DE2617308C2 - - Google Patents
Info
- Publication number
- DE2617308C2 DE2617308C2 DE2617308A DE2617308A DE2617308C2 DE 2617308 C2 DE2617308 C2 DE 2617308C2 DE 2617308 A DE2617308 A DE 2617308A DE 2617308 A DE2617308 A DE 2617308A DE 2617308 C2 DE2617308 C2 DE 2617308C2
- Authority
- DE
- Germany
- Prior art keywords
- allantoin
- amino acid
- basic amino
- compound
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 204
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 108
- 229960000458 allantoin Drugs 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 42
- 150000001413 amino acids Chemical class 0.000 claims description 39
- -1 amino acid compound Chemical class 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 36
- 239000004475 Arginine Substances 0.000 claims description 28
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000004472 Lysine Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 229960003104 ornithine Drugs 0.000 claims description 14
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 13
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 13
- 125000000539 amino acid group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 11
- 235000019441 ethanol Nutrition 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 description 40
- 239000000047 product Substances 0.000 description 22
- 239000000843 powder Substances 0.000 description 19
- 229960003646 lysine Drugs 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002441 X-ray diffraction Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229960005337 lysine hydrochloride Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 229960003244 ornithine hydrochloride Drugs 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 230000006229 amino acid addition Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000035984 keratolysis Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001338 necrotic effect Effects 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
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4850675A JPS5231072A (en) | 1975-04-21 | 1975-04-21 | Synthesis of molecular compounds of allantoin and alginine |
| JP9946675A JPS5225771A (en) | 1975-08-18 | 1975-08-18 | Preparation of molecular compound of allantoin and lysine |
| JP9946775A JPS5934710B2 (ja) | 1975-08-18 | 1975-08-18 | アラントインとオルニチンとの分子化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2617308A1 DE2617308A1 (de) | 1976-11-04 |
| DE2617308C2 true DE2617308C2 (en, 2012) | 1987-12-10 |
Family
ID=27293315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762617308 Granted DE2617308A1 (de) | 1975-04-21 | 1976-04-21 | Verbindungen des allantoins mit basischen aminosaeuren und verfahren zu ihrer herstellung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4038287A (en, 2012) |
| DE (1) | DE2617308A1 (en, 2012) |
| FR (1) | FR2374034A1 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113425614A (zh) * | 2021-06-28 | 2021-09-24 | 广东药科大学 | 氨基酸或氨基酸类似物或其盐在作为提高尿囊素溶解性能的添加剂的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275643A (en) * | 1963-07-19 | 1966-09-27 | Irwin I Lubowe | Allantoin-pantothenate compounds |
| BE737288A (en, 2012) * | 1968-08-08 | 1970-01-16 | ||
| US3578656A (en) * | 1969-02-24 | 1971-05-11 | Schuylkill Chemical Co | Method of making allantoin polygalacturonic acid compounds |
| US3927021A (en) * | 1975-02-24 | 1975-12-16 | Schuylkill Chemical Co | Allantoin glycine complex |
-
1976
- 1976-04-12 US US05/676,134 patent/US4038287A/en not_active Expired - Lifetime
- 1976-04-21 FR FR7611704A patent/FR2374034A1/fr active Granted
- 1976-04-21 DE DE19762617308 patent/DE2617308A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2374034A1 (fr) | 1978-07-13 |
| DE2617308A1 (de) | 1976-11-04 |
| FR2374034B1 (en, 2012) | 1979-03-30 |
| US4038287A (en) | 1977-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0302948B1 (de) | Verfahren zur Gewinnung von Steviosiden aus pflanzlichem Rohmaterial | |
| DE60004620T3 (de) | Verfahren zur Herstellung eines nichtkristallisierbaren Polyolsirups | |
| DE3886711T2 (de) | Verfahren zur Herstellung von hochreiner kristalliner Lactulose und das so erhaltene Produkt. | |
| DE2901730C2 (en, 2012) | ||
| DE2406628C2 (de) | Alkylester von Partricin, Verfahren zu ihrer Herstellung und diese Ester enthaltende pharmazeutische Mittel | |
| DE69912773T2 (de) | Nicht hydratisiertes gabapentin polymorph, herstellungsprozess und verwendung zur herstellung von gabapentin pharmazeutischer reinheit. | |
| DE2431483C3 (de) | Verfahren zur Herstellung von Alkali- oder Ammoniumsalzen von Insulin | |
| DE2002385C3 (de) | Verfahren zur Herstellung von Lactulose-Konzentrat | |
| DE1925230C3 (de) | Verfahren zur Herstellung des Antibiotikums Streptozotocin | |
| DE2725246C2 (en, 2012) | ||
| DE2617308C2 (en, 2012) | ||
| DE1618492B1 (de) | Fruktosegewinnung aus Zucker | |
| DE1493618A1 (de) | Cumarinderivate und ein Verfahren zu ihrer Herstellung | |
| DE1493894A1 (de) | Verfahren zur Herstellung von Ornithinasparaginat | |
| DE3102984A1 (de) | Verfahren zur herstellung von cysteamin-s-substituierten verbindungen und deren derivaten | |
| DE1618492C (de) | Fruktosegewinnung aus Zucker | |
| DE1770351C2 (de) | 2-0-Acyl-clindamycine, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibiotische Zubereitungen | |
| EP1731484B1 (de) | Wässrige Lösung aus einer Bismutverbindung und einer Polyhydroxyverbindung sowie Verfahren zu ihrer Herstellung | |
| DE2837694A1 (de) | Verfahren und extraktionsmittel zur herstellung von reiner phosphorsaeure | |
| DE2949594C2 (de) | Kanamycintannat, Verfahren zu seiner Hersellung und pharmazeutische Mittel | |
| DE2436479A1 (de) | Verfahren zur reinigung von steroidheterosiden | |
| DE2354239C3 (de) | Verfahren zur Herstellung von Methylenglucosen | |
| DE1545652C (de) | 3-(alpha-Hydroxyäthyl)-6-chlor-7sulfamyl-1,2,4-benzothiadiazin-1,1 dioxyd | |
| DE1924174C3 (de) | Magnesiumorotatglycinate | |
| DD237310A1 (de) | Verfahren zur herstellung des natriumsalzes der gamma-hydroxybuttersaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |