LU87035A1 - Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant - Google Patents

Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant Download PDF

Info

Publication number: LU87035A1
Authority: LU; Luxembourg
Prior art keywords: esters; garlic; trans; compounds according; erythromycin
Prior art date: 1987-11-04

Application number

LU87035A

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 LU87035A priority Critical patent/LU87035A1/fr

1988-11-02 Priority to JP63280216A priority patent/JPH01193286A/ja

1988-11-03 Priority to AT88402765T priority patent/ATE113289T1/de

1988-11-03 Priority to ES88402765T priority patent/ES2063055T3/es

1988-11-03 Priority to EP88402765A priority patent/EP0315534B1/de

1988-11-03 Priority to DE3851936T priority patent/DE3851936T2/de

1988-11-03 Priority to CA000582115A priority patent/CA1314874C/fr

1988-11-03 Priority to US07/266,611 priority patent/US5004733A/en

1989-06-14 Publication of LU87035A1 publication Critical patent/LU87035A1/fr

Links

239000000203 mixture Substances 0.000 title claims abstract description 37
239000002537 cosmetic Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 11
239000003242 anti bacterial agent Substances 0.000 title description 8
229940088710 antibiotic agent Drugs 0.000 title description 8
150000002148 esters Chemical class 0.000 claims abstract description 44
239000003120 macrolide antibiotic agent Substances 0.000 claims abstract description 14
208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 13
206010000496 acne Diseases 0.000 claims abstract description 13
-1 alkyl radical Chemical class 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
229940041028 lincosamides Drugs 0.000 claims abstract description 7
229940041033 macrolides Drugs 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
150000003254 radicals Chemical class 0.000 claims abstract description 5
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 3
240000002234 Allium sativum Species 0.000 claims description 25
235000004611 garlic Nutrition 0.000 claims description 25
229960003276 erythromycin Drugs 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
229960002227 clindamycin Drugs 0.000 claims description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
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 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
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 14
229960005287 lincomycin Drugs 0.000 claims description 14
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 13
150000001875 compounds Chemical class 0.000 claims description 12
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 10
239000002253 acid Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
229930006677 Erythromycin A Natural products 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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 6
229960002351 oleandomycin Drugs 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
201000004681 Psoriasis Diseases 0.000 claims description 5
239000004187 Spiramycin Substances 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
229960004144 josamycin Drugs 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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
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
229930191512 spiramycin Natural products 0.000 claims description 4
235000019372 spiramycin Nutrition 0.000 claims description 4
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 4
150000007513 acids Chemical class 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
239000003795 chemical substances by application 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
150000007530 organic bases Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
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 2
230000003255 anti-acne Effects 0.000 claims description 2
230000002682 anti-psoriatic effect Effects 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
239000001913 cellulose Substances 0.000 claims description 2
229920002678 cellulose Polymers 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
235000019367 oleandomycin Nutrition 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
125000005907 alkyl ester group Chemical group 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
235000010755 mineral Nutrition 0.000 claims 1
230000002335 preservative effect Effects 0.000 claims 1
229960001294 spiramycin Drugs 0.000 claims 1
201000004624 Dermatitis Diseases 0.000 abstract description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
230000000699 topical effect Effects 0.000 description 6
210000003491 skin Anatomy 0.000 description 5
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
230000008569 process Effects 0.000 description 4
239000012298 atmosphere Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000006210 lotion Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000004452 microanalysis Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000186427 Cutibacterium acnes Species 0.000 description 2
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
230000009471 action Effects 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
239000000499 gel Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
230000035515 penetration Effects 0.000 description 2
229940055019 propionibacterium acne Drugs 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
OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 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
101150041968 CDC13 gene Proteins 0.000 description 1
101100275770 Caenorhabditis elegans cri-3 gene Proteins 0.000 description 1
235000014493 Crataegus Nutrition 0.000 description 1
241001092040 Crataegus Species 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
125000002252 acyl group Chemical group 0.000 description 1
239000000443 aerosol 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
230000008901 benefit Effects 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
230000002995 comedolytic effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
239000000839 emulsion Substances 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
150000002194 fatty esters Chemical class 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
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
229940049918 linoleate Drugs 0.000 description 1
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
229940040452 linolenate Drugs 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 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
210000000434 stratum corneum Anatomy 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
230000029305 taxis Effects 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
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- 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
- 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

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

LU87035A 1987-11-04 1987-11-04 Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant LU87035A1 (fr)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
LU87035A LU87035A1 (fr)	1987-11-04	1987-11-04	Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
JP63280216A JPH01193286A (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エトレチニック型または近縁エステル、その製法および医薬・化粧品
AT88402765T ATE113289T1 (de)	1987-11-04	1988-11-03	Ester vom etretintyp und ähnliche ester von makroliden antibiotika und linkosamide antibiotika, verfahren zu ihrer herstellung und die sie enthaltenden pharmazeutischen und kosmetischen zusammensetzungen.
ES88402765T ES2063055T3 (es)	1987-11-04	1988-11-03	Esteres de tipo etretinico o emparentado de antibioticos macrolidicos y lincosamidicos, su procedimiento de preparacion y composiciones farmaceuticas y cosmeticas que los contienen.
EP88402765A EP0315534B1 (de)	1987-11-04	1988-11-03	Ester vom Etretintyp und ähnliche Ester von makroliden Antibiotika und linkosamide Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
DE3851936T DE3851936T2 (de)	1987-11-04	1988-11-03	Ester vom Etretintyp und ähnliche Ester von makroliden Antibiotika und linkosamide Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen.
CA000582115A CA1314874C (fr)	1987-11-04	1988-11-03	Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
US07/266,611 US5004733A (en)	1987-11-04	1988-11-03	Esters of the etretinic type or related to macrolidic and lincosamidic antibiotics and pharmaceutical and cosmetic compositions containing said esters

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU87035A LU87035A1 (fr)	1987-11-04	1987-11-04	Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
LU87035		1987-11-04

Publications (1)

Publication Number	Publication Date
LU87035A1 true LU87035A1 (fr)	1989-06-14

Family

ID=19730978

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87035A LU87035A1 (fr)	1987-11-04	1987-11-04	Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

Country Status (8)

Country	Link
US (1)	US5004733A (de)
EP (1)	EP0315534B1 (de)
JP (1)	JPH01193286A (de)
AT (1)	ATE113289T1 (de)
CA (1)	CA1314874C (de)
DE (1)	DE3851936T2 (de)
ES (1)	ES2063055T3 (de)
LU (1)	LU87035A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2644460A1 (fr) *	1989-03-16	1990-09-21	Oreal	Esters retinoiques de d-desosamine, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique
CN116196264B (zh) *	2022-12-21	2025-12-19	江苏远恒药业有限公司	一种炎症响应的制霉素脂肪酸酯阴道栓剂的制备方法及其产品和应用

Family Cites Families (7)

* 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
CH661516A5 (de) *	1983-12-08	1987-07-31	Hoffmann La Roche	Phenylnonatetraenoylzuckerderivate.
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
IT1203634B (it) *	1984-08-13	1989-02-15	Oreal	Derivati 1-sostituiti del 4-metossi-2,3,6-trimetilbenzene loro procedimento di preparazione e composizioni medicamentose e cosmetiche che li contengono
LU85558A1 (fr) *	1984-09-28	1986-04-03	Oreal	Nouveaux derives naphtaleniques a action retinoique,leurs procedes de preparation et compositions medicamenteuse et cosmetique les contenant
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 LU87035A patent/LU87035A1/fr unknown
1988
- 1988-11-02 JP JP63280216A patent/JPH01193286A/ja active Pending
- 1988-11-03 US US07/266,611 patent/US5004733A/en not_active Expired - Fee Related
- 1988-11-03 AT AT88402765T patent/ATE113289T1/de active
- 1988-11-03 ES ES88402765T patent/ES2063055T3/es not_active Expired - Lifetime
- 1988-11-03 EP EP88402765A patent/EP0315534B1/de not_active Expired - Lifetime
- 1988-11-03 CA CA000582115A patent/CA1314874C/fr not_active Expired - Fee Related
- 1988-11-03 DE DE3851936T patent/DE3851936T2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0315534A3 (de)	1991-03-27
EP0315534A2 (de)	1989-05-10
DE3851936D1 (de)	1994-12-01
CA1314874C (fr)	1993-03-23
ES2063055T3 (es)	1995-01-01
EP0315534B1 (de)	1994-10-26
DE3851936T2 (de)	1995-03-09
US5004733A (en)	1991-04-02
ATE113289T1 (de)	1994-11-15
JPH01193286A (ja)	1989-08-03

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
CH666679A5 (fr)	1988-08-15	Derives naphtaleniques a action retinoique, leurs procedes de preparation et compositions medicamenteuse et cosmetique les contenant.
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
EP0315536B1 (de)	1994-10-26	Polyaromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und diese enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
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
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
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
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
EP0404640A1 (de)	1990-12-27	5,6,7,8-Tetrahydro-1-naphthalenolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antioxidationsmittel in kosmetischen und pharmazeutischen 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
CH618978A5 (de)	1980-08-29
BE862019R (fr)	1978-06-19	Nouveaux derives de la vincamine, leur preparation et leur application comme medicaments
FR2499571A1 (fr)	1982-08-13	Nouveaux derives d'apovincaminol, leur preparation et leur application en tant que medicaments
EP0373072B1 (de)	1994-10-26	Lipophile Ether und/oder Ester von D-Desosamin, Verfahren zur Herstellung davon und ihre Verwendung als Fungizide und Bakterizide