LU87036A1 - Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant - Google Patents

Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant Download PDF

Info

Publication number: LU87036A1
Authority: LU; Luxembourg
Prior art keywords: esters; carboxy; benzylidene; butadiene; methyl
Prior art date: 1987-11-04

Application number

LU87036A

Other languages

English (en)

French (fr)

Inventor

Michel Philippe

Henri Sebag

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.)

1987-11-04

Filing date

1987-11-04

Publication date

1989-06-14

1987-11-04 Application filed by Oreal filed Critical Oreal

1987-11-04 Priority to LU87036A priority Critical patent/LU87036A1/fr

1988-11-02 Priority to JP63280218A priority patent/JPH01193288A/ja

1988-11-03 Priority to US07/266,598 priority patent/US5004731A/en

1988-11-03 Priority to CA000582116A priority patent/CA1313660C/fr

1988-11-03 Priority to ES88402766T priority patent/ES2063765T3/es

1988-11-03 Priority to DE3851937T priority patent/DE3851937T2/de

1988-11-03 Priority to AT88402766T priority patent/ATE113290T1/de

1988-11-03 Priority to EP88402766A priority patent/EP0315535B1/de

1989-06-14 Publication of LU87036A1 publication Critical patent/LU87036A1/fr

Links

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238000002360 preparation method Methods 0.000 title claims description 11
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239000003242 anti bacterial agent Substances 0.000 title abstract description 10
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150000002148 esters Chemical class 0.000 claims abstract description 43
208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 13
206010000496 acne Diseases 0.000 claims abstract description 13
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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 claims description 16
229960002227 clindamycin Drugs 0.000 claims description 14
KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 claims description 12
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OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 claims description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
229960004144 josamycin Drugs 0.000 claims description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
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XJSFLOJWULLJQS-NGVXBBESSA-N josamycin Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 XJSFLOJWULLJQS-NGVXBBESSA-N 0.000 claims description 5
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
208000017520 skin disease Diseases 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
239000004104 Oleandomycin Substances 0.000 claims description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
239000004187 Spiramycin Substances 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
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RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 claims description 4
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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150000007529 inorganic bases Chemical class 0.000 claims description 3
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ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical class O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 claims description 2
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239000001913 cellulose Substances 0.000 claims description 2
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150000003839 salts Chemical class 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
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239000002562 thickening agent Substances 0.000 claims description 2
150000003626 triacylglycerols Chemical class 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000005907 alkyl ester group Chemical group 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
SDVVLIIVFBKBMG-UHFFFAOYSA-N penta-2,4-dienoic acid Chemical compound OC(=O)C=CC=C SDVVLIIVFBKBMG-UHFFFAOYSA-N 0.000 claims 1
230000002335 preservative effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000000699 topical effect Effects 0.000 description 6
210000003491 skin Anatomy 0.000 description 5
239000000243 solution Substances 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
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239000006210 lotion Substances 0.000 description 3
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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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HSZLKTCKAYXVBX-LYIMTGTFSA-N Spiramycin III Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]([C@@H](O[C@H]2[C@@H]([C@H]([C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@](C)(O)C3)[C@@H](C)O2)N(C)C)O)[C@@H](CC=O)C[C@H]1C)OC)OC(=O)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 HSZLKTCKAYXVBX-LYIMTGTFSA-N 0.000 description 1
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241000191963 Staphylococcus epidermidis Species 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
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DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Dermatology (AREA)
Crystallography & Structural Chemistry (AREA)
Epidemiology (AREA)
Birds (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Cosmetics (AREA)

LU87036A 1987-11-04 1987-11-04 Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant LU87036A1 (fr)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
LU87036A LU87036A1 (fr)	1987-11-04	1987-11-04	Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
JP63280218A JPH01193288A (ja)	1987-11-04	1988-11-02	マクロライドおよびリンコサミド抗生物質の不飽和脂環式エステル、その製法および医薬・化粧品
US07/266,598 US5004731A (en)	1987-11-04	1988-11-03	Unsaturated cycloaliphatic esters of macrolidic and lincosamidic antibiotics and pharmaceutical and cosmetic compositions containing them
CA000582116A CA1313660C (fr)	1987-11-04	1988-11-03	Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
ES88402766T ES2063765T3 (es)	1987-11-04	1988-11-03	Esteres cicloalifaticos insaturados de antibioticos macrolidicos y lincosamidicos, su procedimiento de preparacion y composiciones farmaceuticas y cosmeticas que los contienen.
DE3851937T DE3851937T2 (de)	1987-11-04	1988-11-03	Nicht gesättigte cycloaliphatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen.
AT88402766T ATE113290T1 (de)	1987-11-04	1988-11-03	Nicht gesättigte cycloaliphatische ester von makroliden antibiotika und linkosamiden antibiotika, verfahren zu ihrer herstellung und die sie enthaltenden pharmazeutischen und kosmetischen zusammensetzungen.
EP88402766A EP0315535B1 (de)	1987-11-04	1988-11-03	Nicht gesättigte cycloaliphatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU87036A LU87036A1 (fr)	1987-11-04	1987-11-04	Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
LU87036		1987-11-04

Publications (1)

