CH615903A5 - - Google Patents
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- Publication number
- CH615903A5 CH615903A5 CH977778A CH977778A CH615903A5 CH 615903 A5 CH615903 A5 CH 615903A5 CH 977778 A CH977778 A CH 977778A CH 977778 A CH977778 A CH 977778A CH 615903 A5 CH615903 A5 CH 615903A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenylalanine
- paraguanidino
- guanidination
- group
- carried out
- Prior art date
Links
- 229960005190 phenylalanine Drugs 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- GTVVZTAFGPQSPC-UHFFFAOYSA-N 4-nitrophenylalanine Chemical compound OC(=O)C(N)CC1=CC=C([N+]([O-])=O)C=C1 GTVVZTAFGPQSPC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- ATRCEYNJCBJGAZ-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)guanidine Chemical compound CC=1C=C(C)N(N=C(N)N)N=1 ATRCEYNJCBJGAZ-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- AVELLUNDPAEEIV-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)guanidine;nitric acid Chemical compound O[N+]([O-])=O.CC=1C=C(C)N(N=C(N)N)N=1 AVELLUNDPAEEIV-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 101000749842 Homo sapiens Leukocyte cell-derived chemotaxin 1 Proteins 0.000 description 1
- 150000008547 L-phenylalanines Chemical class 0.000 description 1
- 102100040448 Leukocyte cell-derived chemotaxin 1 Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- -1 ethylacetamido-4-aminobenzylmalonate Chemical compound 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000025600 response to UV Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7430509A FR2283888A1 (fr) | 1974-09-09 | 1974-09-09 | Nouveaux derives de la phenylalanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615903A5 true CH615903A5 (en, 2012) | 1980-02-29 |
Family
ID=9142895
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1167875A CH612930A5 (en, 2012) | 1974-09-09 | 1975-09-09 | |
| CH977778A CH615903A5 (en, 2012) | 1974-09-09 | 1978-09-19 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1167875A CH612930A5 (en, 2012) | 1974-09-09 | 1975-09-09 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4118575A (en, 2012) |
| JP (1) | JPS5152152A (en, 2012) |
| CH (2) | CH612930A5 (en, 2012) |
| DE (1) | DE2540134C3 (en, 2012) |
| FR (1) | FR2283888A1 (en, 2012) |
| GB (2) | GB1526557A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10005631A1 (de) * | 2000-02-09 | 2001-08-23 | Max Planck Gesellschaft | Arginin-Mimetika als Faktor X¶a¶-Inhibitoren |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3622615A (en) * | 1968-11-06 | 1971-11-23 | Parke Davis & Co | N{11 -(p-tolylsulfonyl)-L-arginine esters |
| GB1268867A (en) * | 1969-07-24 | 1972-03-29 | Sumitomo Chemical Co | THE PREPARATION OF D-THREO-beta-p-METHYLSULPHONYLPHENYLSERINE ESTER |
| CH553161A (de) * | 1970-10-30 | 1974-08-30 | Hoffmann La Roche | Verfahren zur herstellung von phenylalaninderivaten. |
-
1974
- 1974-09-09 FR FR7430509A patent/FR2283888A1/fr active Granted
-
1975
- 1975-09-05 US US05/610,671 patent/US4118575A/en not_active Expired - Lifetime
- 1975-09-08 GB GB36888/75A patent/GB1526557A/en not_active Expired
- 1975-09-08 GB GB16303/78A patent/GB1526558A/en not_active Expired
- 1975-09-09 CH CH1167875A patent/CH612930A5/xx not_active IP Right Cessation
- 1975-09-09 DE DE2540134A patent/DE2540134C3/de not_active Expired
- 1975-09-09 JP JP50108604A patent/JPS5152152A/ja active Pending
-
1978
- 1978-09-19 CH CH977778A patent/CH615903A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5152152A (en) | 1976-05-08 |
| US4118575A (en) | 1978-10-03 |
| GB1526558A (en) | 1978-09-27 |
| GB1526557A (en) | 1978-09-27 |
| DE2540134B2 (de) | 1978-03-30 |
| DE2540134A1 (de) | 1976-03-25 |
| FR2283888A1 (fr) | 1976-04-02 |
| CH612930A5 (en, 2012) | 1979-08-31 |
| FR2283888B1 (en, 2012) | 1979-03-09 |
| DE2540134C3 (de) | 1978-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |