HUP9700816A2 - Interleukin-1béta felszabadulást gátló (3R)-3-amino-4-karboxi-butiraldehid-származékok - Google Patents
Interleukin-1béta felszabadulást gátló (3R)-3-amino-4-karboxi-butiraldehid-származékokInfo
- Publication number
- HUP9700816A2 HUP9700816A2 HU9700816A HUP9700816A HUP9700816A2 HU P9700816 A2 HUP9700816 A2 HU P9700816A2 HU 9700816 A HU9700816 A HU 9700816A HU P9700816 A HUP9700816 A HU P9700816A HU P9700816 A2 HUP9700816 A2 HU P9700816A2
- Authority
- HU
- Hungary
- Prior art keywords
- general formula
- acid
- hydroxy
- acyl
- amino
- Prior art date
Links
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 title 1
- 102000003777 Interleukin-1 beta Human genes 0.000 title 1
- 108090000193 Interleukin-1 beta Proteins 0.000 title 1
- NGEWQZIDQIYUNV-UHFFFAOYSA-N 2-hydroxy-3-methylbutyric acid Chemical compound CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 abstract 2
- RILPIWOPNGRASR-UHFFFAOYSA-N 2-hydroxy-3-methylpentanoic acid Chemical compound CCC(C)C(O)C(O)=O RILPIWOPNGRASR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract 1
- WAMWSIDTKSNDCU-ZETCQYMHSA-N (2s)-2-azaniumyl-2-cyclohexylacetate Chemical compound OC(=O)[C@@H](N)C1CCCCC1 WAMWSIDTKSNDCU-ZETCQYMHSA-N 0.000 abstract 1
- SKEKPUHJRDTHLE-SCSAIBSYSA-N (3r)-3-amino-5-oxopentanoic acid Chemical class O=CC[C@@H](N)CC(O)=O SKEKPUHJRDTHLE-SCSAIBSYSA-N 0.000 abstract 1
- UJPXNCODVPXBRK-UHFFFAOYSA-N 2-cycloheptyl-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1CCCCCC1 UJPXNCODVPXBRK-UHFFFAOYSA-N 0.000 abstract 1
- RRDPWAPIJGSANI-UHFFFAOYSA-N 2-cyclohexyl-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1CCCCC1 RRDPWAPIJGSANI-UHFFFAOYSA-N 0.000 abstract 1
- VOXXWSYKYCBWHO-UHFFFAOYSA-N 3-phenyllactic acid Chemical compound OC(=O)C(O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-UHFFFAOYSA-N 0.000 abstract 1
- 150000008574 D-amino acids Chemical class 0.000 abstract 1
- 108010016626 Dipeptides Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 abstract 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 229940061720 alpha hydroxy acid Drugs 0.000 abstract 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 abstract 1
- 150000001413 amino acids Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229960002743 glutamine Drugs 0.000 abstract 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 abstract 1
- 229960002885 histidine Drugs 0.000 abstract 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 abstract 1
- 229960000448 lactic acid Drugs 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 229960003646 lysine Drugs 0.000 abstract 1
- 229960002510 mandelic acid Drugs 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 229960004452 methionine Drugs 0.000 abstract 1
- 229930182817 methionine Natural products 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- 229940081066 picolinic acid Drugs 0.000 abstract 1
- 229960002429 proline Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000004474 valine Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- 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
- C07K5/0202—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-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A találmány tárgyát az (I) általánős képletű új (3R)-3-aminő-4-karbőxi-bűtiraldehid-származékők -, ahől X jelentése 1-4 szénatőmős alkil-őxi-karbőnil- vagy (helyettesített)fenil-1-2 szénatőmős alkil-őxi-karbőnil-csőpőrt vagy 1-4 szénatőmősalkil-karbőnil- vagy (helyettesített) fenil-1-3 szénatőmős alkil-karbőnil-csőpőrt, n jelentése 1 vagy 0 Y jelentése n=1 esetén valamely Y4-Y3-Y2-Y1 általánős képletűtetrapeptid-, Y3-Y2-Y1 általánős képletű tripeptid- vagy Y2-Y1általánős képletű diepeptid rész vagy valamilyen Y1 általánős képletűaminősav-rész, és n=0 esetén valamely Q4-Y3-Y2-Y1 általánős képletű a-hidrőxi-acil-tripeptid-, Q3-Y2-Y1 általánős képletű a-hidrőxi-acil-tripeptid- vagy Q2-Y1 általánős képletű a-hidrőxi-acil-aminőacil-részahől Y1-Y4 jelentése az alább felsőrőlt L- vagy D-aminősavak bármelyikénekgyöke: alanin, allőizőleűcin, ciklőhexil-glicin, fenil-alann,glűtamin, hisztidin, izőleűcin, lizin, metiőnin, pikőlinsav, prőlin,triőzin vagy valin, és ahől Q2-Q4 jelentése az alább felsőrőlt R vagy S kőnfigűrációjú a-hidrőxi-savak bármelyikéből képzett acil-csőpőrt 2-ciklőheptil-2-hidrőxi-ecetsav, 2-ciklőhexil-2-hidrőxi-ecetsav, 3-ciklőhexil-tejsav, 3-fenil-tejsav, 2-hidrőxi-3-metil-vajsav, 2-hidrőxi-3-metil-valeriánsav,mandűlasav vagy tejsav és ezek szerves vagy szervetlen bázisssal képzett sói, valamint avegyületeket tartalmazó gyógyszerkészítmények képezik. A találmány szerinti (I) általánős képletű vegyületek értékesgyógyászati, közelebbről interleűkin-1b kőnvertáló enzimet gátlóhatással rendelkeznek. ŕ
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9700816A HUP9700816A3 (en) | 1997-04-28 | 1997-04-28 | 3(r)-3-amino-4-carboxy-butiraldehyde derivatives inhibiting release of interleukin-1-beta |
EP98919387A EP0979241B1 (en) | 1997-04-28 | 1998-04-22 | (3r)-3-amino-4-carboxybutyraldehyde derivatives inhibiting the release of interleukin-1/beta |
US09/423,006 US6593300B1 (en) | 1997-04-28 | 1998-04-22 | (3R)-3-amino-4-carboxybutyraldehyde derivatives inhibiting the release of interleukin-1/beta |
PT98919387T PT979241E (pt) | 1997-04-28 | 1998-04-22 | Derivados (3r)-3-amino-4-carboxibutiraldeido que inibem a libertacao de interleuquina-1/beta |
PCT/HU1998/000040 WO1998049189A1 (en) | 1997-04-28 | 1998-04-22 | (3r)-3-amino-4-carboxybutyraldehyde derivatives inhibiting the release of interleukin-1/beta |
DE69833646T DE69833646T2 (de) | 1997-04-28 | 1998-04-22 | (3r)-3-amino-4-carboxybutyraldehydderivate die die il-1/beta freisetzung inhibieren |
CA002288332A CA2288332A1 (en) | 1997-04-28 | 1998-04-22 | (3r)-3-amino-4-carboxybutyraldehyde derivatives inhibiting the release of interleukin-1/beta |
ES98919387T ES2259812T3 (es) | 1997-04-28 | 1998-04-22 | Derivados de (3r)-3-amino-4-carboxibutiraldehido inhibidores de la liberacion de interleuquina-1/beta. |
AT98919387T ATE318837T1 (de) | 1997-04-28 | 1998-04-22 | (3r)-3-amino-4-carboxybutyraldehydderivate die die il-1/beta freisetzung inhibieren |
AU72261/98A AU740954B2 (en) | 1997-04-28 | 1998-04-22 | (3R)-3-amino-4-carboxybutyraldehyde derivatives inhibiting the release of interleukin-1/beta |
DK98919387T DK0979241T3 (da) | 1997-04-28 | 1998-04-22 | (3R)-3-amino-4-carboxybutyraldehydderivativer, som inhiberer frigivelsen af interleukin-1/beta |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9700816A HUP9700816A3 (en) | 1997-04-28 | 1997-04-28 | 3(r)-3-amino-4-carboxy-butiraldehyde derivatives inhibiting release of interleukin-1-beta |
