DE2007273A1 - N(6) Aralkyl adenosin Derivate und Verfahren zur Herstellung derselben - Google Patents
N(6) Aralkyl adenosin Derivate und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2007273A1 DE2007273A1 DE19702007273 DE2007273A DE2007273A1 DE 2007273 A1 DE2007273 A1 DE 2007273A1 DE 19702007273 DE19702007273 DE 19702007273 DE 2007273 A DE2007273 A DE 2007273A DE 2007273 A1 DE2007273 A1 DE 2007273A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- derivatives
- aralkyl
- adenosine
- adenosine derivatives
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- -1 aralkyl adenosine derivatives Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003218 coronary vasodilator agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 11
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 6
- 229960005305 adenosine Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LUJNPFWZXIGIPS-UHFFFAOYSA-N (2,5-dimethylphenyl)methanamine Chemical compound CC1=CC=C(C)C(CN)=C1 LUJNPFWZXIGIPS-UHFFFAOYSA-N 0.000 description 1
- XPKDQBYOXNXKGG-UHFFFAOYSA-N 2-(chloromethyl)-4-methyl-1-methylsulfanylbenzene Chemical compound CSC1=CC=C(C)C=C1CCl XPKDQBYOXNXKGG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000004961 Furin Human genes 0.000 description 1
- 108090001126 Furin Proteins 0.000 description 1
- 150000003835 adenosine derivatives Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702007273 DE2007273A1 (de) | 1970-02-18 | 1970-02-18 | N(6) Aralkyl adenosin Derivate und Verfahren zur Herstellung derselben |
| SU1616102A SU399134A1 (ru) | 1971-01-29 | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ N (б)-АРАЛКИЛАДЕНОЗИНА | |
| US00112424A US3781273A (en) | 1970-02-18 | 1971-02-03 | N(6)-benzyl-adenosine compounds and therapeutic compositions |
| ES388194A ES388194A1 (es) | 1970-02-18 | 1971-02-12 | Procedimiento para la preparacion de nuevos derivados de n (6)-aralcohil-adenosina. |
| DK69471AA DK123357B (da) | 1970-02-18 | 1971-02-16 | Analogifremgangsmåde til fremstilling af N(6)-benzyl-adenosin-derivater. |
| IL36211A IL36211A0 (en) | 1970-02-18 | 1971-02-16 | N(6)-aralkyl-adenosine derivatives,process for the preparation thereof and pharmaceutical compositions containing the same |
| NL7102026A NL7102026A (enExample) | 1970-02-18 | 1971-02-16 | |
| CH284974A CH549600A (de) | 1970-02-18 | 1971-02-16 | Verfahren zur herstellung neuer n (6)-aralkyl-adenosinderivate. |
| CA105,563A CA953714A (en) | 1970-02-18 | 1971-02-16 | N(6)-aralkyl-adenosine derivatives and process for the preparation thereof |
| CH220871A CH549596A (de) | 1970-02-18 | 1971-02-16 | Verfahren zur herstellung neuer n(6)-aralkyl-adenosinderivate. |
| HUBO1274A HU162739B (enExample) | 1970-02-18 | 1971-02-16 | |
| ZA711030A ZA711030B (en) | 1970-02-18 | 1971-02-17 | New n(6)-aralkyl-adenosine derivatives and the preparation thereof |
| AT123372A AT313483B (de) | 1970-02-18 | 1971-02-17 | Verfahren zur Herstellung neuer N(6)-Aralkyl-adenosin-Derivate |
| FR7105318A FR2081524B1 (enExample) | 1970-02-18 | 1971-02-17 | |
| AT137871A AT306251B (de) | 1970-02-18 | 1971-02-17 | Verfahren zur Herstellung von neuer N(6)-Aralkyl-adenosin-Derivate |
| JP46007691A JPS5116440B1 (enExample) | 1970-02-18 | 1971-02-18 | |
| GB21877/71A GB1279946A (en) | 1970-02-18 | 1971-04-19 | N(6) aralkyl-adenosine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702007273 DE2007273A1 (de) | 1970-02-18 | 1970-02-18 | N(6) Aralkyl adenosin Derivate und Verfahren zur Herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2007273A1 true DE2007273A1 (de) | 1971-08-26 |
Family
ID=5762543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702007273 Pending DE2007273A1 (de) | 1970-02-18 | 1970-02-18 | N(6) Aralkyl adenosin Derivate und Verfahren zur Herstellung derselben |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3781273A (enExample) |
| JP (1) | JPS5116440B1 (enExample) |
| AT (2) | AT313483B (enExample) |
| CA (1) | CA953714A (enExample) |
| CH (2) | CH549596A (enExample) |
| DE (1) | DE2007273A1 (enExample) |
| DK (1) | DK123357B (enExample) |
| ES (1) | ES388194A1 (enExample) |
| FR (1) | FR2081524B1 (enExample) |
| GB (1) | GB1279946A (enExample) |
| HU (1) | HU162739B (enExample) |
| IL (1) | IL36211A0 (enExample) |
| NL (1) | NL7102026A (enExample) |
| ZA (1) | ZA711030B (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5030624A (en) * | 1988-10-26 | 1991-07-09 | G. D. Searle & Co. | R-diastereomer of an N6 -[(2-hydroxypropyl)aryl]adenosine and its medicinal uses |
| US5032584A (en) * | 1988-10-26 | 1991-07-16 | G. D. Searle & Co. | S-diastereomer of an n6 -((2-hydroxypropyl)aryl)adenosine and its medicinal uses |
| US5043325A (en) * | 1984-04-18 | 1991-08-27 | Whitby Research, Inc. | N-6 substituted adenosine derivatives as cardiac vasodilators |
| US5066655A (en) * | 1987-04-24 | 1991-11-19 | Whitby Research, Inc. | N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| US5070877A (en) * | 1988-08-11 | 1991-12-10 | Medco Research, Inc. | Novel method of myocardial imaging |
| US5310731A (en) * | 1984-06-28 | 1994-05-10 | Whitby Research, Inc. | N-6 substituted-5'-(N-substitutedcarboxamido)adenosines as cardiac vasodilators and antihypertensive agents |
| US6784165B1 (en) | 1999-11-23 | 2004-08-31 | Aderis Pharmaceuticals, Inc. | Treatment of heart rhythm disturbances with N6-substituted-5′-(N-substituted) carboxamidoadenosines |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988003147A1 (en) * | 1986-10-31 | 1988-05-05 | Warner-Lambert Company | Selected n6-substituted adenosines having selective a2 binding activity |
| US5565566A (en) * | 1987-04-24 | 1996-10-15 | Discovery Therapeutics, Inc. | N6 -substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| CZ294538B6 (cs) * | 2002-12-30 | 2005-01-12 | Ústav Experimentální Botaniky Akademie Vědčeské Re | Substituční deriváty N6-benzyladenosinu, způsob jejich přípravy, jejich použití pro přípravu léčiv, kosmetických přípravků a růstových regulátorů, farmaceutické přípravky, kosmetické přípravky a růstové regulátory tyto sloučeniny obsahující |
| US20050009776A1 (en) * | 2003-04-24 | 2005-01-13 | Aderis Pharmaceuticals, Inc. | Method of treating atrial fibrillation or atrial flutter |
| WO2005025545A2 (en) * | 2003-09-17 | 2005-03-24 | Aderis Pharmaceuticals, Inc. | Pharmaceutical formulation for controlled release of selodenoson |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2881164A (en) * | 1955-07-18 | 1959-04-07 | American Cyanamid Co | Ribofuranosyl derivatives of 6-aralkylamino and 6-heterocyclicalkylaminopurines |
| US3506643A (en) * | 1966-12-09 | 1970-04-14 | Max Thiel | N**6-aralkyl-adenosine derivatives |
-
1970
- 1970-02-18 DE DE19702007273 patent/DE2007273A1/de active Pending
-
1971
- 1971-02-03 US US00112424A patent/US3781273A/en not_active Expired - Lifetime
- 1971-02-12 ES ES388194A patent/ES388194A1/es not_active Expired
- 1971-02-16 IL IL36211A patent/IL36211A0/xx unknown
- 1971-02-16 CH CH220871A patent/CH549596A/xx not_active IP Right Cessation
- 1971-02-16 CH CH284974A patent/CH549600A/xx not_active IP Right Cessation
- 1971-02-16 DK DK69471AA patent/DK123357B/da unknown
- 1971-02-16 HU HUBO1274A patent/HU162739B/hu unknown
- 1971-02-16 NL NL7102026A patent/NL7102026A/xx not_active Application Discontinuation
- 1971-02-16 CA CA105,563A patent/CA953714A/en not_active Expired
- 1971-02-17 AT AT123372A patent/AT313483B/de active
- 1971-02-17 AT AT137871A patent/AT306251B/de not_active IP Right Cessation
- 1971-02-17 FR FR7105318A patent/FR2081524B1/fr not_active Expired
- 1971-02-17 ZA ZA711030A patent/ZA711030B/xx unknown
- 1971-02-18 JP JP46007691A patent/JPS5116440B1/ja active Pending
- 1971-04-19 GB GB21877/71A patent/GB1279946A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5043325A (en) * | 1984-04-18 | 1991-08-27 | Whitby Research, Inc. | N-6 substituted adenosine derivatives as cardiac vasodilators |
| US5310731A (en) * | 1984-06-28 | 1994-05-10 | Whitby Research, Inc. | N-6 substituted-5'-(N-substitutedcarboxamido)adenosines as cardiac vasodilators and antihypertensive agents |
| USRE37045E1 (en) | 1984-06-28 | 2001-02-06 | Discovery Therapeutics, Inc. | N-6 substituted-5′-(N-substituted carboxamide)adenosines as cardiac vasodilator and antihypertensive agents |
| US5066655A (en) * | 1987-04-24 | 1991-11-19 | Whitby Research, Inc. | N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| US5070877A (en) * | 1988-08-11 | 1991-12-10 | Medco Research, Inc. | Novel method of myocardial imaging |
| US5030624A (en) * | 1988-10-26 | 1991-07-09 | G. D. Searle & Co. | R-diastereomer of an N6 -[(2-hydroxypropyl)aryl]adenosine and its medicinal uses |
| US5032584A (en) * | 1988-10-26 | 1991-07-16 | G. D. Searle & Co. | S-diastereomer of an n6 -((2-hydroxypropyl)aryl)adenosine and its medicinal uses |
| US6784165B1 (en) | 1999-11-23 | 2004-08-31 | Aderis Pharmaceuticals, Inc. | Treatment of heart rhythm disturbances with N6-substituted-5′-(N-substituted) carboxamidoadenosines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1279946A (en) | 1972-06-28 |
| AT313483B (de) | 1974-02-25 |
| US3781273A (en) | 1973-12-25 |
| ZA711030B (en) | 1971-11-24 |
| FR2081524A1 (enExample) | 1971-12-03 |
| CH549600A (de) | 1974-05-31 |
| JPS5116440B1 (enExample) | 1976-05-24 |
| DK123357B (da) | 1972-06-12 |
| NL7102026A (enExample) | 1971-08-20 |
| CH549596A (de) | 1974-05-31 |
| FR2081524B1 (enExample) | 1974-09-27 |
| ES388194A1 (es) | 1973-05-01 |
| IL36211A0 (en) | 1971-04-28 |
| HU162739B (enExample) | 1973-04-28 |
| AT306251B (de) | 1973-04-10 |
| SU399134A3 (enExample) | 1973-09-27 |
| CA953714A (en) | 1974-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |