RU2475487C2 - Имидазохинолины с иммуномодулирующими свойствами - Google Patents
Имидазохинолины с иммуномодулирующими свойствами Download PDFInfo
- Publication number
- RU2475487C2 RU2475487C2 RU2009140465/04A RU2009140465A RU2475487C2 RU 2475487 C2 RU2475487 C2 RU 2475487C2 RU 2009140465/04 A RU2009140465/04 A RU 2009140465/04A RU 2009140465 A RU2009140465 A RU 2009140465A RU 2475487 C2 RU2475487 C2 RU 2475487C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- amino
- propyl
- imidazo
- quinolin
- Prior art date
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- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title 1
- 230000002519 immonomodulatory effect Effects 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 73
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 4
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims abstract 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims abstract 2
- 125000003725 azepanyl group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 2
- -1 methoxyethyl Chemical group 0.000 claims 99
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 86
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 74
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 20
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 16
- OAFYFGINDSGHDR-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 OAFYFGINDSGHDR-UHFFFAOYSA-N 0.000 claims 9
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- CARVEAKPQSZLKP-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(1-methylpiperidin-4-yl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C1CCN(C)CC1)CC1=CC=CC(CC(=O)OC)=C1 CARVEAKPQSZLKP-UHFFFAOYSA-N 0.000 claims 2
- JXRWVFKUUVEFAW-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(3-morpholin-4-ylpropyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCOCC1 JXRWVFKUUVEFAW-UHFFFAOYSA-N 0.000 claims 2
- VEDCUJSSWBHNNY-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[3-(4-methylpiperazin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCN(C)CC1 VEDCUJSSWBHNNY-UHFFFAOYSA-N 0.000 claims 2
- LZHLVRRBAUBVRX-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[3-(dimethylamino)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CCCN(C)C)CC1=CC=CC(CC(=O)OC)=C1 LZHLVRRBAUBVRX-UHFFFAOYSA-N 0.000 claims 2
- DPFWTVXXNGIJTB-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[3-[ethyl(methyl)amino]propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CCCN(C)CC)CC1=CC=CC(CC(=O)OC)=C1 DPFWTVXXNGIJTB-UHFFFAOYSA-N 0.000 claims 2
- VIMMXFYSJXUVJE-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propylamino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNCC1=CC=CC(CC(=O)OC)=C1 VIMMXFYSJXUVJE-UHFFFAOYSA-N 0.000 claims 2
- GOXIVZHBIPWDCC-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(1-methylpiperidin-4-yl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C1CCN(C)CC1)CC1=CC=C(CC(=O)OC)C=C1 GOXIVZHBIPWDCC-UHFFFAOYSA-N 0.000 claims 2
- JESLMFCDDXPVAC-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-methylsulfonylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CS(C)(=O)=O)CC1=CC=C(CC(=O)OC)C=C1 JESLMFCDDXPVAC-UHFFFAOYSA-N 0.000 claims 2
- XHNJWZRQHYJISF-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CCN(C)C)CC1=CC=C(CC(=O)OC)C=C1 XHNJWZRQHYJISF-UHFFFAOYSA-N 0.000 claims 2
- XIQQEASYCSFTBJ-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propylamino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNCC1=CC=C(CC(=O)OC)C=C1 XIQQEASYCSFTBJ-UHFFFAOYSA-N 0.000 claims 2
- RRDDJWNSVSLZSN-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 RRDDJWNSVSLZSN-UHFFFAOYSA-N 0.000 claims 2
- NIOHPZFOZHREKH-UHFFFAOYSA-N methyl 2-[4-[[acetyl-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 NIOHPZFOZHREKH-UHFFFAOYSA-N 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- MITQPGKTRNEULN-UHFFFAOYSA-N CCCCC1=NC2=C(N1CCCN(CC3=CC(=CC=C3)OC(=O)C)C(=O)CN4CC(C4)O)C5=CC=CC=C5N=C2N Chemical compound CCCCC1=NC2=C(N1CCCN(CC3=CC(=CC=C3)OC(=O)C)C(=O)CN4CC(C4)O)C5=CC=CC=C5N=C2N MITQPGKTRNEULN-UHFFFAOYSA-N 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- NKRDSOWWBRATKT-UHFFFAOYSA-N S1(=O)(=O)NC(=O)C2=CC=CC=C12.S1(=O)(=O)NC(=O)C2=CC=CC=C12.C(C)(=O)O Chemical compound S1(=O)(=O)NC(=O)C2=CC=CC=C12.S1(=O)(=O)NC(=O)C2=CC=CC=C12.C(C)(=O)O NKRDSOWWBRATKT-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- VUCWMAJEUOWLEY-UHFFFAOYSA-N 1-$l^{1}-azanylpiperidine Chemical group [N]N1CCCCC1 VUCWMAJEUOWLEY-UHFFFAOYSA-N 0.000 abstract 2
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 abstract 2
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000001575 pathological effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic 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
- C07D471/02—Heterocyclic 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
- C07D471/04—Ortho-condensed 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Ophthalmology & Optometry (AREA)
- Biotechnology (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91658607P | 2007-05-08 | 2007-05-08 | |
| US60/916,586 | 2007-05-08 | ||
| US2495708P | 2008-01-31 | 2008-01-31 | |
| US61/024,957 | 2008-01-31 | ||
| PCT/GB2008/050328 WO2008135791A1 (en) | 2007-05-08 | 2008-05-06 | Imidazoquinolines with immuno-modulating properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009140465A RU2009140465A (ru) | 2011-06-20 |
| RU2475487C2 true RU2475487C2 (ru) | 2013-02-20 |
Family
ID=39596464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009140465/04A RU2475487C2 (ru) | 2007-05-08 | 2008-05-06 | Имидазохинолины с иммуномодулирующими свойствами |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US8436178B2 (OSRAM) |
| EP (1) | EP2155743B1 (OSRAM) |
| JP (1) | JP5400763B2 (OSRAM) |
| KR (1) | KR20100016289A (OSRAM) |
| CN (1) | CN101687867B (OSRAM) |
| AR (1) | AR066492A1 (OSRAM) |
| AU (1) | AU2008247165B2 (OSRAM) |
| BR (1) | BRPI0811125A2 (OSRAM) |
| CA (1) | CA2686163A1 (OSRAM) |
| CL (1) | CL2008001357A1 (OSRAM) |
| CO (1) | CO6251247A2 (OSRAM) |
| CY (1) | CY1113339T1 (OSRAM) |
| DK (1) | DK2155743T3 (OSRAM) |
| EC (1) | ECSP099750A (OSRAM) |
| ES (1) | ES2393037T3 (OSRAM) |
| HR (1) | HRP20120895T1 (OSRAM) |
| IL (1) | IL201572A0 (OSRAM) |
| MX (1) | MX2009011802A (OSRAM) |
| MY (1) | MY150519A (OSRAM) |
| PE (1) | PE20090276A1 (OSRAM) |
| PL (1) | PL2155743T3 (OSRAM) |
| PT (1) | PT2155743E (OSRAM) |
| RU (1) | RU2475487C2 (OSRAM) |
| TW (1) | TW200902529A (OSRAM) |
| UY (1) | UY31069A1 (OSRAM) |
| WO (1) | WO2008135791A1 (OSRAM) |
| ZA (1) | ZA200907547B (OSRAM) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11136397B2 (en) | 2016-01-07 | 2021-10-05 | Birdie Pharmaceuticals, Inc. | Anti-EGFR combinations for treating tumors |
| US11220552B2 (en) | 2016-01-07 | 2022-01-11 | Birdie Biopharmaceuticals, Inc. | Anti-CD20 combinations for treating tumors |
| US11279761B2 (en) | 2014-07-09 | 2022-03-22 | Birdie Biopharmaceuticals, Inc. | Anti-PD-L1 combinations for treating tumors |
| RU2785124C1 (ru) * | 2019-07-17 | 2022-12-05 | Пфайзер Инк. | Производные имидазо[4,5-с]пиридина в качестве агонистов toll-подобного рецептора |
| US11517567B2 (en) | 2017-06-23 | 2022-12-06 | Birdie Biopharmaceuticals, Inc. | Pharmaceutical compositions |
| US11633495B2 (en) | 2014-01-10 | 2023-04-25 | Birdie Biopharmaceuticals, Inc. | Compounds and compositions for immunotherapy |
| US11834448B2 (en) | 2017-04-27 | 2023-12-05 | Birdie Biopharmaceuticals, Inc. | 2-amino-quinoline derivatives |
| US11976064B2 (en) | 2019-07-17 | 2024-05-07 | Pfizer Inc. | Toll-like receptor agonists |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2559036C (en) | 2004-03-26 | 2013-08-20 | Dainippon Sumitomo Pharma Co., Ltd. | 9-substituted 8-oxoadenine compound |
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| US20040204438A1 (en) * | 1999-06-10 | 2004-10-14 | 3M Innovative Properties Company | Sulfonamide substituted imidazoquinolines |
| US20040229897A1 (en) * | 1999-06-10 | 2004-11-18 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
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| US11517567B2 (en) | 2017-06-23 | 2022-12-06 | Birdie Biopharmaceuticals, Inc. | Pharmaceutical compositions |
| US12295950B2 (en) | 2017-06-23 | 2025-05-13 | Birdie Biopharmaceuticals, Inc. | Pharmaceutical compositions |
| RU2785124C1 (ru) * | 2019-07-17 | 2022-12-05 | Пфайзер Инк. | Производные имидазо[4,5-с]пиридина в качестве агонистов toll-подобного рецептора |
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