JP5491421B2 - ５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス - Google Patents
５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス Download PDFInfo
- Publication number
- JP5491421B2 JP5491421B2 JP2010549649A JP2010549649A JP5491421B2 JP 5491421 B2 JP5491421 B2 JP 5491421B2 JP 2010549649 A JP2010549649 A JP 2010549649A JP 2010549649 A JP2010549649 A JP 2010549649A JP 5491421 B2 JP5491421 B2 JP 5491421B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- reacting
- ethanol
- propan
- bromide
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 94
- 230000008569 process Effects 0.000 title claims description 93
- 238000002360 preparation method Methods 0.000 title description 10
- XTTZERNUQAFMOF-QMMMGPOBSA-N lorcaserin Chemical compound C[C@H]1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-QMMMGPOBSA-N 0.000 title description 8
- 239000000543 intermediate Substances 0.000 title description 6
- 239000002485 serotonin 2C agonist Substances 0.000 title 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 176
- HZFRKZWBVUJYDA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1 HZFRKZWBVUJYDA-UHFFFAOYSA-N 0.000 claims description 88
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 88
- YAFMYKFAUNCQPU-UHFFFAOYSA-N 1-(2-bromoethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CCBr)C=C1 YAFMYKFAUNCQPU-UHFFFAOYSA-N 0.000 claims description 73
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 45
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 42
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 26
- URWKQIHYBHDHPD-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethylamino]propan-2-ol Chemical compound CC(O)CNCCC1=CC=C(Cl)C=C1 URWKQIHYBHDHPD-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- ARSNVFGYXNWTPK-UHFFFAOYSA-N 2-chloro-n-[2-(4-chlorophenyl)ethyl]propan-1-amine;hydrochloride Chemical compound [Cl-].CC(Cl)C[NH2+]CCC1=CC=C(Cl)C=C1 ARSNVFGYXNWTPK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- -1 4-chloro-phenethyl-amino Chemical group 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- CLHHGPFQMDSVGA-UHFFFAOYSA-N propan-2-ol thionyl dichloride Chemical compound CC(C)O.S(=O)(Cl)Cl CLHHGPFQMDSVGA-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 description 24
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 6
- BONQOKQKRRFITB-UHFFFAOYSA-N 1-[bis[2-(4-chlorophenyl)ethyl]amino]propan-2-ol Chemical compound C=1C=C(Cl)C=CC=1CCN(CC(O)C)CCC1=CC=C(Cl)C=C1 BONQOKQKRRFITB-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000003518 caustics Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 239000012455 biphasic mixture Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 208000008589 Obesity Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004305 normal phase HPLC Methods 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- MVOSNPUNXINWAD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(Cl)C=C1 MVOSNPUNXINWAD-UHFFFAOYSA-N 0.000 description 2
- IMMGGYIXPZKRMM-UHFFFAOYSA-N 2-chloro-n-[2-(4-chlorophenyl)ethyl]propan-1-amine Chemical compound CC(Cl)CNCCC1=CC=C(Cl)C=C1 IMMGGYIXPZKRMM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- KMCQIOFKQGIPTG-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]propan-1-amine Chemical compound CCCNCCC1=CC=C(Cl)C=C1 KMCQIOFKQGIPTG-UHFFFAOYSA-N 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 239000000018 receptor agonist Substances 0.000 description 2
- 229940044601 receptor agonist Drugs 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 210000002987 choroid plexus Anatomy 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960004597 dexfenfluramine Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000001263 extrapyramidal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000011813 knockout mouse model Methods 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029556 regulation of feeding behavior Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 210000001103 thalamus Anatomy 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6810208P | 2008-03-04 | 2008-03-04 | |
| US61/068,102 | 2008-03-04 | ||
| PCT/US2009/001340 WO2009111004A1 (en) | 2008-03-04 | 2009-03-03 | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513402A JP2011513402A (ja) | 2011-04-28 |
| JP2011513402A5 JP2011513402A5 (OSRAM) | 2013-03-21 |
| JP5491421B2 true JP5491421B2 (ja) | 2014-05-14 |
Family
ID=40589739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549649A Expired - Fee Related JP5491421B2 (ja) | 2008-03-04 | 2009-03-03 | ５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8822727B2 (OSRAM) |
| EP (1) | EP2288585A1 (OSRAM) |
| JP (1) | JP5491421B2 (OSRAM) |
| CN (1) | CN102015591B (OSRAM) |
| WO (1) | WO2009111004A1 (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2332921T3 (en) | 2003-06-17 | 2016-05-09 | Arena Pharm Inc | 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepine hydrochloride |
| KR101519441B1 (ko) | 2004-12-23 | 2015-05-12 | 아레나 파마슈티칼스, 인크. | 5ｈｔ２ｃ 수용체 조정물질 조성물 및 그의 사용 방법 |
| CN101466684B (zh) | 2006-04-03 | 2012-06-20 | 艾尼纳制药公司 | 8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的制备工艺和其相关中间体 |
| WO2009111004A1 (en) | 2008-03-04 | 2009-09-11 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| WO2010148207A2 (en) | 2009-06-18 | 2010-12-23 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| MX2013002430A (es) | 2010-09-01 | 2013-07-22 | Arena Pharm Inc | Formas de dosis de disolucion de rápida de agonistas de 5-ht2c. |
| NZ630494A (en) | 2010-09-01 | 2016-05-27 | Arena Pharm Inc | Administration of lorcaserin to individuals with renal impairment |
| SG10201506874UA (en) | 2010-09-01 | 2015-10-29 | Arena Pharm Inc | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| SG10201506865WA (en) | 2010-09-01 | 2015-10-29 | Arena Pharm Inc | Non-hygroscopic salts of 5-ht2c agonists |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| MX2013002422A (es) | 2010-09-01 | 2013-05-17 | Arena Pharm Inc | Sales de lorcaserina con acidos opticamente activos. |
| MY181736A (en) | 2012-10-09 | 2021-01-05 | Arena Pharm Inc | Method of weight management |
| CN105431415A (zh) | 2013-05-20 | 2016-03-23 | 斯洛文尼亚莱柯制药股份有限公司 | 通过烯烃的弗瑞德-克来福特烷基化进行的8-氯-3-苯并[d]氮杂*的新合成方法 |
| EP3010887A1 (en) | 2013-06-21 | 2016-04-27 | LEK Pharmaceuticals d.d. | Preparation of chiral 1-methyl-2,3,4,5-1h-benzodiazepines via asymmetric reduction of alpha-substituted styrenes |
| CN103901151A (zh) * | 2014-04-23 | 2014-07-02 | 湖北朗昕生化药业有限公司 | 一种hplc法检测氯卡色林盐酸盐含量的方法 |
| WO2015170346A1 (en) | 2014-05-09 | 2015-11-12 | Council Of Scientific & Industrial Research | A process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-benzo[d]azepine its enantiomers |
| TW201618787A (zh) | 2014-10-30 | 2016-06-01 | 艾尼納製藥公司 | 組合物及方法 |
| CN107673949B (zh) * | 2017-10-25 | 2021-02-23 | 南京恒旺生物医药有限公司 | 一种1-氯-3-甲基-2-丁烯的制备方法 |
| CN112358406A (zh) * | 2020-10-28 | 2021-02-12 | 山东省药学科学院 | 一种氯卡色林中间体的制备方法 |
| CN115784911A (zh) * | 2022-10-19 | 2023-03-14 | 山东省药学科学院 | 一种1-[2-(4-氯苯基)-乙基氨基]-2-丙醇的合成方法 |
Family Cites Families (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2900415A (en) | 1954-12-14 | 1959-08-18 | Lakeside Lab Inc | Synthesized antispasmodic compounds |
| CH481110A (de) | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
| CH498122A (de) | 1968-02-09 | 1970-10-31 | Geigy Ag J R | Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates |
| CH500194A (de) | 1968-02-15 | 1970-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von Tetrahydroazepinderivaten |
| US4233217A (en) | 1968-03-11 | 1980-11-11 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H, 3 benzazepines |
| CA974989A (en) | 1968-03-11 | 1975-09-23 | Wallace And Tiernan Inc. | Process for preparing 1,2,4,5-tetrahydro-3h,3-benzazepines and products obtained thereby |
| FR314F (OSRAM) | 1968-03-22 | 1970-05-25 | ||
| FR7736M (OSRAM) | 1968-09-02 | 1970-03-09 | ||
| US3716639A (en) | 1970-03-11 | 1973-02-13 | Ciba Geigy Corp | Anorexigenic tetrahydrobenzazepines |
| US3795683A (en) | 1970-08-19 | 1974-03-05 | Hoffmann La Roche | 2,3,4,5-tetrahydro-1h-3-benzazepines |
| LU65954A1 (OSRAM) | 1972-08-25 | 1974-03-07 | ||
| US4210749A (en) | 1974-11-12 | 1980-07-01 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines |
| SE7510988L (sv) | 1975-10-01 | 1977-04-02 | Draco Ab | Nya farmaceutiskt aktiva foreningar |
| US4111957A (en) | 1977-02-02 | 1978-09-05 | Smithkline Corporation | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds |
| US4108989A (en) | 1977-04-01 | 1978-08-22 | Smithkline Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones |
| DE2758001A1 (de) | 1977-12-24 | 1979-07-12 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| CA1090797A (en) | 1978-06-20 | 1980-12-02 | Kenneth G. Holden | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1h- 3-benzazepine compounds |
| AU515236B2 (en) | 1978-06-26 | 1981-03-26 | Smithkline Corporation | Substituted-1-thienyl and furyl-2,3,4,5-tetrahydro-14-3 benzazepine derivatives |
| ZA792785B (en) | 1978-07-07 | 1980-08-27 | Smithkline Corp | Mercapto substituted-2,3,4,5-tetrahydro-1h-3-benzazepines |
| IE50355B1 (en) | 1979-10-20 | 1986-04-02 | Wyeth John & Brother Ltd | Morpholine derivatives |
| US4477378A (en) | 1980-02-05 | 1984-10-16 | Schering Corp. | Esters of substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
| DE3272044D1 (de) | 1981-11-27 | 1986-08-21 | Smithkline Beckman Corp | 3-benzazepines as alpha-2 antagonists |
| ZA827887B (en) | 1981-11-27 | 1983-11-30 | Smithkline Beckman Corp | Pharmaceutical compositions and method of producing alpha2 antagonism |
| FR2518544A1 (fr) | 1981-12-22 | 1983-06-24 | Lipha | Benzodiazepines-1,3 thione-2, procede de preparation et medicament les contenant |
| FR2525603A1 (fr) | 1982-04-27 | 1983-10-28 | Adir | Benzoazacycloalkyl-spiro-imidazolinines, leur preparation et leur application en therapeutique |
| US4988690A (en) | 1982-06-14 | 1991-01-29 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines and anti-depressant use thereof |
| DE3418270A1 (de) | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US4541954A (en) | 1984-09-05 | 1985-09-17 | Smithkline Beckman Corporation | Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| EP0204349A3 (de) | 1985-06-01 | 1990-01-03 | Dr. Karl Thomae GmbH | Neue heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| EG18188A (en) | 1986-05-01 | 1992-09-30 | Pfizer Ltd | Process for preparation anti-arhythmia agents |
| US4762845A (en) | 1986-05-21 | 1988-08-09 | Abbott Laboratories | 7-(3-Substituted imino-1-pyrrolidinyl)-quinolone-3-carboxylic acids |
| EP0285287A3 (en) | 1987-03-23 | 1990-08-16 | Smithkline Beecham Corporation | 3-benzazepine compounds for use in treating gastrointestinal motility disorders |
| ZA882080B (en) | 1987-03-27 | 1989-04-26 | Schering Corp | Substituted benzazepines,their preparation and pharmaceutical compositions containing them |
| US5015639A (en) | 1987-03-27 | 1991-05-14 | Schering Corporation | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
| US5247080A (en) | 1987-03-27 | 1993-09-21 | Schering Corporation | Substituted benzazepines useful as intermediates for producing pharmaceutically active compounds |
| AU1700688A (en) | 1987-04-09 | 1988-11-04 | Smithkline Beckman Corporation | Sulfinyl and sulfonyl substituted 3-benzazepines |
| US4957914A (en) | 1987-05-15 | 1990-09-18 | Syntex (U.S.A.) Inc. | 1,9-alkano-bridged-2,3,4,5-tetrahydro-1H-3-benzazepines |
| DK107688D0 (da) | 1988-03-01 | 1988-03-01 | Novo Industri As | Carbaminsyreestere af substituerede 7-hydroxy-2,3,4,5-tetrahydro-1h-3-benzazepiner |
| US5422355A (en) | 1989-06-02 | 1995-06-06 | John Wyeth & Brother, Limited | Composition for treating depression with (N-heteroaryl)alkylamines |
| US5178786A (en) | 1989-08-04 | 1993-01-12 | The Lubrizol Corporation | Corrosion-inhibiting compositions and functional fluids containing same |
| CA2037162A1 (en) | 1990-03-12 | 1991-09-13 | Steven Howard Shaber | Heterocyclicacetonitriles and fungicidal use |
| WO1991019698A1 (en) | 1990-06-15 | 1991-12-26 | Schering Corporation | 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substitued benzazepines and pharmaceutical compositions containing them |
| JP2502723Y2 (ja) | 1990-06-25 | 1996-06-26 | 油谷重工株式会社 | 建設機械のピン結合装置 |
| US5275915A (en) | 1991-06-05 | 1994-01-04 | Dainippon Ink And Chemicals, Inc. | Developer for light-sensitive material |
| PT100602A (pt) | 1991-06-21 | 1993-09-30 | Smithkline Beecham Plc | Uso de derivados de tetra-hidrobenzazepinas, derivados de tetra-hidrobenzazepinas,sua preparacao e composicoes farmaceuticas que os contem |
| GB9116824D0 (en) | 1991-08-05 | 1991-09-18 | Smithkline Beecham Corp | Chemical compounds |
| EP0558824A1 (en) | 1992-02-04 | 1993-09-08 | Duphar International Research B.V | Method for the preparation of vicinal aminoalcohols and optically active O-protected derivatives thereof |
| US5241065A (en) | 1992-02-25 | 1993-08-31 | Schering Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepines having anti-psychotic activity |
| US5218385A (en) * | 1992-03-17 | 1993-06-08 | Lii Jein Hei | Flash light eyeglasses with hinge switch |
| EP0615166B1 (en) * | 1993-02-26 | 1998-09-23 | Mitsui Chemicals, Inc. | Resins for electrophotographic toners |
| US6087346A (en) | 1993-06-23 | 2000-07-11 | Cambridge Neuroscience, Inc. | Sigma receptor ligands and the use thereof |
| US5387685A (en) | 1993-07-16 | 1995-02-07 | American Cyanamid Co | MDR reversal agents |
| GB9322976D0 (en) | 1993-11-08 | 1994-01-05 | Pfizer Ltd | Therapeutic agents |
| US5421119A (en) * | 1994-05-31 | 1995-06-06 | Miner; Donald W. | Rifle firing pin |
| DE4419247A1 (de) | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie |
| DE4419315A1 (de) | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE4419246A1 (de) | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE4427838A1 (de) | 1994-08-05 | 1996-02-08 | Thomae Gmbh Dr K | Kondensierte Azepinderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE4429079A1 (de) | 1994-08-17 | 1996-02-22 | Thomae Gmbh Dr K | Cyclische Harnstoffderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| GB9508622D0 (en) | 1995-04-28 | 1995-06-14 | Pfizer Ltd | Therapeutic agants |
| FR2740531B1 (fr) * | 1995-10-27 | 1997-11-21 | Legris Sa | Perfectionnement a un dispositif de liaison d'un tube a un embout |
| CA2190708A1 (en) | 1995-12-08 | 1997-06-09 | Johannes Aebi | Aminoalkyl substituted benzo-heterocyclic compounds |
| US5892116A (en) | 1996-01-03 | 1999-04-06 | Georgetown University | Gelators |
| US5925651A (en) | 1996-04-03 | 1999-07-20 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5691362A (en) | 1996-06-05 | 1997-11-25 | Schering-Plough Corporation | Substituted benzene-fused hetero- and carbocyclics as nuerokinin antagonists |
| WO1998006701A1 (en) | 1996-08-15 | 1998-02-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| US5908830A (en) | 1996-10-31 | 1999-06-01 | Merck & Co., Inc. | Combination therapy for the treatment of diabetes and obesity |
| WO1998040385A1 (en) | 1997-03-07 | 1998-09-17 | Novo Nordisk A/S | 4,5,6,7-TETRAHYDRO-THIENO[3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE |
| US5795895A (en) | 1997-06-13 | 1998-08-18 | Anchors; J. Michael | Combination anorexiant drug therapy for obesity using phentermine and an SSRI drug |
| AUPP020297A0 (en) | 1997-11-05 | 1997-11-27 | University Of Melbourne, The | A novel receptor, and compounds which bind thereto |
| AU3275999A (en) | 1998-03-10 | 1999-09-27 | Ono Pharmaceutical Co. Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| CA2325741C (en) | 1998-03-26 | 2007-05-08 | Santen Pharmaceutical Co., Ltd. | Urea derivatives having tnf- .alpha. production inhibitory effects |
| EP0987235B1 (en) | 1998-08-25 | 2003-03-12 | MERCK PATENT GmbH | Method for the conversion of arenes or alkenes with iodoalkenes, aryl iodides or arenediazonium salts |
| JP2000159702A (ja) * | 1998-11-25 | 2000-06-13 | Mitsubishi Chemicals Corp | １−（４−クロロフェニル）−ω−ブロモアルカンの製造方法 |
| ES2209728T3 (es) | 1999-08-06 | 2004-07-01 | F. Hoffmann-La Roche Ag | Tetrahidro-benzo(d)azepinas y su uso como antagonistas de receptores de glutamato metabotropico. |
| EP1074549B1 (en) | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors |
| US6403657B1 (en) | 1999-10-04 | 2002-06-11 | Martin C. Hinz | Comprehensive pharmacologic therapy for treatment of obesity |
| DE10003708A1 (de) | 2000-01-28 | 2001-08-02 | Solvent Innovation Gmbh | Neuartige chirale ionische Flüssigkeiten und Verfahren zu ihrer Darstellung in enantiomerenreiner oder enantiomerenangereicherter Form |
| CZ300945B6 (cs) | 2000-06-30 | 2009-09-23 | Glaxo Group Limited | Zpusob prípravy 5-(6-chinazolinyl)-furan-2-karbaldehydu |
| CZ20031311A3 (cs) | 2000-11-14 | 2004-04-14 | Smithkline Beecham P. L. C. | Deriváty tetrahydroazepinu, užitečné jako modulátory receptorů dopaminu D3 (antipsychotická činidla) |
| DE10057751A1 (de) | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Carbamat-substituierte Pyrazolopyridinderivate |
| GB0030710D0 (en) | 2000-12-15 | 2001-01-31 | Hoffmann La Roche | Piperazine derivatives |
| JPWO2002074746A1 (ja) | 2001-03-16 | 2004-07-08 | 山之内製薬株式会社 | ベンゾアゼピン誘導体 |
| US6825198B2 (en) | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
| JP2003034681A (ja) * | 2001-07-18 | 2003-02-07 | Tosoh Corp | Ｎ−（ω−ブロモアルキル）フタルイミド類の製造方法 |
| MXPA04002785A (es) | 2001-09-24 | 2004-07-29 | Elan Pharm Inc | Aminas sustituidas para tratamiento de enfermedad de alzheimer. |
| WO2003062205A1 (en) | 2001-12-21 | 2003-07-31 | Smithkline Beecham P.L.C. | 7-sulfonyl-3-benzazepine derivatives as modulators of the dopamine receptor and their use for the treatment of cns disorders |
| WO2003057161A2 (en) | 2001-12-28 | 2003-07-17 | Bayer Pharmaceuticals Corporation | BENZOTHIENO [3,2-c]PYRAZOLYL AND BENZOFURANO [3,2-c] PYRAZOLYL COMPOUNDS, THEIR USE IN DISEASES ASSOCIATED WITH THE 5-HT2C RECEPTOR AND INTERMEDIATE COMPOUNDS THEREOF |
| CA2473740A1 (en) | 2002-01-18 | 2003-07-31 | David Solow-Cordero | Methods of treating conditions associated with an edg receptor |
| WO2003077847A2 (en) | 2002-03-12 | 2003-09-25 | Merck & Co., Inc. | Substituted amides |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| JP4188060B2 (ja) * | 2002-11-08 | 2008-11-26 | 北興化学工業株式会社 | １−置換フェニル−ω−ブロモアルカンの製造法 |
| DE10261131A1 (de) | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Substituierte 5-Aminomethyl-1H-pyrrol-2-carbonsäureamide |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| JP4782003B2 (ja) | 2003-06-17 | 2011-09-28 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５ｈｔ２ｃレセプター関連疾患の処置に有用なベンズアゼピン誘導体 |
| DK2332921T3 (en) | 2003-06-17 | 2016-05-09 | Arena Pharm Inc | 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepine hydrochloride |
| TW200510324A (en) | 2003-08-11 | 2005-03-16 | Lilly Co Eli | 6-(2,2,2-trifluoroethylamino)-7-chiloro-2, 3, 4, 5-tetrahydro-1h-benzo[d]azepine as a 5-ht2c receptor agonist |
| WO2005042491A1 (en) | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| US20070275949A1 (en) | 2003-10-22 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases |
| US20090143276A1 (en) * | 2007-10-08 | 2009-06-04 | Anaphore, Inc. | Trimeric IL-1Ra |
| EP2479168B1 (en) | 2004-02-25 | 2014-04-09 | Eli Lilly And Company | 6-Substituted 2,3,4,5-Tetrahydro-1H-Benzo [d]Azepines as 5-HT2C Receptor Agonists |
| SE0401871D0 (sv) | 2004-07-15 | 2004-07-15 | Glucogene Medical Hfm Ab | New compositions |
| US20080269282A1 (en) | 2004-08-02 | 2008-10-30 | Genmedica Therapeutics Sl | Compounds for Inhibiting Copper-Containing Amine Oxidases and Uses Thereof |
| JPWO2006043710A1 (ja) | 2004-10-19 | 2008-05-22 | 株式会社リバース・プロテオミクス研究所 | 創薬標的タンパク質及び標的遺伝子、並びにスクリーニング方法 |
| RS50996B (sr) | 2004-12-21 | 2010-10-31 | Arena Pharmaceuticals Inc. | Kristalni oblici (r)-8-hloro-1-metil-2,3,4,5-tetrahidro-1h-benzazepin hlorhidrat |
| KR101519441B1 (ko) | 2004-12-23 | 2015-05-12 | 아레나 파마슈티칼스, 인크. | 5ｈｔ２ｃ 수용체 조정물질 조성물 및 그의 사용 방법 |
| JP4984567B2 (ja) * | 2006-02-24 | 2012-07-25 | 東ソー株式会社 | 分岐アルキルブロミドの製造方法 |
| CN101466684B (zh) | 2006-04-03 | 2012-06-20 | 艾尼纳制药公司 | 8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的制备工艺和其相关中间体 |
| ES2522587T3 (es) | 2006-12-05 | 2014-11-17 | Arena Pharmaceuticals, Inc. | Procesos para preparar (R)-8-cloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzacepina e intermedios de la misma |
| JP5339263B2 (ja) | 2007-07-26 | 2013-11-13 | コクヨ株式会社 | 引き戸の取付構造、引き戸及び収納装置 |
| US8166624B2 (en) * | 2008-01-17 | 2012-05-01 | Jon Andreasen | Linearly extendible impact anchor driving pole and anchor system |
| WO2009111004A1 (en) | 2008-03-04 | 2009-09-11 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| WO2010148207A2 (en) | 2009-06-18 | 2010-12-23 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| NZ630494A (en) | 2010-09-01 | 2016-05-27 | Arena Pharm Inc | Administration of lorcaserin to individuals with renal impairment |
| CN102126988A (zh) | 2010-12-17 | 2011-07-20 | 张家港瀚康化工有限公司 | 4-(4-氯苯基)-2-溴甲基-2-苯基丁腈的制备方法 |
-
2009
- 2009-03-03 WO PCT/US2009/001340 patent/WO2009111004A1/en not_active Ceased
- 2009-03-03 EP EP09717615A patent/EP2288585A1/en not_active Withdrawn
- 2009-03-03 JP JP2010549649A patent/JP5491421B2/ja not_active Expired - Fee Related
- 2009-03-03 US US12/921,101 patent/US8822727B2/en not_active Expired - Fee Related
- 2009-03-03 CN CN200980116092.7A patent/CN102015591B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8822727B2 (en) | 2014-09-02 |
| WO2009111004A1 (en) | 2009-09-11 |
| CN102015591A (zh) | 2011-04-13 |
| EP2288585A1 (en) | 2011-03-02 |
| CN102015591B (zh) | 2014-01-29 |
| US20110015438A1 (en) | 2011-01-20 |
| JP2011513402A (ja) | 2011-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5491421B2 (ja) | ５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス | |
| US8168782B2 (en) | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates related thereto | |
| US8367657B2 (en) | Processes for preparing 3-benzazepines | |
| CN101547892B (zh) | 制备(r)-8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的方法和其中间体 | |
| US8952197B2 (en) | Processes for the preparation of 5-HT2C receptor agonists | |
| EP2155696A2 (en) | Piperazine salts as d3/d2 antagonists | |
| IE67288B1 (en) | 1-indolyalkyl-4-(alkoxypyrimidinyl) piperazines | |
| CN104470913A (zh) | 用于制造羟基化的环戊基嘧啶化合物的方法 | |
| US7030243B1 (en) | Process for making camptothecin derivatives | |
| EP1412340A2 (en) | Process for the preparation of citalopram hydrobromide | |
| EP1694684B1 (en) | Process for making camptothecin derivatives | |
| HK1176604A (en) | Process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine | |
| HK1160838B (en) | 8-chloro-1 -methyl-2,3,4,5-tetrahydro-1 h-3benzazapine hydrochloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120215 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120215 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130123 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130717 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130719 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131018 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131025 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140108 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140131 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140227 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5491421 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |