JPH0137391B2 - - Google Patents
Info
- Publication number
- JPH0137391B2 JPH0137391B2 JP60254326A JP25432685A JPH0137391B2 JP H0137391 B2 JPH0137391 B2 JP H0137391B2 JP 60254326 A JP60254326 A JP 60254326A JP 25432685 A JP25432685 A JP 25432685A JP H0137391 B2 JPH0137391 B2 JP H0137391B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxybenzenesulfonamide
- methanol
- formula
- aminopropyl
- solvent
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 17
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 10
- IORITYIZDHJCGT-SSDOTTSWSA-N 5-[(2r)-2-aminopropyl]-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(C[C@@H](C)N)C=C1S(N)(=O)=O IORITYIZDHJCGT-SSDOTTSWSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical class O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical class NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KEFIGZIQAGNFAX-UHFFFAOYSA-N 1-(2,2-diethoxyethoxy)-2-ethoxybenzene Chemical compound CCOC(OCC)COC1=CC=CC=C1OCC KEFIGZIQAGNFAX-UHFFFAOYSA-N 0.000 description 2
- MKQNYQGIPARLKO-UHFFFAOYSA-N 2-methoxybenzenesulfonamide Chemical compound COC1=CC=CC=C1S(N)(=O)=O MKQNYQGIPARLKO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 150000001299 aldehydes Chemical class 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- NEGYEDYHPHMHGK-UHFFFAOYSA-N para-methoxyamphetamine Chemical compound COC1=CC=C(CC(C)N)C=C1 NEGYEDYHPHMHGK-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- KYRRNJIOCLALJQ-UHFFFAOYSA-N 5-(2-aminopropyl)-2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C(CC(C)N)C=C1S(N)(=O)=O KYRRNJIOCLALJQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YGLMBIHCBHUNBV-UHFFFAOYSA-N n-[1-(4-methoxyphenyl)propan-2-yl]acetamide Chemical compound COC1=CC=C(CC(C)NC(C)=O)C=C1 YGLMBIHCBHUNBV-UHFFFAOYSA-N 0.000 description 1
- LFLZOWIFJOBEPN-UHFFFAOYSA-N nitrate, nitrate Chemical compound O[N+]([O-])=O.O[N+]([O-])=O LFLZOWIFJOBEPN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229950006768 phenylethanolamine Drugs 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000002889 sympathetic effect Effects 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254326A JPS62114952A (ja) | 1985-11-13 | 1985-11-13 | 置換フエネチルアミン誘導体の製造法 |
| KR1019860005460A KR940007746B1 (ko) | 1985-11-13 | 1986-07-07 | 치환된 펜에틸아민 유도체의 제조방법 |
| AT0203286A AT397960B (de) | 1985-11-13 | 1986-07-28 | Verfahren zur herstellung des neuen r-(-)-5-(2-((2-(o-äthoxyphenoxy)-äthyl)-amino)- propyl)-2-methoxybenzolsulfonamids |
| ES8600685A ES2000382A6 (es) | 1985-11-13 | 1986-07-29 | Un procedimiento para la produccion de derivados de fenetilamina substituidos |
| CA000515041A CA1282077C (en) | 1985-11-13 | 1986-07-31 | Process for producing substituted-phenethylamine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254326A JPS62114952A (ja) | 1985-11-13 | 1985-11-13 | 置換フエネチルアミン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62114952A JPS62114952A (ja) | 1987-05-26 |
| JPH0137391B2 true JPH0137391B2 (ko) | 1989-08-07 |
Family
ID=17263445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60254326A Granted JPS62114952A (ja) | 1985-11-13 | 1985-11-13 | 置換フエネチルアミン誘導体の製造法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS62114952A (ko) |
| KR (1) | KR940007746B1 (ko) |
| AT (1) | AT397960B (ko) |
| CA (1) | CA1282077C (ko) |
| ES (1) | ES2000382A6 (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006004093A1 (ja) * | 2004-07-07 | 2006-01-12 | Hamari Chemicals, Ltd. | 光学活性フェニルプロピルアミン誘導体の製法 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4971990A (en) * | 1988-02-19 | 1990-11-20 | Hokuriku Pharmaceutical Co., Ltd. | Phenoxyethylamine derivatives, for preparing the same and composition for exhibiting excellent α1 -blocking activity containing the same |
| US5288759A (en) * | 1992-08-27 | 1994-02-22 | Alcon Laboratories, Inc. | Use of certain sulfamoyl-substituted phenethylamine derivatives to reverse drug-induced mydriasis |
| TW536402B (en) | 1998-06-26 | 2003-06-11 | Yamanouchi Pharma Co Ltd | Pharmaceutical composition for the therapy of voiding dysfunction |
| KR100525493B1 (ko) | 2001-02-23 | 2005-11-02 | 연성정밀화학(주) | 설파모일 치환 페네틸아민 유도체의 제조 방법 |
| CZ20013848A3 (cs) * | 2001-10-25 | 2003-05-14 | Léčiva, A.S. | Způsob výroby (R)-(-)-5-[2-[2-(2-ethoxyfenoxy)ethylamino]propyl]-2-methoxybenzensulfonamidu |
| ES2200699B1 (es) * | 2002-07-12 | 2005-10-01 | Ragactives, S.L | Procedimiento para la separacion de r(-) y s(+)-5-(2-((2-(etoxifenoxi)etil)amino)propil-2-metoxibenceno-sulfonamida. |
| WO2004016582A1 (en) * | 2002-08-14 | 2004-02-26 | Natco Pharma Limited | An improved process for the preparation of tamsulosin hydrochloride |
| KR100503639B1 (ko) | 2003-02-12 | 2005-07-26 | 보령제약 주식회사 | 탐술로신의 정제 방법 |
| WO2005056521A1 (en) | 2003-12-09 | 2005-06-23 | Cj Corporation | Method of preparing optically pure phenethylamine derivatives |
| SI21655A (sl) * | 2003-12-29 | 2005-06-30 | LEK farmacevtska dru�ba d.d. | Sinteza optično čistega (R)-5-(2-aminopropil)-2-metoksibenzensulfonamida |
| SI21656A (sl) * | 2003-12-29 | 2005-06-30 | LEK farmacevtska družba d.d. | Priprava (R)-5-(2-(2-(2-etoksifenoksi) etilamino)-1-propil)-2-metoksibenzensulfonamida hidroklorida z visoko kemijsko čistoto |
| CZ2004197A3 (cs) * | 2004-02-05 | 2005-08-17 | Zentiva, A. S. | Způsob výroby (R)-(-)-5-(2-aminopropyl)-2-methoxybenzensulfonamidu |
| WO2005080323A1 (en) * | 2004-02-23 | 2005-09-01 | Cadila Healthcare Limited | Process for manufacturing optically pure (r) or (s)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide |
| CN100545148C (zh) | 2004-08-16 | 2009-09-30 | 神隆新加坡私人有限公司 | 一种抗良性前列腺肥大药物坦索罗辛之合成方法 |
| US8273918B2 (en) | 2005-09-12 | 2012-09-25 | Avrobindo Pharma Ltd. | Process for preparing tamsulosin hydrochloride |
| WO2008152653A2 (en) * | 2007-06-11 | 2008-12-18 | Matrix Laboratories Ltd | An improved process for the preparation of tamsulosin hydrochloride |
| CN102307579B (zh) | 2009-02-04 | 2013-10-16 | 安斯泰来制药株式会社 | 经口给药用医药组合物 |
| EP2255793A1 (en) | 2009-05-28 | 2010-12-01 | Krka Tovarna Zdravil, D.D., Novo Mesto | Pharmaceutical composition comprising tamsulosin |
| JP5661773B2 (ja) * | 2009-09-12 | 2015-01-28 | サンド・アクチエンゲゼルシヤフト | インドリン誘導体の調製方法およびこれらの中間体 |
| DE202023102187U1 (de) | 2023-04-25 | 2023-05-02 | Nusrath Anjum | Auf Tamsulosin basierende Derivatformulierung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1147342A (en) * | 1977-10-12 | 1983-05-31 | Kazuo Imai | Process of producing novel phenylethanolamine derivatives |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| US4558156A (en) * | 1980-02-08 | 1985-12-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl-substituted phenethylamine derivatives |
-
1985
- 1985-11-13 JP JP60254326A patent/JPS62114952A/ja active Granted
-
1986
- 1986-07-07 KR KR1019860005460A patent/KR940007746B1/ko not_active IP Right Cessation
- 1986-07-28 AT AT0203286A patent/AT397960B/de not_active IP Right Cessation
- 1986-07-29 ES ES8600685A patent/ES2000382A6/es not_active Expired
- 1986-07-31 CA CA000515041A patent/CA1282077C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006004093A1 (ja) * | 2004-07-07 | 2006-01-12 | Hamari Chemicals, Ltd. | 光学活性フェニルプロピルアミン誘導体の製法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62114952A (ja) | 1987-05-26 |
| ES2000382A6 (es) | 1988-02-16 |
| KR940007746B1 (ko) | 1994-08-24 |
| KR870004949A (ko) | 1987-06-02 |
| ATA203286A (de) | 1993-12-15 |
| AT397960B (de) | 1994-08-25 |
| CA1282077C (en) | 1991-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
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