RU2012152633A - Способ получения бимосиамозы - Google Patents

Способ получения бимосиамозы Download PDF

Info

Publication number: RU2012152633A
Authority: RU; Russia
Prior art keywords: bis; hexane; carboethoxymethylphenyl; mannopyranosyloxy; phenyl
Prior art date: 2010-05-07

Application number

RU2012152633/04A

Other languages

English (en)

Russian (ru)

Inventor

Ремо КРАНИХ

Даниель БОК

Original Assignee

Ревотар Биофармасьютикалз Аг

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.)

2010-05-07

Filing date

2011-05-04

Publication date

2014-06-20

2011-05-04 Application filed by Ревотар Биофармасьютикалз Аг filed Critical Ревотар Биофармасьютикалз Аг

2014-06-20 Publication of RU2012152633A publication Critical patent/RU2012152633A/ru

Links

238000000034 method Methods 0.000 title claims abstract 16
RYWCQJDEHXJHRI-XJMXIVSISA-N 2-[3-[5-[6-[3-[3-(carboxymethyl)phenyl]-4-[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hexyl]-2-[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC(C(=C1)C=2C=C(CC(O)=O)C=CC=2)=CC=C1CCCCCCC(C=C1C=2C=C(CC(O)=O)C=CC=2)=CC=C1O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 RYWCQJDEHXJHRI-XJMXIVSISA-N 0.000 claims abstract 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract 28
-1 ethyl (2'-methoxybiphenyl-3-yl) acetic acid Chemical compound 0.000 claims abstract 17
229950007225 bimosiamose Drugs 0.000 claims abstract 14
AGFBLMOECRWVDT-UHFFFAOYSA-N 2-[3-(2-methoxyphenyl)phenyl]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=CC(CC(O)=O)=C1 AGFBLMOECRWVDT-UHFFFAOYSA-N 0.000 claims abstract 11
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims abstract 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
PDHXVYUQWHNFRV-UHFFFAOYSA-N ethyl 2-[3-[5-[6-[3-[3-(2-ethoxy-2-oxoethyl)phenyl]-4-hydroxyphenyl]hexyl]-2-hydroxyphenyl]phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(C=2C(=CC=C(CCCCCCC=3C=C(C(O)=CC=3)C=3C=C(CC(=O)OCC)C=CC=3)C=2)O)=C1 PDHXVYUQWHNFRV-UHFFFAOYSA-N 0.000 claims abstract 9
RGLYBOVAJQTZBO-UHFFFAOYSA-N ethyl 2-[3-[5-[6-[3-[3-(2-ethoxy-2-oxoethyl)phenyl]-4-methoxyphenyl]hexyl]-2-methoxyphenyl]phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(C=2C(=CC=C(CCCCCCC=3C=C(C(OC)=CC=3)C=3C=C(CC(=O)OCC)C=CC=3)C=2)OC)=C1 RGLYBOVAJQTZBO-UHFFFAOYSA-N 0.000 claims abstract 9
WYLVUWWIGIGCBK-UHFFFAOYSA-N ethyl 2-[3-[5-[6-[3-[3-(2-ethoxy-2-oxoethyl)phenyl]-4-methoxyphenyl]-6-oxohexanoyl]-2-methoxyphenyl]phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(C=2C(=CC=C(C=2)C(=O)CCCCC(=O)C=2C=C(C(OC)=CC=2)C=2C=C(CC(=O)OCC)C=CC=2)OC)=C1 WYLVUWWIGIGCBK-UHFFFAOYSA-N 0.000 claims abstract 8
239000002904 solvent Substances 0.000 claims abstract 8
150000001875 compounds Chemical class 0.000 claims abstract 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 7
PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 claims abstract 6
239000003960 organic solvent Substances 0.000 claims abstract 5
230000002378 acidificating effect Effects 0.000 claims abstract 4
238000002955 isolation Methods 0.000 claims abstract 4
125000004494 ethyl ester group Chemical group 0.000 claims abstract 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
239000000203 mixture Substances 0.000 claims 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
206010061218 Inflammation Diseases 0.000 claims 5
230000004054 inflammatory process Effects 0.000 claims 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
239000000047 product Substances 0.000 claims 4
206010001889 Alveolitis Diseases 0.000 claims 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
208000025865 Ulcer Diseases 0.000 claims 3
230000000172 allergic effect Effects 0.000 claims 3
208000010668 atopic eczema Diseases 0.000 claims 3
239000003054 catalyst Substances 0.000 claims 3
239000013078 crystal Substances 0.000 claims 3
201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 3
208000030533 eye disease Diseases 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
201000003651 pulmonary sarcoidosis Diseases 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
239000002841 Lewis acid Substances 0.000 claims 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
230000003197 catalytic effect Effects 0.000 claims 2
238000003745 diagnosis Methods 0.000 claims 2
150000007517 lewis acids Chemical class 0.000 claims 2
229910052751 metal Inorganic materials 0.000 claims 2
239000002184 metal Substances 0.000 claims 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
238000011282 treatment Methods 0.000 claims 2
231100000397 ulcer Toxicity 0.000 claims 2
ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 claims 1
KYNNBXCGXUOREX-UHFFFAOYSA-N 2-(3-bromophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1 KYNNBXCGXUOREX-UHFFFAOYSA-N 0.000 claims 1
206010002198 Anaphylactic reaction Diseases 0.000 claims 1
BBRRGKQZSUJDJR-UHFFFAOYSA-N C=1C=C(O)C(C=2C=C(CC(=O)OCC)C=CC=2)=CC=1C(CCCCC)C(C=1)=CC=C(O)C=1C1=CC=CC(CC(=O)OCC)=C1 Chemical compound C=1C=C(O)C(C=2C=C(CC(=O)OCC)C=CC=2)=CC=1C(CCCCC)C(C=1)=CC=C(O)C=1C1=CC=CC(CC(=O)OCC)=C1 BBRRGKQZSUJDJR-UHFFFAOYSA-N 0.000 claims 1
208000035473 Communicable disease Diseases 0.000 claims 1
208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
206010013774 Dry eye Diseases 0.000 claims 1
206010014561 Emphysema Diseases 0.000 claims 1
206010033078 Otitis media Diseases 0.000 claims 1
206010035664 Pneumonia Diseases 0.000 claims 1
201000002154 Pterygium Diseases 0.000 claims 1
201000007737 Retinal degeneration Diseases 0.000 claims 1
206010064996 Ulcerative keratitis Diseases 0.000 claims 1
206010046851 Uveitis Diseases 0.000 claims 1
210000000683 abdominal cavity Anatomy 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
230000036783 anaphylactic response Effects 0.000 claims 1
208000003455 anaphylaxis Diseases 0.000 claims 1
238000009835 boiling Methods 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
206010009887 colitis Diseases 0.000 claims 1
239000007859 condensation product Substances 0.000 claims 1
210000004087 cornea Anatomy 0.000 claims 1
201000007717 corneal ulcer Diseases 0.000 claims 1
201000003146 cystitis Diseases 0.000 claims 1
239000000539 dimer Substances 0.000 claims 1
208000025245 disorder of lacrimal gland Diseases 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
239000005414 inactive ingredient Substances 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
210000004400 mucous membrane Anatomy 0.000 claims 1
208000028169 periodontal disease Diseases 0.000 claims 1
230000002265 prevention Effects 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
230000004258 retinal degeneration Effects 0.000 claims 1
239000012265 solid product Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract 2
LDERXAIJKAWVIH-UHFFFAOYSA-N ethyl 2-[3-(2-methoxyphenyl)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(C=2C(=CC=CC=2)OC)=C1 LDERXAIJKAWVIH-UHFFFAOYSA-N 0.000 abstract 1

Classifications

- 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
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

RU2012152633/04A 2010-05-07 2011-05-04 Способ получения бимосиамозы RU2012152633A (ru)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP10162276		2010-05-07
EP10162276.9		2010-05-07
PCT/EP2011/057130 WO2011138365A1 (fr)	2010-05-07	2011-05-04	Procédé d'élaboration de bimosiamose

Publications (1)

Publication Number	Publication Date
RU2012152633A true RU2012152633A (ru)	2014-06-20

Family

ID=44276097

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RU2012152633/04A RU2012152633A (ru)	2010-05-07	2011-05-04	Способ получения бимосиамозы

Country Status (8)

Country	Link
EP (1)	EP2566580A1 (fr)
JP (1)	JP2013525467A (fr)
KR (1)	KR20130056238A (fr)
CN (1)	CN103002951A (fr)
AU (1)	AU2011249843A1 (fr)
CA (1)	CA2798383A1 (fr)
RU (1)	RU2012152633A (fr)
WO (1)	WO2011138365A1 (fr)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5444050A (en) *	1994-04-29	1995-08-22	Texas Biotechnology Corporation	Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa
WO1997001335A1 (fr)	1995-06-29	1997-01-16	Texas Biotechnology Corporation	Inhibiteurs de selectine a petites molecules bivalents et trivalents
US5712387A (en) *	1996-05-20	1998-01-27	Texas Biotechnology Corporation	High yield stereospecific mannosylation
US5919768A (en)	1996-06-26	1999-07-06	Texas Biotechnology Corporation	Di- and trivalent small molecule selectin inhibitors
EP1897533A1 (fr) *	2006-09-08	2008-03-12	Revotar Biopharmaceuticals AG	Utilisation de 1,6-Bis[3-(3-carboxyméthylphényl)-4-(2-alpha-D-mannopyranosyl-oxy)-phényl]hexane pour la préparation des compositions cosmétiques.
EP1903049A1 (fr)	2006-09-08	2008-03-26	Revotar Biopharmaceuticals AG	Formes crystallines de 1,6-Bis [3-(3-carboxymethylphenyl)-4-(2-alpha -D-mannopyranosyloxy)-phenyl] hexane
EP1958637A1 (fr) *	2007-02-14	2008-08-20	Revotar Biopharmaceuticals AG	Composition pharmaceutique pour le traitement de maladies induites par IL-8

2011
- 2011-05-04 EP EP11720069A patent/EP2566580A1/fr not_active Withdrawn
- 2011-05-04 CA CA2798383A patent/CA2798383A1/fr not_active Abandoned
- 2011-05-04 KR KR1020127029201A patent/KR20130056238A/ko not_active Withdrawn
- 2011-05-04 CN CN2011800230987A patent/CN103002951A/zh active Pending
- 2011-05-04 RU RU2012152633/04A patent/RU2012152633A/ru not_active Application Discontinuation
- 2011-05-04 JP JP2013508490A patent/JP2013525467A/ja not_active Withdrawn
- 2011-05-04 AU AU2011249843A patent/AU2011249843A1/en not_active Abandoned
- 2011-05-04 WO PCT/EP2011/057130 patent/WO2011138365A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP2566580A1 (fr)	2013-03-13
JP2013525467A (ja)	2013-06-20
WO2011138365A1 (fr)	2011-11-10
KR20130056238A (ko)	2013-05-29
CN103002951A (zh)	2013-03-27
CA2798383A1 (fr)	2011-11-10
AU2011249843A1 (en)	2012-11-29

Legal Events

Date	Code	Title	Description
2014-06-20	FA93	Acknowledgement of application withdrawn (no request for examination)	Effective date: 20140505

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