IL97944A - Peptides with bradykinin-antagonistic action their preparation and pharmaceutical compositions containing them - Google Patents
Peptides with bradykinin-antagonistic action their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL97944A IL97944A IL9794491A IL9794491A IL97944A IL 97944 A IL97944 A IL 97944A IL 9794491 A IL9794491 A IL 9794491A IL 9794491 A IL9794491 A IL 9794491A IL 97944 A IL97944 A IL 97944A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- substituted
- amino
- peptide
- aryl
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract description 34
- 230000009471 action Effects 0.000 title abstract description 7
- 150000001413 amino acids Chemical class 0.000 claims abstract description 23
- 101800004538 Bradykinin Proteins 0.000 claims abstract description 9
- 102400000967 Bradykinin Human genes 0.000 claims abstract description 9
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims abstract description 9
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 230000001404 mediated effect Effects 0.000 claims abstract description 4
- 230000001575 pathological effect Effects 0.000 claims abstract description 4
- 101710097732 Bradykinin-related peptides Proteins 0.000 claims abstract 2
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- 229940024606 amino acid Drugs 0.000 claims description 26
- 125000006239 protecting group Chemical group 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 12
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 9
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
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- 125000003277 amino group Chemical group 0.000 claims description 8
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 7
- 125000003435 aroyl group Chemical group 0.000 claims description 7
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 210000004899 c-terminal region Anatomy 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
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- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 4
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- 239000012634 fragment Substances 0.000 claims description 4
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- TXHAHOVNFDVCCC-UHFFFAOYSA-N 2-(tert-butylazaniumyl)acetate Chemical compound CC(C)(C)NCC(O)=O TXHAHOVNFDVCCC-UHFFFAOYSA-N 0.000 claims description 3
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- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 3
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- BVAUMRCGVHUWOZ-ZETCQYMHSA-N (2s)-2-(cyclohexylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NC1CCCCC1 BVAUMRCGVHUWOZ-ZETCQYMHSA-N 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- QUOGESRFPZDMMT-YFKPBYRVSA-O L-homoarginine(1+) Chemical group OC(=O)[C@@H](N)CCCCNC([NH3+])=N QUOGESRFPZDMMT-YFKPBYRVSA-O 0.000 claims description 2
- LEIKGVHQTKHOLM-IUCAKERBSA-N Pro-Pro-Gly Chemical compound OC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 LEIKGVHQTKHOLM-IUCAKERBSA-N 0.000 claims description 2
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- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4013270A DE4013270A1 (de) | 1990-04-26 | 1990-04-26 | Peptide mit bradykinin-antagonistischer wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97944A0 IL97944A0 (en) | 1992-06-21 |
| IL97944A true IL97944A (en) | 1995-05-26 |
Family
ID=6405107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9794491A IL97944A (en) | 1990-04-26 | 1991-04-24 | Peptides with bradykinin-antagonistic action their preparation and pharmaceutical compositions containing them |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0455133B1 (cs) |
| JP (1) | JP2552402B2 (cs) |
| KR (1) | KR100195569B1 (cs) |
| CN (1) | CN1034416C (cs) |
| AT (1) | ATE149519T1 (cs) |
| AU (1) | AU641004B2 (cs) |
| CA (1) | CA2041268C (cs) |
| CY (1) | CY2113B1 (cs) |
| CZ (1) | CZ280682B6 (cs) |
| DE (2) | DE4013270A1 (cs) |
| DK (1) | DK0455133T3 (cs) |
| ES (1) | ES2099102T3 (cs) |
| FI (1) | FI109541B (cs) |
| GR (1) | GR3023172T3 (cs) |
| HK (1) | HK1006843A1 (cs) |
| HU (1) | HU208028B (cs) |
| IE (1) | IE911387A1 (cs) |
| IL (1) | IL97944A (cs) |
| LV (1) | LV10290B (cs) |
| NO (1) | NO300779B1 (cs) |
| NZ (1) | NZ237928A (cs) |
| PT (1) | PT97466B (cs) |
| RU (1) | RU2056432C1 (cs) |
| SK (1) | SK279286B6 (cs) |
| ZA (1) | ZA913121B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06508116A (ja) * | 1991-04-01 | 1994-09-14 | コルテク,インコーポレイテッド | ブラジキニンアンタゴニスト |
| TW199863B (cs) * | 1991-12-21 | 1993-02-11 | Hoechst Ag | |
| TW258739B (cs) * | 1992-04-04 | 1995-10-01 | Hoechst Ag | |
| KR100360639B1 (ko) * | 1994-03-09 | 2003-01-30 | 코르텍, 인크. | N-치환글리신함유브라디키닌길항제펩티드 |
| FR2739553B1 (fr) * | 1995-10-06 | 1998-01-02 | Oreal | Utilisation d'antagonistes de la bradykinine pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
| DE19612067A1 (de) * | 1996-03-27 | 1997-10-02 | Hoechst Ag | Verwendung von Bradykinin-Antagonisten zur Herstellung von Arzneimitteln zur Behandlung von chronisch fibrogenetischen Lebererkrankungen und akuten Lebererkrankungen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4923963A (en) * | 1987-09-02 | 1990-05-08 | Nova Technology Limited Partnership | Bradykinin antagonist peptides |
| IE63490B1 (en) * | 1988-11-24 | 1995-05-03 | Hoechst Ag | Peptides having bradykinin antagonist action |
| DE3926822A1 (de) * | 1989-08-14 | 1991-02-21 | Hoechst Ag | Peptide mit bradykinin-antagonistischer wirkung |
-
1990
- 1990-04-26 DE DE4013270A patent/DE4013270A1/de not_active Withdrawn
-
1991
- 1991-04-24 FI FI911978A patent/FI109541B/fi active
- 1991-04-24 AU AU75304/91A patent/AU641004B2/en not_active Expired
- 1991-04-24 CZ CS911165A patent/CZ280682B6/cs not_active IP Right Cessation
- 1991-04-24 PT PT97466A patent/PT97466B/pt not_active IP Right Cessation
- 1991-04-24 IL IL9794491A patent/IL97944A/en not_active IP Right Cessation
- 1991-04-24 SK SK1165-91A patent/SK279286B6/sk not_active IP Right Cessation
- 1991-04-24 NZ NZ237928A patent/NZ237928A/xx unknown
- 1991-04-25 ZA ZA913121A patent/ZA913121B/xx unknown
- 1991-04-25 EP EP91106663A patent/EP0455133B1/de not_active Expired - Lifetime
- 1991-04-25 AT AT91106663T patent/ATE149519T1/de not_active IP Right Cessation
- 1991-04-25 CA CA002041268A patent/CA2041268C/en not_active Expired - Lifetime
- 1991-04-25 IE IE138791A patent/IE911387A1/en unknown
- 1991-04-25 NO NO911649A patent/NO300779B1/no not_active IP Right Cessation
- 1991-04-25 ES ES91106663T patent/ES2099102T3/es not_active Expired - Lifetime
- 1991-04-25 CN CN91102638A patent/CN1034416C/zh not_active Expired - Lifetime
- 1991-04-25 DE DE59108573T patent/DE59108573D1/de not_active Expired - Lifetime
- 1991-04-25 DK DK91106663.7T patent/DK0455133T3/da active
- 1991-04-25 JP JP3121848A patent/JP2552402B2/ja not_active Expired - Lifetime
- 1991-04-25 KR KR1019910006649A patent/KR100195569B1/ko not_active Expired - Lifetime
- 1991-04-25 HU HU911392A patent/HU208028B/hu unknown
-
1992
- 1992-07-27 RU SU925052268A patent/RU2056432C1/ru active
- 1992-12-23 LV LVP-92-699A patent/LV10290B/lv unknown
-
1997
- 1997-04-18 GR GR970400829T patent/GR3023172T3/el unknown
-
1998
- 1998-06-22 HK HK98105879A patent/HK1006843A1/xx not_active IP Right Cessation
- 1998-09-29 CY CY9800030A patent/CY2113B1/xx unknown
Also Published As
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| KR0139632B1 (ko) | 브라디키닌 길항 작용을 갖는 펩티드 | |
| CA2023194C (en) | Peptides having bradykinin antagonist action | |
| US5597803A (en) | Bradykinin peptides with modifications at the N terminus | |
| US5648333A (en) | Peptides having bradykinin antagonist action | |
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| LT3872B (en) | Novel peptides and pharmaceutical compositions containing them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |