chelates metalliques pour la liaison a la glycoproteine iib/iiia specifique des plaquettes |
| KR102548998B1 (ko) | 2020-03-31 | 2023-06-29 | 재단법인 아산사회복지재단 | 혈전영상을 위한 방사성의약품 및 조성물 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2037153A1 (fr) * | 1990-03-09 | 1991-09-10 | Leo Alig | Derives de l'acide acetique |
| WO1992019595A1 (fr) * | 1991-05-07 | 1992-11-12 | Merck & Co., Inc. | Antagonistes de recepteur de fibrinogene |
| DE69429328T2 (de) * | 1993-09-22 | 2002-06-13 | Fujisawa Pharmaceutical Co., Ltd. | N-(3-piperidinylcarbonyl)-b-alanin derivate als paf-antagonisten |
| AU7862794A (en) * | 1993-10-19 | 1995-05-08 | Sumitomo Pharmaceuticals Company, Limited | 2,3-diaminopropionic acid derivative |
| US5770575A (en) * | 1994-03-16 | 1998-06-23 | Ortho Pharmaceutical Corporation | Nipecotic acid derivatives as antithrombotic compounds |
| IL117495A (en) * | 1995-03-17 | 2002-05-23 | Fujisawa Pharmaceutical Co | History of b-alanine, the process for their preparation and the pharmaceutical preparations containing them |
-
1997
- 1997-03-12 EP EP97907277A patent/EP0888302A1/fr not_active Withdrawn
- 1997-03-12 CA CA002248809A patent/CA2248809A1/fr not_active Abandoned
- 1997-03-12 JP JP9532437A patent/JP2000506524A/ja active Pending
- 1997-03-12 WO PCT/JP1997/000769 patent/WO1997033869A1/fr not_active Ceased
- 1997-03-12 KR KR1019980707159A patent/KR19990087694A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0888302A1 (fr) | 1999-01-07 |
| WO1997033869A1 (fr) | 1997-09-18 |
| KR19990087694A (ko) | 1999-12-27 |
| JP2000506524A (ja) | 2000-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |