RU2200153C2 - Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи - Google Patents
Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи Download PDFInfo
- Publication number
- RU2200153C2 RU2200153C2 RU99118221/04A RU99118221A RU2200153C2 RU 2200153 C2 RU2200153 C2 RU 2200153C2 RU 99118221/04 A RU99118221/04 A RU 99118221/04A RU 99118221 A RU99118221 A RU 99118221A RU 2200153 C2 RU2200153 C2 RU 2200153C2
- Authority
- RU
- Russia
- Prior art keywords
- aminophenylamino
- compound
- benzophenone
- nmr
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 160
- 238000011282 treatment Methods 0.000 title claims abstract description 16
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 title abstract 3
- 238000011321 prophylaxis Methods 0.000 title abstract 3
- -1 alkylphenyl-sulfonyl Chemical group 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 206010012434 Dermatitis allergic Diseases 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 4
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 3
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 3
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims abstract 2
- 150000007513 acids Chemical class 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 229
- 239000004480 active ingredient Substances 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 8
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- LHCRNWZLVYDHFQ-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-pentan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)CCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N LHCRNWZLVYDHFQ-UHFFFAOYSA-N 0.000 claims description 3
- MVALDVBMYCYENV-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2,2,2-trifluoroacetamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)C(F)(F)F MVALDVBMYCYENV-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 102000003777 Interleukin-1 beta Human genes 0.000 claims description 2
- 108090000193 Interleukin-1 beta Proteins 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000011970 concomitant therapy Methods 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 259
- 239000007858 starting material Substances 0.000 description 204
- 238000000746 purification Methods 0.000 description 120
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 87
- 238000004587 chromatography analysis Methods 0.000 description 80
- 239000003480 eluent Substances 0.000 description 79
- 238000005160 1H NMR spectroscopy Methods 0.000 description 68
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 68
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 66
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 63
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 27
- 238000002425 crystallisation Methods 0.000 description 24
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- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 12
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- 210000004027 cell Anatomy 0.000 description 6
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
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- HYWPRMOPWZFAML-UHFFFAOYSA-N [4-(4-aminoanilino)phenyl]-(2-hydroxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 HYWPRMOPWZFAML-UHFFFAOYSA-N 0.000 description 3
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9701453.4A GB9701453D0 (en) | 1997-01-24 | 1997-01-24 | Aminobenzophenones |
| GB9701453.4 | 1997-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99118221A RU99118221A (ru) | 2001-06-27 |
| RU2200153C2 true RU2200153C2 (ru) | 2003-03-10 |
Family
ID=10806523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99118221/04A RU2200153C2 (ru) | 1997-01-24 | 1998-01-08 | Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6313174B1 (enExample) |
| EP (1) | EP0966424B1 (enExample) |
| JP (1) | JP4250204B2 (enExample) |
| KR (1) | KR100544046B1 (enExample) |
| CN (1) | CN1188388C (enExample) |
| AT (1) | ATE269844T1 (enExample) |
| AU (1) | AU733561B2 (enExample) |
| CA (1) | CA2278798C (enExample) |
| DE (1) | DE69824705T2 (enExample) |
| DK (1) | DK0966424T3 (enExample) |
| ES (1) | ES2223116T3 (enExample) |
| GB (1) | GB9701453D0 (enExample) |
| HU (1) | HUP0000678A3 (enExample) |
| NZ (1) | NZ336754A (enExample) |
| PL (1) | PL334806A1 (enExample) |
| PT (1) | PT966424E (enExample) |
| RO (1) | RO120195B1 (enExample) |
| RU (1) | RU2200153C2 (enExample) |
| WO (1) | WO1998032730A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003505362A (ja) * | 1999-07-16 | 2003-02-12 | レオ・ファーマ・アクティーゼルスカブ | ＩＬ−１βおよびＴＮＦ−αの抑制剤としてのアミノベンゾフェノン |
| DK1210320T3 (da) * | 1999-07-16 | 2005-01-31 | Leo Pharma As | Aminobenzofenoner som inhibitorer for IL-1beta og TNF-alfa |
| US6897236B1 (en) | 1999-07-16 | 2005-05-24 | Leo Pharmaceutical Products, Ltd. | Aminobenzophenones as inhibitors of IL-1β and TNF-α |
| US6750253B1 (en) | 1999-07-16 | 2004-06-15 | Leo Pharmaceutical Products Ltd. A/S | Aminobenzophenones as inhibitors of il-1β and tnf-α |
| EP1202954B1 (en) * | 1999-07-16 | 2003-10-01 | Leo Pharma A/S | Novel aminobenzophenones |
| AU768816B2 (en) * | 1999-07-16 | 2004-01-08 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha |
| AU776395B2 (en) * | 1999-12-06 | 2004-09-09 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha |
| EP1250332A1 (en) * | 1999-12-17 | 2002-10-23 | Abbott Laboratories | Inhibitors of interleukin 5 gene expression |
| JP2003519143A (ja) * | 1999-12-28 | 2003-06-17 | ファーマコピーア，インコーポレーティッド | ピリミジン及びトリアジン系キナーゼ阻害剤 |
| CA2408727A1 (en) * | 2000-05-22 | 2001-11-29 | Leo Pharma A/S | Benzophenones as inhibitors of il-1.beta. and tnf-.alpha. |
| US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| SE0100569D0 (sv) * | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | New compounds |
| GB0107368D0 (en) * | 2001-03-23 | 2001-05-16 | Novartis Ag | Organic compounds |
| AU2002338286A1 (en) * | 2001-04-10 | 2002-10-28 | Leo Pharma A/S | Novel aminophenyl ketone derivatives |
| MXPA04001912A (es) * | 2001-08-28 | 2004-07-23 | Leo Pharma As | Aminobenzofenonas novedosas. |
| CN1753861A (zh) * | 2002-12-20 | 2006-03-29 | 利奥制药有限公司 | 新颖的氨基二苯酮化合物 |
| WO2005009940A1 (en) * | 2003-07-24 | 2005-02-03 | Leo Pharma A/S | Novel aminobenzophenone compounds |
| DK1828148T3 (da) * | 2004-12-13 | 2010-05-17 | Leo Pharma As | Triazolsubstituerede aminobenzophenonforbindelser |
| DE102005022020A1 (de) * | 2005-05-12 | 2006-11-23 | Merckle Gmbh | Dibenzocycloheptanverbindungen und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| KR101057546B1 (ko) * | 2007-06-05 | 2011-08-17 | 주식회사 엘지화학 | 광학 이방성 화합물 및 이를 포함하는 수지 조성물 |
| EP2206534A1 (de) | 2008-10-09 | 2010-07-14 | c-a-i-r biosciences GmbH | Dibenzocycloheptanonderivate und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| WO2012167133A2 (en) * | 2011-06-01 | 2012-12-06 | The Regents Of The University Of California | Inhibitors of anandamide transport and their therapeutic uses |
| MX354772B (es) | 2011-08-19 | 2018-03-21 | Univ California | Inhibidores de la amida de acidos grasos (faah) restringidos perifericamente por bifenil metasustituido. |
| EP3988540A1 (en) | 2014-04-07 | 2022-04-27 | The Regents of the University of California | Inhibitors of fatty acid amide hydrolase (faah) enzyme with improved oral bioavailability and their use as medicaments |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1535401A (en) * | 1977-07-28 | 1978-12-13 | Holliday & Co Ltd L | Nitrodiphenylamine carboxylic acid disperse dyes |
| SU790620A1 (ru) * | 1979-06-01 | 1981-07-30 | Ордена Трудового Красного Знамени Институт Медицинскойпаразитологии И Торпической Медицины Им.E.И.Марциновского | Дихлор аминобензофенон как исходный продуктдл пОлучЕНи лЕКАРСТВЕННыХ пРЕпАРАТОВ C АНТигЕльМиНТНыМдЕйСТВиЕМ |
| DE3739402C2 (de) * | 1986-11-21 | 1989-01-12 | Ricoh Kk | Faerbende phthalid-verbindungen, verfahren zu ihrer herstellung und diese enthaltende aufzeichnungsmaterialien |
-
1997
- 1997-01-24 GB GBGB9701453.4A patent/GB9701453D0/en active Pending
-
1998
- 1998-01-08 EP EP98900270A patent/EP0966424B1/en not_active Expired - Lifetime
- 1998-01-08 DK DK98900270T patent/DK0966424T3/da active
- 1998-01-08 CN CNB988028301A patent/CN1188388C/zh not_active Expired - Fee Related
- 1998-01-08 RO RO99-00839A patent/RO120195B1/ro unknown
- 1998-01-08 ES ES98900270T patent/ES2223116T3/es not_active Expired - Lifetime
- 1998-01-08 DE DE69824705T patent/DE69824705T2/de not_active Expired - Lifetime
- 1998-01-08 AT AT98900270T patent/ATE269844T1/de active
- 1998-01-08 HU HU0000678A patent/HUP0000678A3/hu unknown
- 1998-01-08 US US09/341,923 patent/US6313174B1/en not_active Expired - Fee Related
- 1998-01-08 AU AU54781/98A patent/AU733561B2/en not_active Ceased
- 1998-01-08 PT PT98900270T patent/PT966424E/pt unknown
- 1998-01-08 RU RU99118221/04A patent/RU2200153C2/ru not_active IP Right Cessation
- 1998-01-08 KR KR1019997006672A patent/KR100544046B1/ko not_active Expired - Fee Related
- 1998-01-08 JP JP53149998A patent/JP4250204B2/ja not_active Expired - Fee Related
- 1998-01-08 WO PCT/DK1998/000008 patent/WO1998032730A1/en not_active Ceased
- 1998-01-08 NZ NZ336754A patent/NZ336754A/xx not_active IP Right Cessation
- 1998-01-08 CA CA002278798A patent/CA2278798C/en not_active Expired - Fee Related
- 1998-01-08 PL PL98334806A patent/PL334806A1/xx not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1535401A (en) * | 1977-07-28 | 1978-12-13 | Holliday & Co Ltd L | Nitrodiphenylamine carboxylic acid disperse dyes |
| SU790620A1 (ru) * | 1979-06-01 | 1981-07-30 | Ордена Трудового Красного Знамени Институт Медицинскойпаразитологии И Торпической Медицины Им.E.И.Марциновского | Дихлор аминобензофенон как исходный продуктдл пОлучЕНи лЕКАРСТВЕННыХ пРЕпАРАТОВ C АНТигЕльМиНТНыМдЕйСТВиЕМ |
| DE3739402C2 (de) * | 1986-11-21 | 1989-01-12 | Ricoh Kk | Faerbende phthalid-verbindungen, verfahren zu ihrer herstellung und diese enthaltende aufzeichnungsmaterialien |
Also Published As
| Publication number | Publication date |
|---|---|
| DK0966424T3 (da) | 2004-11-01 |
| ES2223116T3 (es) | 2005-02-16 |
| US6313174B1 (en) | 2001-11-06 |
| JP4250204B2 (ja) | 2009-04-08 |
| DE69824705T2 (de) | 2005-07-07 |
| RO120195B1 (ro) | 2005-10-28 |
| AU5478198A (en) | 1998-08-18 |
| NZ336754A (en) | 2001-03-30 |
| KR100544046B1 (ko) | 2006-01-23 |
| CN1188388C (zh) | 2005-02-09 |
| HUP0000678A2 (hu) | 2001-10-28 |
| CN1248966A (zh) | 2000-03-29 |
| EP0966424A1 (en) | 1999-12-29 |
| ATE269844T1 (de) | 2004-07-15 |
| JP2001511771A (ja) | 2001-08-14 |
| WO1998032730A1 (en) | 1998-07-30 |
| CA2278798A1 (en) | 1998-07-30 |
| HUP0000678A3 (en) | 2001-11-28 |
| KR20000070437A (ko) | 2000-11-25 |
| EP0966424B1 (en) | 2004-06-23 |
| PT966424E (pt) | 2004-09-30 |
| CA2278798C (en) | 2007-07-03 |
| GB9701453D0 (en) | 1997-03-12 |
| PL334806A1 (en) | 2000-03-13 |
| AU733561B2 (en) | 2001-05-17 |
| HK1025306A1 (en) | 2000-11-10 |
| DE69824705D1 (de) | 2004-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130109 |