AR009302A1 - Tripeptido inhibidor del estado de transicion de trombina que comprende un residuo de lisina o de 4-aminociclohexilglicina y que ademas comprende unacetofuncionalidad electrofilica en el c-termino, su utilizacion y una composicion farmaceutica que lo comprende - Google Patents
Tripeptido inhibidor del estado de transicion de trombina que comprende un residuo de lisina o de 4-aminociclohexilglicina y que ademas comprende unacetofuncionalidad electrofilica en el c-termino, su utilizacion y una composicion farmaceutica que lo comprendeInfo
- Publication number
- AR009302A1 AR009302A1 ARP970103820A ARP970103820A AR009302A1 AR 009302 A1 AR009302 A1 AR 009302A1 AR P970103820 A ARP970103820 A AR P970103820A AR P970103820 A ARP970103820 A AR P970103820A AR 009302 A1 AR009302 A1 AR 009302A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkylene
- alkyl
- lysine
- acid
- tripeptide
- Prior art date
Links
- SNQBKCVWLYISGN-UHFFFAOYSA-N 2-[(4-aminocyclohexyl)amino]acetic acid Chemical compound NC1CCC(NCC(O)=O)CC1 SNQBKCVWLYISGN-UHFFFAOYSA-N 0.000 title abstract 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title abstract 3
- 239000004472 Lysine Substances 0.000 title abstract 3
- 230000007704 transition Effects 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 239000002699 waste material Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 abstract 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 abstract 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 1
- 108090000190 Thrombin Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 abstract 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 abstract 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 1
- 229960004072 thrombin Drugs 0.000 abstract 1
Classifications
-
- 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
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Tripéptido inhibidor del estado de transicion de trombina que comprende un residuo de lisina o de 4-aminociclohexilglicina y que además comprende uncetofuncionalidad electrofílica en el c-término que posee la formula (I), donde Ra es -NR1R2 y Rb esR3; o R3 es R1 y Rb es -NH-(SO2)m-R3; m es 0 o 1; donde R1es -(SO2)n-alquileno (C1-6)-COOH o un derivado éster del mismo; n es 0 o 1; y m y n no son 1 en forma simultánea; R2 se selecciona entre H, alquilo(C1-12),alquenilo (C2-12), cicloalquilo(C3-8 ), alquileno (C1-6) cicloalquilo(C3-8), arilo (C6-14), aralquilo (C7-15) y alquileno (C1-6)-COOH- o un derivado ésterdel mismo; R3 es una mitad hidrofobica; o R3 y R3 son cadenas cerradas que poseen 5- o 6-miembros junto con N-C al quese enc uentran unidas, dichacadena cerrada puede encontrarse fundida con una cadena cerrada de 6 miembros alifática o aromática; A es un aminoácido que se selecciona entre prolina, queopcionalmente contiene un segundo heteroátomo que se seleccionaentre N , O o S; y opcionalmente se encuentra sustituido con alquilo(C1-6), alcoxi (C1-6) ohalogeno, 3,4-de-hidroprolina, ácido 2-azetidina carboxílico, ácido pipecolínico, ácido octahidroindol-2-carboxílico, ácido 2-amino isobutíricoovalina; B es lisina o 4-aminociclohexilglicina; y X es -CHF2, -CF3, -COOR4 o -CONR5R6, donde R4 es H o alquilo (C2-6); y R5 y R6 son, de maneraindependiente H, alquilo (C1-6) o alquileno (C1-6)-C6H5; o R5 y R6 son, en forma conjunta,alquileno (C3-6); o X es un heterociclo que se selecciona entre2-tiazol, 2-tiazolina, 2-benzotiazol, 2-oxazol, 2-oxazolina, 2-benzoxazol y 2-benzimidazol, dichos heterociclos se encuentran opcionalmente sustituidos conuno o más alquilo (C1-6),alcoxi u oxo (C1-6); o una sal farmacéuticamente aceptable de los mismos. Se refiere además a la utilizacion de dicho tripéptido
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96202336 | 1996-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR009302A1 true AR009302A1 (es) | 2000-04-12 |
Family
ID=8224306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP970103820A AR009302A1 (es) | 1996-08-23 | 1997-08-22 | Tripeptido inhibidor del estado de transicion de trombina que comprende un residuo de lisina o de 4-aminociclohexilglicina y que ademas comprende unacetofuncionalidad electrofilica en el c-termino, su utilizacion y una composicion farmaceutica que lo comprende |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0956293B1 (es) |
| AR (1) | AR009302A1 (es) |
| AT (1) | ATE282629T1 (es) |
| AU (1) | AU4618197A (es) |
| DE (1) | DE69731664D1 (es) |
| ID (1) | ID18075A (es) |
| IL (1) | IL121474A0 (es) |
| TW (1) | TW515803B (es) |
| WO (1) | WO1998007308A2 (es) |
| ZA (1) | ZA977209B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5877156A (en) * | 1997-04-24 | 1999-03-02 | Akzo Nobel, N.V. | Thrombin inhibitors |
| EP0884325A1 (en) * | 1997-04-24 | 1998-12-16 | Akzo Nobel N.V. | Thrombin inhibitors containing a peptidyl heterocycle |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| EP2019837B1 (en) * | 2006-05-23 | 2011-03-23 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
| EP2027143A2 (en) | 2006-05-23 | 2009-02-25 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
| CA2677487A1 (en) | 2007-02-09 | 2008-08-14 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
| CN117143179B (zh) * | 2023-09-18 | 2024-07-12 | 安徽峆一药业股份有限公司 | 一种凝血酶发色底物s-2238的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5672582A (en) * | 1993-04-30 | 1997-09-30 | Merck & Co., Inc. | Thrombin inhibitors |
| SE9301916D0 (sv) * | 1993-06-03 | 1993-06-03 | Ab Astra | New peptides derivatives |
| ZA951617B (en) * | 1994-03-04 | 1997-02-27 | Lilly Co Eli | Antithrombotic agents. |
| AU4250896A (en) * | 1994-12-22 | 1996-07-10 | Biochem Pharma Inc. | Heterocyclic keto arginine peptides as thrombin inhibitors |
| US5827860A (en) * | 1995-06-07 | 1998-10-27 | Ortho Pharmaceutical Corporation | Peptidyl heterocycles useful in the treatment of thrombin related disorders |
| IL119466A (en) * | 1995-11-03 | 2001-08-26 | Akzo Nobel Nv | Thrombin inhibitors, their preparation and pharmaceutical compositions containing them |
-
1997
- 1997-08-05 IL IL12147497A patent/IL121474A0/xx unknown
- 1997-08-12 ZA ZA9707209A patent/ZA977209B/xx unknown
- 1997-08-19 DE DE69731664T patent/DE69731664D1/de not_active Expired - Lifetime
- 1997-08-19 AU AU46181/97A patent/AU4618197A/en not_active Abandoned
- 1997-08-19 AT AT97944781T patent/ATE282629T1/de not_active IP Right Cessation
- 1997-08-19 EP EP97944781A patent/EP0956293B1/en not_active Expired - Lifetime
- 1997-08-19 WO PCT/EP1997/004579 patent/WO1998007308A2/en not_active Ceased
- 1997-08-22 ID IDP972947A patent/ID18075A/id unknown
- 1997-08-22 AR ARP970103820A patent/AR009302A1/es unknown
- 1997-08-30 TW TW086112645A patent/TW515803B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| ID18075A (id) | 1998-02-26 |
| WO1998007308A3 (en) | 2000-08-24 |
| IL121474A0 (en) | 1998-02-08 |
| EP0956293B1 (en) | 2004-11-17 |
| DE69731664D1 (de) | 2004-12-23 |
| WO1998007308A2 (en) | 1998-02-26 |
| ATE282629T1 (de) | 2004-12-15 |
| AU4618197A (en) | 1998-03-06 |
| TW515803B (en) | 2003-01-01 |
| ZA977209B (en) | 1998-02-20 |
| EP0956293A1 (en) | 1999-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |