CH635514A5 - Verfahren zur herstellung neuer desamino-derivate des kallikrein-trypsin-inhibitors. - Google Patents
Verfahren zur herstellung neuer desamino-derivate des kallikrein-trypsin-inhibitors. Download PDFInfo
- Publication number
- CH635514A5 CH635514A5 CH517977A CH517977A CH635514A5 CH 635514 A5 CH635514 A5 CH 635514A5 CH 517977 A CH517977 A CH 517977A CH 517977 A CH517977 A CH 517977A CH 635514 A5 CH635514 A5 CH 635514A5
- Authority
- CH
- Switzerland
- Prior art keywords
- bpti
- desamino
- derivatives
- reaction
- solution
- Prior art date
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- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
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- FKMJXALNHKIDOD-LBPRGKRZSA-N TAMe Chemical compound NC(=N)NCCC[C@@H](C(=O)OC)NS(=O)(=O)C1=CC=C(C)C=C1 FKMJXALNHKIDOD-LBPRGKRZSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 102000057032 Tissue Kallikreins Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940019748 antifibrinolytic proteinase inhibitors Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical group NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000005786 degenerative changes Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical group O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- SBBWEQLNKVHYCX-JTQLQIEISA-N ethyl L-tyrosinate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=C(O)C=C1 SBBWEQLNKVHYCX-JTQLQIEISA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000000951 immunodiffusion Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 230000002956 necrotizing effect Effects 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
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- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/81—Protease inhibitors
- C07K14/8107—Endopeptidase (E.C. 3.4.21-99) inhibitors
- C07K14/811—Serine protease (E.C. 3.4.21) inhibitors
- C07K14/8114—Kunitz type inhibitors
- C07K14/8117—Bovine/basic pancreatic trypsin inhibitor (BPTI, aprotinin)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/26—Containing cys-cys disulfide bridge between nonadjacent cysteine residues
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762619246 DE2619246A1 (de) | 1976-04-30 | 1976-04-30 | Desamino-derivate des kallikrein- trypsin-inhibitors, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH635514A5 true CH635514A5 (de) | 1983-04-15 |
Family
ID=5976820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH517977A CH635514A5 (de) | 1976-04-30 | 1977-04-26 | Verfahren zur herstellung neuer desamino-derivate des kallikrein-trypsin-inhibitors. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4118481A (https=) |
| JP (1) | JPS52134009A (https=) |
| AT (1) | AT361118B (https=) |
| BE (1) | BE854102A (https=) |
| CH (1) | CH635514A5 (https=) |
| DE (1) | DE2619246A1 (https=) |
| DK (1) | DK188077A (https=) |
| FR (1) | FR2349598A1 (https=) |
| GB (1) | GB1533358A (https=) |
| NL (1) | NL7704690A (https=) |
| SE (1) | SE442301B (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2748294A1 (de) * | 1977-10-27 | 1979-05-03 | Bayer Ag | Neue derivate des bpti, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2748295A1 (de) * | 1977-10-27 | 1979-05-03 | Bayer Ag | Neue derivate des bpti |
| US4997537A (en) * | 1986-10-21 | 1991-03-05 | Northeastern University | High performance microcapillary gel electrophoresis |
| US5665216A (en) * | 1986-10-21 | 1997-09-09 | Northeastern University | Capillary column for high performance electrophoretic separation and detection of SDS proteins and system and using the same |
| US6057287A (en) * | 1994-01-11 | 2000-05-02 | Dyax Corp. | Kallikrein-binding "Kunitz domain" proteins and analogues thereof |
| PT739355E (pt) * | 1994-01-11 | 2005-01-31 | Dyax Corp | Proteinas de 'dominio de kunitz' inibidoras de calicreina e seus analogos |
| ES2229236T3 (es) | 1994-01-11 | 2005-04-16 | Dyax Corporation | Inhibidores de la plasmina humana derivados de los dominios de kunitz. |
| US20040054082A1 (en) * | 2001-12-03 | 2004-03-18 | Bank David H | Toughened polymer blends with improved surface properties |
| US7153829B2 (en) * | 2002-06-07 | 2006-12-26 | Dyax Corp. | Kallikrein-inhibitor therapies |
| WO2003103475A2 (en) | 2002-06-07 | 2003-12-18 | Dyax Corp. | Prevention and reduction of blood loss |
| JP2005537006A (ja) * | 2002-08-28 | 2005-12-08 | ダイアックス、コープ | 臓器及び組織の保存方法 |
| US7235530B2 (en) | 2004-09-27 | 2007-06-26 | Dyax Corporation | Kallikrein inhibitors and anti-thrombolytic agents and uses thereof |
| US7276480B1 (en) | 2005-12-30 | 2007-10-02 | Dyax Corp. | Prevention and reduction of blood loss |
| US20070213275A1 (en) * | 2006-03-10 | 2007-09-13 | Dyax Corp. | Formulations for ecallantide |
| CA2696208A1 (en) * | 2007-08-21 | 2009-02-26 | Genzyme Corporation | Treatment with kallikrein inhibitors |
| CA2695012A1 (en) * | 2007-08-23 | 2009-02-26 | Genzyme Corporation | Treatment with kallikrein inhibitors |
| CA2744235A1 (en) * | 2009-01-06 | 2010-07-15 | Dyax Corp. | Treatment of mucositis with kallikrein inhibitors |
| EP3459564B1 (en) | 2010-01-06 | 2021-10-27 | Takeda Pharmaceutical Company Limited | Plasma kallikrein binding proteins |
| CA2823776A1 (en) | 2011-01-06 | 2012-07-12 | Dyax Corp. | Plasma kallikrein binding proteins |
| IL295414B2 (en) | 2014-03-27 | 2026-02-01 | Takeda Pharmaceuticals Co | Compositions and methods for treating macular edema due to diabetes |
| AU2016366557B2 (en) | 2015-12-11 | 2024-01-25 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof for treating hereditary angioedema attack |
| US12528880B2 (en) | 2020-01-13 | 2026-01-20 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof for treating pediatric hereditary angioedema attack |
-
1976
- 1976-04-30 DE DE19762619246 patent/DE2619246A1/de not_active Withdrawn
-
1977
- 1977-04-25 GB GB17095/77A patent/GB1533358A/en not_active Expired
- 1977-04-26 CH CH517977A patent/CH635514A5/de not_active IP Right Cessation
- 1977-04-28 JP JP4859777A patent/JPS52134009A/ja active Pending
- 1977-04-28 SE SE7704928A patent/SE442301B/xx not_active IP Right Cessation
- 1977-04-28 NL NL7704690A patent/NL7704690A/xx not_active Application Discontinuation
- 1977-04-29 FR FR7713037A patent/FR2349598A1/fr active Granted
- 1977-04-29 BE BE177127A patent/BE854102A/xx not_active IP Right Cessation
- 1977-04-29 DK DK188077A patent/DK188077A/da not_active Application Discontinuation
- 1977-04-29 US US05/792,296 patent/US4118481A/en not_active Expired - Lifetime
- 1977-04-29 AT AT305477A patent/AT361118B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2349598B1 (https=) | 1980-02-22 |
| GB1533358A (en) | 1978-11-22 |
| NL7704690A (nl) | 1977-11-01 |
| SE442301B (sv) | 1985-12-16 |
| AT361118B (de) | 1981-02-25 |
| US4118481A (en) | 1978-10-03 |
| BE854102A (fr) | 1977-10-31 |
| FR2349598A1 (fr) | 1977-11-25 |
| SE7704928L (sv) | 1977-10-31 |
| JPS52134009A (en) | 1977-11-09 |
| DE2619246A1 (de) | 1977-11-10 |
| ATA305477A (de) | 1980-07-15 |
| DK188077A (da) | 1977-10-31 |
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