HRP20020453A2 - 1,3-diaza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof - Google Patents
1,3-diaza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof Download PDFInfo
- Publication number
- HRP20020453A2 HRP20020453A2 HR20020453A HRP20020453A HRP20020453A2 HR P20020453 A2 HRP20020453 A2 HR P20020453A2 HR 20020453 A HR20020453 A HR 20020453A HR P20020453 A HRP20020453 A HR P20020453A HR P20020453 A2 HRP20020453 A2 HR P20020453A2
- Authority
- HR
- Croatia
- Prior art keywords
- diaza
- dibenzo
- azulen
- ylmethoxy
- oxa
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- NKTGZAKMRRHEKM-UHFFFAOYSA-N 3,5-diazatetracyclo[12.4.0.02,6.08,13]octadeca-1(18),2,4,6,8,10,12,14,16-nonaene Chemical compound N1=CN=C2C3=C(C4=C(C=C12)C=CC=C4)C=CC=C3 NKTGZAKMRRHEKM-UHFFFAOYSA-N 0.000 title claims description 6
- 108060008682 Tumor Necrosis Factor Proteins 0.000 title description 39
- 239000003112 inhibitor Substances 0.000 title description 4
- 102000003390 tumor necrosis factor Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 112
- 238000006243 chemical reaction Methods 0.000 claims description 38
- -1 C1-C4-alkoxycarbonyl Chemical group 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000003435 aroyl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 150000003573 thiols Chemical class 0.000 claims description 9
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000001575 pathological effect Effects 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- BIVWPRXKQRBVEH-UHFFFAOYSA-N 3-[(17-chloro-13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),3,7,9,11,15,17-octaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1NC(COCCCN(C)C)=N2 BIVWPRXKQRBVEH-UHFFFAOYSA-N 0.000 claims description 4
- 102000004127 Cytokines Human genes 0.000 claims description 4
- 108090000695 Cytokines Proteins 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000022244 formylation Effects 0.000 claims description 4
- 238000006170 formylation reaction Methods 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
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- RMAHZQMRRPRZRD-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1N(COCC[Si](C)(C)C)C(COCCCN)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1N(COCC[Si](C)(C)C)C(COCCCN)=N2 RMAHZQMRRPRZRD-UHFFFAOYSA-N 0.000 claims description 3
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- FXWQMARYUXECQS-UHFFFAOYSA-N [2-(5-chloro-1h-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy)-ethyl]-dimethyl-amine Chemical compound C12=CC=CC=C2SC2=CC=C(Cl)C=C2C2=C1NC(COCCN(C)C)=N2 FXWQMARYUXECQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- FLZNAYFRLFLERO-UHFFFAOYSA-N dimethyl-[2-(1h-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy) -ethyl]-amine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1NC(COCCN(C)C)=N2 FLZNAYFRLFLERO-UHFFFAOYSA-N 0.000 claims description 3
- AJQUWOHVSQDLGD-UHFFFAOYSA-N dimethyl-[3-(1h-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy)-propyl]-amine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1NC(COCCCN(C)C)=N2 AJQUWOHVSQDLGD-UHFFFAOYSA-N 0.000 claims description 3
- GXXQXWNMEXZJPR-UHFFFAOYSA-N dimethyl-{2-[1-(2-trimethylsilyl-ethoxymethyl)-1h-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy]-ethyl}-amine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1N(COCC[Si](C)(C)C)C(COCCN(C)C)=N2 GXXQXWNMEXZJPR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- WVWURONCALWJAZ-UHFFFAOYSA-N (5-methyl-13-thia-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl)methanol Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1N(C)C(CO)=N2 WVWURONCALWJAZ-UHFFFAOYSA-N 0.000 claims description 2
- PWDUUYKZJOXCPH-UHFFFAOYSA-N 3-[5-(2-phenylethyl)-13-thia-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl]propan-1-ol Chemical compound OCCCC1=NC(C2=CC=CC=C2SC2=CC=CC=C22)=C2N1CCC1=CC=CC=C1 PWDUUYKZJOXCPH-UHFFFAOYSA-N 0.000 claims description 2
- YQJORVCNVDPTIH-UHFFFAOYSA-N 3-[[9-chloro-5-(2-trimethylsilylethoxymethyl)-13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7(12),8,10,14,16-octaen-4-yl]methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1N(COCC[Si](C)(C)C)C(COCCCN(C)C)=N2 YQJORVCNVDPTIH-UHFFFAOYSA-N 0.000 claims description 2
- QLSDGQDZVXIBRM-UHFFFAOYSA-N 5-(2-trimethylsilylethoxymethyl)-13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaene-4-carbaldehyde Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1N(COCC[Si](C)(C)C)C(C=O)=N2 QLSDGQDZVXIBRM-UHFFFAOYSA-N 0.000 claims description 2
- SIFSXWCHQQZTRM-UHFFFAOYSA-N 5-methyl-13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaene-4-carbaldehyde Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1N(C)C(C=O)=N2 SIFSXWCHQQZTRM-UHFFFAOYSA-N 0.000 claims description 2
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- ZZCXSGZOTZKQCU-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1N(COCC[Si](C)(C)C)C(CO)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1N(COCC[Si](C)(C)C)C(CO)=N2 ZZCXSGZOTZKQCU-UHFFFAOYSA-N 0.000 claims description 2
- HTRDNAOLQNJGJH-UHFFFAOYSA-N CN(C)CCCOCCCC1=NC(C2=CC=CC=C2SC2=CC=CC=C22)=C2N1C(C)C1=CC=CC=C1 Chemical compound CN(C)CCCOCCCC1=NC(C2=CC=CC=C2SC2=CC=CC=C22)=C2N1C(C)C1=CC=CC=C1 HTRDNAOLQNJGJH-UHFFFAOYSA-N 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- MQCZFDLHWUMYIU-UHFFFAOYSA-N N,N-dimethyl-2-[1-(13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl)-2-phenylpropoxy]ethanamine Chemical compound N=1C(C2=CC=CC=C2OC2=CC=CC=C22)=C2NC=1C(OCCN(C)C)C(C)C1=CC=CC=C1 MQCZFDLHWUMYIU-UHFFFAOYSA-N 0.000 claims description 2
- NAUQHHZDSQAFAH-UHFFFAOYSA-N N,N-dimethyl-2-[2-phenyl-1-(13-thia-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl)propoxy]ethanamine Chemical compound N=1C(C2=CC=CC=C2SC2=CC=CC=C22)=C2NC=1C(OCCN(C)C)C(C)C1=CC=CC=C1 NAUQHHZDSQAFAH-UHFFFAOYSA-N 0.000 claims description 2
- XVYURZSESJLIFV-UHFFFAOYSA-N N,N-dimethyl-3-[1-(13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl)-2-phenylpropoxy]propan-1-amine Chemical compound N=1C(C2=CC=CC=C2OC2=CC=CC=C22)=C2NC=1C(OCCCN(C)C)C(C)C1=CC=CC=C1 XVYURZSESJLIFV-UHFFFAOYSA-N 0.000 claims description 2
- NAJFIWSKPFSRGQ-UHFFFAOYSA-N N,N-dimethyl-3-[2-phenyl-1-(13-thia-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl)propoxy]propan-1-amine Chemical compound N=1C(C2=CC=CC=C2SC2=CC=CC=C22)=C2NC=1C(OCCCN(C)C)C(C)C1=CC=CC=C1 NAJFIWSKPFSRGQ-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- BVEZUPBFVUJKKT-UHFFFAOYSA-N [17-chloro-5-(2-trimethylsilylethoxymethyl)-13-oxa-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),3,7,9,11,15,17-octaen-4-yl]methanol Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1N(COCC[Si](C)(C)C)C(CO)=N2 BVEZUPBFVUJKKT-UHFFFAOYSA-N 0.000 claims description 2
- DKGDJLVJIKVSOS-UHFFFAOYSA-N [3-(5- chloro-1h-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy)-propyl]-dimethyl-amine Chemical compound C12=CC=CC=C2SC2=CC=C(Cl)C=C2C2=C1NC(COCCCN(C)C)=N2 DKGDJLVJIKVSOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- MPPWLDVLNMYZJZ-UHFFFAOYSA-N dimethyl-{3-[1-(2-trimethylsilyl-ethoxymethyl)-1h-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy]-propyl}-amine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1N(COCC[Si](C)(C)C)C(COCCCN(C)C)=N2 MPPWLDVLNMYZJZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- VQDCGJFARWEXDP-UHFFFAOYSA-N methyl 3-[5-(2-phenylethyl)-13-thia-3,5-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),3,7,9,11,14,16-octaen-4-yl]prop-2-enoate Chemical compound COC(=O)C=CC1=NC(C2=CC=CC=C2SC2=CC=CC=C22)=C2N1CCC1=CC=CC=C1 VQDCGJFARWEXDP-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- 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
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- 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
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- 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
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- 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
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- 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
- A61P17/04—Antipruritics
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- 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
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20020453A HRP20020453A2 (en) | 2002-05-23 | 2002-05-23 | 1,3-diaza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof |
| AU2003232372A AU2003232372A1 (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| CA002487017A CA2487017A1 (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| YU100104A RS100104A (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| CNB038161214A CN100354277C (zh) | 2002-05-23 | 2003-05-20 | 作为肿瘤坏死因子产生抑制剂的1,3－二氮杂－二苯并薁类和制备该抑制剂的中间体 |
| US10/515,711 US7166583B2 (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| AT03755236T ATE409191T1 (de) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulene als inhibitoren der produktion von tumornekrosefaktor und zwischenprodukte für deren herstellung |
| PCT/HR2003/000025 WO2003099823A2 (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| ES03755236T ES2314237T3 (es) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenos como inhibidroes de la produccion de factor de necrosis tumoral e intermedios para su preparacion. |
| PL03374504A PL374504A1 (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| DE60323748T DE60323748D1 (de) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulene als inhibitoren der produfür deren herstellung |
| JP2004507480A JP2005531586A (ja) | 2002-05-23 | 2003-05-20 | 腫瘍壊死因子産生の阻害剤としての１，３−ジアザ−ジベンゾアズレン類及びその製造用中間体 |
| EP03755236A EP1509528B1 (en) | 2002-05-23 | 2003-05-20 | 1,3-diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| ARP030101804A AR040040A1 (es) | 2002-05-23 | 2003-05-23 | 1,3-diaza-dibenzoazulenos para la inhibicion de la produccion del factor de necrosis tumoral e intermediarios para su preparacion |
| IS7568A IS7568A (is) | 2002-05-23 | 2004-11-29 | 1,3-díasa-díbensóasúlen sem latar æxlisdrepþáttarframleiðslu og milliefni til framleiðslu á þeim |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20020453A HRP20020453A2 (en) | 2002-05-23 | 2002-05-23 | 1,3-diaza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020453A2 true HRP20020453A2 (en) | 2003-12-31 |
Family
ID=29559974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020453A HRP20020453A2 (en) | 2002-05-23 | 2002-05-23 | 1,3-diaza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7166583B2 (ja) |
| EP (1) | EP1509528B1 (ja) |
| JP (1) | JP2005531586A (ja) |
| CN (1) | CN100354277C (ja) |
| AR (1) | AR040040A1 (ja) |
| AT (1) | ATE409191T1 (ja) |
| AU (1) | AU2003232372A1 (ja) |
| CA (1) | CA2487017A1 (ja) |
| DE (1) | DE60323748D1 (ja) |
| ES (1) | ES2314237T3 (ja) |
| HR (1) | HRP20020453A2 (ja) |
| IS (1) | IS7568A (ja) |
| PL (1) | PL374504A1 (ja) |
| RS (1) | RS100104A (ja) |
| WO (1) | WO2003099823A2 (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1129190E (pt) | 1998-11-13 | 2007-08-08 | Immunex Corp | Adn e polipéptidos de tslp humanos. |
| JP5329016B2 (ja) | 2001-07-23 | 2013-10-30 | イミュネックス・コーポレーション | 修飾したヒト胸腺ストローマ細胞リンホポエチン |
| HRP20020304B1 (en) * | 2002-04-10 | 2008-04-30 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 1-oxa-3-aza-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the production thereof |
| HRP20030958A2 (en) * | 2003-11-21 | 2005-08-31 | Pliva-Istra�iva�ki institut d.o.o. | USE OF 1,3-DIAZA-DIBENZO[e,h]AZULENES FOR THE MANUFACTURE OF THE TREATMENT AND PREVENTION OF CENTRAL NERVOUS SYSTEM DISEASES AND DISORDERS |
| CA2577631A1 (en) * | 2004-08-20 | 2006-03-02 | Amgen Inc. | Methods and compositions for treating allergic inflammation |
| JP2008532927A (ja) * | 2005-01-13 | 2008-08-21 | グラクソスミスクライン・イストラジヴァッキ・センタル・ザグレブ・ドルズバ・ゼー・オメイェノ・オドゴヴォルノスティオ | 抗炎症マクロライド接合体 |
| US20090286772A1 (en) * | 2006-02-24 | 2009-11-19 | Anh Chau | 2-(Phenyl or Heterocyclic)-1H-Phenanthro[9,10-D]Imidazoles |
| US7982016B2 (en) | 2007-09-10 | 2011-07-19 | Amgen Inc. | Antigen binding proteins capable of binding thymic stromal lymphopoietin |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3711489A (en) * | 1971-03-31 | 1973-01-16 | Pfizer | Certain 8,9-dihydro(3,4,7,8)cycloocta(1,2-d)imidazoles |
| FR2211218A1 (en) * | 1972-12-21 | 1974-07-19 | Pfizer | Dibenzocyclooctaimidazoles - useful as anti inflammatories |
| US4215135A (en) * | 1979-06-08 | 1980-07-29 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-1H-phenanthro[9,10-d]imidazoles |
| US4198421A (en) * | 1978-11-30 | 1980-04-15 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-dibenzo[2,3:6,7]oxepino[4,5-d]imidazoles |
| US4305954A (en) * | 1981-02-11 | 1981-12-15 | E. I. Du Pont De Nemours And Company | Antiinflammatory 3,4-dihydro(or 1,4-dihydro)-2-[(substituted)thio]-[1]benzopyrano[3,4-d]imidazoles and their corresponding sulfoxides and sulfones |
| US5166214A (en) | 1988-12-05 | 1992-11-24 | Du Pont Merck Pharmaceutical Company | Use of imidazoles for the treatment of atherosclerosis |
| CA2003283A1 (en) | 1988-12-05 | 1990-06-05 | C. Anne Higley | Imidazoles for the treatment of atherosclerosis |
| KR100568438B1 (ko) | 1997-04-24 | 2006-04-07 | 오르토-맥네일 파마슈티칼, 인코퍼레이티드 | 염증성 질환의 치료에 유용한 치환된 이미다졸, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
| HRP20000310A2 (en) | 2000-05-17 | 2002-02-28 | Pliva Farmaceutska Ind Dioniko | New dibenzoazulene compounds as tumor necrosis factor inhibitors |
-
2002
- 2002-05-23 HR HR20020453A patent/HRP20020453A2/hr not_active Application Discontinuation
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2003
- 2003-05-20 CN CNB038161214A patent/CN100354277C/zh not_active Expired - Fee Related
- 2003-05-20 PL PL03374504A patent/PL374504A1/xx not_active Application Discontinuation
- 2003-05-20 CA CA002487017A patent/CA2487017A1/en not_active Abandoned
- 2003-05-20 WO PCT/HR2003/000025 patent/WO2003099823A2/en active IP Right Grant
- 2003-05-20 RS YU100104A patent/RS100104A/sr unknown
- 2003-05-20 JP JP2004507480A patent/JP2005531586A/ja active Pending
- 2003-05-20 ES ES03755236T patent/ES2314237T3/es not_active Expired - Lifetime
- 2003-05-20 DE DE60323748T patent/DE60323748D1/de not_active Expired - Fee Related
- 2003-05-20 AT AT03755236T patent/ATE409191T1/de not_active IP Right Cessation
- 2003-05-20 EP EP03755236A patent/EP1509528B1/en not_active Expired - Lifetime
- 2003-05-20 US US10/515,711 patent/US7166583B2/en not_active Expired - Fee Related
- 2003-05-20 AU AU2003232372A patent/AU2003232372A1/en not_active Abandoned
- 2003-05-23 AR ARP030101804A patent/AR040040A1/es not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1509528B1 (en) | 2008-09-24 |
| CN1665513A (zh) | 2005-09-07 |
| JP2005531586A (ja) | 2005-10-20 |
| WO2003099823A3 (en) | 2004-04-29 |
| DE60323748D1 (de) | 2008-11-06 |
| CN100354277C (zh) | 2007-12-12 |
| CA2487017A1 (en) | 2003-12-04 |
| RS100104A (en) | 2006-10-27 |
| ES2314237T3 (es) | 2009-03-16 |
| US20050227963A1 (en) | 2005-10-13 |
| IS7568A (is) | 2004-11-29 |
| EP1509528A2 (en) | 2005-03-02 |
| PL374504A1 (en) | 2005-10-31 |
| AU2003232372A1 (en) | 2003-12-12 |
| AR040040A1 (es) | 2005-03-09 |
| ATE409191T1 (de) | 2008-10-15 |
| US7166583B2 (en) | 2007-01-23 |
| WO2003099823A2 (en) | 2003-12-04 |
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