FR2515187A1 - Complexes d'inclusion de steroides avec de la g-cyclodextrine, procede pour leur preparation et compositions pharmaceutiques les contenant - Google Patents

Complexes d'inclusion de steroides avec de la g-cyclodextrine, procede pour leur preparation et compositions pharmaceutiques les contenant Download PDF

Info

Publication number: FR2515187A1
Authority: FR; France
Prior art keywords: cyclodextrin; complex; steroid; steroids; water
Prior art date: 1981-10-27
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

FR8217943A

Other languages

English (en)

French (fr)

Inventor

Agnes Stadler-Nee-Szoke

Jozsef Szejtli

Ilona Habon

Gyozo Hortobagyi

Ilona Kolbe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Richter Gedeon Vegyeszeti Gyar Nyrt

Original Assignee

Richter Gedeon Vegyeszeti Gyar RT

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.)

1981-10-27

Filing date

1982-10-26

Publication date

1983-04-29

1982-10-26 Application filed by Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT

1983-04-29 Publication of FR2515187A1 publication Critical patent/FR2515187A1/fr

Status Withdrawn legal-status Critical Current

Links

150000003431 steroids Chemical class 0.000 title claims abstract description 60
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 title claims abstract description 57
238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 18
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
239000000243 solution Substances 0.000 claims abstract description 28
239000007864 aqueous solution Substances 0.000 claims abstract description 14
238000002156 mixing Methods 0.000 claims abstract description 3
229920000858 Cyclodextrin Polymers 0.000 claims description 110
229940080345 gamma-cyclodextrin Drugs 0.000 claims description 71
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 34
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 claims description 24
229960002256 spironolactone Drugs 0.000 claims description 23
229960003957 dexamethasone Drugs 0.000 claims description 18
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 18
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239000000203 mixture Substances 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 16
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OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 16
GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 claims description 11
GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims description 11
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150000001875 compounds Chemical class 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 2
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GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 2
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HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 16
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HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 6
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244000309464 bull Species 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 3
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WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 3
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NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 3
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JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
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BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
235000011175 beta-cyclodextrine Nutrition 0.000 description 2
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Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Nanotechnology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Crystallography & Structural Chemistry (AREA)
Biotechnology (AREA)
General Engineering & Computer Science (AREA)
Medical Informatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

FR8217943A 1981-10-27 1982-10-26 Complexes d'inclusion de steroides avec de la g-cyclodextrine, procede pour leur preparation et compositions pharmaceutiques les contenant Withdrawn FR2515187A1 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU813147A HU190356B (en)	1981-10-27	1981-10-27	Process for preparing steroid-gamma-cyclodextrin inclusion complexes with high water-solubility

Publications (1)

Publication Number	Publication Date
FR2515187A1 true FR2515187A1 (fr)	1983-04-29

Family

ID=10962794

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FR8217943A Withdrawn FR2515187A1 (fr)	1981-10-27	1982-10-26	Complexes d'inclusion de steroides avec de la g-cyclodextrine, procede pour leur preparation et compositions pharmaceutiques les contenant

Country Status (12)

Country	Link
JP (1)	JPS5883699A (it)
BE (1)	BE894825A (it)
DD (1)	DD208549A5 (it)
DE (1)	DE3238800A1 (it)
DK (1)	DK474782A (it)
ES (1)	ES8308571A1 (it)
FR (1)	FR2515187A1 (it)
GB (1)	GB2109381A (it)
HU (1)	HU190356B (it)
IT (1)	IT1191049B (it)
NL (1)	NL8204122A (it)
SE (1)	SE8206055L (it)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0147851A2 (de) *	1983-12-29	1985-07-10	CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT.	Wasserlösliche Formen von Polyenantibiotika und Verfahren zu ihrer Herstellung
EP1216712A1 (en) *	2000-12-20	2002-06-26	Schering Aktiengesellschaft	Cyclodextrin-drospirenone inclusion complexes
WO2002049674A1 (en) *	2000-12-20	2002-06-27	Schering Aktiengesellschaft	Cyclodextrin-drospirenone inclusion complexes
US6958326B2 (en)	2000-12-20	2005-10-25	Schering Ag	Cyclodextrin-drospirenone inclusion complexes
WO2013135248A3 (en) *	2012-03-13	2014-01-09	Amphidex A/S	Production of stabilized channel type cyclodextrin crystals

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2162529B (en) *	1984-06-08	1988-03-02	Nitrokemia Ipartelepek	B-cyclodextrin complex of benzene sulphonyl urea derivatives
US5223295A (en) *	1988-01-22	1993-06-29	Asterol International	Process for the elimination of steroid compounds contained in substance of biological origin
US5229370A (en) *	1988-08-15	1993-07-20	Ammeraal Robert N	Water soluble branched beta cyclodextrin steroid complex
WO1990001320A1 (en) *	1988-08-15	1990-02-22	American Maize-Products Company	Water soluble branched beta cyclodextrin steroid complex
EP0540751A4 (en) *	1991-05-20	1994-10-26	Eisai Co Ltd	Steroid compound combined with polysaccharide
US20040152664A1 (en) *	1998-09-02	2004-08-05	Allergan, Inc.	Prednisolone compositions
US20040048830A1 (en) *	2000-11-02	2004-03-11	Mingqiang Zhang	Use of cortisol-sequestering agents for the treatment of hypercortisolaemia related disorders
US20070020299A1 (en) *	2003-12-31	2007-01-25	Pipkin James D	Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid
US20070020298A1 (en) *	2003-12-31	2007-01-25	Pipkin James D	Inhalant formulation containing sulfoalkyl ether gamma-cyclodextrin and corticosteroid

1981
- 1981-10-27 HU HU813147A patent/HU190356B/hu not_active IP Right Cessation
1982
- 1982-10-20 DE DE19823238800 patent/DE3238800A1/de not_active Withdrawn
- 1982-10-25 SE SE8206055A patent/SE8206055L/xx not_active Application Discontinuation
- 1982-10-26 FR FR8217943A patent/FR2515187A1/fr not_active Withdrawn
- 1982-10-26 NL NL8204122A patent/NL8204122A/nl not_active Application Discontinuation
- 1982-10-26 GB GB08230513A patent/GB2109381A/en not_active Withdrawn
- 1982-10-26 DK DK474782A patent/DK474782A/da not_active Application Discontinuation
- 1982-10-26 IT IT23942/82A patent/IT1191049B/it active
- 1982-10-26 ES ES516840A patent/ES8308571A1/es not_active Expired
- 1982-10-26 DD DD82244272A patent/DD208549A5/de unknown
- 1982-10-27 JP JP57187658A patent/JPS5883699A/ja active Pending
- 1982-10-27 BE BE0/209341A patent/BE894825A/fr not_active IP Right Cessation

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0147851A2 (de) *	1983-12-29	1985-07-10	CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT.	Wasserlösliche Formen von Polyenantibiotika und Verfahren zu ihrer Herstellung
EP0147851A3 (en) *	1983-12-29	1986-12-30	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.	Water soluble forms of polyene antibiotics, and process for preparing them
EP1216712A1 (en) *	2000-12-20	2002-06-26	Schering Aktiengesellschaft	Cyclodextrin-drospirenone inclusion complexes
WO2002049674A1 (en) *	2000-12-20	2002-06-27	Schering Aktiengesellschaft	Cyclodextrin-drospirenone inclusion complexes
US6610670B2 (en)	2000-12-20	2003-08-26	Schering Aktiengesellschaft	Cyclodextrin-drospirenone inclusion complexes
US6958326B2 (en)	2000-12-20	2005-10-25	Schering Ag	Cyclodextrin-drospirenone inclusion complexes
US7163931B2 (en)	2000-12-20	2007-01-16	Schering Aktiengesellchaft	Compositions of estrogen-cyclodextrin complexes
US7569557B2 (en)	2000-12-20	2009-08-04	Bayer Schering Pharma Ag	Compositions of estrogen-cyclodextrin complexes
WO2013135248A3 (en) *	2012-03-13	2014-01-09	Amphidex A/S	Production of stabilized channel type cyclodextrin crystals

Also Published As

Publication number	Publication date
IT8223942A0 (it)	1982-10-26
SE8206055D0 (sv)	1982-10-25
ES516840A0 (es)	1983-09-16
DD208549A5 (de)	1984-04-04
HU190356B (en)	1986-08-28
DK474782A (da)	1983-04-28
GB2109381A (en)	1983-06-02
DE3238800A1 (de)	1983-05-05
NL8204122A (nl)	1983-05-16
ES8308571A1 (es)	1983-09-16
BE894825A (fr)	1983-02-14
SE8206055L (sv)	1983-04-28
JPS5883699A (ja)	1983-05-19
IT1191049B (it)	1988-02-24

Publication	Publication Date	Title
FR2515187A1 (fr)	1983-04-29	Complexes d'inclusion de steroides avec de la g-cyclodextrine, procede pour leur preparation et compositions pharmaceutiques les contenant
Montassier et al.	1997	Inclusion complexes of tretinoin with cyclodextrins
Arias et al.	1997	Investigation of the triamterene–β-cyclodextrin system prepared by co-grinding
FR2808691A1 (fr)	2001-11-16	Cyclodextrines substituees preferentiellement sur leur face primaire par des fonctions acide ou amine
CA2343426A1 (fr)	2001-10-10	Composition, notamment cosmetique, renfermant un steroide et un 2-alkyl alcanol ou un ester
WO2000066635A1 (fr)	2000-11-09	Cyclodextrines amphiphiles, leur preparation et leur utilisation pour solubiliser des systemes organises et incorporer des molecules hydrophobes
PT796238E (pt)	2000-09-29	Processo de estabilizacao de acidos gordos poli-insaturados e utilizacao desses produtos estabilizados em terapeutica e em cosmetologia
CA2647089A1 (fr)	2007-09-27	Association de substance oleagineuse avec un melange d'au moins deux cyclodextrines
EP1675876A2 (fr)	2006-07-05	Derives amphiphiles de cyclodextrines, leur procede de preparation et leurs utilisations
EP1165620A1 (fr)	2002-01-02	Complexes d'inclusion d'acides gras polyinsatures et de leurs derives avec la y-cyclodextrine
EP2486064B1 (fr)	2022-05-25	Procede de preparation de derives acetyles de matiere amylacee
Szejtli	1985	Cyclodextrins: a new group of industrial basic materials
FR2495160A1 (fr)	1982-06-04	Derive de bisglucosylmoranoline et compositions pharmaceutiques pour le traitement du diabete sucre qui le renferment
FR2681868A1 (fr)	1993-04-02	Nouvelles substances amphiphiles derivees de cyclodextrines et leur utilisation dans des compositions cosmetiques.
EP1469823B1 (fr)	2008-01-16	Utilisation cosmetique ou dermatologique de la vitamine a ou de ses esters, en association avec une beta-cyclodextrine partiellement methylee
US20210315248A1 (en)	2021-10-14	System and method for hovenia dulcis extraction
EP1401561B1 (fr)	2006-05-03	Nouvelle utilisation de complexes d'inclusion de cyclodextrine
EP1023039B1 (fr)	2002-08-14	Utilisation d'alkyl monoglucosides en tant que vecteurs moleculaires
CA1047505A (fr)	1979-01-30	Production et applications de sulfoxydes organiques
WO1999038892A1 (fr)	1999-08-05	Cellulose de parenchyme substituee par des groupements carboxyalkyle et procede pour la preparer
FR2714066A1 (fr)	1995-06-23	Utilisation de mono-3,6-anhydrocyclodextrines pour solubiliser un composé hydrophobe et pour contrôler la pureté d'un énantiomère, et procédé de préparation de ces cyclodextrines.
FR2775686A1 (fr)	1999-09-10	Exploitation industrielle et commerciale des lipides cuticulaires de la baie de raisin en pharmacologie et cosmetologie
WO1995004107A1 (fr)	1995-02-09	Procede pour la solubilisation du poly(1-3)glucopyranose
RU2042687C1 (ru)	1995-08-27	Способ получения дегидроаналогов стероидов
CH619471A5 (en)	1980-09-30	Water-soluble compositions, with the exception of medicinal products, containing an N<4>-acylcytosine arabinoside, process for preparing them and use of these compositions

Legal Events

Date	Code	Title	Description
1984-08-24	ST	Notification of lapse