LU87041A1 - Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant - Google Patents

Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant Download PDF

Info

Publication number: LU87041A1
Authority: LU; Luxembourg
Prior art keywords: retinoyl; esters; trans; garlic; josamycin
Prior art date: 1987-11-04

Application number

LU87041A

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 LU87041A priority Critical patent/LU87041A1/fr

1988-08-24 Priority to US07/235,853 priority patent/US5045533A/en

1988-11-02 Priority to JP63276360A priority patent/JP2736258B2/ja

1988-11-03 Priority to CA000582109A priority patent/CA1313662C/fr

1988-11-03 Priority to DE198888402771T priority patent/DE315540T1/de

1988-11-03 Priority to EP88402771A priority patent/EP0315540B1/de

1988-11-03 Priority to DE8888402771T priority patent/DE3870582D1/de

1988-11-03 Priority to AT88402771T priority patent/ATE75482T1/de

1988-11-03 Priority to ES198888402771T priority patent/ES2009730T3/es

1989-06-14 Publication of LU87041A1 publication Critical patent/LU87041A1/fr

1990-01-30 Priority to GR89300130T priority patent/GR890300130T1/el

1992-07-13 Priority to GR920401501T priority patent/GR3005156T3/el

Links

239000000203 mixture Substances 0.000 title claims abstract description 31
239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 13
229940041033 macrolides Drugs 0.000 title claims abstract description 7
239000002537 cosmetic Substances 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title description 9
150000002148 esters Chemical class 0.000 claims abstract description 31
208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 12
206010000496 acne Diseases 0.000 claims abstract description 12
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims abstract description 5
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 abstract description 3
229930006677 Erythromycin A Natural products 0.000 claims abstract description 3
229960003276 erythromycin Drugs 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 3
SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical class OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims abstract 2
240000002234 Allium sativum Species 0.000 claims description 18
235000004611 garlic Nutrition 0.000 claims description 18
229960004144 josamycin Drugs 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
239000004187 Spiramycin Substances 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
239000004104 Oleandomycin Substances 0.000 claims description 7
229960002351 oleandomycin Drugs 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 claims description 5
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
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 5
235000019367 oleandomycin Nutrition 0.000 claims description 5
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
229960001294 spiramycin Drugs 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
229930002330 retinoic acid Natural products 0.000 claims description 4
229930191512 spiramycin Natural products 0.000 claims description 4
235000019372 spiramycin Nutrition 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
229960001727 tretinoin Drugs 0.000 claims description 4
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 compound 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 3
239000002253 acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
150000004665 fatty acids Chemical class 0.000 claims description 3
ACTOXUHEUCPTEW-UHFFFAOYSA-N spiramycins Chemical class CC1CC(CC=O)C(OC2C(C(C(OC3OC(C)C(O)C(C)(O)C3)C(C)O2)N(C)C)O)C(OC)C(O)CC(=O)OC(C)CC=CC=CC1OC1CCC(N(C)C)C(C)O1 ACTOXUHEUCPTEW-UHFFFAOYSA-N 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
239000000058 anti acne agent Substances 0.000 claims description 2
229940124340 antiacne agent Drugs 0.000 claims description 2
239000001913 cellulose Substances 0.000 claims description 2
229920002678 cellulose Polymers 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
239000002304 perfume Substances 0.000 claims description 2
229920001296 polysiloxane Polymers 0.000 claims description 2
229920000909 polytetrahydrofuran Polymers 0.000 claims description 2
239000003755 preservative agent Substances 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
239000002562 thickening agent Substances 0.000 claims description 2
150000003626 triacylglycerols Chemical class 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims 2
150000007530 organic bases Chemical class 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
230000002335 preservative effect Effects 0.000 claims 1
201000004624 Dermatitis Diseases 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
210000003491 skin Anatomy 0.000 description 4
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
239000006210 lotion Substances 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
FPPBCRLXUHYGHR-UHFFFAOYSA-N 2-tert-butyl-3-hydroxycyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=C(O)C(=O)C=CC1=O FPPBCRLXUHYGHR-UHFFFAOYSA-N 0.000 description 1
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
235000014493 Crataegus Nutrition 0.000 description 1
241001092040 Crataegus Species 0.000 description 1
241000186427 Cutibacterium acnes Species 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
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
ZPCCSZFPOXBNDL-LWXQEXJOSA-N Spiramycin-II Natural products CO[C@H]1[C@@H](CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C)OC(=O)C ZPCCSZFPOXBNDL-LWXQEXJOSA-N 0.000 description 1
HSZLKTCKAYXVBX-VPIGJTHDSA-N Spiramycin-III Natural products CCC(=O)O[C@@H]1CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C)[C@H]1OC HSZLKTCKAYXVBX-VPIGJTHDSA-N 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000013475 authorization Methods 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
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
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
229940055019 propionibacterium acne Drugs 0.000 description 1
ACTOXUHEUCPTEW-ZOTSFZJCSA-N spiramycin I Natural products CO[C@H]1[C@H](O)CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C ACTOXUHEUCPTEW-ZOTSFZJCSA-N 0.000 description 1
ZPCCSZFPOXBNDL-RSMXASMKSA-N spiramycin II Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([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)OC(C)=O)[C@H]1CC[C@H](N(C)C)[C@H](C)O1 ZPCCSZFPOXBNDL-RSMXASMKSA-N 0.000 description 1
229950001955 spiramycin i Drugs 0.000 description 1
229950006796 spiramycin ii Drugs 0.000 description 1
229950003659 spiramycin iii Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

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
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
- 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

Landscapes

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)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Dermatology (AREA)
Crystallography & Structural Chemistry (AREA)
Birds (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Cosmetics (AREA)
Pyrrole Compounds (AREA)
Pyrane Compounds (AREA)

LU87041A 1986-05-06 1987-11-04 Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant LU87041A1 (fr)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
LU87041A LU87041A1 (fr)	1987-11-04	1987-11-04	Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
US07/235,853 US5045533A (en)	1986-05-06	1988-08-24	Retinoic esters of antibiotics and pharmaceutical and cosmetic compositions containing them
JP63276360A JP2736258B2 (ja)	1987-11-04	1988-11-02	マクロライドのレチノイン酸エステル、その製造方法及びこれを含有する化粧料組成物
EP88402771A EP0315540B1 (de)	1987-11-04	1988-11-03	Retinoesäure-Ester von Makroliden, ihre Verfahren zur Herstellung und sie enthaltende pharmazeutische und kosmetische Zusammensetzungen
DE198888402771T DE315540T1 (de)	1987-11-04	1988-11-03	Retinoesaeure-ester von makroliden, ihre verfahren zur herstellung und sie enthaltende pharmazeutische und kosmetische zusammensetzungen.
CA000582109A CA1313662C (fr)	1987-11-04	1988-11-03	Esters retinoiques de macrolides, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
DE8888402771T DE3870582D1 (de)	1987-11-04	1988-11-03	Retinoesaeure-ester von makroliden, ihre verfahren zur herstellung und sie enthaltende pharmazeutische und kosmetische zusammensetzungen.
AT88402771T ATE75482T1 (de)	1987-11-04	1988-11-03	Retinoesaeure-ester von makroliden, ihre verfahren zur herstellung und sie enthaltende pharmazeutische und kosmetische zusammensetzungen.
ES198888402771T ES2009730T3 (es)	1987-11-04	1988-11-03	Esteres retinoicos de macrolidos, su procedimiento de preparacion y composiciones farmaceuticas y cosmeticas que los contienen.
GR89300130T GR890300130T1 (en)	1987-11-04	1990-01-30	Retinoic esters of macrolides, method for their preparation and pharmaceutical and cosmetic compositions containing them
GR920401501T GR3005156T3 (de)	1987-11-04	1992-07-13

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU87041		1987-11-04
LU87041A LU87041A1 (fr)	1987-11-04	1987-11-04	Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

Publications (1)

Publication Number	Publication Date
LU87041A1 true LU87041A1 (fr)	1989-06-14

Family

ID=19730984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87041A LU87041A1 (fr)	1986-05-06	1987-11-04	Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

Country Status (9)

Country	Link
US (1)	US5045533A (de)
EP (1)	EP0315540B1 (de)
JP (1)	JP2736258B2 (de)
AT (1)	ATE75482T1 (de)
CA (1)	CA1313662C (de)
DE (2)	DE3870582D1 (de)
ES (1)	ES2009730T3 (de)
GR (2)	GR890300130T1 (de)
LU (1)	LU87041A1 (de)

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* Cited by examiner, † Cited by third party
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GB2282596B (en) *	1993-10-06	1998-04-15	Ciba Geigy Ag	Water-soluble retinoids
US6565882B2 (en)	2000-02-24	2003-05-20	Advancis Pharmaceutical Corp	Antibiotic composition with inhibitor
US6544555B2 (en)	2000-02-24	2003-04-08	Advancis Pharmaceutical Corp.	Antibiotic product, use and formulation thereof
US6541014B2 (en)	2000-10-13	2003-04-01	Advancis Pharmaceutical Corp.	Antiviral product, use and formulation thereof
US20020068078A1 (en)	2000-10-13	2002-06-06	Rudnic Edward M.	Antifungal product, use and formulation thereof
AU2004258953B2 (en)	2003-07-21	2011-02-10	Shionogi, Inc.	Antibiotic product, use and formulation thereof
AU2004258949B2 (en)	2003-07-21	2011-02-10	Shionogi, Inc.	Antibiotic product, use and formulation thereof
JP2006528185A (ja)	2003-07-21	2006-12-14	アドバンシスファーマスーティカルコーポレイション	抗生物質製剤、その使用法及び作成方法
CA2535177A1 (en)	2003-08-11	2005-02-24	Advancis Pharmaceutical Corporation	Robust pellet
US8062672B2 (en)	2003-08-12	2011-11-22	Shionogi Inc.	Antibiotic product, use and formulation thereof
AU2004270170B2 (en) *	2003-08-29	2011-01-27	Shionogi, Inc.	Antibiotic product, use and formulation thereof
CA2538064C (en)	2003-09-15	2013-12-17	Advancis Pharmaceutical Corporation	Antibiotic product, use and formulation thereof
CA2572292A1 (en)	2004-07-02	2006-02-09	Advancis Pharmaceutical Corporation	Tablet for pulsed delivery
US8778924B2 (en)	2006-12-04	2014-07-15	Shionogi Inc.	Modified release amoxicillin products
US8357394B2 (en)	2005-12-08	2013-01-22	Shionogi Inc.	Compositions and methods for improved efficacy of penicillin-type antibiotics
US8299052B2 (en) *	2006-05-05	2012-10-30	Shionogi Inc.	Pharmaceutical compositions and methods for improved bacterial eradication
US11072575B1 (en) *	2020-09-19	2021-07-27	Xi'an Taikomed Pharmaceutical Technology Co., Ltd.	Method of preparing a cinnamyl alcohol retinoic acid ester with antioxidant and antibacterial activities
WO2023187197A1 (en) *	2022-03-31	2023-10-05	Université De Genève	Conjugates of antimicrobial agents with a tocopheryl or tocotrienyl group

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4056616A (en) *	1976-03-05	1977-11-01	Schering Corporation	Rosamicin derivatives and method of using same
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
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 LU87041A patent/LU87041A1/fr unknown
1988
- 1988-08-24 US US07/235,853 patent/US5045533A/en not_active Expired - Lifetime
- 1988-11-02 JP JP63276360A patent/JP2736258B2/ja not_active Expired - Lifetime
- 1988-11-03 DE DE8888402771T patent/DE3870582D1/de not_active Expired - Lifetime
- 1988-11-03 CA CA000582109A patent/CA1313662C/fr not_active Expired - Lifetime
- 1988-11-03 AT AT88402771T patent/ATE75482T1/de not_active IP Right Cessation
- 1988-11-03 EP EP88402771A patent/EP0315540B1/de not_active Expired - Lifetime
- 1988-11-03 ES ES198888402771T patent/ES2009730T3/es not_active Expired - Lifetime
- 1988-11-03 DE DE198888402771T patent/DE315540T1/de active Pending
1990
- 1990-01-30 GR GR89300130T patent/GR890300130T1/el unknown
1992
- 1992-07-13 GR GR920401501T patent/GR3005156T3/el unknown

Also Published As

Publication number	Publication date
US5045533A (en)	1991-09-03
ES2009730T3 (es)	1993-08-01
JPH01193293A (ja)	1989-08-03
JP2736258B2 (ja)	1998-04-02
EP0315540A1 (de)	1989-05-10
GR3005156T3 (de)	1993-05-24
DE315540T1 (de)	1989-10-05
CA1313662C (fr)	1993-02-16
ES2009730A4 (es)	1989-10-16
EP0315540B1 (de)	1992-04-29
DE3870582D1 (de)	1992-06-04
ATE75482T1 (de)	1992-05-15
GR890300130T1 (en)	1990-01-31

Publication	Publication Date	Title
LU87041A1 (fr)	1989-06-14	Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
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
LU85558A1 (fr)	1986-04-03	Nouveaux derives naphtaleniques a action retinoique,leurs procedes de preparation et compositions medicamenteuse et cosmetique les contenant
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
BE1001203A3 (fr)	1989-08-16	Composition a base de derives d'hydroxypyridone pour diminuer la chute des cheveux.
EP0409728A2 (de)	1991-01-23	Bi-aromatische Ester, Verfahren zu ihrer Herstellung und ihre Verwendung in der menschlichen oder tierischen Heilkunde und in der Kosmetik
LU86945A1 (fr)	1989-03-08	Compositions pharmaceutiques et cosmetiques a base de pyridones et d'agents antibacteriens
EP0315536B1 (de)	1994-10-26	Polyaromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und diese enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
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.
CA1313657C (fr)	1993-02-16	Esters bioaromatiques d'antibiotiques macrolidiques et lincosamidiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
EP0315535B1 (de)	1994-10-26	Nicht gesättigte cycloaliphatische Ester von makroliden Antibiotika und linkosamiden 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
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
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
CA1273580A (fr)	1990-09-04	Compositions pharmaceutiques contenant a titre de principe actif au moins un mono, di ou tri-ester de dihydroxy-1,8 phenyl-10 anthrone-9 ou anthranol-9
CH668420A5 (fr)	1988-12-30	Hydroxy-1 acyloxy-8 acyl-10 anthrones, leur preparation et compositions therapeutiques et cosmetiques les contenant.
CH651290A5 (fr)	1985-09-13	Derives de la serie des dihydroxy-1,8 anthrones-9 substituees en position 10 par un radical insature.
EP0373072A1 (de)	1990-06-13	Lipophile Ether und/oder Ester von D-Desosamin, Verfahren zur Herstellung davon und ihre Verwendung als Fungizide und Bakterizide