NL193946C - Alkeenzuuresters van een antibioticum alsmede farmaceutische en cosmetische preparaten die dergelijke esters bevatten. - Google Patents
Alkeenzuuresters van een antibioticum alsmede farmaceutische en cosmetische preparaten die dergelijke esters bevatten. Download PDFInfo
- Publication number
- NL193946C NL193946C NL8701054A NL8701054A NL193946C NL 193946 C NL193946 C NL 193946C NL 8701054 A NL8701054 A NL 8701054A NL 8701054 A NL8701054 A NL 8701054A NL 193946 C NL193946 C NL 193946C
- Authority
- NL
- Netherlands
- Prior art keywords
- retinoyl
- erythromycin
- cis
- trans
- clindamycin
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 31
- 239000003242 anti bacterial agent Substances 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 25
- 239000002253 acid Substances 0.000 title claims description 15
- 230000003115 biocidal effect Effects 0.000 title claims description 11
- 239000002537 cosmetic Substances 0.000 title claims description 8
- 150000001336 alkenes Chemical class 0.000 title description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 3
- 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 58
- 229960003276 erythromycin Drugs 0.000 claims description 58
- 229960002227 clindamycin Drugs 0.000 claims description 43
- 229960005287 lincomycin Drugs 0.000 claims description 36
- 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 29
- 229930006677 Erythromycin A Natural products 0.000 claims description 27
- 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 26
- 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 26
- 239000000203 mixture Substances 0.000 claims description 25
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 13
- SHGAZHPCJJPHSC-XFYACQKRSA-N isotretinoin Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-XFYACQKRSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 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 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
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- 229940088710 antibiotic agent Drugs 0.000 description 22
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- 230000000694 effects Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
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- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 210000003491 skin Anatomy 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 229930002330 retinoic acid Natural products 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000186427 Cutibacterium acnes Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 6
- 229940055019 propionibacterium acne Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 retinoic acid imidazolides Chemical class 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
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- 238000005886 esterification reaction Methods 0.000 description 4
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- 239000003960 organic solvent Substances 0.000 description 4
- 125000001444 retinoyl group Chemical group O=C([*])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- 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
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8606528 | 1986-05-06 | ||
| FR8606528A FR2598420B1 (fr) | 1986-05-06 | 1986-05-06 | Nouveaux esters retinoiques d'antibiotiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8701054A NL8701054A (nl) | 1987-12-01 |
| NL193946B NL193946B (nl) | 2000-11-01 |
| NL193946C true NL193946C (nl) | 2001-03-02 |
Family
ID=9334966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8701054A NL193946C (nl) | 1986-05-06 | 1987-05-04 | Alkeenzuuresters van een antibioticum alsmede farmaceutische en cosmetische preparaten die dergelijke esters bevatten. |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JP2504990B2 (no) |
| BE (1) | BE1004152A4 (no) |
| CA (1) | CA1300131C (no) |
| CH (1) | CH674847A5 (no) |
| DE (1) | DE3714937C2 (no) |
| DK (1) | DK169345B1 (no) |
| ES (1) | ES2006478A6 (no) |
| FR (1) | FR2598420B1 (no) |
| GB (1) | GB2191483B (no) |
| IT (1) | IT1204556B (no) |
| NL (1) | NL193946C (no) |
| NO (1) | NO168041C (no) |
| SE (1) | SE470379B (no) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU87041A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87039A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters biaromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87036A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87035A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87040A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87038A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters aromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87037A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters polyaromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87070A1 (fr) * | 1987-12-10 | 1989-07-07 | Oreal | Association de derives de pyrimidine et d'agents pour induire et stimuler la croissance des cheveux et diminuer leur chute |
| 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 |
| GB2282596B (en) * | 1993-10-06 | 1998-04-15 | Ciba Geigy Ag | Water-soluble retinoids |
| FR2931662B1 (fr) * | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise. |
| FR2931661B1 (fr) * | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide. |
| AU2012272804B2 (en) | 2011-06-22 | 2017-07-06 | Vyome Therapeutics Limited | Conjugate-based antifungal and antibacterial prodrugs |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2862921A (en) * | 1953-08-13 | 1958-12-02 | Upjohn Co | Erythromycin esters |
| US3598806A (en) * | 1969-04-15 | 1971-08-10 | Upjohn Co | Process for preparing lincomycin-3-monoacylates |
| FR2378523A1 (fr) * | 1977-01-26 | 1978-08-25 | Grupper Charles | Medicament pour le traitement de l'acne |
| 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 |
-
1986
- 1986-05-06 FR FR8606528A patent/FR2598420B1/fr not_active Expired - Lifetime
-
1987
- 1987-05-02 JP JP62107980A patent/JP2504990B2/ja not_active Expired - Lifetime
- 1987-05-04 NL NL8701054A patent/NL193946C/nl not_active IP Right Cessation
- 1987-05-05 CH CH1705/87A patent/CH674847A5/fr not_active IP Right Cessation
- 1987-05-05 NO NO871870A patent/NO168041C/no unknown
- 1987-05-05 DK DK229387A patent/DK169345B1/da not_active IP Right Cessation
- 1987-05-05 ES ES8701603A patent/ES2006478A6/es not_active Expired
- 1987-05-05 CA CA000536348A patent/CA1300131C/fr not_active Expired - Lifetime
- 1987-05-05 DE DE3714937A patent/DE3714937C2/de not_active Expired - Lifetime
- 1987-05-05 IT IT20389/87A patent/IT1204556B/it active
- 1987-05-05 SE SE8701845A patent/SE470379B/sv not_active IP Right Cessation
- 1987-05-06 BE BE8700486A patent/BE1004152A4/fr not_active IP Right Cessation
- 1987-05-06 GB GB8710673A patent/GB2191483B/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3714937C2 (de) | 1998-02-26 |
| BE1004152A4 (fr) | 1992-10-06 |
| IT8720389A0 (it) | 1987-05-05 |
| CA1300131C (fr) | 1992-05-05 |
| JPS62289593A (ja) | 1987-12-16 |
| GB8710673D0 (en) | 1987-06-10 |
| JP2504990B2 (ja) | 1996-06-05 |
| NO871870L (no) | 1987-11-09 |
| SE8701845L (sv) | 1987-11-07 |
| DE3714937A1 (de) | 1987-11-12 |
| FR2598420B1 (fr) | 1991-06-07 |
| FR2598420A1 (fr) | 1987-11-13 |
| NO871870D0 (no) | 1987-05-05 |
| DK229387A (da) | 1987-11-07 |
| SE8701845D0 (sv) | 1987-05-05 |
| DK229387D0 (da) | 1987-05-05 |
| IT1204556B (it) | 1989-03-10 |
| NL8701054A (nl) | 1987-12-01 |
| GB2191483B (en) | 1990-05-30 |
| SE470379B (sv) | 1994-02-07 |
| NO168041C (no) | 1992-01-08 |
| NL193946B (nl) | 2000-11-01 |
| DK169345B1 (da) | 1994-10-10 |
| CH674847A5 (no) | 1990-07-31 |
| GB2191483A (en) | 1987-12-16 |
| ES2006478A6 (es) | 1989-05-01 |
| NO168041B (no) | 1991-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| V4 | Discontinued because of reaching the maximum lifetime of a patent |
Effective date: 20070504 |