DE2102173A1 - Pyrrolidone carboxylic acid alkyl esters prepn - having therapeutic and cosmetic activity esp for the skin - Google Patents
Pyrrolidone carboxylic acid alkyl esters prepn - having therapeutic and cosmetic activity esp for the skinInfo
- Publication number
- DE2102173A1 DE2102173A1 DE19712102173 DE2102173A DE2102173A1 DE 2102173 A1 DE2102173 A1 DE 2102173A1 DE 19712102173 DE19712102173 DE 19712102173 DE 2102173 A DE2102173 A DE 2102173A DE 2102173 A1 DE2102173 A1 DE 2102173A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carboxylic acid
- carried out
- pyrrolidone
- general 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.)
- Ceased
Links
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 title claims description 4
- 230000000694 effects Effects 0.000 title abstract description 4
- 239000002537 cosmetic Substances 0.000 title abstract description 3
- 230000001225 therapeutic effect Effects 0.000 title abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract description 3
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 230000003019 stabilising effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- -1 alkyl pyrrolidonecarboxylates Chemical class 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229940071139 pyrrolidone carboxylate Drugs 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RLGWLHOLFDTULQ-UHFFFAOYSA-N 1-heptadecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCCCCCCN1CCCC1=O RLGWLHOLFDTULQ-UHFFFAOYSA-N 0.000 description 1
- YPJPWJJRCJXTOR-UHFFFAOYSA-N 1-tridecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCCN1CCCC1=O YPJPWJJRCJXTOR-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000002086 anti-sebum Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102173 DE2102173A1 (en) | 1971-01-18 | 1971-01-18 | Pyrrolidone carboxylic acid alkyl esters prepn - having therapeutic and cosmetic activity esp for the skin |
| NO485071A NO137639C (no) | 1971-01-18 | 1971-12-27 | Kosmetisk preparat. |
| ES398930A ES398930A1 (es) | 1971-01-18 | 1972-01-17 | Procedimiento para la preparacion de nuevos esteres alcohi-licos de acido pirrolidon-carboxilixo. |
| CH65372A CH566983A5 (enExample) | 1971-01-18 | 1972-01-17 | |
| SE51272A SE388541B (sv) | 1971-01-18 | 1972-01-17 | Anvendning av pyrrolidonkarboxylsyraalkylestrar som aktiva komponenter ihudkosmetiska kompositioner |
| CH740975A CH567467A5 (enExample) | 1971-01-18 | 1972-01-17 | |
| ES398929A ES398929A1 (es) | 1971-01-18 | 1972-01-17 | Procedimiento para la preparacion de nuevos esteres alcohi-licos de acido pirrolidon-carboxilico. |
| AT35972A AT311329B (de) | 1971-01-18 | 1972-01-17 | Verfahren zur Herstellung von neuen 5-Pyrrolidon-(2)-carbonsäurealkylestern |
| AT1057172A AT316537B (de) | 1971-01-18 | 1972-01-17 | Verfahren zur Herstellung von neuen 5-Pyrrolidon-(2)-carbonsäurealkylestern |
| FI9572A FI55765C (fi) | 1971-01-18 | 1972-01-17 | Kosmetisk vaerdefulla i hudvaordsmedel anvaenda pyrrolidonkarboxylsyraalkylestrar |
| DK23272A DK128850B (da) | 1971-01-18 | 1972-01-17 | Analogifremgangsmåde til fremstilling af pyrrolidinoncarboxylsyrealkylestere. |
| DK130673A DK133536C (da) | 1971-01-18 | 1973-03-09 | Middel til kosmetisk hudpleje |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102173 DE2102173A1 (en) | 1971-01-18 | 1971-01-18 | Pyrrolidone carboxylic acid alkyl esters prepn - having therapeutic and cosmetic activity esp for the skin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2102173A1 true DE2102173A1 (en) | 1972-08-17 |
Family
ID=5796207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712102173 Ceased DE2102173A1 (en) | 1971-01-18 | 1971-01-18 | Pyrrolidone carboxylic acid alkyl esters prepn - having therapeutic and cosmetic activity esp for the skin |
Country Status (7)
| Country | Link |
|---|---|
| CH (2) | CH566983A5 (enExample) |
| DE (1) | DE2102173A1 (enExample) |
| DK (1) | DK128850B (enExample) |
| ES (2) | ES398929A1 (enExample) |
| FI (1) | FI55765C (enExample) |
| NO (1) | NO137639C (enExample) |
| SE (1) | SE388541B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4015008A (en) * | 1974-02-01 | 1977-03-29 | National Patent Development Corporation | N,N-dichloro substituted aminocarboxylic acids as microbiocides |
| DE3536669A1 (de) * | 1984-10-26 | 1986-04-30 | Nitto Electric Industrial Co., Ltd., Ibaraki, Osaka | Zusammensetzung fuer die perkutane verabreichung von medikamenten und verfahren zur foerderung der perkutanen absorption von medikamenten |
-
1971
- 1971-01-18 DE DE19712102173 patent/DE2102173A1/de not_active Ceased
- 1971-12-27 NO NO485071A patent/NO137639C/no unknown
-
1972
- 1972-01-17 ES ES398929A patent/ES398929A1/es not_active Expired
- 1972-01-17 SE SE51272A patent/SE388541B/xx unknown
- 1972-01-17 DK DK23272A patent/DK128850B/da unknown
- 1972-01-17 ES ES398930A patent/ES398930A1/es not_active Expired
- 1972-01-17 FI FI9572A patent/FI55765C/fi active
- 1972-01-17 CH CH65372A patent/CH566983A5/xx not_active IP Right Cessation
- 1972-01-17 CH CH740975A patent/CH567467A5/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4015008A (en) * | 1974-02-01 | 1977-03-29 | National Patent Development Corporation | N,N-dichloro substituted aminocarboxylic acids as microbiocides |
| DE3536669A1 (de) * | 1984-10-26 | 1986-04-30 | Nitto Electric Industrial Co., Ltd., Ibaraki, Osaka | Zusammensetzung fuer die perkutane verabreichung von medikamenten und verfahren zur foerderung der perkutanen absorption von medikamenten |
Also Published As
| Publication number | Publication date |
|---|---|
| SE388541B (sv) | 1976-10-11 |
| DK128850C (enExample) | 1975-01-20 |
| NO137639B (no) | 1977-12-19 |
| ES398930A1 (es) | 1974-10-01 |
| DK128850B (da) | 1974-07-15 |
| CH566983A5 (enExample) | 1975-09-30 |
| FI55765B (fi) | 1979-06-29 |
| ES398929A1 (es) | 1974-10-01 |
| NO137639C (no) | 1978-03-29 |
| CH567467A5 (enExample) | 1975-10-15 |
| FI55765C (fi) | 1979-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |