LU87040A1 - Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant - Google Patents

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

Info

Publication number: LU87040A1
Authority: LU; Luxembourg
Prior art keywords: esters; tetrahydro; tetramethyl; erythromycin; compounds according
Prior art date: 1987-11-04

Application number

LU87040A

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 LU87040A priority Critical patent/LU87040A1/fr

1988-11-02 Priority to JP63280220A priority patent/JPH01193290A/ja

1988-11-03 Priority to AT88402770T priority patent/ATE113294T1/de

1988-11-03 Priority to ES88402770T priority patent/ES2063767T3/es

1988-11-03 Priority to EP88402770A priority patent/EP0315539B1/de

1988-11-03 Priority to DE3851941T priority patent/DE3851941T2/de

1988-11-03 Priority to US07/266,599 priority patent/US5004730A/en

1988-11-03 Priority to CA000582110A priority patent/CA1313656C/fr

1989-06-14 Publication of LU87040A1 publication Critical patent/LU87040A1/fr

Links

239000000203 mixture Substances 0.000 title claims description 35
238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 11
239000002537 cosmetic Substances 0.000 title claims description 9
230000008569 process Effects 0.000 title claims description 7
239000003242 anti bacterial agent Substances 0.000 title abstract description 11
229940088710 antibiotic agent Drugs 0.000 title abstract description 11
208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 13
206010000496 acne Diseases 0.000 claims abstract description 13
150000002148 esters Chemical class 0.000 claims description 30
229960003276 erythromycin Drugs 0.000 claims description 24
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
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
-1 roxythromycin Chemical compound 0.000 claims description 14
239000003120 macrolide antibiotic agent Substances 0.000 claims description 13
229960002227 clindamycin Drugs 0.000 claims description 12
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
229960005287 lincomycin Drugs 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
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
229930006677 Erythromycin A Natural products 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
239000002253 acid Substances 0.000 claims description 7
229960004144 josamycin Drugs 0.000 claims description 7
239000004187 Spiramycin Substances 0.000 claims description 6
229940041028 lincosamides Drugs 0.000 claims description 6
229940041033 macrolides Drugs 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
239000004104 Oleandomycin 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
229960002351 oleandomycin Drugs 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical group C#C HSFWRNGVRCDJHI-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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
125000004433 nitrogen atom Chemical group N* 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
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
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
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
235000019367 oleandomycin Nutrition 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000002971 oxazolyl group Chemical group 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
150000003839 salts Chemical class 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
229960001294 spiramycin Drugs 0.000 claims description 2
239000002562 thickening agent Substances 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
150000003626 triacylglycerols Chemical class 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000005870 benzindolyl group Chemical group 0.000 claims 1
HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
235000010755 mineral Nutrition 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000003367 polycyclic group Chemical group 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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
239000006210 lotion Substances 0.000 description 3
241000186427 Cutibacterium acnes Species 0.000 description 2
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
230000009471 action Effects 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000000499 gel Substances 0.000 description 2
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230000002458 infectious effect Effects 0.000 description 2
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229940055019 propionibacterium acne Drugs 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
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
235000014493 Crataegus Nutrition 0.000 description 1
241001092040 Crataegus Species 0.000 description 1
201000004624 Dermatitis Diseases 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
241000446386 Patis Species 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
125000002252 acyl group Chemical group 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
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
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000002995 comedolytic effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product 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
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 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
238000004128 high performance liquid chromatography Methods 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
238000011835 investigation Methods 0.000 description 1
238000002955 isolation 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
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239000002674 ointment Substances 0.000 description 1
239000012074 organic phase 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
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229940002612 prodrug Drugs 0.000 description 1
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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
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229950003659 spiramycin iii Drugs 0.000 description 1
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238000003756 stirring Methods 0.000 description 1
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239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
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230000009466 transformation Effects 0.000 description 1
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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
- A61K8/60—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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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
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Animal Behavior & Ethology (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Dermatology (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Cosmetics (AREA)

LU87040A 1987-11-04 1987-11-04 Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant LU87040A1 (fr)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
LU87040A LU87040A1 (fr)	1987-11-04	1987-11-04	Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
JP63280220A JPH01193290A (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多環式芳香族エステル、その製法、並びに医薬・化粧品
AT88402770T ATE113294T1 (de)	1987-11-04	1988-11-03	Polycyclische aromatische ester von makroliden antibiotika und linkosamiden antibiotika, verfahren zu ihrer herstellung und die sie enthaltenden pharmazeutischen und kosmetischen zusammensetzungen.
ES88402770T ES2063767T3 (es)	1987-11-04	1988-11-03	Esteres aromaticos policiclicos de antibioticos macrolidicos y lincosamidicos, su procedimiento de preparacion y composiciones farmaceuticas y cosmeticas que los contienen.
EP88402770A EP0315539B1 (de)	1987-11-04	1988-11-03	Polycyclische aromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen
DE3851941T DE3851941T2 (de)	1987-11-04	1988-11-03	Polycyclische aromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen.
US07/266,599 US5004730A (en)	1987-11-04	1988-11-03	Polycyclic aromatic esters of macrolidic and lincosamidic antibiotics and pharmaceutical and cosmetic compositions containing them
CA000582110A CA1313656C (fr)	1987-11-04	1988-11-03	Estersaromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU87040A LU87040A1 (fr)	1987-11-04	1987-11-04	Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant
LU87040		1987-11-04

Publications (1)

Publication Number	Publication Date
LU87040A1 true LU87040A1 (fr)	1989-06-14

Family

ID=19730983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87040A LU87040A1 (fr)	1987-11-04	1987-11-04	Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant

Country Status (8)

Country	Link
US (1)	US5004730A (de)
EP (1)	EP0315539B1 (de)
JP (1)	JPH01193290A (de)
AT (1)	ATE113294T1 (de)
CA (1)	CA1313656C (de)
DE (1)	DE3851941T2 (de)
ES (1)	ES2063767T3 (de)
LU (1)	LU87040A1 (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2614618B1 (fr) *	1987-04-30	1989-07-07	Cird	Derives heterocycliques polycycliques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire
EP0638071B1 (de) *	1992-12-28	1997-04-09	Eisai Co., Ltd.	Heterocyclische carbonsäure-derivate, die an rar rezeptoren binden können
US5770382A (en) *	1994-12-30	1998-06-23	Ligand Pharmaceuticals, Inc.	Tricyclic retinoids, methods for their production and use
US5770383A (en) *	1994-12-30	1998-06-23	Ligand Pharmaceuticals, Inc.	Tricyclic retinoids, methods for their production and use
US5770378A (en) *	1994-12-30	1998-06-23	Ligand Pharmaceuticals, Inc.	Tricyclic retinoids, methods for their production and use
WO1996034007A1 (es) *	1995-04-27	1996-10-31	Laboratorios Aranda, S.A. De C.V.	Derivados de quinolonilcarboxieritromicina y composiciones farmaceuticas que los contienen
AU726450B2 (en)	1995-10-06	2000-11-09	Ligand Pharmaceuticals Incorporated	Dimer-selective RXR modulators and methods for their use
CA2334545A1 (en) *	1998-06-12	1999-12-16	Ligand Pharmaceuticals Incorporated	Treatment of anti-estrogen resistant breast cancer using rxr modulators
US6566372B1 (en)	1999-08-27	2003-05-20	Ligand Pharmaceuticals Incorporated	Bicyclic androgen and progesterone receptor modulator compounds and methods
EP1212322A2 (de)	1999-08-27	2002-06-12	Ligand Pharmaceuticals Incorporated	8-substituierte-6-trifluoromethyl-9-pyrido[3,2-g]chiolinverbindungen als androgen rezeptormodulatoren
MXPA02002032A (es)	1999-08-27	2003-05-19	Ligand Pharm Inc	Compuestos moduladores del receptor de androgeno y metodos.
US6593493B1 (en)	1999-09-14	2003-07-15	Ligand Pharmaceuticals, Inc.	RXR modulators with improved pharmacologic profile
US9050310B2 (en) *	2004-06-25	2015-06-09	Minas Theodore Coroneo	Treatment of ocular lesions
US20060204474A1 (en) *	2005-02-25	2006-09-14	Coroneo Minas T	Treatment of epithelial layer lesions
US11045441B2 (en)	2015-10-13	2021-06-29	Wisconsin Alumni Research Foundation	Use of retinoic acid and analogs thereof to treat central neural apneas
US11566039B2 (en)	2017-08-10	2023-01-31	President And Fellows Of Harvard College	Lincosamide antibiotics and uses thereof
WO2019032936A1 (en) *	2017-08-10	2019-02-14	President Adn Fellows Of Harvard College	LINCONSAMIDE ANTIBIOTICS AND USES THEREOF

Family Cites Families (5)

* 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
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
LU86022A1 (fr) *	1985-07-25	1987-02-04	Cird	Derives aromatiques polycyliques,leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique
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 LU87040A patent/LU87040A1/fr unknown
1988
- 1988-11-02 JP JP63280220A patent/JPH01193290A/ja active Pending
- 1988-11-03 DE DE3851941T patent/DE3851941T2/de not_active Expired - Fee Related
- 1988-11-03 EP EP88402770A patent/EP0315539B1/de not_active Expired - Lifetime
- 1988-11-03 US US07/266,599 patent/US5004730A/en not_active Expired - Fee Related
- 1988-11-03 AT AT88402770T patent/ATE113294T1/de active
- 1988-11-03 CA CA000582110A patent/CA1313656C/fr not_active Expired - Fee Related
- 1988-11-03 ES ES88402770T patent/ES2063767T3/es not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE3851941T2 (de)	1995-04-27
EP0315539B1 (de)	1994-10-26
CA1313656C (fr)	1993-02-16
ES2063767T3 (es)	1995-01-16
JPH01193290A (ja)	1989-08-03
EP0315539A2 (de)	1989-05-10
EP0315539A3 (de)	1991-03-20
DE3851941D1 (de)	1994-12-01
ATE113294T1 (de)	1994-11-15
US5004730A (en)	1991-04-02

Publication	Publication Date	Title
CA2102454C (fr)	2001-02-27	Derives de l'erythromycine, leur procede de preparation, leur application comme medicaments
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
EP0210929B1 (de)	1992-06-03	Aromatische polycyclische Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen und kosmetischen Zubereitungen
EP0315540B1 (de)	1992-04-29	Retinoesäure-Ester von Makroliden, ihre Verfahren zur Herstellung und sie enthaltende pharmazeutische und kosmetische Zusammensetzungen
EP0596802A1 (de)	1994-05-11	Erythromycinderivate, ihr Verfahren zur Herstellung und ihre Verwendung als Arzneimitteln
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.
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
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
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
EP0772630B1 (de)	2001-09-19	Streptograminderivate, ihre herstellung und sie enthaltende pharmazeutische zubereitungen
CA2012218A1 (fr)	1990-09-16	Esters retinoiques de l-cladinose, 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
BE862019R (fr)	1978-06-19	Nouveaux derives de la vincamine, leur preparation et leur application comme medicaments