DE2800480C2 - - Google Patents
Info
- Publication number
- DE2800480C2 DE2800480C2 DE2800480A DE2800480A DE2800480C2 DE 2800480 C2 DE2800480 C2 DE 2800480C2 DE 2800480 A DE2800480 A DE 2800480A DE 2800480 A DE2800480 A DE 2800480A DE 2800480 C2 DE2800480 C2 DE 2800480C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- substituted
- compounds
- imidazo
- Prior art date
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- -1 4-substituted imidazo [1,2-a] quinoxaline Chemical class 0.000 claims description 11
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- VKXZCHMZYHIJSG-UHFFFAOYSA-N 4-(4-chlorophenyl)imidazo[1,2-a]quinoxaline Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=CC=C2N2C1=NC=C2 VKXZCHMZYHIJSG-UHFFFAOYSA-N 0.000 claims 1
- LCIFAJPMIUOMPP-UHFFFAOYSA-N 4-(4-fluorophenyl)imidazo[1,2-a]quinoxaline Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CC=C2N2C1=NC=C2 LCIFAJPMIUOMPP-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- VTNBGTYLJIUATL-UHFFFAOYSA-N imidazo[1,2-a]quinoxaline Chemical class C1=CC=C2N3C=CN=C3C=NC2=C1 VTNBGTYLJIUATL-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- 206010030113 Oedema Diseases 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003018 immunosuppressive agent Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 210000002683 foot Anatomy 0.000 description 4
- 229960003444 immunosuppressant agent Drugs 0.000 description 4
- 230000021633 leukocyte mediated immunity Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HVECTIQVQPUSEX-UHFFFAOYSA-N 2-imidazol-1-ylaniline Chemical compound NC1=CC=CC=C1N1C=NC=C1 HVECTIQVQPUSEX-UHFFFAOYSA-N 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 208000006313 Delayed Hypersensitivity Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 241000159243 Toxicodendron radicans Species 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000001716 anti-fugal effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000003228 hemolysin Substances 0.000 description 2
- 230000001861 immunosuppressant effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 241001260018 Arthroderma uncinatum Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 206010005913 Body tinea Diseases 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000005232 Glossitis Diseases 0.000 description 1
- 206010019755 Hepatitis chronic active Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 206010043866 Tinea capitis Diseases 0.000 description 1
- 201000010618 Tinea cruris Diseases 0.000 description 1
- 206010049591 Tinea imbricata Diseases 0.000 description 1
- 206010067197 Tinea manuum Diseases 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 201000003465 angular cheilitis Diseases 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000656 anti-yeast Effects 0.000 description 1
- 230000005875 antibody response Effects 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000002479 balanitis Diseases 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 208000007287 cheilitis Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000008348 humoral response Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 206010021198 ichthyosis Diseases 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 229940124589 immunosuppressive drug Drugs 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 208000003265 stomatitis Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 201000009642 tinea barbae Diseases 0.000 description 1
- 201000003875 tinea corporis Diseases 0.000 description 1
- 208000009189 tinea favosa Diseases 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229960001005 tuberculin Drugs 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000005951 type IV hypersensitivity Effects 0.000 description 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75764077A | 1977-01-07 | 1977-01-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2800480A1 DE2800480A1 (de) | 1978-07-13 |
| DE2800480C2 true DE2800480C2 (en, 2012) | 1990-04-12 |
Family
ID=25048641
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782800480 Granted DE2800480A1 (de) | 1977-01-07 | 1978-01-05 | 4-substituierte imidazo eckige klammer auf 1,2-a eckige klammer zu -chinoxaline, zwischenprodukte, verfahren zu deren herstellung und diese enthaltende mittel |
| DE2858766A Expired - Fee Related DE2858766C2 (en, 2012) | 1977-01-07 | 1978-01-05 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2858766A Expired - Fee Related DE2858766C2 (en, 2012) | 1977-01-07 | 1978-01-05 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4160097A (en, 2012) |
| JP (2) | JPS5387398A (en, 2012) |
| AU (1) | AU521807B2 (en, 2012) |
| BE (1) | BE862608A (en, 2012) |
| CA (1) | CA1149385A (en, 2012) |
| CH (2) | CH636102A5 (en, 2012) |
| CS (1) | CS200232B2 (en, 2012) |
| DE (2) | DE2800480A1 (en, 2012) |
| DK (1) | DK157024C (en, 2012) |
| FI (1) | FI64374C (en, 2012) |
| FR (1) | FR2376858A1 (en, 2012) |
| GB (2) | GB1579499A (en, 2012) |
| GR (1) | GR73168B (en, 2012) |
| IE (1) | IE46191B1 (en, 2012) |
| LU (1) | LU78813A1 (en, 2012) |
| NL (1) | NL7800114A (en, 2012) |
| SE (2) | SE436359B (en, 2012) |
| YU (1) | YU44663B (en, 2012) |
| ZA (1) | ZA7827B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE439308B (sv) * | 1978-08-02 | 1985-06-10 | Roussel Uclaf | Imidazo(1,2-a)kinoxaliner och farmaceutiska kompositioner derav |
| JPS5569567A (en) * | 1978-11-21 | 1980-05-26 | Eisai Co Ltd | Novel imidazole compound, and antidepressant containing the same |
| IT1209431B (it) * | 1980-11-28 | 1989-07-16 | Angeli Inst Spa | Imidazolilfenil amidine, processi per la loro preparazione e loro impiego farmaceutico, ed intermedi di preparazione. |
| DE3830054A1 (de) * | 1988-09-03 | 1990-03-15 | Boehringer Mannheim Gmbh | Phenylamide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| JPH0349309U (en, 2012) * | 1989-09-21 | 1991-05-14 | ||
| US6235740B1 (en) | 1997-08-25 | 2001-05-22 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
| US6635626B1 (en) | 1997-08-25 | 2003-10-21 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
| CN1285834A (zh) | 1997-11-11 | 2001-02-28 | 小野药品工业株式会社 | 稠合吡嗪化合物 |
| ES2324846T3 (es) * | 1998-03-04 | 2009-08-17 | Bristol-Myers Squibb Company | Inhibidores de la proteina tirosina quinasa de imidazopirazina heterociclo-sustituida. |
| US6869956B2 (en) * | 2000-10-03 | 2005-03-22 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK) |
| EP1325009B1 (en) | 2000-10-03 | 2006-03-08 | Bristol-Myers Squibb Company | Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same |
| CA2436770A1 (en) * | 2001-02-01 | 2002-08-08 | James R. Burke | Methods of treating inflammatory and immune diseases using inhibitors of ikb kinase (ikk) |
| WO2008039794A1 (en) * | 2006-09-25 | 2008-04-03 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541109A (en) * | 1968-06-25 | 1970-11-17 | Du Pont | 1-substituted imidazoles useful in acth reserve assay |
| US4011236A (en) * | 1968-09-09 | 1977-03-08 | Merck & Co., Inc. | N-(benzimidazol-2-yl)arylcarboxamides as ultraviolet (uv) light absorbers |
| GB1347493A (en) * | 1971-02-11 | 1974-02-27 | Aspro Nicholas Ltd | Benzazine derivatives |
| US3994893A (en) | 1975-11-03 | 1976-11-30 | E. R. Squibb & Sons, Inc. | 4-Amino derivatives of pyrozolo[1,5-a]quinoxaline-3-carboxylic acid and esters |
-
1977
- 1977-12-08 US US05/858,515 patent/US4160097A/en not_active Expired - Lifetime
- 1977-12-23 GR GR55051A patent/GR73168B/el unknown
- 1977-12-28 JP JP15758177A patent/JPS5387398A/ja active Granted
- 1977-12-28 CA CA000293972A patent/CA1149385A/en not_active Expired
-
1978
- 1978-01-03 BE BE184085A patent/BE862608A/xx not_active IP Right Cessation
- 1978-01-04 DK DK004278A patent/DK157024C/da not_active IP Right Cessation
- 1978-01-04 NL NL7800114A patent/NL7800114A/xx not_active Application Discontinuation
- 1978-01-04 FI FI780023A patent/FI64374C/fi not_active IP Right Cessation
- 1978-01-04 ZA ZA00780027A patent/ZA7827B/xx unknown
- 1978-01-05 DE DE19782800480 patent/DE2800480A1/de active Granted
- 1978-01-05 SE SE7800138A patent/SE436359B/sv not_active IP Right Cessation
- 1978-01-05 LU LU78813A patent/LU78813A1/xx unknown
- 1978-01-05 DE DE2858766A patent/DE2858766C2/de not_active Expired - Fee Related
- 1978-01-06 CH CH15278A patent/CH636102A5/fr not_active IP Right Cessation
- 1978-01-06 YU YU21/78A patent/YU44663B/xx unknown
- 1978-01-06 GB GB13335/79A patent/GB1579499A/en not_active Expired
- 1978-01-06 GB GB492/78A patent/GB1579498A/en not_active Expired
- 1978-01-06 IE IE37/78A patent/IE46191B1/en unknown
- 1978-01-06 FR FR7800308A patent/FR2376858A1/fr active Granted
- 1978-01-09 CS CS78169A patent/CS200232B2/cs unknown
- 1978-01-11 AU AU32331/78A patent/AU521807B2/en not_active Expired
-
1983
- 1983-01-18 CH CH27483A patent/CH640229A5/fr not_active IP Right Cessation
- 1983-02-21 SE SE8300945A patent/SE460477B/sv not_active IP Right Cessation
-
1986
- 1986-01-17 JP JP61006590A patent/JPS61171470A/ja active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69132961T2 (de) | Styrylsubstituierte heteroarylverbindungen, welche egf-rezeptor-tyrosinkinase inhibieren | |
| DE69011914T2 (de) | Olefinisch substitierte 1H-Imidazo[4,5-c]chinolin-4-amine. | |
| DE2800480C2 (en, 2012) | ||
| EP0515901A1 (de) | Antimykotische Mittel, die Phenylessigsäurederivate enthalten | |
| DE1770447A1 (de) | In 1-Stellung substituierte 1,4-Dihydro-6,7-methylendioxy-4-oxo-chinolin-3-carbonsaeure-Derivate | |
| DD146293A5 (de) | Verfahren zur herstellung von 5-(4-pyridyl)-6-(4-fluorphenyl)-2,3-dihydroimidazo eckige klammer auf 2,1-b eckige klammer zu thiazol,seiner salze und seiner oxide | |
| DE3125471A1 (de) | "piperazinderivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten" | |
| EP0036153A1 (de) | 1,1-Diphenyl-2-(1,2,4-triazol-1-yl)-äthan-1-ole als Antimykotika | |
| DE2921660A1 (de) | 5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel | |
| DE69114405T2 (de) | 3-(1,2-Benzisoxazol-3-yl)-4-Pyridinamine und Derivate. | |
| DE69110219T2 (de) | 3-(1H-Indazol-3-yl)-4-pyridiname, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Arzneimittel. | |
| DE2318784A1 (de) | N-(2,4-dihydroxybenzoyl)-4-aminosalizylsaeure | |
| DE2702790A1 (de) | Neue therapeutika auf der basis des imidazo(1,2-a)pyridins | |
| DE3347658A1 (de) | 1.4-naphthochinonderivate mit entzuendungshemmender wirkung | |
| EP0037049A1 (de) | Biphenylyl-imidazolylethan-Derivate, Verfahren zu ihrer Herstellung und diese Verbindingungen enthaltende Arzneimittel | |
| EP0276466A2 (de) | Aminoazolderivate, Verfahren zu deren Herstellung und deren Verwendung als antimykotische Mittel | |
| DE3012190A1 (de) | Pharmazeutisches mittel auf der basis 1,3,5-substituierter biuret-verbindungen | |
| AT383806B (de) | Verfahren zur herstellung neuer verbindungen von furo-(3,4-c)-pyridinderivaten und von deren salzen | |
| DE1806995C3 (de) | Bisimidazolyl-bisphenylmethane und deren Salze | |
| DE2113489B2 (de) | 2-Nitro-benzofuranderivate, ein Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| DE2656678C2 (de) | 4-Amino-trans-decahydrochinolin-Derivate und Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2506256C2 (de) | 5-Nitro-imidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0111205B1 (de) | Acridanon-Derivate | |
| DE2510130A1 (de) | Imidazolderivate und verfahren zu ihrer herstellung | |
| DE2930039A1 (de) | Entzuendungshemmendes mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 2858766 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 2858766 |
|
| AH | Division in |
Ref country code: DE Ref document number: 2858766 Format of ref document f/p: P |
|
| AH | Division in |
Ref country code: DE Ref document number: 2858766 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BRISTOL-MYERS SQUIBB CO. (N.D.GES.D.STAATES DELAWA |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: KINZEBACH, W., DIPL.-CHEM. DR.PHIL. RIEDL, P., DIPL.-CHEM.DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |