DE2102171A1 - Pyrrolidonecarboxylic acid alkyl esters - cosmetic agents - Google Patents
Pyrrolidonecarboxylic acid alkyl esters - cosmetic agentsInfo
- Publication number
- DE2102171A1 DE2102171A1 DE19712102171 DE2102171A DE2102171A1 DE 2102171 A1 DE2102171 A1 DE 2102171A1 DE 19712102171 DE19712102171 DE 19712102171 DE 2102171 A DE2102171 A DE 2102171A DE 2102171 A1 DE2102171 A1 DE 2102171A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carried out
- general formula
- pyrrolidone
- alkyl esters
- 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.)
- Pending
Links
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 title claims description 4
- 239000002537 cosmetic Substances 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 claims abstract description 7
- 150000004820 halides Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- -1 nonadecyl ester Chemical class 0.000 abstract description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract description 3
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 210000002374 sebum Anatomy 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 210000004907 gland Anatomy 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 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
- 239000003208 petroleum Substances 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
- 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
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000002086 anti-sebum Effects 0.000 description 1
- 150000007942 carboxylates 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
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940071139 pyrrolidone carboxylate Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Pyrrole Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102171 DE2102171A1 (en) | 1971-01-18 | 1971-01-18 | Pyrrolidonecarboxylic acid alkyl esters - cosmetic agents |
| CH57172A CH568287A5 (OSRAM) | 1971-01-18 | 1972-01-14 | |
| CH747675A CH566312A5 (OSRAM) | 1971-01-18 | 1972-01-14 | |
| ES398931A ES398931A1 (es) | 1971-01-18 | 1972-01-17 | Procedimiento para la preparacion de nuevos esteres alcoho-licos de acido pirrolidon-carboxilixo. |
| ES398932A ES398932A1 (es) | 1971-01-18 | 1972-01-17 | Procedimiento para la preparacion de nuevos esteres alcohi-licos de acido pirrolidon-carboxilico. |
| DK23372A DK135713C (da) | 1971-01-18 | 1972-01-17 | Analogifremgangsmade til fremstilling af pyrrolidoncarboxylsyrealkylestere |
| SE51172A SE388540B (sv) | 1971-01-18 | 1972-01-17 | Anvendning av pyrrolidonkarboxylsyraalkylestrar som aktiva komponenter i hudkosmetiska kompositioner |
| AT1057172A AT316537B (de) | 1971-01-18 | 1972-01-17 | Verfahren zur Herstellung von neuen 5-Pyrrolidon-(2)-carbonsäurealkylestern |
| AT35972A AT311329B (de) | 1971-01-18 | 1972-01-17 | Verfahren zur Herstellung von neuen 5-Pyrrolidon-(2)-carbonsäurealkylestern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102171 DE2102171A1 (en) | 1971-01-18 | 1971-01-18 | Pyrrolidonecarboxylic acid alkyl esters - cosmetic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2102171A1 true DE2102171A1 (en) | 1972-07-27 |
Family
ID=5796205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712102171 Pending DE2102171A1 (en) | 1971-01-18 | 1971-01-18 | Pyrrolidonecarboxylic acid alkyl esters - cosmetic agents |
Country Status (5)
| Country | Link |
|---|---|
| CH (2) | CH568287A5 (OSRAM) |
| DE (1) | DE2102171A1 (OSRAM) |
| DK (1) | DK135713C (OSRAM) |
| ES (2) | ES398932A1 (OSRAM) |
| SE (1) | SE388540B (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0227531A3 (en) * | 1985-11-29 | 1987-09-16 | Merck & Co. Inc. | Pyroglutamic acid esters used as dermal penetration enhancers for drugs |
| EP0342055A3 (en) * | 1988-05-13 | 1990-08-29 | Unilever Plc | Treatment of skin disorders |
-
1971
- 1971-01-18 DE DE19712102171 patent/DE2102171A1/de active Pending
-
1972
- 1972-01-14 CH CH57172A patent/CH568287A5/xx not_active IP Right Cessation
- 1972-01-14 CH CH747675A patent/CH566312A5/xx not_active IP Right Cessation
- 1972-01-17 SE SE51172A patent/SE388540B/xx unknown
- 1972-01-17 DK DK23372A patent/DK135713C/da active
- 1972-01-17 ES ES398932A patent/ES398932A1/es not_active Expired
- 1972-01-17 ES ES398931A patent/ES398931A1/es not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0227531A3 (en) * | 1985-11-29 | 1987-09-16 | Merck & Co. Inc. | Pyroglutamic acid esters used as dermal penetration enhancers for drugs |
| EP0342055A3 (en) * | 1988-05-13 | 1990-08-29 | Unilever Plc | Treatment of skin disorders |
| AU617466B2 (en) * | 1988-05-13 | 1991-11-28 | Unilever Plc | Treatment of skin disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| DK135713C (da) | 1977-11-14 |
| SE388540B (sv) | 1976-10-11 |
| CH566312A5 (OSRAM) | 1975-09-15 |
| ES398932A1 (es) | 1974-08-16 |
| ES398931A1 (es) | 1974-08-16 |
| DK135713B (da) | 1977-06-13 |
| CH568287A5 (OSRAM) | 1975-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |