WO1998008854B1 - Sugar derivatives as sialyl lewis x mimetics - Google Patents
Sugar derivatives as sialyl lewis x mimeticsInfo
- Publication number
- WO1998008854B1 WO1998008854B1 PCT/EP1997/004649 EP9704649W WO9808854B1 WO 1998008854 B1 WO1998008854 B1 WO 1998008854B1 EP 9704649 W EP9704649 W EP 9704649W WO 9808854 B1 WO9808854 B1 WO 9808854B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pharmaceutically acceptable
- compound according
- alkyl
- acceptable salt
- substituted
- Prior art date
Links
- NIGUVXFURDGQKZ-UQTBNESHSA-N alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@]3(O[C@H]([C@H](NC(C)=O)[C@@H](O)C3)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O NIGUVXFURDGQKZ-UQTBNESHSA-N 0.000 title abstract 2
- 102000003800 Selectins Human genes 0.000 claims abstract 2
- 108090000184 Selectins Proteins 0.000 claims abstract 2
- 230000001413 cellular effect Effects 0.000 claims abstract 2
- 230000001404 mediated effect Effects 0.000 claims abstract 2
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 230000003278 mimic effect Effects 0.000 abstract 1
- 125000005630 sialyl group Chemical group 0.000 abstract 1
Abstract
Sialyl Lewis X mimetics which mimic the inhibition of selectin-mediated cellular adhesion by sialyl X having a core of formula (I).
Claims
1. A compound of the formula I
Y is C╬╣-C4alkylene which is substituted by one or two substituents selected from OR3 
R2 is -NHR╬▓;
R3 is aralkyl with C C6alkyl and C6-C10aryl or CH2C(O)NHCrC2oalkyl which is unsubstituted or substituted by one or two OC(O)C10-C╬╣6alkyl;
R╬╕ is C(O)CHR8NHC(O)(CH2)qC(O)0H;
R8 is CrC╬╡alkyl unsubstituted or substituted with one or two OH; m is a number from 1 to 6; and q is 2 or 3; or
Y is unsubstituted d-C alkylene; Ra is -NR6R7;
R7 is (CH2)mC(O)NHC10-C16alkyl,- and Re and m have the above meanings.
2. A process for the preparation of a compound according to claim 1 wherein the corresponding radical -Y-R2 is coupled, optionally via more than one step, to the corresponding sugar moiety.
3. A compound according to claim 1 or a pharmaceutically acceptable salt thereof for use as a pharmaceutical.
4. A method for preventing or treating conditions or diseases which are mediated by the binding of selectin in cellular adhesion in a subject in need of such treatment, which method comprises administering to said subject an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
5. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound according to claim 1 or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable diluent or carrier.
6. A compound according to claim 1 or a pharmaceutically acceptable salt thereof for use in the manufacturing of a medicament for use in the method according to claim 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU47004/97A AU4700497A (en) | 1996-08-26 | 1997-08-26 | Organic compounds |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2455696P | 1996-08-26 | 1996-08-26 | |
| US60/024,556 | 1996-08-26 | ||
| US08/744,744 US5830871A (en) | 1996-10-28 | 1996-10-28 | Inhibitors of E-, P- and L-selectin binding |
| US08/764,315 US5837862A (en) | 1996-12-12 | 1996-12-12 | Sialyl Lewis X mimetics incorporating mannopeptides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1998008854A2 WO1998008854A2 (en) | 1998-03-05 |
| WO1998008854A3 WO1998008854A3 (en) | 1998-08-20 |
| WO1998008854B1 true WO1998008854B1 (en) | 1998-10-01 |
Family
ID=27362340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/004649 WO1998008854A2 (en) | 1996-08-26 | 1997-08-26 | Sugar derivatives as sialyl lewis x mimetics |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU4700497A (en) |
| WO (1) | WO1998008854A2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5888984A (en) * | 1994-05-12 | 1999-03-30 | Dermal Research Laboratories, Inc. | Pharmaceutical composition of complex carbohydrates and essential oils and methods of using the same |
| WO1999010359A2 (en) * | 1997-08-26 | 1999-03-04 | Novartis Ag | Liposomic based sialyl lewis x mimetics |
| ATE361082T1 (en) | 1999-02-01 | 2007-05-15 | Dermal Res Lab Inc | PHARMACEUTICAL COMPOSITION OF COMPLEX CARBOHYDRATES ITS APPLICATION |
| US7879824B2 (en) | 2001-07-31 | 2011-02-01 | Dermal Research Laboratories, Inc. | Methods of preventing or treating diseases and conditions using complex carbohydrates |
| CA2501842C (en) * | 2002-10-11 | 2012-07-17 | Yamanouchi Europe B.V. | Glucose-based compounds with affinity to p-selectin |
| CN115197185B (en) * | 2021-04-12 | 2024-03-22 | 中国科学院大连化学物理研究所 | A kind of preparation method of transition metal catalyzed pyranoside derivatives |
-
1997
- 1997-08-26 WO PCT/EP1997/004649 patent/WO1998008854A2/en active Application Filing
- 1997-08-26 AU AU47004/97A patent/AU4700497A/en not_active Abandoned
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