Publications (3)
Publication Number | Publication Date |
---|---|
HU9700816D0 HU9700816D0 (en) | 1997-06-30 |
HUP9700816A2 true HUP9700816A2 (hu) | 1999-01-28 |
HUP9700816A3 HUP9700816A3 (en) | 1999-06-28 |
Family
ID=89995060
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU9700816A HUP9700816A3 (en) | 1997-04-28 | 1997-04-28 | 3(r)-3-amino-4-carboxy-butiraldehyde derivatives inhibiting release of interleukin-1-beta |
Country Status (11)
Country | Link |
---|---|
US (1) | US6593300B1 (hu) |
EP (1) | EP0979241B1 (hu) |
AT (1) | ATE318837T1 (hu) |
AU (1) | AU740954B2 (hu) |
CA (1) | CA2288332A1 (hu) |
DE (1) | DE69833646T2 (hu) |
DK (1) | DK0979241T3 (hu) |
ES (1) | ES2259812T3 (hu) |
HU (1) | HUP9700816A3 (hu) |
PT (1) | PT979241E (hu) |
WO (1) | WO1998049189A1 (hu) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69925581T2 (de) | 1998-03-09 | 2006-04-27 | Vertex Pharmaceuticals Inc., Cambridge | 1,2-diazepanderivate als inhibitoren des interleukin-1beta umwandelnden enzyms |
EP2261232A3 (en) | 1998-03-19 | 2011-04-20 | Vertex Pharmaceuticals Incorporated | Inhibitors of caspases |
PE20011350A1 (es) | 2000-05-19 | 2002-01-15 | Vertex Pharma | PROFARMACO DE UN INHIBIDOR DE ENZIMA CONVERTIDORA DE INTERLEUCINA-1ß (ICE) |
US8627256B2 (en) * | 2011-04-25 | 2014-01-07 | Lsi Corporation | Method for computing IO redistribution routing |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0519748B1 (en) * | 1991-06-21 | 1998-09-02 | Merck & Co. Inc. | Peptidyl derivatives as inhibitors of interleukin-1B converting enzyme |
US5716929A (en) * | 1994-06-17 | 1998-02-10 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
AU5122196A (en) | 1995-03-31 | 1996-10-16 | Takeda Chemical Industries Ltd. | Cysteine protease inhibitor |
-
1997
- 1997-04-28 HU HU9700816A patent/HUP9700816A3/hu unknown
-
1998
- 1998-04-22 CA CA002288332A patent/CA2288332A1/en not_active Abandoned
- 1998-04-22 US US09/423,006 patent/US6593300B1/en not_active Expired - Fee Related
- 1998-04-22 AT AT98919387T patent/ATE318837T1/de not_active IP Right Cessation
- 1998-04-22 AU AU72261/98A patent/AU740954B2/en not_active Ceased
- 1998-04-22 DE DE69833646T patent/DE69833646T2/de not_active Expired - Fee Related
- 1998-04-22 WO PCT/HU1998/000040 patent/WO1998049189A1/en active IP Right Grant
- 1998-04-22 DK DK98919387T patent/DK0979241T3/da active
- 1998-04-22 EP EP98919387A patent/EP0979241B1/en not_active Expired - Lifetime
- 1998-04-22 ES ES98919387T patent/ES2259812T3/es not_active Expired - Lifetime
- 1998-04-22 PT PT98919387T patent/PT979241E/pt unknown
Also Published As
Publication number | Publication date |
---|---|
CA2288332A1 (en) | 1998-11-05 |
HUP9700816A3 (en) | 1999-06-28 |
ATE318837T1 (de) | 2006-03-15 |
DK0979241T3 (da) | 2006-06-26 |
DE69833646T2 (de) | 2006-12-28 |
WO1998049189A1 (en) | 1998-11-05 |
EP0979241A1 (en) | 2000-02-16 |
ES2259812T3 (es) | 2006-10-16 |
AU740954B2 (en) | 2001-11-15 |
EP0979241B1 (en) | 2006-03-01 |
PT979241E (pt) | 2006-07-31 |
US6593300B1 (en) | 2003-07-15 |
HU9700816D0 (en) | 1997-06-30 |
DE69833646D1 (de) | 2006-04-27 |
AU7226198A (en) | 1998-11-24 |
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Legal Events
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FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |