EA002123B1 - Соединения, усиливающие активность ретиноидов - Google Patents
Соединения, усиливающие активность ретиноидов Download PDFInfo
- Publication number
- EA002123B1 EA002123B1 EA199800318A EA199800318A EA002123B1 EA 002123 B1 EA002123 B1 EA 002123B1 EA 199800318 A EA199800318 A EA 199800318A EA 199800318 A EA199800318 A EA 199800318A EA 002123 B1 EA002123 B1 EA 002123B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- group
- hexano
- benzoic acid
- dimethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 230000003389 potentiating effect Effects 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 36
- DLFBCHSYAZBTSS-UHFFFAOYSA-N 4-(5,7,7,10,10-pentamethyl-8,9-dihydronaphtho[2,3-b][1,5]benzodiazepin-12-yl)benzoic acid Chemical compound C12=CC(C(CCC3(C)C)(C)C)=C3C=C2N(C)C2=CC=CC=C2N=C1C1=CC=C(C(O)=O)C=C1 DLFBCHSYAZBTSS-UHFFFAOYSA-N 0.000 claims abstract description 34
- -1 pyridinediyl group Chemical group 0.000 claims abstract description 31
- 229930002330 retinoic acid Natural products 0.000 claims abstract description 28
- 229960001727 tretinoin Drugs 0.000 claims abstract description 28
- SHGAZHPCJJPHSC-YCNIQYBTSA-N retinoic acid group Chemical group C\C(=C/C(=O)O)\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims abstract description 27
- 230000000694 effects Effects 0.000 claims abstract description 26
- 239000003814 drug Substances 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000013543 active substance Substances 0.000 claims abstract description 11
- 230000002708 enhancing effect Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 230000001766 physiological effect Effects 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 241000124008 Mammalia Species 0.000 claims abstract 4
- 229960003512 nicotinic acid Drugs 0.000 claims abstract 2
- 239000011664 nicotinic acid Substances 0.000 claims abstract 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 34
- 229940079593 drug Drugs 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 76
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- 239000012044 organic layer Substances 0.000 description 51
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- 239000002904 solvent Substances 0.000 description 40
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 238000010898 silica gel chromatography Methods 0.000 description 29
- 102100030817 Liver carboxylesterase 1 Human genes 0.000 description 26
- 101710169844 Sesquipedalian-1 Proteins 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 150000004492 retinoid derivatives Chemical class 0.000 description 21
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- 239000000243 solution Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 230000024245 cell differentiation Effects 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 8
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- 102000005962 receptors Human genes 0.000 description 8
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 6
- 230000001939 inductive effect Effects 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- JXMZUNPWVXQADG-UHFFFAOYSA-N 1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1I JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- DNMZJIGSDQVGSA-UHFFFAOYSA-N methoxymethane;hydrochloride Chemical compound Cl.COC DNMZJIGSDQVGSA-UHFFFAOYSA-N 0.000 description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/20—[b, f]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D281/16—[b, f]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thin Film Transistor (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24263995 | 1995-09-21 | ||
| JP15058296 | 1996-06-12 | ||
| PCT/JP1996/002709 WO1997011061A1 (en) | 1995-09-21 | 1996-09-20 | Compounds potentiating retinoid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199800318A1 EA199800318A1 (ru) | 1998-10-29 |
| EA002123B1 true EA002123B1 (ru) | 2001-12-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199800318A EA002123B1 (ru) | 1995-09-21 | 1996-09-20 | Соединения, усиливающие активность ретиноидов |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US5929069A (OSRAM) |
| EP (1) | EP0906907B1 (OSRAM) |
| KR (1) | KR100484294B1 (OSRAM) |
| CN (1) | CN1121395C (OSRAM) |
| AT (1) | ATE214055T1 (OSRAM) |
| AU (1) | AU7001596A (OSRAM) |
| CA (1) | CA2233012A1 (OSRAM) |
| DE (1) | DE69619711T2 (OSRAM) |
| DK (1) | DK0906907T3 (OSRAM) |
| EA (1) | EA002123B1 (OSRAM) |
| NO (1) | NO981269L (OSRAM) |
| TW (1) | TW420667B (OSRAM) |
| WO (1) | WO1997011061A1 (OSRAM) |
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| CN1121395C (zh) * | 1995-09-21 | 2003-09-17 | 药物分子设计研究所株式会社 | 类视色素作用增强性化合物 |
| JP4398585B2 (ja) * | 1997-11-12 | 2010-01-13 | 有限会社ケムフィズ | レチノイドレセプター作用剤 |
| JP4204657B2 (ja) | 1997-12-05 | 2009-01-07 | 有限会社ケムフィズ | 糖尿病の予防・治療剤 |
| US6083973A (en) * | 1998-03-09 | 2000-07-04 | Syntex (U.S.A.) Inc. | Methods for inhibiting mucin secretion using RAR α selective antagonists |
| US6869959B1 (en) | 1999-04-28 | 2005-03-22 | Institute Of Medicinal Molecular Design Inc. | Heterocyclic carboxylic acid derivatives |
| JP5127096B2 (ja) | 1999-04-30 | 2013-01-23 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | アポトーシスにより誘導される自己免疫疾患を処置するためのベンゾジアゼピンの使用 |
| US7572788B2 (en) | 1999-04-30 | 2009-08-11 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| US20060025388A1 (en) | 1999-04-30 | 2006-02-02 | Glick Gary D | Compositions and methods relating to novel compounds and targets thereof |
| CA2523986A1 (en) * | 2003-03-20 | 2004-09-30 | Research Foundation Itsuu Laboratory | Method for forming organ |
| GB0308335D0 (en) | 2003-04-10 | 2003-05-14 | Novartis Ag | Organic compounds |
| WO2005087219A1 (ja) | 2004-03-10 | 2005-09-22 | Research Foundation Itsuu Laboratory | 記憶固定促進剤 |
| WO2005099759A1 (ja) * | 2004-04-16 | 2005-10-27 | Institute Of Medicinal Molecular Design. Inc. | 動脈硬化症の予防及び／又は治療のための医薬 |
| CA2611031A1 (en) | 2005-06-01 | 2007-05-10 | The Regents Of The University Of Michigan | Unsolvated benzodiazepine compositions and methods |
| JP5042839B2 (ja) | 2005-09-09 | 2012-10-03 | 有限会社ケムフィズ | 腸疾患の予防及び／又は治療のための医薬 |
| AU2006308655B2 (en) | 2005-11-01 | 2010-09-23 | The Regents Of The University Of Michigan | Novel 1,4-benzodiazepine-2,5-diones with therapeutic properties |
| JP5264716B2 (ja) | 2006-06-09 | 2013-08-14 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 化合物およびその標的に関連する組成物および方法 |
| JP2008081427A (ja) * | 2006-09-27 | 2008-04-10 | R&R Inc | 分泌障害性疾患の予防及び／又は治療のための医薬 |
| US7902260B2 (en) * | 2007-02-28 | 2011-03-08 | Kemphys Ltd. | Medicament for preventive and/or therapeutic treatment of lower urinary tract symptom |
| AU2008226532B2 (en) | 2007-03-09 | 2011-09-22 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| TW200927709A (en) | 2007-08-15 | 2009-07-01 | Res Found Itsuu Lab | Tricyclic amine compound |
| ES2614498T3 (es) | 2007-09-14 | 2017-05-31 | The Regents Of The University Of Michigan | Inhibidores de ATPasa F1F0 y métodos relacionados |
| US8188072B2 (en) | 2007-11-06 | 2012-05-29 | The Regents Of The University Of Michigan | Benzodiazepinone compounds useful in the treatment of skin conditions |
| WO2010030891A2 (en) | 2008-09-11 | 2010-03-18 | The Regents Of The University Of Michigan | Aryl guanidine f1f0-atpase inhibitors and related methods |
| US8604023B2 (en) | 2009-04-17 | 2013-12-10 | The Regents Of The University Of Michigan | 1,4-benzodiazepinone compounds and their use in treating cancer |
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| US9062024B2 (en) | 2009-09-28 | 2015-06-23 | Nippon Soda Co., Ltd. | Nitrogen-containing heterocyclic compound and salt thereof, and a fungicide for agricultural and horticultural use |
| US9126978B2 (en) | 2009-11-17 | 2015-09-08 | The Regents Of The University Of Michigan | 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties |
| AU2010322287B2 (en) | 2009-11-17 | 2014-04-03 | The Regents Of The University Of Michigan | 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties |
| AR084070A1 (es) | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| WO2012075456A1 (en) | 2010-12-02 | 2012-06-07 | Constellation Pharmaceuticals | Bromodomain inhibitors and uses thereof |
| US20130324520A1 (en) * | 2011-02-14 | 2013-12-05 | Sloan-Kettering Institute For Cancer Research | Rxrg modulators for the treatment of cancer |
| US9422292B2 (en) | 2011-05-04 | 2016-08-23 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| US9328117B2 (en) | 2011-06-17 | 2016-05-03 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| TWI602820B (zh) | 2012-06-06 | 2017-10-21 | 星宿藥物公司 | 溴域抑制劑及其用途 |
| WO2013184878A1 (en) | 2012-06-06 | 2013-12-12 | Constellation Pharmaceuticals, Inc. | Benzo [b] isoxazoloazepine bromodomain inhibitors and uses thereof |
| CN103304494B (zh) * | 2013-06-20 | 2015-05-27 | 河北大学 | 茚(1,2-b)喹喔啉-11-酮肟衍生物及其制备方法和用途 |
| SI3157928T1 (sl) | 2014-06-20 | 2019-06-28 | Constellation Pharmaceuticals, Inc. | Kristalinične oblike 2-((4S)-6-(4-klorofenil)-1-metil-4H-benzo(C)izoksazolo(4,5-E)azepin-4-il acetamida |
| KR200489267Y1 (ko) | 2018-09-20 | 2019-05-23 | 김은진 | 폭 조절형 옷걸이 |
| KR200490993Y1 (ko) | 2019-06-14 | 2020-02-04 | 이현봉 | 구김방지기능을 구비한 바지걸이 |
| CN114702454A (zh) * | 2022-03-29 | 2022-07-05 | 江西师范大学 | 5-烷基-11-芳基-5H-二苯并[b,e][1,4]二氮杂卓衍生物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04211071A (ja) * | 1990-03-05 | 1992-08-03 | Hokuriku Seiyaku Co Ltd | 多環式化合物 |
| CN1121395C (zh) * | 1995-09-21 | 2003-09-17 | 药物分子设计研究所株式会社 | 类视色素作用增强性化合物 |
| JP4204657B2 (ja) * | 1997-12-05 | 2009-01-07 | 有限会社ケムフィズ | 糖尿病の予防・治療剤 |
-
1996
- 1996-09-20 CN CN96198386A patent/CN1121395C/zh not_active Expired - Fee Related
- 1996-09-20 TW TW085111550A patent/TW420667B/zh not_active IP Right Cessation
- 1996-09-20 EA EA199800318A patent/EA002123B1/ru not_active IP Right Cessation
- 1996-09-20 AT AT96931263T patent/ATE214055T1/de not_active IP Right Cessation
- 1996-09-20 KR KR10-1998-0702114A patent/KR100484294B1/ko not_active Expired - Fee Related
- 1996-09-20 US US08/710,657 patent/US5929069A/en not_active Expired - Lifetime
- 1996-09-20 EP EP96931263A patent/EP0906907B1/en not_active Expired - Lifetime
- 1996-09-20 WO PCT/JP1996/002709 patent/WO1997011061A1/ja not_active Ceased
- 1996-09-20 AU AU70015/96A patent/AU7001596A/en not_active Abandoned
- 1996-09-20 CA CA002233012A patent/CA2233012A1/en not_active Abandoned
- 1996-09-20 DE DE69619711T patent/DE69619711T2/de not_active Expired - Lifetime
- 1996-09-20 DK DK96931263T patent/DK0906907T3/da active
-
1998
- 1998-03-20 NO NO981269A patent/NO981269L/no unknown
-
1999
- 1999-04-09 US US09/288,618 patent/US6121256A/en not_active Expired - Fee Related
-
2001
- 2001-04-20 US US09/838,272 patent/US6476017B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0906907A1 (en) | 1999-04-07 |
| DK0906907T3 (da) | 2002-04-22 |
| DE69619711T2 (de) | 2002-10-17 |
| WO1997011061A1 (en) | 1997-03-27 |
| AU7001596A (en) | 1997-04-09 |
| NO981269L (no) | 1998-05-20 |
| DE69619711D1 (de) | 2002-04-11 |
| ATE214055T1 (de) | 2002-03-15 |
| EP0906907A4 (OSRAM) | 1999-04-07 |
| EP0906907B1 (en) | 2002-03-06 |
| TW420667B (en) | 2001-02-01 |
| US20010039272A1 (en) | 2001-11-08 |
| CA2233012A1 (en) | 1997-03-27 |
| NO981269D0 (no) | 1998-03-20 |
| KR100484294B1 (ko) | 2005-09-09 |
| US6476017B2 (en) | 2002-11-05 |
| KR19990063661A (ko) | 1999-07-26 |
| CN1202160A (zh) | 1998-12-16 |
| CN1121395C (zh) | 2003-09-17 |
| US5929069A (en) | 1999-07-27 |
| EA199800318A1 (ru) | 1998-10-29 |
| US6121256A (en) | 2000-09-19 |
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