CA2493457A1 - Composes d'acide acetylamino benzoique et leur utilisation pour la suppression de non-sens et le traitement de maladie - Google Patents
Composes d'acide acetylamino benzoique et leur utilisation pour la suppression de non-sens et le traitement de maladie Download PDFInfo
- Publication number
- CA2493457A1 CA2493457A1 CA002493457A CA2493457A CA2493457A1 CA 2493457 A1 CA2493457 A1 CA 2493457A1 CA 002493457 A CA002493457 A CA 002493457A CA 2493457 A CA2493457 A CA 2493457A CA 2493457 A1 CA2493457 A1 CA 2493457A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- benzoic acid
- phenoxy
- hydrogen
- 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.)
- Abandoned
Links
Classifications
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/42—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne de nouveaux composés d'acide acétyl amino benzoïque, des procédés d'utilisation d'un dérivé d'acide acétyl amino benzoïque et des compositions pharmaceutiques comprenant ce dernier. Il s'agit notamment de procédés de traitement ou de prévention d'une maladie qui sont améliorés par la modulation de la terminaison de translation prématurée ou la dégradation de l'ARNm médiée par les non-sens, ou qui améliorent au moins un symptôme qui y est associé.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39826702P | 2002-07-24 | 2002-07-24 | |
US60/398,267 | 2002-07-24 | ||
PCT/US2003/023183 WO2004009533A1 (fr) | 2002-07-24 | 2003-07-23 | Composes d'acide acetylamino benzoique et leur utilisation pour la suppression de non-sens et le traitement de maladie |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2493457A1 true CA2493457A1 (fr) | 2004-01-29 |
Family
ID=30771207
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002493457A Abandoned CA2493457A1 (fr) | 2002-07-24 | 2003-07-23 | Composes d'acide acetylamino benzoique et leur utilisation pour la suppression de non-sens et le traitement de maladie |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1525185A1 (fr) |
AU (1) | AU2003254157A1 (fr) |
CA (1) | CA2493457A1 (fr) |
WO (1) | WO2004009533A1 (fr) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7247741B2 (en) * | 2005-01-21 | 2007-07-24 | Ptc Therapeutics, Inc. | Acetylamino benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
US20060025480A1 (en) | 2004-08-02 | 2006-02-02 | Boehringer Ingelheim International Gmbh | Benzoic acid derivatives as non nucleoside reverse transcriptase inhibitors |
NZ552501A (en) | 2004-08-11 | 2010-03-26 | Kyorin Seiyaku Kk | Novel cyclic aminobenzoic acid derivative |
EP1799659A1 (fr) * | 2004-10-13 | 2007-06-27 | PTC Therapeutics, Inc. | Composés permettant de supprimer les effets des mutations non-sens, et méthodes d emploi desdits composés |
WO2007047706A2 (fr) * | 2005-10-17 | 2007-04-26 | Children's Hospital | Procedes et compositions de regulation de l'expression genique |
KR101384572B1 (ko) * | 2005-12-30 | 2014-04-24 | 아버 비타 코포레이션 | Pdz 상호작용의 소형 분자 억제제 |
US8633160B2 (en) | 2005-12-30 | 2014-01-21 | Nono Inc. | Small molecule inhibitors of PDZ interactions |
MX2008012515A (es) | 2006-03-30 | 2008-11-19 | Ptc Therapeutics Inc | Metodos para la produccion de proteina funcional a partir de adn que tiene una mutacion sin sentido y el tratamiento de trastornos asociados con la misma. |
KR100787131B1 (ko) * | 2006-07-04 | 2007-12-21 | 한국생명공학연구원 | Hif―1 활성을 저해하는 화합물, 이의 제조방법 및이를 유효성분으로 함유하는 약학적 조성물 |
FR2912745A1 (fr) * | 2007-02-19 | 2008-08-22 | Centre Nat Rech Scient | Nouveaux composes derives d'indole et compositions pharmaceutiques les contenant |
WO2008135448A1 (fr) * | 2007-05-03 | 2008-11-13 | Neurosearch A/S | Nouveaux dérivés de béta-céto-amide servant de modulateurs de canaux ioniques |
EP2062578A1 (fr) * | 2007-11-12 | 2009-05-27 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Utilisation de composés chimiques pour traiter le SIDA |
MX2010005298A (es) * | 2007-11-16 | 2010-06-30 | Rigel Pharmaceuticals Inc | Compuestos de carboxamida, sulfonamida y amina para trastornos metabolicos. |
CN102464618B (zh) | 2010-11-03 | 2014-07-23 | 中国中化股份有限公司 | 吡唑酰胺类化合物及其应用 |
JP6045828B2 (ja) * | 2012-07-11 | 2016-12-14 | 千葉県 | 抗癌剤 |
JP2015530378A (ja) * | 2012-08-29 | 2015-10-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 変形性関節症の処置のためのddr2インヒビター |
AU2014291711B2 (en) | 2013-07-18 | 2017-02-02 | Novartis Ag | Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core |
CN103554043B (zh) * | 2013-09-03 | 2015-04-01 | 浙江医药高等专科学校 | 苯基取代的三唑酰胺类化合物及用途 |
CN103467399B (zh) * | 2013-09-03 | 2015-01-07 | 浙江医药高等专科学校 | 三唑酰胺类化合物、其制备方法和其用途 |
WO2016172437A2 (fr) * | 2015-04-24 | 2016-10-27 | The Johns Hopkins University | Composés à petites molécules ciblant le complexe transcriptionnel pbx1 |
CN106478447B (zh) * | 2015-09-01 | 2018-10-30 | 上海医药工业研究院 | 羧酸衍生物及其作为fxr拮抗剂的应用 |
WO2017049409A1 (fr) * | 2015-09-25 | 2017-03-30 | The Centre For Drug Research And Development | Compositions permettant de favoriser la translecture de codons de terminaison prématurée, et leurs procédés d'utilisation |
CA3048204A1 (fr) | 2015-12-23 | 2017-06-29 | Moonshot Pharma Llc | Procedes pour induire une reponse immunitaire |
EP3641752A4 (fr) | 2017-06-22 | 2021-03-17 | Moonshot Pharma LLC | Méthodes de traitement du cancer au moyen de compositions comprenant de l'amlexanox et des immunomodulateurs |
JP2021529814A (ja) * | 2018-07-09 | 2021-11-04 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドGlaxosmithkline Intellectual Property Development Limited | 化学化合物 |
CN114716343B (zh) * | 2020-12-22 | 2023-03-21 | 清华大学 | 新型nampt酶激动剂及其制备与用途 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51149240A (en) * | 1975-06-17 | 1976-12-22 | Mitsubishi Yuka Yakuhin Kk | Process for preparing new 3-substituted aminophenylacetic acid derivat ives |
JPH07138221A (ja) * | 1993-11-11 | 1995-05-30 | Fujisawa Pharmaceut Co Ltd | アミジノ化合物 |
DE19624155A1 (de) * | 1996-06-18 | 1998-01-08 | Hoechst Ag | Substituierte Benzoesäurederivate, Verfahren zu ihrer Herstellung und die Anwendung der Verbindungen zur Behandlung von Krankheiten |
JP2001510450A (ja) * | 1996-10-23 | 2001-07-31 | ザイモジェネティクス,インコーポレイテッド | 骨欠損状態を処置するための組成物および方法 |
US6458538B1 (en) * | 1999-12-14 | 2002-10-01 | Ptc Therapeutics, Inc. | Methods of assaying for compounds that inhibit premature translation termination and nonsense-mediated RNA decay |
WO2002018321A2 (fr) * | 2000-08-29 | 2002-03-07 | Abbott Laboratories | Inhibiteurs de proteine tyrosine phosphatase d'acide amino(oxo)acetique |
-
2003
- 2003-07-23 EP EP03766013A patent/EP1525185A1/fr not_active Withdrawn
- 2003-07-23 CA CA002493457A patent/CA2493457A1/fr not_active Abandoned
- 2003-07-23 AU AU2003254157A patent/AU2003254157A1/en not_active Abandoned
- 2003-07-23 WO PCT/US2003/023183 patent/WO2004009533A1/fr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2004009533A1 (fr) | 2004-01-29 |
EP1525185A1 (fr) | 2005-04-27 |
AU2003254157A1 (en) | 2004-02-09 |
AU2003254157A8 (en) | 2004-02-09 |
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EP1542667B1 (fr) | Composes d'acide benzoique a substitution ureido et leur utilisation pour la suppression de non-sens et le traitement de maladie | |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |
Effective date: 20130723 |
|
FZDE | Discontinued |
Effective date: 20130723 |