AR056262A1 - Preparacion de alcoholes propargilicos y esteres intermediarios de analogos de himbacina - Google Patents
Preparacion de alcoholes propargilicos y esteres intermediarios de analogos de himbacinaInfo
- Publication number
- AR056262A1 AR056262A1 ARP060100126A ARP060100126A AR056262A1 AR 056262 A1 AR056262 A1 AR 056262A1 AR P060100126 A ARP060100126 A AR P060100126A AR P060100126 A ARP060100126 A AR P060100126A AR 056262 A1 AR056262 A1 AR 056262A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- formula
- compound
- group
- mono
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 3
- 150000001298 alcohols Chemical class 0.000 title 1
- FMPNFDSPHNUFOS-LPJDIUFZSA-N himbacine Chemical class C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-LPJDIUFZSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- -1 propargyl alcohols Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229940088598 enzyme Drugs 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004982 dihaloalkyl group Chemical group 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- 239000003856 thrombin receptor antagonist Substances 0.000 abstract 1
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Esta revela un proceso para la conversion de una serie de alcoholes propargílicos racémicos en los correspondientes enantiomeros (R). Esta presente también revela la esterificacion enantioselectiva de un alcohol propargílico a partir de su racemato para preparar un éster (R). La enantiselectividad se aumenta mediante el uso de enzimas determinadas experimentalmente. Los alcoholes propargílicos y los ésteres quirales pueden ser utiles en la preparacion de compuestos tales como, por ejemplo, antagonistas del receptor de trombina. Reivindicacion1: Un proceso para la preparacion de un compuesto de formula (1), a partir de un compuesto de formula (2), comprendiendo dicho proceso: a) hacer reaccionar un compuesto de formula (3), con un acetato en presencia de un enzima de resolucion para producir compuestos de formulas (4) y (5), b) sulfonar el compuesto de formula (5) para producir un compuesto sulfonato de formula (6), siendo dicho compuesto sulfonato de formula (6) extraído por lavado con agua o convertido en un compuesto acetato de formula (4) por desplazamiento del grupo sulfonato a grupo acetato; c) convertir el compuesto de formula (4) al compuesto de formula (2); y d) esterificar un compuesto de formula (7), con el compuesto de formula (2) para producir el compuesto de formula (1), donde R1 y R2 se seleccionan cada uno independientemente del grupo que consiste en los grupos hidrogeno, halogeno, alquilo, haloalquilo, alcoxi, mono- y di-alcoxialquilo, alquenilo, alquinillo, mono- y di-alquilamino, mono- y di-arilamino, (aril)alquilamino, (alquil)arilamino, amido, mono- y di-alquilamido, y mono- y di-arilamido; R3 se selecciona del grupo que consiste en los grupos alquilo, arilo, arilalquilo y heteroarilo; R4 y R5 se seleccionan cada uno independientemente del grupo que consiste en H, hidroxilo, amino, nitro, amido, halogeno, alquilo, alquenilo, alcoxi, mono- y di-alcoxialquilo, halo(alquilo C1-6)-, dihaloalquilo, trihaloalquilo, cicloalquilo, cicloalquilalquilo, arilo, alquilarilo, aril-alquilo-, tioalquilo, alquil-tioalquilo, alquenilo, hidroxil-alquilo, aminoalquilo, -C(O)OR7, -C(O)NR8R9, -alquil-C(O)NR8R9, -NR10R11, y NR10R11-alquilo, o R4 y R5, juntos con el carbono al cual están unidos, forman un grupo heteroarilo o heterocíclico de 5 a 10 átomos que comprenden átomos de hidrogeno, C1-9 y 1 a 4 heteroátomos seleccionados independientemente del grupo que consiste en N, O, y S, donde un nitrogeno del anillo puede formar un N- oxido o un grupo cuaternario con un grupo alquilo 1-4; R7, R8, y R9 se seleccionan independientemente del grupo que consiste en H, alquilo C1-6, fenilo y bencilo; y R10 y R11 se seleccionan cada uno independientemente del grupo que consiste en H y alquilo C1-6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64392705P | 2005-01-14 | 2005-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR056262A1 true AR056262A1 (es) | 2007-10-03 |
Family
ID=36580053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060100126A AR056262A1 (es) | 2005-01-14 | 2006-01-12 | Preparacion de alcoholes propargilicos y esteres intermediarios de analogos de himbacina |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060172397A1 (es) |
| EP (1) | EP1848683A2 (es) |
| JP (1) | JP2008526254A (es) |
| CN (1) | CN101137614A (es) |
| AR (1) | AR056262A1 (es) |
| CA (1) | CA2594742A1 (es) |
| MX (1) | MX2007008630A (es) |
| WO (1) | WO2006076565A2 (es) |
| ZA (1) | ZA200705788B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7488742B2 (en) * | 2000-06-15 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
| CA2594807A1 (en) | 2005-01-14 | 2006-07-20 | Schering Corporation | An exo-selective synthesis of himbacine analogs |
| CN102618596A (zh) * | 2012-03-20 | 2012-08-01 | 中国药科大学 | 一种非水相体系中生物转化制备关附庚素的方法 |
| CN106966899A (zh) * | 2017-03-01 | 2017-07-21 | 山东裕欣药业有限公司 | 一种呱西替柳的制备方法 |
| WO2020255164A1 (en) * | 2019-06-21 | 2020-12-24 | Council Of Scientific And Industrial Research | A chemo-enzymatic process for the preparation of homopropargylic alcohol |
| CN112142694B (zh) * | 2020-09-23 | 2025-06-10 | 中国科学院成都有机化学有限公司 | 一种多取代四氢呋喃与四氢吡喃双烯体类化合物及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995033845A1 (en) * | 1994-06-02 | 1995-12-14 | Taisho Pharmaceutical Co., Ltd. | Process for producing optically active propargyl alcohol compound |
| US6063847A (en) * | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
| GB9908327D0 (en) * | 1999-04-12 | 1999-06-09 | Chirotech Technology Ltd | Process for the preparation of prostaglandin precursors |
| US7235567B2 (en) * | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
| ATE455774T1 (de) * | 2002-04-16 | 2010-02-15 | Schering Corp | Trizyklische thrombinrezeptorantagonisten |
-
2006
- 2006-01-12 MX MX2007008630A patent/MX2007008630A/es unknown
- 2006-01-12 CN CNA2006800080851A patent/CN101137614A/zh active Pending
- 2006-01-12 WO PCT/US2006/001209 patent/WO2006076565A2/en not_active Ceased
- 2006-01-12 AR ARP060100126A patent/AR056262A1/es not_active Application Discontinuation
- 2006-01-12 EP EP06718300A patent/EP1848683A2/en not_active Withdrawn
- 2006-01-12 US US11/330,936 patent/US20060172397A1/en not_active Abandoned
- 2006-01-12 CA CA002594742A patent/CA2594742A1/en not_active Abandoned
- 2006-01-12 JP JP2007551397A patent/JP2008526254A/ja not_active Withdrawn
-
2007
- 2007-07-13 ZA ZA200705788A patent/ZA200705788B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1848683A2 (en) | 2007-10-31 |
| MX2007008630A (es) | 2007-09-12 |
| JP2008526254A (ja) | 2008-07-24 |
| CA2594742A1 (en) | 2006-07-20 |
| ZA200705788B (en) | 2008-09-25 |
| WO2006076565A2 (en) | 2006-07-20 |
| WO2006076565A3 (en) | 2006-12-07 |
| CN101137614A (zh) | 2008-03-05 |
| US20060172397A1 (en) | 2006-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |