RU2003116648A - Substituted imidazopyridines - Google Patents

Substituted imidazopyridines Download PDF

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Publication number
RU2003116648A
RU2003116648A RU2003116648/04A RU2003116648A RU2003116648A RU 2003116648 A RU2003116648 A RU 2003116648A RU 2003116648/04 A RU2003116648/04 A RU 2003116648/04A RU 2003116648 A RU2003116648 A RU 2003116648A RU 2003116648 A RU2003116648 A RU 2003116648A
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alkyl
aryl
compound
alkenyl
heteroaryl
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RU2003116648/04A
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Russian (ru)
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RU2294934C2 (en
Inventor
Кайл Дж. ЛИНДСТРОМ (US)
Кайл Дж. ЛИНДСТРОМ
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ЗМ Инновейтив Пропертиз Компани (US)
Зм Инновейтив Пропертиз Компани
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Priority to US60/254,228 priority
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Claims (34)

1. The compound of formula (I)
Figure 00000001
where X is an alkylene or alkenylene group;
Y is —CO—, —CS— or —SO 2 —groups;
Z - represents a single bond or groups —O—, —S— or –NR 5 -; R 1 represents an aryl, heteroaryl, heterocyclyl, C 1-20 alkyl or C 2-20 alkenyl group, each of these groups may be unsubstituted or contain one or more substituents independently selected from the group consisting of:
alkyl;
alkenyl;
- aryl;
heteroaryl;
heterocyclyl;
- substituted cycloalkyl;
-O-alkyl;
-O- (alkyl) 0-1 aryl;
-O- (alkyl) 0-1- heteroaryl;
-O- (alkyl) 0-1- heterocyclyl;
-COOH;
-CO-O-alkyl;
-CO-alkyl;
-S (O) 0-2 -alkyl;
-S (O) 0-2 - (alkyl) 0-1 -aryl;
-S (O) 0-2 - (alkyl) 0-1- heteroaryl;
-S (O) 0-2 - (alkyl) 0-1- heterocyclyl;
- (alkyl) 0-1 —N (R 5 ) 2 ;
- (alkyl) 0-1 -NR 5 -CO-O-alkyl;
- (alkyl) 0-1 -NR 5 -CO-alkyl;
- (alkyl) 0-1 -NR 5 -CO-aryl;
- (alkyl) 0-1 -NR 5 -CO-heteroaryl;
-N 3 ;
a halogen atom;
haloalkyl;
haloalkoxyl;
-CO-haloalkyl;
-CO-haloalkoxyl;
-NO 2 ;
-CN;
-HE;
-SH; and in the case of alkyl, alkenyl and heterocyclyl groups, also an oxo group;
Deputy R 2 selected from the group including:
a hydrogen atom;
alkyl;
alkenyl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
alkyl-O-aryl;
-alkyl-S-aryl;
-alkyl-O-alkenyl;
-alkyl-S-alkenyl; and
-alkyl or alkenyl containing one or more substituents selected from the groups including:
-HE;
-halogen
-N (R 5 ) 2 ;
-CO-N (R 5 ) 2 ;
-CS-N (R 5 ) 2 ;
-SO 2 -N (R 5 ) 2 ;
-NR 5 -CO-C 1-10 alkyl;
-NR 5 -CS-C 1-10 alkyl;
-NR 5 -SO 2 -C 1-10 alkyl;
-CO-C 1-10 alkyl;
-CO-OC 1-10 alkyl;
-N 3 ;
aryl;
heteroaryl;
heterocyclyl;
-CO-aryl; and
-CO-heteroaryl;
the substituents R 3 and R 4 are independently selected from the group consisting of alkyl, alkenyl, halogen, alkoxy, amino, alkylamino, dialkylamino and alkylthiol groups, and each substituent R 5 represents a hydrogen atom or C 1-10 an alkyl group;
or a pharmaceutical grade salt based on these groups.
2. The compound or salt according to claim 1, characterized in that Y represents a group -CO-.
3. The compound or salt according to claim 1, characterized in that Y is a —CO— group, and Z is a single bond.
4. The compound or salt according to claim 3, characterized in that the substituent R 1 represents an alkyl, aryl or substituted aryl group.
5. The compound or salt according to claim 1, characterized in that Y represents a group-CS-.
6. The compound or salt according to claim 1, characterized in that Y represents a —CS— group and Z represents a –NR 5 - group.
7. The compound or salt according to claim 6, characterized in that the substituent R 5 represents a hydrogen atom, and the substituent R 1 represents an aryl or substituted aryl group.
8. The compound or salt according to claim 1, characterized in that Y represents a group -SO 2 -.
9. The compound or salt according to claim 1, characterized in that Y represents a group —SO 2 -, and Z is a single bond.
10. The compound or salt according to claim 9, characterized in that the substituent R 1 represents an alkyl, aryl or substituted aryl group.
11. The compound or salt of claim 10, wherein the substituent R 1 represents an alkyl group.
12. The compound or salt according to claim 1, characterized in that Y represents a group -SO 2 -, and Z - -NR 5 -.
13. The compound or salt according to p. 12, characterized in that the substituent R 5 represents an alkyl group, and the substituent R 1 is also an alkyl group.
14. The compound or salt according to claim 1, characterized in that the substituent R 2 represents a hydrogen atom, an alkyl or alkyl-O-alkyl group.
15. The compound or salt according to claim 1, characterized in that X represents a - (CH 2 ) 2-4 - group.
16. The compound or salt according to claim 1, characterized in that the substituents R 3 and R 4 independently from each other represent a hydrogen atom or an alkyl group.
17. A compound selected from the group consisting of:
N- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] benzamide;
N- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] methanesulfonamide;
N- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] -4-fluorobenzenesulfonamide monohydrate;
N- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] -N’-phenylthiourea monohydrate;
N ’- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] -N, N-dimethyl sulfamide;
N- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] -N’-phenylurea;
N- [4- (4-amino-2,6,7-trimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] methanesulfonamide;
N- [4- (4-amino-2-butyl-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl) butyl] -4 - [[2- (dimethylamino) ethoxy] (phenyl) methyl] benzamide; and
N- {4- [4-amino-2- (ethoxymethyl) -6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl] butyl} methanesulfonamide;
or salts of pharmaceutical quality based on them.
18. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
19. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 9 in combination with a pharmaceutically acceptable carrier.
20. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 17 in combination with a pharmaceutically acceptable carrier.
21. A method of stimulating the biosynthesis of cytokine in the animal’s body, which consists in introducing into the animal’s body a therapeutically effective amount of a compound according to claim 1.
22. A method of treating a viral disease in animals, comprising administering to the animal an organism a therapeutically effective amount of a compound according to claim 1.
23. A method of treating a tumorous disease in animals, comprising administering to the animal an therapeutically effective amount of a compound according to claim 1.
24. A method of stimulating the biosynthesis of cytokine in the animal’s body, which consists in introducing into the animal’s body a therapeutically effective amount of a compound according to claim 9.
25. A method of treating a viral disease in animals, comprising administering to the animal an therapeutically effective amount of a compound according to claim 9.
26. A method of treating a tumorous disease in animals, comprising administering to the animal's body a therapeutically effective amount of a compound according to claim 9.
27. A method of stimulating the cytokine biosynthesis in an animal organism, which method comprises administering to the animal organism a therapeutically effective amount of a compound according to claim 17.
28. A method of treating a viral disease in animals, comprising administering to the animal an therapeutically effective amount of a compound according to claim 17.
29. A method of treating a tumorous disease in animals, which comprises administering to the animal's body a therapeutically effective amount of a compound according to claim 17.
30. The compound of formula (II)
Figure 00000002
where X is an alkylene or alkenylene group;
Deputy R 2 selected from the group including:
a hydrogen atom;
alkyl;
alkenyl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
alkyl-O-aryl;
-alkyl-S-aryl;
-alkyl-O-alkenyl;
-alkyl-S-alkenyl; and
- alkyl or alkenyl containing one or more substituents selected from the group consisting of:
-HE;
-halogen
-N (R 5 ) 2 ;
-CO-N (R 5 ) 2 ;
-CS-N (R 5 ) 2 ;
-SO 2 -N (R 5 ) 2 ;
-NR 5 -CO-C 1-10 alkyl;
-NR 5 -CS-C 1-10 alkyl;
-NR 5 -SO 2 -C 1-10 alkyl;
-CO-C 1-10 alkyl;
-CO-OC 1-10 alkyl;
-N 3 ;
aryl;
heteroaryl;
heterocyclyl;
-CO-aryl; and
-CO-heteroaryl;
the substituents R 3 and R 4 are independently selected from the group consisting of alkyl, alkenyl, halogen, alkoxy, amino, alkylamino, dialkylamino and alkylthiol groups, and
each substituent R 5 is independently a hydrogen atom
or
A C 1-10 alkyl group;
or a pharmaceutical grade salt based on these groups.
31. The compound of formula (III)
Figure 00000003
in which: Q represents NO 2 or NH 2 groups;
X is an alkylene or alkenylene group;
the substituents R 3 and R 4 are independently selected from the group consisting of alkyl, alkenyl, halogen, alkoxy, amino, alkylamino, dialkylamino and alkylthiol groups; and each substituent R 5 independently represents a hydrogen atom or a C 1-10 alkyl group;
or a pharmaceutical grade salt based on these groups.
32. The compound of formula (IV)
Figure 00000004
where X is an alkylene or alkenylene group;
Deputy R 2 selected from the group including:
a hydrogen atom;
alkyl;
alkenyl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
alkyl-O-aryl;
-alkyl-S-aryl;
-alkyl-O-alkenyl;
-alkyl-S-alkenyl; and
- alkyl or alkenyl containing one or more substituents selected from the group consisting of:
-HE;
-halogen
-N (R 5 ) 2 ;
-CO-N (R 5 ) 2 ;
-CS-N (R 5 ) 2 ;
-SO 2 -N (R 5 ) 2 ;
-NR 5 -CO-C 1-10 alkyl;
-NR 5 -CS-C 1-10 alkyl;
-NR 5 -SO 2 -C 1-10 alkyl;
-CO-C 1-10 alkyl;
-CO-OC 1-10 alkyl;
-N 3 ;
aryl;
heteroaryl;
heterocyclyl;
-CO-aryl; and
-CO-heteroaryl;
the substituents R 3 and R 4 are independently selected from the group consisting of alkyl, alkenyl, halogen, alkoxy, amino, alkylamino, dialkylamino and alkylthiol groups, and
each substituent R 5 is independently a hydrogen atom
or
A C 1-10 alkyl group;
or a pharmaceutical grade salt based on these groups.
33. The compound of formula (V)
Figure 00000005
in which X is an alkylene or alkenylene group;
Deputy R 2 selected from the group including:
a hydrogen atom;
alkyl;
alkenyl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
alkyl-O-aryl;
-alkyl-S-aryl;
-alkyl-O-alkenyl;
-alkyl-S-alkenyl; and
- alkyl or alkenyl containing one or more substituents selected from the group consisting of:
-HE;
-halogen
-N (R 5 ) 2 ;
-CO-N (R 5 ) 2 ;
-CS-N (R 5 ) 2 ;
-SO 2 -N (R 5 ) 2 ;
-NR 5 -CO-C 1-10 alkyl;
-NR 5 -CS-C 1-10 alkyl;
-NR 5 -SO 2 -C 1-10 alkyl;
-CO-C 1-10 alkyl;
-CO-OC 1-10 alkyl;
-N 3 ;
aryl;
heteroaryl;
heterocyclyl;
-CO-aryl; and
-CO-heteroaryl;
the substituents R 3 and R 4 are independently selected from the group consisting of alkyl, alkenyl, halogen, alkoxy, amino, alkylamine, dialkylamino and alkylthiol groups, and each R 5 is independently a hydrogen atom
or
A C 1-10 alkyl group;
or a pharmaceutical grade salt based on these groups.
34. The compound of formula (VI)
Figure 00000006
in which X is an alkylene or alkenylene group;
R 1 represents an aryl, heteroaryl, heterocyclyl, C 1-20 alkyl or C 2-20 alkenyl group, each of these groups may be unsubstituted or contain one or more substituents independently selected from the group consisting of:
alkyl;
alkenyl;
aryl;
heteroaryl;
heterocyclyl;
- substituted cycloalkyl;
-O-alkyl;
-O- (alkyl) 0-1 aryl;
-O- (alkyl) 0-1- heteroaryl;
-O- (alkyl) 0-1- heterocyclyl;
-COOH;
-CO-O-alkyl;
-CO-alkyl;
-S (O) 0-2 -alkyl;
-S (O) 0-2 - (alkyl) 0-1 -aryl;
-S (O) 0-2 - (alkyl) 0-1- heteroaryl;
-S (O) 0-2 - (alkyl) 0-1- heterocyclyl;
- (alkyl) 0-1 —N (R 5 ) 2 ;
- (alkyl) 0-1 -NR 5 -CO-O-alkyl;
- (alkyl) 0-1 -NR 5 -CO-alkyl;
- (alkyl) 0-1 -NR 5 -CO-aryl;
- (alkyl) 0-1 -NR 5 -CO-heteroaryl;
-N 3 ;
a halogen atom;
haloalkyl;
haloalkoxyl;
-CO-haloalkyl;
-CO-haloalkoxyl;
-NO 2 ;
-CN;
-HE;
-SH; and in the case of alkyl, alkenyl and heterocyclyl groups, also an oxo group;
Deputy R 2 selected from the group including:
a hydrogen atom;
alkyl;
alkenyl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
alkyl-O-aryl;
-alkyl-S-aryl;
-alkyl-O-alkenyl;
-alkyl-S-alkenyl; and
-alkyl or alkenyl containing one or more substituents selected from the group consisting of:
-HE;
-halogen
-N (R 5 ) 2 ;
-CO-N (R 5 ) 2 ;
-CS-N (R 5 ) 2 ;
-SO 2 -N (R 5 ) 2 ;
-NR 5 -CO-C 1-10 alkyl;
-NR 5 -CS-C 1-10 alkyl;
-NR 5 -SO 2 -C 1-10 alkyl;
-CO-C 1-10 alkyl;
-CO-O-C 1-10 alkyl;
-N 3 ;
aryl;
heteroaryl;
heterocyclyl;
-CO-aryl; and
-CO-heteroaryl;
the substituents R 3 and R 4 are independently selected from the group consisting of alkyl, alkenyl, halogen, alkoxy, amino, alkylamine, dialkylamino and alkylthiol groups, and each substituent R 5 represents a hydrogen atom or C 1-10 an alkyl group;
or a pharmaceutical grade salt based on these groups.
RU2003116648/04A 2000-12-08 2001-12-06 Substituted imidazopyridines RU2294934C2 (en)

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US60/254,228 2000-12-08

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Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5741908A (en) 1996-06-21 1998-04-21 Minnesota Mining And Manufacturing Company Process for reparing imidazoquinolinamines
HU0101155A3 (en) 1997-12-11 2002-10-28 Minnesota Mining & Mfg Imidazonaphthyridines, pharmaceutical compositions thereof and intermediates
US6541485B1 (en) 1999-06-10 2003-04-01 3M Innovative Properties Company Urea substituted imidazoquinolines
US6331539B1 (en) 1999-06-10 2001-12-18 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US6756382B2 (en) 1999-06-10 2004-06-29 3M Innovative Properties Company Amide substituted imidazoquinolines
US6660735B2 (en) 2000-12-08 2003-12-09 3M Innovative Properties Company Urea substituted imidazoquinoline ethers
US6677348B2 (en) 2000-12-08 2004-01-13 3M Innovative Properties Company Aryl ether substituted imidazoquinolines
US6664265B2 (en) 2000-12-08 2003-12-16 3M Innovative Properties Company Amido ether substituted imidazoquinolines
US6664264B2 (en) 2000-12-08 2003-12-16 3M Innovative Properties Company Thioether substituted imidazoquinolines
US6545017B1 (en) 2000-12-08 2003-04-08 3M Innovative Properties Company Urea substituted imidazopyridines
US6667312B2 (en) 2000-12-08 2003-12-23 3M Innovative Properties Company Thioether substituted imidazoquinolines
US20020107262A1 (en) * 2000-12-08 2002-08-08 3M Innovative Properties Company Substituted imidazopyridines
HU0700062A2 (en) 2000-12-08 2007-05-02 3M Innovative Properties Co Aryl ether substituted imidazoquinolines and pharmaceutical compositions thereof
US6525064B1 (en) 2000-12-08 2003-02-25 3M Innovative Properties Company Sulfonamido substituted imidazopyridines
US6677347B2 (en) 2000-12-08 2004-01-13 3M Innovative Properties Company Sulfonamido ether substituted imidazoquinolines
US6545016B1 (en) 2000-12-08 2003-04-08 3M Innovative Properties Company Amide substituted imidazopyridines
MXPA04005023A (en) 2001-11-29 2004-08-11 3M Innovative Properties Co Pharmaceutical formulations comprising an immune response modifier.
