JPS6176440A - 安息香酸誘導体 - Google Patents
安息香酸誘導体Info
- Publication number
- JPS6176440A JPS6176440A JP19708984A JP19708984A JPS6176440A JP S6176440 A JPS6176440 A JP S6176440A JP 19708984 A JP19708984 A JP 19708984A JP 19708984 A JP19708984 A JP 19708984A JP S6176440 A JPS6176440 A JP S6176440A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- derivative
- compound
- acid
- 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.)
- Granted
Links
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- -1 p-nitrosobenzoic acid ester Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 230000004069 differentiation Effects 0.000 claims abstract description 6
- 150000008062 acetophenones Chemical class 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 208000032839 leukemia Diseases 0.000 claims abstract description 3
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract 4
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 230000001939 inductive effect Effects 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- NLRKCXQQSUWLCH-IDEBNGHGSA-N nitrosobenzene Chemical class O=N[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 NLRKCXQQSUWLCH-IDEBNGHGSA-N 0.000 claims description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- JPXMTWWFLBLUCD-UHFFFAOYSA-N nitro blue tetrazolium(2+) Chemical compound COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 JPXMTWWFLBLUCD-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- CAFWWZWJFFJXTF-UHFFFAOYSA-N methyl 4-nitrosobenzoate Chemical compound COC(=O)C1=CC=C(N=O)C=C1 CAFWWZWJFFJXTF-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- SNBCETWLOKEFMT-UHFFFAOYSA-N 3,4-diethylbenzoyl chloride Chemical compound CCC1=CC=C(C(Cl)=O)C=C1CC SNBCETWLOKEFMT-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- JMHSCWJIDIKGNZ-UHFFFAOYSA-N 4-carbamoylbenzoic acid Chemical class NC(=O)C1=CC=C(C(O)=O)C=C1 JMHSCWJIDIKGNZ-UHFFFAOYSA-N 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 208000001126 Keratosis Diseases 0.000 description 1
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 1
- 229910018106 Ni—C Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003760 tallow Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19708984A JPS6176440A (ja) | 1984-09-19 | 1984-09-19 | 安息香酸誘導体 |
| AT85108383T ATE57522T1 (de) | 1984-07-07 | 1985-07-05 | Benzoesaeurederivate. |
| DE8585108383T DE3580134D1 (de) | 1984-07-07 | 1985-07-05 | Benzoesaeurederivate. |
| EP85108383A EP0170105B1 (en) | 1984-07-07 | 1985-07-05 | Benzoic acid derivatives |
| US06/753,036 US4703110A (en) | 1984-07-07 | 1985-07-08 | Benzoic acid derivatives having a para substituent which is a substituted phenyl group connected by a linking radical; useful in neoplastic cell differentiation and diagnosis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19708984A JPS6176440A (ja) | 1984-09-19 | 1984-09-19 | 安息香酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6176440A true JPS6176440A (ja) | 1986-04-18 |
| JPH0458459B2 JPH0458459B2 (enrdf_load_stackoverflow) | 1992-09-17 |
Family
ID=16368539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19708984A Granted JPS6176440A (ja) | 1984-07-07 | 1984-09-19 | 安息香酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6176440A (enrdf_load_stackoverflow) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4939156A (en) * | 1987-07-11 | 1990-07-03 | Meiji Seika Kaisha, Ltd. | New tetramethyl-cis-diaza-bicyclo{4.2.0}octane-3,5-dione derivatives having differentiation-inducing activity and antiviral activity |
| WO1991014673A1 (fr) * | 1990-03-20 | 1991-10-03 | Shionogi & Co., Ltd. | Procede nouveau pour fabriquer un derive d'acide benzoique |
| US6869959B1 (en) | 1999-04-28 | 2005-03-22 | Institute Of Medicinal Molecular Design Inc. | Heterocyclic carboxylic acid derivatives |
| WO2005087220A1 (ja) * | 2004-03-11 | 2005-09-22 | R & R Inc. | 抗しわ剤 |
| US7084133B2 (en) | 2001-02-09 | 2006-08-01 | Hiroyuki Kagechika | Dicarba-closo-dodecaborane derivatives |
| AU2001284416B2 (en) * | 2000-09-01 | 2007-02-15 | Toko Pharmaceuticals Ind. Co., Ltd | Process for the production of crystals of a benzoic acid derivative |
| US7259187B2 (en) | 2000-12-26 | 2007-08-21 | Research Foundation Itsuu Laboratory | Tropolone derivatives |
| JP2008179570A (ja) * | 2007-01-25 | 2008-08-07 | R&R Inc | 内臓癒着の予防及び／又は治療のための医薬 |
| WO2008120711A1 (ja) | 2007-03-30 | 2008-10-09 | Tmrc Co., Ltd. | タミバロテンカプセル剤 |
| WO2009022722A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ３環系アミン化合物 |
| WO2009022720A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ５員複素環化合物 |
| US7902260B2 (en) | 2007-02-28 | 2011-03-08 | Kemphys Ltd. | Medicament for preventive and/or therapeutic treatment of lower urinary tract symptom |
| US8071647B2 (en) | 2005-09-09 | 2011-12-06 | Kemphys Ltd. | Method for treatment of adhesion of the intestines |
| US8232300B2 (en) | 2007-08-15 | 2012-07-31 | Research Foundation Itsuu Laboratory | Tricyclic amide compound |
| WO2013005753A1 (ja) | 2011-07-05 | 2013-01-10 | 公益財団法人乙卯研究所 | 重水素化フェニルプロピオン酸誘導体 |
| US8633335B2 (en) | 2007-10-31 | 2014-01-21 | Research Founation Itsuu Laboratory | Retinoid prodrug compound |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5528911A (en) * | 1978-08-21 | 1980-02-29 | Nippon Chemiphar Co Ltd | New penicillin and cephalosporin derivative and their preparation |
| JPS58128340A (ja) * | 1982-01-23 | 1983-07-30 | バスフ アクチエンゲゼルシヤフト | フェニルエチレン誘導体及びその製法 |
| JPS58164603A (ja) * | 1982-03-24 | 1983-09-29 | Tatatomi Nishikubo | 自己増感型感光性樹脂の製造法 |
| JPS6122047A (ja) * | 1984-07-07 | 1986-01-30 | Koichi Shiyudo | 安息香酸誘導体 |
-
1984
- 1984-09-19 JP JP19708984A patent/JPS6176440A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5528911A (en) * | 1978-08-21 | 1980-02-29 | Nippon Chemiphar Co Ltd | New penicillin and cephalosporin derivative and their preparation |
| JPS58128340A (ja) * | 1982-01-23 | 1983-07-30 | バスフ アクチエンゲゼルシヤフト | フェニルエチレン誘導体及びその製法 |
| JPS58164603A (ja) * | 1982-03-24 | 1983-09-29 | Tatatomi Nishikubo | 自己増感型感光性樹脂の製造法 |
| JPS6122047A (ja) * | 1984-07-07 | 1986-01-30 | Koichi Shiyudo | 安息香酸誘導体 |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4939156A (en) * | 1987-07-11 | 1990-07-03 | Meiji Seika Kaisha, Ltd. | New tetramethyl-cis-diaza-bicyclo{4.2.0}octane-3,5-dione derivatives having differentiation-inducing activity and antiviral activity |
| WO1991014673A1 (fr) * | 1990-03-20 | 1991-10-03 | Shionogi & Co., Ltd. | Procede nouveau pour fabriquer un derive d'acide benzoique |
| US6869959B1 (en) | 1999-04-28 | 2005-03-22 | Institute Of Medicinal Molecular Design Inc. | Heterocyclic carboxylic acid derivatives |
| AU2001284416B2 (en) * | 2000-09-01 | 2007-02-15 | Toko Pharmaceuticals Ind. Co., Ltd | Process for the production of crystals of a benzoic acid derivative |
| KR100715092B1 (ko) * | 2000-09-01 | 2007-05-07 | 도코 야쿠힌 고교 가부시키가이샤 | 안식향산 유도체 결정의 제조방법 |
| US7314639B2 (en) | 2000-09-01 | 2008-01-01 | Toko Pharmaceutical Ind. Co., Ltd. | Process for the production of crystals of a benzoic acid derivative |
| US7259187B2 (en) | 2000-12-26 | 2007-08-21 | Research Foundation Itsuu Laboratory | Tropolone derivatives |
| US7084133B2 (en) | 2001-02-09 | 2006-08-01 | Hiroyuki Kagechika | Dicarba-closo-dodecaborane derivatives |
| US8030360B2 (en) | 2004-03-11 | 2011-10-04 | Kemphys Ltd. | Anti-wrinkle agent |
| WO2005087220A1 (ja) * | 2004-03-11 | 2005-09-22 | R & R Inc. | 抗しわ剤 |
| US8071647B2 (en) | 2005-09-09 | 2011-12-06 | Kemphys Ltd. | Method for treatment of adhesion of the intestines |
| US8168677B2 (en) | 2005-09-09 | 2012-05-01 | Kemphys Ltd. | Method for treatment of inflammatory bowel disease |
| JP2008179570A (ja) * | 2007-01-25 | 2008-08-07 | R&R Inc | 内臓癒着の予防及び／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 |
| WO2008120711A1 (ja) | 2007-03-30 | 2008-10-09 | Tmrc Co., Ltd. | タミバロテンカプセル剤 |
| US8252837B2 (en) | 2007-03-30 | 2012-08-28 | Tmrc Co., Ltd. | Tamibarotene capsule preparation |
| WO2009022722A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ３環系アミン化合物 |
| WO2009022720A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ５員複素環化合物 |
| US8143260B2 (en) | 2007-08-15 | 2012-03-27 | Research Foundation Itsuu Laboratory | Tricyclic amine compound |
| US8232300B2 (en) | 2007-08-15 | 2012-07-31 | Research Foundation Itsuu Laboratory | Tricyclic amide compound |
| US8722730B2 (en) | 2007-08-15 | 2014-05-13 | Research Foundation Itsuu Laboratory | 5-membered heterocyclic compound |
| US8633335B2 (en) | 2007-10-31 | 2014-01-21 | Research Founation Itsuu Laboratory | Retinoid prodrug compound |
| WO2013005753A1 (ja) | 2011-07-05 | 2013-01-10 | 公益財団法人乙卯研究所 | 重水素化フェニルプロピオン酸誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0458459B2 (enrdf_load_stackoverflow) | 1992-09-17 |
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