Publication Number	Publication Date
LU87036A1 true LU87036A1 (fr)	1989-06-14

Family

ID=19730979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87036A LU87036A1 (fr)	1987-11-04	1987-11-04	Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

Country Status (8)

Country	Link
US (1)	US5004731A (de)
EP (1)	EP0315535B1 (de)
JP (1)	JPH01193288A (de)
AT (1)	ATE113290T1 (de)
CA (1)	CA1313660C (de)
DE (1)	DE3851937T2 (de)
ES (1)	ES2063765T3 (de)
LU (1)	LU87036A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003264917A1 (en) *	2002-07-08	2004-01-23	Pliva - Istrazivacki Institut D.O.O.	Hybrid molecules of macrolides with steroid/non-steroid anti-inflammatory, antineoplastic and antiviral active molecules
RS20050008A (sr) *	2002-07-08	2007-06-04	Pliva-Istraživački Institut D.O.O.,	Nova jedinjenja,kompozicije i metode za lečenje inflamatornih oboljenja i stanja
EP1521763A2 (de) *	2002-07-08	2005-04-13	Pliva - Istrazivacki Institut d.o.o.	Nicht-steroidische entzündungshemmende wirkstoffe, zusammensetzungen und verfahren zu deren verwendung

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2169104A1 (en) *	1972-01-22	1973-09-07	Tanabe Seiyaku Co	Semi-synthetic macrolide antibiotics and disinfectants - - active against gram positive bacteria
JPS60126296A (ja) *	1983-12-13	1985-07-05	Kyowa Hakko Kogyo Co Ltd	３，３”，４”−トリ−ｏ−アシルスピラマイシン１
LU85144A1 (fr) *	1983-12-16	1985-09-12	Oreal	Derives insatures du camphre,leurs procedes de preparation et leur application dans le domaine therapeutique et cosmetique
LU85777A1 (fr) *	1985-02-20	1986-09-02	Oreal	Derives insatures cycloaliphatiques,leurs procedes de preparation et leur utilisation
FR2582000B1 (fr) *	1985-05-14	1987-06-26	Oreal	Esters gras bi ou tri-eniques d'erythromycine a, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
FR2598420B1 (fr) *	1986-05-06	1991-06-07	Oreal	Nouveaux esters retinoiques d'antibiotiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

1987
- 1987-11-04 LU LU87036A patent/LU87036A1/fr unknown
1988
- 1988-11-02 JP JP63280218A patent/JPH01193288A/ja active Pending
- 1988-11-03 CA CA000582116A patent/CA1313660C/fr not_active Expired - Fee Related
- 1988-11-03 US US07/266,598 patent/US5004731A/en not_active Expired - Fee Related
- 1988-11-03 AT AT88402766T patent/ATE113290T1/de active
- 1988-11-03 ES ES88402766T patent/ES2063765T3/es not_active Expired - Lifetime
- 1988-11-03 DE DE3851937T patent/DE3851937T2/de not_active Expired - Fee Related
- 1988-11-03 EP EP88402766A patent/EP0315535B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0315535A3 (de)	1991-03-27
JPH01193288A (ja)	1989-08-03
DE3851937D1 (de)	1994-12-01
ATE113290T1 (de)	1994-11-15
DE3851937T2 (de)	1995-03-09
US5004731A (en)	1991-04-02
CA1313660C (fr)	1993-02-16
EP0315535A2 (de)	1989-05-10
ES2063765T3 (es)	1995-01-16
EP0315535B1 (de)	1994-10-26

Publication	Publication Date	Title
EP0315540B1 (de)	1992-04-29	Retinoesäure-Ester von Makroliden, ihre Verfahren zur Herstellung und sie enthaltende pharmazeutische und kosmetische Zusammensetzungen
EP0315539B1 (de)	1994-10-26	Polycyclische aromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
CA1253492A (fr)	1989-05-02	Esters gras bi ou tri-eniques d'erythromycine a, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
JPS63502593A (ja)	1988-09-29	マノアリド類似体
BE1001203A3 (fr)	1989-08-16	Composition a base de derives d'hydroxypyridone pour diminuer la chute des cheveux.
CA1300131C (fr)	1992-05-05	Esters retinoiques d'antibiotiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
LU86945A1 (fr)	1989-03-08	Compositions pharmaceutiques et cosmetiques a base de pyridones et d'agents antibacteriens
LU87036A1 (fr)	1989-06-14	Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
EP0315536B1 (de)	1994-10-26	Polyaromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und diese enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
EP0315538B1 (de)	1994-10-26	Biaromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihren Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
EP0315534B1 (de)	1994-10-26	Ester vom Etretintyp und ähnliche Ester von makroliden Antibiotika und linkosamide Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
EP0315537B1 (de)	1994-10-26	Aromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
EP0388314B1 (de)	1994-05-11	Retinsäureester von l-Cladinos, Verfahren zu deren Herstellung und ihre Verwendung in der Human- oder Veterinärmedizin und in der Kosmetik
CA2012219C (fr)	1999-10-12	Esters retinoiques de d-desosamine, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique
EP0373072B1 (de)	1994-10-26	Lipophile Ether und/oder Ester von D-Desosamin, Verfahren zur Herstellung davon und ihre Verwendung als Fungizide und Bakterizide