CA2365732A1 (en) 2001-12-20 2003-06-20 Harm Sluiman Testing measurements
JP2005531599A (en) * 2002-05-29 2005-10-20 スリーエム イノベイティブ プロパティズ カンパニー Method for imidazo [4,5-c] pyridin-4-amine
EP1615665A4 (en) 2003-04-10 2010-10-06 3M Innovative Properties Co Delivery of immune response modifier compounds
NZ538812A (en) 2002-08-15 2009-02-28 3M Innovative Properties Co Immunostimulatory compositions and methods of stimulating an immune response
AU2003299082A1 (en) * 2002-09-26 2004-04-19 3M Innovative Properties Company 1h-imidazo dimers
JP2006513212A (en) 2002-12-20 2006-04-20 スリーエム イノベイティブ プロパティズ カンパニー Aryl / hetaryl substituted imidazoquinolines
EP1578419A4 (en) 2002-12-30 2008-11-12 3M Innovative Properties Co Immunostimulatory combinations
AU2004218349A1 (en) 2003-03-04 2004-09-16 3M Innovative Properties Company Prophylactic treatment of UV-induced epidermal neoplasia
CA2518082C (en) * 2003-03-13 2013-02-12 3M Innovative Properties Company Methods for diagnosing skin lesions
US8426457B2 (en) 2003-03-13 2013-04-23 Medicis Pharmaceutical Corporation Methods of improving skin quality
US20040192585A1 (en) 2003-03-25 2004-09-30 3M Innovative Properties Company Treatment for basal cell carcinoma
WO2004110991A2 (en) 2003-06-06 2004-12-23 3M Innovative Properties Company PROCESS FOR IMIDAZO[4,5-c]PYRIDIN-4-AMINES
MXPA06001674A (en) 2003-08-12 2006-05-12 3M Innovative Properties Co Hydroxylamine substituted imidazo-containing compounds.
AU2004268616B2 (en) 2003-08-25 2010-10-07 3M Innovative Properties Company Delivery of immune response modifier compounds
MXPA06002199A (en) 2003-08-27 2006-05-22 3M Innovative Properties Co Aryloxy and arylalkyleneoxy substituted imidazoquinolines.
EP1660026A4 (en) 2003-09-05 2008-07-16 3M Innovative Properties Co Treatment for cd5+ b cell lymphoma
BRPI0414856A (en) 2003-10-03 2006-11-21 3M Innovative Properties Co alkoxy-substituted imidazoquinolines
US7544697B2 (en) 2003-10-03 2009-06-09 Coley Pharmaceutical Group, Inc. Pyrazolopyridines and analogs thereof
AU2004291122A1 (en) 2003-11-14 2005-06-02 3M Innovative Properties Company Hydroxylamine substituted imidazo ring compounds
CA2545774A1 (en) 2003-11-14 2005-06-02 3M Innovative Properties Company Oxime substituted imidazo ring compounds
WO2005051317A2 (en) 2003-11-25 2005-06-09 3M Innovative Properties Company Substituted imidazo ring systems and methods
WO2005055932A2 (en) 2003-12-02 2005-06-23 3M Innovative Properties Company Therapeutic combinations and methods including irm compounds
EP1701955A1 (en) 2003-12-29 2006-09-20 3M Innovative Properties Company Arylalkenyl and arylalkynyl substituted imidazoquinolines
US7888349B2 (en) * 2003-12-29 2011-02-15 3M Innovative Properties Company Piperazine, [1,4]Diazepane, [1,4]Diazocane, and [1,5]Diazocane fused imidazo ring compounds
WO2005066169A2 (en) 2003-12-30 2005-07-21 3M Innovative Properties Company Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides
CA2559863A1 (en) 2004-03-24 2005-10-13 3M Innovative Properties Company Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
WO2005123080A2 (en) 2004-06-15 2005-12-29 3M Innovative Properties Company Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
US7915281B2 (en) 2004-06-18 2011-03-29 3M Innovative Properties Company Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method
US7897609B2 (en) 2004-06-18 2011-03-01 3M Innovative Properties Company Aryl substituted imidazonaphthyridines
US8026366B2 (en) 2004-06-18 2011-09-27 3M Innovative Properties Company Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
AU2005326708C1 (en) 2004-12-30 2012-08-30 3M Innovative Properties Company Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds
WO2006074003A2 (en) 2004-12-30 2006-07-13 3M Innovative Properties Company CHIRAL FUSED [1,2]IMIDAZO[4,5-c] RING COMPOUNDS
WO2006084251A2 (en) 2005-02-04 2006-08-10 Coley Pharmaceutical Group, Inc. Aqueous gel formulations containing immune reponse modifiers
EP1846405A2 (en) 2005-02-11 2007-10-24 3M Innovative Properties Company Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods
JP2008535832A (en) 2005-04-01 2008-09-04 コーリー ファーマシューティカル グループ,インコーポレイテッド Pyrazolopyridine-1,4-diamine and analogs thereof
JP2008538550A (en) 2005-04-01 2008-10-30 コーリー ファーマシューティカル グループ,インコーポレイテッド 1-Substituted pyrazolo (3,4-c) cyclic compounds as modulators of cytokine biosynthesis for treating viral infections and neoplastic diseases
KR20080048551A (en) * 2005-09-23 2008-06-02 콜레이 파마시티컬 그룹, 인코포레이티드 Method for 1h-imidazo[4,5-c]pyridines and analogs thereof
CN100344325C (en) * 2005-10-17 2007-10-24 华南师范大学 Medicine for treating cervical carcinoma, its preparation process and application
WO2008008432A2 (en) 2006-07-12 2008-01-17 Coley Pharmaceutical Group, Inc. Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods
WO2009034411A1 (en) * 2007-09-12 2009-03-19 Centre National De La Recherche Scientifique Perharidines as cdk inhibitors
CN112587658A (en) 2012-07-18 2021-04-02 博笛生物科技有限公司 Targeted immunotherapy for cancer
ES2809535T3 (en) * 2013-12-09 2021-03-04 UCB Biopharma SRL Imidazopyridine derivatives as modulators of TNF activity
EP3092254A4 (en) 2014-01-10 2017-09-20 Birdie Biopharmaceuticals Inc. Compounds and compositions for treating her2 positive tumors
WO2016004876A1 (en) 2014-07-09 2016-01-14 Shanghai Birdie Biotech, Inc. Anti-pd-l1 combinations for treating tumors
CN112546238A (en) 2014-09-01 2021-03-26 博笛生物科技有限公司 anti-PD-L1 conjugates for the treatment of tumors

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL73534A (en) * 1983-11-18 1990-12-23 Riker Laboratories Inc 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds
US4929624A (en) * 1989-03-23 1990-05-29 Minnesota Mining And Manufacturing Company Olefinic 1H-imidazo(4,5-c)quinolin-4-amines
US5389640A (en) * 1991-03-01 1995-02-14 Minnesota Mining And Manufacturing Company 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines
US5268376A (en) * 1991-09-04 1993-12-07 Minnesota Mining And Manufacturing Company 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines
CZ288182B6 (en) * 1993-07-15 2001-05-16 Minnesota Mining & Mfg Imidazo[4,5-c]pyridine-4-amines and pharmaceutical preparations based thereon
EP0894797A4 (en) * 1997-01-09 2001-08-16 Terumo Corp Novel amide derivatives and intermediates for the synthesis thereof
HU0101155A3 (en) * 1997-12-11 2002-10-28 Minnesota Mining & Mfg Imidazonaphthyridines, pharmaceutical compositions thereof and intermediates
US6541485B1 (en) * 1999-06-10 2003-04-01 3M Innovative Properties Company Urea substituted imidazoquinolines
US6451810B1 (en) * 1999-06-10 2002-09-17 3M Innovative Properties Company Amide substituted imidazoquinolines
US6331539B1 (en) * 1999-06-10 2001-12-18 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines

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