JPS6122047A - 安息香酸誘導体 - Google Patents
安息香酸誘導体Info
- Publication number
- JPS6122047A JPS6122047A JP14119484A JP14119484A JPS6122047A JP S6122047 A JPS6122047 A JP S6122047A JP 14119484 A JP14119484 A JP 14119484A JP 14119484 A JP14119484 A JP 14119484A JP S6122047 A JPS6122047 A JP S6122047A
- Authority
- JP
- Japan
- Prior art keywords
- group
- derivative
- formula
- acid
- tables
- 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 abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 230000004069 differentiation Effects 0.000 claims abstract description 6
- -1 terephthalaldehydic acid ester Chemical class 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
- 239000002253 acid Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003377 acid catalyst Substances 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
- 239000000126 substance Substances 0.000 claims 9
- 238000007796 conventional method Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 13
- 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 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-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
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FIUWNZQAIGJKSK-UHFFFAOYSA-N 3,4-diethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1CC FIUWNZQAIGJKSK-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
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 206010020751 Hypersensitivity 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 description 1
- 101150085390 RPM1 gene Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- OORGGNYDIUQRDG-UHFFFAOYSA-N [3-[4-[(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)methyl]benzoyl]phenyl]-[3-[4-[(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)methyl]benzoyl]phenyl]imino-oxidoazanium Chemical compound O1C(=O)C=2C(C)=CSC=2N=C1CC(C=C1)=CC=C1C(=O)C(C=1)=CC=CC=1N=[N+]([O-])C(C=1)=CC=CC=1C(=O)C(C=C1)=CC=C1CC(OC1=O)=NC2=C1C(C)=CS2 OORGGNYDIUQRDG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007815 allergy 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
- 125000004429 atom Chemical group 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
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 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
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CAFWWZWJFFJXTF-UHFFFAOYSA-N methyl 4-nitrosobenzoate Chemical compound COC(=O)C1=CC=C(N=O)C=C1 CAFWWZWJFFJXTF-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000011164 ossification Effects 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
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 238000010186 staining Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14119484A JPS6122047A (ja) | 1984-07-07 | 1984-07-07 | 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 |
|---|---|---|---|
| JP14119484A JPS6122047A (ja) | 1984-07-07 | 1984-07-07 | 安息香酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6122047A true JPS6122047A (ja) | 1986-01-30 |
| JPH0458458B2 JPH0458458B2 (enrdf_load_stackoverflow) | 1992-09-17 |
Family
ID=15286342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14119484A Granted JPS6122047A (ja) | 1984-07-07 | 1984-07-07 | 安息香酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6122047A (enrdf_load_stackoverflow) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6176440A (ja) * | 1984-09-19 | 1986-04-18 | Koichi Shiyudo | 安息香酸誘導体 |
| JP2004529085A (ja) * | 2001-01-18 | 2004-09-24 | ウェリケム バイオテック インコーポレーテッド | 免疫性疾患を治療するための新規な１，２−ジフェニルエテン誘導体 |
| 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 |
| US7259187B2 (en) | 2000-12-26 | 2007-08-21 | Research Foundation Itsuu Laboratory | Tropolone derivatives |
| US7314639B2 (en) | 2000-09-01 | 2008-01-01 | Toko Pharmaceutical Ind. Co., Ltd. | Process for the production of crystals of a benzoic acid derivative |
| 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 |
| WO2009022720A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ５員複素環化合物 |
| WO2009022722A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ３環系アミン化合物 |
| 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 |
| JP2017160261A (ja) * | 2017-06-12 | 2017-09-14 | チョンシー ユー | 非常に高い皮膚浸透率を有するレチノイド及びレチノイド様化合物の正に荷電した水溶性プロドラッグ |
Citations (3)
| 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 |
-
1984
- 1984-07-07 JP JP14119484A patent/JPS6122047A/ja active Granted
Patent Citations (3)
| 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 |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6176440A (ja) * | 1984-09-19 | 1986-04-18 | Koichi Shiyudo | 安息香酸誘導体 |
| US6869959B1 (en) | 1999-04-28 | 2005-03-22 | Institute Of Medicinal Molecular Design Inc. | Heterocyclic carboxylic acid derivatives |
| 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 |
| JP2004529085A (ja) * | 2001-01-18 | 2004-09-24 | ウェリケム バイオテック インコーポレーテッド | 免疫性疾患を治療するための新規な１，２−ジフェニルエテン誘導体 |
| WO2005087220A1 (ja) * | 2004-03-11 | 2005-09-22 | R & R Inc. | 抗しわ剤 |
| US8030360B2 (en) | 2004-03-11 | 2011-10-04 | Kemphys Ltd. | Anti-wrinkle agent |
| 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 |
| WO2009022722A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ３環系アミン化合物 |
| US8143260B2 (en) | 2007-08-15 | 2012-03-27 | Research Foundation Itsuu Laboratory | Tricyclic amine compound |
| WO2009022720A1 (ja) | 2007-08-15 | 2009-02-19 | Research Foundation Itsuu Laboratory | ５員複素環化合物 |
| 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 |
| JP2017160261A (ja) * | 2017-06-12 | 2017-09-14 | チョンシー ユー | 非常に高い皮膚浸透率を有するレチノイド及びレチノイド様化合物の正に荷電した水溶性プロドラッグ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0458458B2 (enrdf_load_stackoverflow) | 1992-09-17 |
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