CH677113A5 - - Google Patents

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Info

Publication number: CH677113A5
Authority: CH; Switzerland
Prior art keywords: thiamorpholinone; ethoxycarbonyl; formula; carboxylate; compounds
Prior art date: 1987-07-21

Application number

CH2771/88A

Other languages

English (en)

French (fr)

Inventor

Jean Maignan

Gerard Malle

Gerard Lang

Original Assignee

Oreal

Priority date (The priority date 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 date listed.)

1987-07-21

Filing date

1988-07-20

Publication date

1991-04-15

1988-07-20 Application filed by Oreal filed Critical Oreal

1991-04-15 Publication of CH677113A5 publication Critical patent/CH677113A5/fr

Links

150000001875 compounds Chemical class 0.000 claims abstract description 36
150000002148 esters Chemical class 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 6
230000003287 optical effect Effects 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 41
229910052757 nitrogen Inorganic materials 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
239000002537 cosmetic Substances 0.000 claims description 11
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
125000001400 nonyl 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])[H] 0.000 claims description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
239000003755 preservative agent Substances 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000000058 anti acne agent Substances 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 claims description 3
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239000003963 antioxidant agent Substances 0.000 claims description 3
230000003115 biocidal effect Effects 0.000 claims description 3
235000021466 carotenoid Nutrition 0.000 claims description 3
150000001747 carotenoids Chemical class 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
159000000011 group IA salts Chemical class 0.000 claims description 3
230000003659 hair regrowth Effects 0.000 claims description 3
230000003020 moisturizing effect Effects 0.000 claims description 3
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
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239000002260 anti-inflammatory agent Substances 0.000 claims 2
230000003078 antioxidant effect Effects 0.000 claims 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 2
229910052801 chlorine Chemical group 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 2
208000002874 Acne Vulgaris Diseases 0.000 abstract description 4
206010039792 Seborrhoea Diseases 0.000 abstract description 4
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
-1 alkyl radical Chemical class 0.000 description 14
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000243 solution Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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238000004587 chromatography analysis Methods 0.000 description 6
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
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238000003756 stirring Methods 0.000 description 6
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238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
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238000000921 elemental analysis Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
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150000003254 radicals Chemical class 0.000 description 3
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VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
JFQNETYDIXLTTR-UHFFFAOYSA-N 2-methylthiomorpholin-3-one Chemical compound CC1SCCNC1=O JFQNETYDIXLTTR-UHFFFAOYSA-N 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
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239000013078 crystal Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
230000037312 oily skin Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
HBDDRESWUAFAHY-UHFFFAOYSA-N thiomorpholin-3-one Chemical compound O=C1CSCCN1 HBDDRESWUAFAHY-UHFFFAOYSA-N 0.000 description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
JJVXHDTWVIPRBZ-VKHMYHEASA-N (2r)-2-[carboxy(methyl)amino]-3-sulfanylpropanoic acid Chemical compound OC(=O)N(C)[C@@H](CS)C(O)=O JJVXHDTWVIPRBZ-VKHMYHEASA-N 0.000 description 1
125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
VOYVSADGIRQSIM-OWOJBTEDSA-N (e)-4-[(1,1-dioxothiolan-3-yl)amino]-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)NC1CCS(=O)(=O)C1 VOYVSADGIRQSIM-OWOJBTEDSA-N 0.000 description 1
PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
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NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
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CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
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GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)

CH2771/88A 1987-07-21 1988-07-20 CH677113A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8710302A FR2618434B1 (fr)	1987-07-21	1987-07-21	Esters d'acide thiamorpholinone carboxylique et de ses derives, leur procede de preparation et leur utilisation dans le domaine cosmetique et dermo-pharmaceutique

Publications (1)

Publication Number	Publication Date
CH677113A5 true CH677113A5 (de)	1991-04-15

Family

ID=9353374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH2771/88A CH677113A5 (de)	1987-07-21	1988-07-20

Country Status (5)

Country	Link
BE (1)	BE1006721A3 (de)
CH (1)	CH677113A5 (de)
FR (1)	FR2618434B1 (de)
GB (1)	GB2207134B (de)
IT (1)	IT1227158B (de)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU83327A1 (fr) *	1981-04-29	1983-03-24	Midit	Procede de preparation de derives de 1,4-thiazine,leur utilisation ainsi que compositions contenant ces derives
FR2525106B1 (fr) *	1982-04-15	1985-06-07	Oreal	Composition cosmetique contenant en tant qu'agent actif sur l'elasticite et la souplesse de la peau, de la thiamorpholinone ou l'un de ses derives
FR2525220A1 (fr) *	1982-04-15	1983-10-21	Oreal	Nouveaux derives substitues de la thiamorpholinone et leurs procedes de preparation

1987
- 1987-07-21 FR FR8710302A patent/FR2618434B1/fr not_active Expired - Fee Related
1988
- 1988-07-20 BE BE8800852A patent/BE1006721A3/fr not_active IP Right Cessation
- 1988-07-20 CH CH2771/88A patent/CH677113A5/fr not_active IP Right Cessation
- 1988-07-20 GB GB8817266A patent/GB2207134B/en not_active Expired - Fee Related
- 1988-07-20 IT IT8821430A patent/IT1227158B/it active

Also Published As

Publication number	Publication date
IT8821430A0 (it)	1988-07-20
GB2207134B (en)	1991-04-24
FR2618434B1 (fr)	1991-02-08
GB8817266D0 (en)	1988-08-24
FR2618434A1 (fr)	1989-01-27
IT1227158B (it)	1991-03-20
BE1006721A3 (fr)	1994-11-29
GB2207134A (en)	1989-01-25

Legal Events

Date	Code	Title	Description
2007-03-15	PL	Patent ceased

Publication	Publication Date	Title
CA1337344C (fr)	1995-10-17	Composes benzamido aromatique, leur procede de preparation et leur utilisation en cosmetique
EP0199636B1 (de)	1989-02-08	Benzoenaphthalinderivate, Verfahren zu deren Herstellung und ihre Verwendung in Pharmazie und Kosmetik
EP0420707B1 (de)	1993-12-15	2-Aminopyrimidin-3-oxid-Derivate enthaltende Zusammensetzungen zur Verwendung zum Vermindern des Haarausfalles und zum Induzieren und Stimulieren des Haarwuchses und neue von 2-Aminopyrimidin-3-oxid abgeleitete Verbindungen
EP0210929A2 (de)	1987-02-04	Aromatische polycyclische Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen und kosmetischen Zubereitungen
FR2689131A1 (fr)	1993-10-01	Procédé de préparation de monoesters majoritairement en position 6' du D-maltose et leur utilisation dans les domaines cosmétique, bucco-dentaire, pharmaceutique et alimentaire.
BE1004273A4 (fr)	1992-10-27	Nouveaux derives aromatiques bicycliques, leur procede de preparation et leur utilisation en cosmetique et en medecine humaine et veterinaire.
FR2614618A1 (fr)	1988-11-04	Derives heterocycliques polycycliques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire
EP0304665B1 (de)	1992-04-15	2,4,6-Triaminopyrimidin N-3-oxid-Harnstoff-Derivate, deren Herstellung und deren kosmetische und dermopharmazeutische Verwendung
EP0409728B1 (de)	1995-03-01	Bi-aromatische Ester, Verfahren zu ihrer Herstellung und ihre Verwendung in der menschlichen oder tierischen Heilkunde und in der Kosmetik
EP0209770A1 (de)	1987-01-28	Eicosatriynester und Amide und deren Verwendung in der Pharmazie und Kosmetik
EP0342115B1 (de)	1992-09-09	Sulfurierte Eicosanoide und deren Verwendung in Arzneimitteln und Kosmetika
EP0122827B1 (de)	1986-07-23	1-(2-Ethoxycarbonyl-4-phenylalkylamido)-3-amino-2-Propanole, deren Herstellungen und deren pharmazeutische Verwendungen
CA1201979A (fr)	1986-03-18	Composition pour une application topique contenant en tant qu'agent actif sur l'elasticite et la souplesse de la peau, de la thiamorpholinone ou l'un de ses derives
BE1006721A3 (fr)	1994-11-29	Esters d'acide thiamorpholine carboxylique et de ses derives, leur procede de preparation et leur utilisation dans le domaine cosmetique et dermopharmaceutique.
CH656132A5 (fr)	1986-06-13	Derives de n-carbamoyl d'isothiazolo-(5,4b) pyridine one-3 leur procede de preparation, et compositions cosmetiques les contenant.
EP0279954B1 (de)	1993-03-17	Eicosattraynsäureamide, ihre Verwendung in der Arzneimittelkunde und Kosmetika, ihre Herstellung und Verfahren zur Herstellung von Eicosattraynsäure
EP0342105A1 (de)	1989-11-15	2-Adamantyl-3-isothyazolin-4-one-Derivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Bakterizide und Fungizide
CA1196331A (fr)	1985-11-05	Derives substitues de la thiamorpholinone et leurs procedes de preparation
EP0071500B1 (de)	1985-05-22	Verfahren zur Herstellung von 4-Amino-buttersäureamide
EP0349418B1 (de)	1992-09-09	4-Hydroxy-isoxazol-Derivate, deren Herstellung und kosmetische und pharmazeutische Zusammensetzungen, die sie enthalten
FR2565584A1 (fr)	1985-12-13	Derives d'acide heptanoique, leur procede de preparation ainsi que leur utilisation
CA2064910A1 (fr)	1991-12-20	Derives de diamino-2,4 triazine 1,3,5 et leur utilisation pour le traitement et la prevention de la chute des cheveux
FR2528042A1 (fr)	1983-12-09	Procede de preparation de derives de la cystamine a activite oncostatique
CH620911A5 (en)	1980-12-31	Process for the preparation of derivatives of quinoxaline 1,4-dioxide
CH340816A (fr)	1959-09-15	Procédé de préparation de nouveaux thiodérivés de colchicéines