DE3833972C2 - - Google Patents
Info
- Publication number
- DE3833972C2 DE3833972C2 DE3833972A DE3833972A DE3833972C2 DE 3833972 C2 DE3833972 C2 DE 3833972C2 DE 3833972 A DE3833972 A DE 3833972A DE 3833972 A DE3833972 A DE 3833972A DE 3833972 C2 DE3833972 C2 DE 3833972C2
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- pyroglutamate
- trihydrate
- solution
- water
- 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 - Lifetime
Links
- 150000004684 trihydrates Chemical class 0.000 claims abstract description 10
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000011734 sodium Substances 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 5
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 5
- -1 Sodium L-2-pyrrolidone-5-carboxylate trihydrate Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 18
- CRPCXAMJWCDHFM-DFWYDOINSA-M sodium;(2s)-5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)[C@@H]1CCC(=O)N1 CRPCXAMJWCDHFM-DFWYDOINSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UFPSXMQHIIVCEO-QVTWQEFQSA-M sodium;(2s)-5-oxopyrrolidine-2-carboxylate;trihydrate Chemical compound O.O.O.[Na+].[O-]C(=O)[C@@H]1CCC(=O)N1 UFPSXMQHIIVCEO-QVTWQEFQSA-M 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ODHCTXKNWHHXJC-GSVOUGTGSA-N 5-oxo-D-proline Chemical compound OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005356 chiral GC Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940045635 sodium pyroglutamate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CRPCXAMJWCDHFM-AENDTGMFSA-M sodium;(2r)-5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)[C@H]1CCC(=O)N1 CRPCXAMJWCDHFM-AENDTGMFSA-M 0.000 description 1
- GJBHGUUFMNITCI-QTNFYWBSSA-M sodium;(2s)-2-aminopentanedioate;hydron;hydrate Chemical compound O.[Na+].OC(=O)[C@@H](N)CCC([O-])=O GJBHGUUFMNITCI-QTNFYWBSSA-M 0.000 description 1
- CRPCXAMJWCDHFM-UHFFFAOYSA-M sodium;5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC(=O)N1 CRPCXAMJWCDHFM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3833972A DE3833972A1 (de) | 1988-10-06 | 1988-10-06 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung |
| EP89117716A EP0362668B1 (de) | 1988-10-06 | 1989-09-26 | Derivate der 2-Pyrrolidon-5-carbonsäure und Verfahren zu ihrer Gewinnung |
| DE8989117716T DE58903397D1 (de) | 1988-10-06 | 1989-09-26 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung. |
| AT89117716T ATE85046T1 (de) | 1988-10-06 | 1989-09-26 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung. |
| ES89117716T ES2044006T3 (es) | 1988-10-06 | 1989-09-26 | Procedimiento para la obtencion de derivados del acido 2-pirrolidon-5-carboxilico. |
| US07/417,089 US4952706A (en) | 1988-10-06 | 1989-10-04 | Derivatives of 2-pyrrolidone-5-carboxylic acid and method of obtaining them |
| CA002000184A CA2000184C (en) | 1988-10-06 | 1989-10-05 | Trihydrates of sodium l- and d-2-pyrrolidone-5-carboxylate |
| JP1258977A JPH02145565A (ja) | 1988-10-06 | 1989-10-05 | ２‐ピロリドン‐５‐カルボン酸の誘導体及びその製法 |
| GR930400449T GR3007204T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-06 | 1993-03-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3833972A DE3833972A1 (de) | 1988-10-06 | 1988-10-06 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3833972A1 DE3833972A1 (de) | 1990-04-12 |
| DE3833972C2 true DE3833972C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-12-20 |
Family
ID=6364487
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3833972A Granted DE3833972A1 (de) | 1988-10-06 | 1988-10-06 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung |
| DE8989117716T Expired - Fee Related DE58903397D1 (de) | 1988-10-06 | 1989-09-26 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8989117716T Expired - Fee Related DE58903397D1 (de) | 1988-10-06 | 1989-09-26 | Derivate der 2-pyrrolidon-5-carbonsaeure und verfahren zu ihrer gewinnung. |
Country Status (8)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2694194B1 (fr) * | 1992-07-31 | 1994-11-04 | Health Business Dev | Gel hydratant, médicament et composition cosmétique le contenant, procédé de préparation dudit gel. |
| FR2839644B1 (fr) * | 2002-05-14 | 2005-09-09 | Oreal | Utilisation d'un sel organique particulier et composition le comprenant pour le lavage et/ou le conditionnement des matieres keratiniques. |
| JP2021008408A (ja) * | 2017-10-05 | 2021-01-28 | 味の素株式会社 | 光学活性ピロリドンカルボン酸またはそのアルカリ金属塩の製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185703A (en) * | 1965-05-25 | Racemization op optically-active pyroglutamic acid | ||
| US2806855A (en) * | 1957-09-17 | Production of pyrrolidone carboxylic | ||
| US2984684A (en) * | 1958-06-12 | 1961-05-16 | Int Minerals & Chem Corp | Resolution of dl-glutamic acid |
| US3153049A (en) * | 1961-10-10 | 1964-10-13 | Rohm & Haas | Recovery of pyrrolidone carboxylic acid from weakly basic anion exchanger eluates |
| US3235563A (en) * | 1962-12-18 | 1966-02-15 | Inst Noguchi | Process for producing dl-2-pyrrolidone-carboxylic acid by heating glutamic acid withfrom 0.5 to 15 parts by weight of water per part of glutamic acid |
| JPS5136274B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-03-13 | 1976-10-07 | ||
| US3952011A (en) * | 1971-12-08 | 1976-04-20 | Ajinomoto Company, Ltd. | Process for producing hemi-alkali metal salt of 2-pyrrolidone-5-carboxylic acid |
| US4097490A (en) * | 1975-09-25 | 1978-06-27 | Merck & Co., Inc. | Pyroglutamic acid salts of t-butylamino-2,3-dihydroxypropane |
| JPS64559A (en) * | 1987-02-17 | 1989-01-05 | Fuji Photo Film Co Ltd | Image recording device |
| DE3735263C1 (de) * | 1987-10-17 | 1988-08-25 | Degussa | Verfahren zur Herstellung von Alkalimetallsalzen der L-2-Pyrrolidon-5-carbonsaeure |
| DE3735264C1 (de) * | 1987-10-17 | 1988-08-25 | Degussa | Verfahren zur Herstellung von Erdalkalimetallsalzen der L-2-Pyrrolidon-5-carbonsaeure |
-
1988
- 1988-10-06 DE DE3833972A patent/DE3833972A1/de active Granted
-
1989
- 1989-09-26 AT AT89117716T patent/ATE85046T1/de not_active IP Right Cessation
- 1989-09-26 ES ES89117716T patent/ES2044006T3/es not_active Expired - Lifetime
- 1989-09-26 DE DE8989117716T patent/DE58903397D1/de not_active Expired - Fee Related
- 1989-09-26 EP EP89117716A patent/EP0362668B1/de not_active Expired - Lifetime
- 1989-10-04 US US07/417,089 patent/US4952706A/en not_active Expired - Fee Related
- 1989-10-05 JP JP1258977A patent/JPH02145565A/ja active Granted
- 1989-10-05 CA CA002000184A patent/CA2000184C/en not_active Expired - Fee Related
-
1993
- 1993-03-02 GR GR930400449T patent/GR3007204T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE58903397D1 (de) | 1993-03-11 |
| CA2000184A1 (en) | 1990-04-06 |
| EP0362668B1 (de) | 1993-01-27 |
| DE3833972A1 (de) | 1990-04-12 |
| GR3007204T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-07-30 |
| JPH02145565A (ja) | 1990-06-05 |
| CA2000184C (en) | 1997-07-08 |
| ATE85046T1 (de) | 1993-02-15 |
| EP0362668A1 (de) | 1990-04-11 |
| ES2044006T3 (es) | 1994-01-01 |
| US4952706A (en) | 1990-08-28 |
| JPH0583546B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |