AR054374A1 - Procedimientos utiles para sintesis de compuestos farmaceuticos en especial inhibidores de renina (aliskiren), intermediarios y compuestos farmaceuticos - Google Patents
Procedimientos utiles para sintesis de compuestos farmaceuticos en especial inhibidores de renina (aliskiren), intermediarios y compuestos farmaceuticosInfo
- Publication number
- AR054374A1 AR054374A1 ARP060102357A ARP060102357A AR054374A1 AR 054374 A1 AR054374 A1 AR 054374A1 AR P060102357 A ARP060102357 A AR P060102357A AR P060102357 A ARP060102357 A AR P060102357A AR 054374 A1 AR054374 A1 AR 054374A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- salt
- manufacture
- pharmaceutical compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 21
- 238000000034 method Methods 0.000 title abstract 4
- UXOWGYHJODZGMF-QORCZRPOSA-N Aliskiren Chemical compound COCCCOC1=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)C(C)C)=CC=C1OC UXOWGYHJODZGMF-QORCZRPOSA-N 0.000 title abstract 2
- 229960004601 aliskiren Drugs 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 15
- 238000004519 manufacturing process Methods 0.000 abstract 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002461 renin inhibitor Substances 0.000 abstract 1
- 229940086526 renin-inhibitors Drugs 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- -1 thionyl halide Chemical class 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
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- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
La presente se refiere a procedimientos, compuestos e intermediarios utiles en la síntesis de compuestos farmacéuticamente activos, en especial inhibidores de renina, tales como aliskiren. Reivindicacion 1: un procedimiento para la fabricacion de un compuesto de la formula (3) en donde R es H, alquilo o alcoxialquilo; R1 es H, alquilo o alcoxialquilo; R2 es H o de preferencia un grupo hidroxilo-protector; R3 es H o alquilo no sustituido o sustituido; y PG es un grupo amino-protector, especialmente uno que se puede remover a través de hidrolisis, por ejemplo alcoxicarbonilo inferior, tal como ter-butoxicarbonilo o benciloxicarbonilo; o una sal del mismo; dicho procedimiento comprende hacer reaccionar un compuesto en la formula (1) en donde R, R1, R2, R3 y PG son como se definieron para un compuesto de la formula (3), con u residuo capaz de transformar el hidroxi en la formula I a X, en donde X es un grupo distinto a hidroxi o H, especialmente un grupo saliente, en especial un reactor seleccionado de ácido hidrohálico, una halogenuro de tionilo, PX*3, POX*3, PX*5 o POX*5 en donde X* es un halogenuro, una combinacion de trifenilfosfina y halogeno, y un derivado activo de un ácido sulfonico orgánico. Reivindicacion 61: La fabricacion de un compuesto de la formula (15), en donde R, R1, y PG son como se definieron para un compuesto de la formula (3) en cualquiera de las reivindicaciones 1 a 3 o como se da en la reivindicacion 4, o una sal del mismo, que comprende uno o más, por ejemplo todos los pasos de: (i) la fabricacion de un compuesto de la formula (3) de acuerdo con cualquiera de las reivindicaciones 1 a 3, o una sal del mismo, la fabricacion de un compuesto de la formula (4) de acuerdo con a reivindicacion 5, o una sal del mismo, o (ii) la fabricacion de un compuesto de la formula (4S) de acuerdo con la reivindicacion 8, o una sal del mismo, la fabricacion de un compuesto de la formula (4) de acuerdo con la reivindicacion 9, o una sal del mismo, la fabricacion de un compuesto de la formula (5) o una sal del mismo, de acuerdo con la reivindicacion 10, la fabricacion de un compuesto de la formula (23) o una sal del mismo, de acuerdo con la reivindicacion 56, la fabricacion de un compuesto de la formula (24) o una sal del mismo, de acuerdo con la reivindicacion 58, la fabricacion de un compuesto de la formula (20), o una sal del mismo, de acuerdo con la reivindicacion 60, la fabricacion de un compuesto de la formula (14) o una sal del mismo, de acuerdo con la reivindicacion 47, y la desproteccion del mismo de acuerdo con la reivindicacion 33 a un compuesto de la formula (15), o una sal del mismo, y si se desea, convertir un compuesto libre obtenible de la formula (15) a una sal, o una sal obtenible al compuesto libre de la formula (15) o una sal diferente del mismo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0511686.8A GB0511686D0 (en) | 2005-06-08 | 2005-06-08 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR054374A1 true AR054374A1 (es) | 2007-06-20 |
Family
ID=34835327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060102357A AR054374A1 (es) | 2005-06-08 | 2006-06-06 | Procedimientos utiles para sintesis de compuestos farmaceuticos en especial inhibidores de renina (aliskiren), intermediarios y compuestos farmaceuticos |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7767831B2 (es) |
| EP (2) | EP2080754A3 (es) |
| JP (2) | JP2008542415A (es) |
| KR (1) | KR20080014011A (es) |
| CN (1) | CN101193860B (es) |
| AR (1) | AR054374A1 (es) |
| AU (1) | AU2006256938B2 (es) |
| BR (1) | BRPI0611919A2 (es) |
| CA (1) | CA2608575A1 (es) |
| EC (1) | ECSP077986A (es) |
| GB (1) | GB0511686D0 (es) |
| GT (1) | GT200600208A (es) |
| IL (1) | IL187004A0 (es) |
| MA (1) | MA29563B1 (es) |
| MX (1) | MX2007015418A (es) |
| NO (1) | NO20080080L (es) |
| NZ (2) | NZ562889A (es) |
| PE (2) | PE20070075A1 (es) |
| RU (1) | RU2418785C2 (es) |
| SG (1) | SG155209A1 (es) |
| TN (1) | TNSN07465A1 (es) |
| TW (1) | TW200716544A (es) |
| WO (1) | WO2006131304A2 (es) |
| ZA (1) | ZA200709076B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0521083D0 (en) | 2005-10-17 | 2005-11-23 | Novartis Ag | Organic compounds |
| DE102007049039A1 (de) | 2007-10-11 | 2009-04-16 | Reuter Chemischer Apparatebau Kg | Verfahren zur Herstellung von 8-Hydrazino-8-Aryl-Octanoylderivaten und deren Verwendung |
| EP2062874B1 (en) | 2007-11-20 | 2014-12-17 | KRKA, tovarna zdravil, d.d., Novo mesto | Process and intermediates for the preparation of aliskiren |
| EP2225200B1 (en) | 2007-12-24 | 2013-10-16 | DSM IP Assets B.V. | Convergent synthesis of renin inhibitors and intermediates useful therein |
| SI2189442T1 (sl) | 2008-11-20 | 2015-03-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Postopek in intermediati za pripravo aliskirena |
| EP2464623B1 (en) | 2009-08-11 | 2020-11-04 | Novartis AG | The ring opening of lactones and lactams |
| US8203005B2 (en) | 2009-10-29 | 2012-06-19 | Carbo Design Llc | Manufacturing process for enantiomerically pure 8-aryloctanoic acids as Aliskiren |
| EP2523934A1 (en) * | 2010-02-10 | 2012-11-21 | Ratiopharm GmbH | Salts of aliskiren |
| US8703976B2 (en) | 2011-10-02 | 2014-04-22 | Milan Soukup | Manufacturing process for 8-aryloctanoic acids such as Aliskiren |
| CN111423325A (zh) * | 2020-04-26 | 2020-07-17 | 江苏凯迪恩医药科技有限公司 | 基于蒽醌类药物的双醋瑞因合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4570108A (en) * | 1982-07-06 | 1986-02-11 | Stroede Aake | Protection device for electrical incandescent lamps |
| US5659065A (en) | 1994-04-18 | 1997-08-19 | Novartis Corporation | Alpha-aminoalkanoic acids and reduction products |
| MY119161A (en) | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| US5606078A (en) | 1994-04-18 | 1997-02-25 | Ciba-Geigy Corporation | 3,5-Disubstituted tetrahydrofuran-2-ones |
| CA2121898A1 (en) * | 1994-04-21 | 1995-10-22 | Stephen Hanessian | Synthesis of prototypes for renin inhibitors |
| IT1292426B1 (it) * | 1997-06-27 | 1999-02-08 | Nicox Sa | Sali nitrati di ace-inibitori |
| JP2005231999A (ja) * | 2000-03-08 | 2005-09-02 | Banyu Pharmaceut Co Ltd | カルバペネム誘導体の製造方法 |
| PL212898B1 (pl) | 2000-07-05 | 2012-12-31 | Speedel Pharma Ag | Sposób otrzymywania podstawionych amidów oktanoilowych oraz zwiazki posrednie wykorzystane w tym sposobie |
| US8168616B1 (en) * | 2000-11-17 | 2012-05-01 | Novartis Ag | Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension |
| ATE342887T1 (de) * | 2000-12-14 | 2006-11-15 | Speedel Pharma Ag | Verfahren zur herstellung von aryloctanoyl-amiden |
| GB0419361D0 (en) | 2004-08-31 | 2004-10-06 | Novartis Ag | Organic compounds |
-
2005
- 2005-06-08 GB GBGB0511686.8A patent/GB0511686D0/en not_active Ceased
-
2006
- 2006-05-18 GT GT200600208A patent/GT200600208A/es unknown
- 2006-06-06 WO PCT/EP2006/005370 patent/WO2006131304A2/en not_active Ceased
- 2006-06-06 CA CA002608575A patent/CA2608575A1/en not_active Abandoned
- 2006-06-06 RU RU2007148226/04A patent/RU2418785C2/ru not_active IP Right Cessation
- 2006-06-06 AR ARP060102357A patent/AR054374A1/es not_active Application Discontinuation
- 2006-06-06 MX MX2007015418A patent/MX2007015418A/es active IP Right Grant
- 2006-06-06 PE PE2006000621A patent/PE20070075A1/es not_active Application Discontinuation
- 2006-06-06 EP EP09005946A patent/EP2080754A3/en not_active Withdrawn
- 2006-06-06 BR BRPI0611919-0A patent/BRPI0611919A2/pt not_active IP Right Cessation
- 2006-06-06 CN CN2006800202505A patent/CN101193860B/zh not_active Expired - Fee Related
- 2006-06-06 KR KR1020077028644A patent/KR20080014011A/ko not_active Ceased
- 2006-06-06 US US11/916,875 patent/US7767831B2/en not_active Expired - Fee Related
- 2006-06-06 JP JP2008515124A patent/JP2008542415A/ja active Pending
- 2006-06-06 NZ NZ562889A patent/NZ562889A/en not_active IP Right Cessation
- 2006-06-06 SG SG200905377-8A patent/SG155209A1/en unknown
- 2006-06-06 NZ NZ591010A patent/NZ591010A/en not_active IP Right Cessation
- 2006-06-06 EP EP06754143A patent/EP1896411A2/en not_active Withdrawn
- 2006-06-06 PE PE2009000932A patent/PE20091359A1/es not_active Application Discontinuation
- 2006-06-06 AU AU2006256938A patent/AU2006256938B2/en not_active Ceased
- 2006-06-07 TW TW095120194A patent/TW200716544A/zh unknown
-
2007
- 2007-10-22 ZA ZA200709076A patent/ZA200709076B/xx unknown
- 2007-10-29 IL IL187004A patent/IL187004A0/en unknown
- 2007-12-07 TN TNP2007000465A patent/TNSN07465A1/en unknown
- 2007-12-07 EC EC2007007986A patent/ECSP077986A/es unknown
- 2007-12-26 MA MA30506A patent/MA29563B1/fr unknown
-
2008
- 2008-01-04 NO NO20080080A patent/NO20080080L/no not_active Application Discontinuation
-
2010
- 2010-06-25 US US12/823,518 patent/US20100274027A1/en not_active Abandoned
-
2012
- 2012-08-07 JP JP2012175078A patent/JP2013028607A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |