JPS6049192B2 - 新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬 - Google Patents
新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬Info
- Publication number
- JPS6049192B2 JPS6049192B2 JP54005483A JP548379A JPS6049192B2 JP S6049192 B2 JPS6049192 B2 JP S6049192B2 JP 54005483 A JP54005483 A JP 54005483A JP 548379 A JP548379 A JP 548379A JP S6049192 B2 JPS6049192 B2 JP S6049192B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- formula
- pyrrolidinylmethyl
- methoxy
- ethylsulfonylbenzamide
- 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
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229940001470 psychoactive drug Drugs 0.000 title claims description 5
- 239000004089 psychotropic agent Substances 0.000 title claims description 5
- 239000004480 active ingredient Substances 0.000 title claims description 4
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 31
- -1 heterocyclic amine Chemical class 0.000 claims description 27
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 19
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- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 11
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- 239000003420 antiserotonin agent Substances 0.000 claims description 8
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- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229940095064 tartrate Drugs 0.000 claims description 6
- BAXPWPBNRAGVGF-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxy-n-[(1-methylpyrrolidin-2-yl)methyl]benzamide Chemical compound C1=C(N)C(S(=O)(=O)CC)=CC(C(=O)NCC2N(CCC2)C)=C1OC BAXPWPBNRAGVGF-UHFFFAOYSA-N 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003814 drug Chemical class 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- QEVBNUFEGDVWRM-UHFFFAOYSA-N 4-amino-2-methoxy-5-methylsulfonylbenzamide Chemical compound COC1=C(C(=O)N)C=C(C(=C1)N)S(=O)(=O)C QEVBNUFEGDVWRM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003354 anti-apomorphinic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- LCUIMXDQQZOHJR-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxybenzamide Chemical compound CCS(=O)(=O)C1=CC(C(N)=O)=C(OC)C=C1N LCUIMXDQQZOHJR-UHFFFAOYSA-N 0.000 claims 2
- 230000001568 sexual effect Effects 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 206010027599 migraine Diseases 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
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- 230000002829 reductive effect Effects 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- 241000700198 Cavia Species 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 208000007107 Stomach Ulcer Diseases 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
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- 238000001953 recrystallisation Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
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- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 description 3
- JEZWENIMQLYTHI-UHFFFAOYSA-N 4-amino-2-methoxy-5-methylbenzenecarbothioic s-acid Chemical compound COC1=CC(N)=C(C)C=C1C(O)=S JEZWENIMQLYTHI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
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- 230000001225 therapeutic effect Effects 0.000 description 3
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- QOWLKTWQYURQLI-UHFFFAOYSA-N 4-amino-2-methoxy-5-sulfanylbenzoic acid Chemical compound COC1=CC(N)=C(S)C=C1C(O)=O QOWLKTWQYURQLI-UHFFFAOYSA-N 0.000 description 2
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- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 229940126214 compound 3 Drugs 0.000 description 1
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- 229960002069 diamorphine Drugs 0.000 description 1
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- 229940040102 levulinic acid Drugs 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006902 nitrogenation reaction Methods 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003368 psychostimulant agent Substances 0.000 description 1
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- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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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
- C07D207/04—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
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
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)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7801632 | 1978-01-20 | ||
| FR7801632A FR2415099A1 (fr) | 1978-01-20 | 1978-01-20 | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54145658A JPS54145658A (en) | 1979-11-14 |
| JPS6049192B2 true JPS6049192B2 (ja) | 1985-10-31 |
Family
ID=9203689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54005483A Expired JPS6049192B2 (ja) | 1978-01-20 | 1979-01-19 | 新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬 |
Country Status (42)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| NZ199080A (en) * | 1980-12-12 | 1984-07-31 | Beecham Group Ltd | 2-alkoxy-4-amino-5-alkylsulphonyl-n-(3beta-(8-hydrocarbyl-8-azabicyclo (3,2,1)octyl))benzamides |
| FR2550447B1 (fr) * | 1983-08-10 | 1986-01-17 | Ile De France | Application du n-(ally-2-pyrrolidinylmethyl) 2-methoxy 4-amino 5-methylsulfamoyl benzamide comme antiagregant plaquettaire |
| FR2574795B1 (fr) * | 1984-12-18 | 1987-11-20 | Ile De France | Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide |
| FR2584401B1 (fr) * | 1985-07-04 | 1987-11-20 | Ile De France | Nouveau benzamide, son procede de preparation et son application dans le domaine therapeutique |
| US5227388A (en) * | 1989-12-26 | 1993-07-13 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| US5260319A (en) * | 1989-12-26 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| FR2678266A1 (fr) * | 1991-06-28 | 1992-12-31 | Delagrange Laboratoires | Nouveaux derives de 2-hydroxy 4-amino 5-ethylsulfonyl benzamide utiles comme anxiolytiques. |
| FR2699533A1 (fr) * | 1992-12-21 | 1994-06-24 | Mouhtaram Mohamed | Dérivés de N-((1,4-dialkyl-6-arylpipérazine-2-yl)méthyl)benzamides. (Isomères cis et trans) Propriétés pharmacologiques et applications. |
| FR2753376B1 (fr) * | 1996-09-18 | 1998-10-16 | Synthelabo | Compositions pharmaceutiques comprenant de l'amisulpride et leurs applications therapeutiques |
| FR2762213B1 (fr) * | 1997-04-18 | 1999-05-14 | Synthelabo | Composition pharmaceutique a retention gastrique |
| US6169094B1 (en) * | 1998-07-14 | 2001-01-02 | Sanofi-Synthelabo | Compositions of (S) (-)-amisulpride |
| DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| CN1791430A (zh) * | 2003-05-16 | 2006-06-21 | 辉瑞产品公司 | 非典型抗精神病药物和gaba调节剂、抗惊厥药物或苯并二氮杂䓬类的治疗性组合 |
| FR2857263B1 (fr) * | 2003-07-09 | 2005-09-09 | Sanofi Synthelabo | Nouvelle composition pharmaceutique solide comprenant de l'amisulpride |
| CA2565996A1 (en) * | 2004-05-11 | 2005-11-17 | Pfizer Products Inc. | Combination of atypical antipsychotics and 5-ht1b receptor antagonists |
| CN101198323A (zh) * | 2005-04-22 | 2008-06-11 | 惠氏公司 | 用于治疗或预防精神障碍的治疗组合 |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| US7825156B2 (en) * | 2007-02-02 | 2010-11-02 | Copharms | Method of treating bipolar depression with a benzamide derivative |
| JP2011526881A (ja) * | 2008-06-25 | 2011-10-20 | ファイザー・インク | ジアリール化合物およびそれらの使用 |
| US20100105755A1 (en) * | 2008-09-12 | 2010-04-29 | Auspex Pharmaceuticals, Inc. | Substituted benzamide modulators of dopamine receptor |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
| CN101898991B (zh) * | 2009-05-31 | 2013-09-25 | 江苏天士力帝益药业有限公司 | 一种(s)(-)-氨磺必利d-(-)-酒石酸盐的合成方法 |
| CN101628886B (zh) * | 2009-08-25 | 2012-12-12 | 北京紫萌同达科技有限公司 | 一种2-甲氧基-4-氨基-5-乙砜基苯甲酸的合成方法 |
| AU2016216578B2 (en) * | 2010-03-11 | 2017-11-23 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
| AU2014202535B2 (en) * | 2010-03-11 | 2016-05-26 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
| GB201004020D0 (en) | 2010-03-11 | 2010-04-21 | Acacia Pharma Ltd | New therapeutic use |
| BR112012031959A2 (pt) | 2010-06-17 | 2015-09-22 | Lupin Ltd | um processo aperfeiçoado para preparação de amisulpride |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| CN103319384A (zh) * | 2013-06-18 | 2013-09-25 | 苏州诚和医药化学有限公司 | 制备2-甲氧基-4-氨基-5-乙砜基苯甲酸的方法 |
| CN103304453A (zh) * | 2013-06-18 | 2013-09-18 | 苏州诚和医药化学有限公司 | 两步法合成2-甲氧基-4-氨基-5-乙砜基苯甲酸 |
| CN103450058B (zh) * | 2013-09-18 | 2015-10-14 | 广安凯特医药化工有限公司 | 一种氨磺必利酸的制备方法 |
| CN104725292B (zh) * | 2015-03-23 | 2017-07-25 | 湖北荆江源制药股份有限公司 | 一种(s)(‑)‑氨磺必利的制备方法 |
| GB201618425D0 (en) * | 2016-11-01 | 2016-12-14 | Acacia Pharma Ltd | method |
| US11377421B2 (en) | 2016-11-28 | 2022-07-05 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
| MA46901A (fr) | 2016-11-28 | 2019-10-02 | Lb Pharmaceuticals Inc | Agents psychotropes et leurs utilisations |
| CN106995397B (zh) * | 2016-12-12 | 2020-01-14 | 河北医科大学 | R-氨磺必利药用盐、制备方法、晶型及其用途 |
| GB201702250D0 (en) | 2017-02-10 | 2017-03-29 | Acacia Pharma Ltd | Method |
| CA3088356A1 (en) | 2017-12-05 | 2019-06-13 | Sunovion Pharmaceuticals Inc. | Crystal forms and production methods thereof |
| CN118593482A (zh) | 2017-12-05 | 2024-09-06 | 赛诺维信制药公司 | 非外消旋混合物及其用途 |
| CN110790693A (zh) * | 2018-08-02 | 2020-02-14 | 北京万全德众医药生物技术有限公司 | 一种(s)(-)-氨磺必利的制备方法 |
| JP2022535893A (ja) | 2019-06-04 | 2022-08-10 | サノビオン ファーマシューティカルズ インク | 放出調節製剤およびその使用 |
| USD1047552S1 (en) * | 2021-04-23 | 2024-10-22 | Krueger International, Inc. | Furniture leg with frame |
| CN116003304A (zh) * | 2023-02-08 | 2023-04-25 | 浙江皓华制药有限公司 | 一种氨磺必利的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| FR2313935A1 (fr) * | 1975-06-10 | 1977-01-07 | Ile De France | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
| FR2244760B1 (OSRAM) * | 1973-09-25 | 1980-06-27 | Ile De France | |
| FR2299862B1 (en) * | 1975-02-07 | 1978-07-21 | Soc Et Scient Et Ind | Substd. N-(1-benzylpyrrolidinyl-2-alkyl)benzamides - used as antiemetics, anti-ulcer agents and CNS active |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
| IE42210B1 (en) * | 1974-12-18 | 1980-06-18 | Synthelabo | 2-methoxy-benzamide derivatives |
-
1978
- 1978-01-20 FR FR7801632A patent/FR2415099A1/fr active Granted
- 1978-12-07 BE BE1009179A patent/BE872585A/xx not_active IP Right Cessation
-
1979
- 1979-01-10 BG BG042018A patent/BG31496A3/xx unknown
- 1979-01-10 AR AR275115A patent/AR221354A1/es active
- 1979-01-10 BG BG043588A patent/BG31497A3/xx unknown
- 1979-01-11 YU YU50/79A patent/YU42172B/xx unknown
- 1979-01-11 IL IL56411A patent/IL56411A/xx unknown
- 1979-01-11 ES ES476755A patent/ES476755A1/es not_active Expired
- 1979-01-11 IN IN21/CAL/79A patent/IN150226B/en unknown
- 1979-01-12 PT PT69068A patent/PT69068A/pt unknown
- 1979-01-13 DE DE2901181A patent/DE2901181C2/de not_active Expired
- 1979-01-15 AU AU43373/79A patent/AU528561B2/en not_active Expired
- 1979-01-15 CH CH37379A patent/CH637927A5/fr active Protection Beyond IP Right Term
- 1979-01-15 GR GR58090A patent/GR64431B/el unknown
- 1979-01-15 NZ NZ189378A patent/NZ189378A/xx unknown
- 1979-01-15 LU LU80786A patent/LU80786A1/xx unknown
- 1979-01-16 RO RO7996297A patent/RO76393A/ro unknown
- 1979-01-16 SE SE7900380A patent/SE448874B/sv not_active IP Right Cessation
- 1979-01-16 RO RO79103170A patent/RO80311A/ro unknown
- 1979-01-16 MC MC791357A patent/MC1232A1/xx unknown
- 1979-01-17 EG EG29/79A patent/EG14045A/xx active
- 1979-01-17 CY CY1201A patent/CY1201A/en unknown
- 1979-01-17 GB GB8118999A patent/GB2083458B/en not_active Expired
- 1979-01-17 GB GB791690A patent/GB2012765B/en not_active Expired
- 1979-01-18 ZM ZM5/79A patent/ZM579A1/xx unknown
- 1979-01-18 DK DK020979A patent/DK158346C/da not_active IP Right Cessation
- 1979-01-18 US US06/004,397 patent/US4294828A/en not_active Expired - Lifetime
- 1979-01-18 IT IT47706/79A patent/IT1164655B/it active Protection Beyond IP Right Term
- 1979-01-18 NO NO790180A patent/NO151320C/no unknown
- 1979-01-19 CS CS79443A patent/CS226181B2/cs unknown
- 1979-01-19 PL PL1979224894A patent/PL118151B1/pl unknown
- 1979-01-19 MX MX797669U patent/MX5793E/es unknown
- 1979-01-19 MX MX7911208U patent/MX7623E/es unknown
- 1979-01-19 CA CA319,969A patent/CA1101430A/en not_active Expired
- 1979-01-19 SU SU792714652A patent/SU820659A3/ru active
- 1979-01-19 AT AT0039879A patent/AT377977B/de not_active IP Right Cessation
- 1979-01-19 PL PL1979212899A patent/PL116532B1/pl unknown
- 1979-01-19 FI FI790182A patent/FI71126C/fi not_active IP Right Cessation
- 1979-01-19 OA OA56717A patent/OA06156A/xx unknown
- 1979-01-19 NL NL7900457A patent/NL191707C/xx not_active IP Right Cessation
- 1979-01-19 HU HU79SO1241A patent/HU179793B/hu unknown
- 1979-01-19 JP JP54005483A patent/JPS6049192B2/ja not_active Expired
- 1979-01-19 ZA ZA79219A patent/ZA79219B/xx unknown
- 1979-01-22 DD DD79210583A patent/DD141520A5/de unknown
- 1979-01-30 IE IE92/79A patent/IE47798B1/en active Protection Beyond IP Right Term
- 1979-02-16 ES ES477782A patent/ES477782A1/es not_active Expired
- 1979-08-16 AR AR277738A patent/AR220574A1/es active
- 1979-11-06 PH PH23252A patent/PH15725A/en unknown
-
1980
- 1980-08-20 PH PH24465A patent/PH22287A/en unknown
-
1981
- 1981-10-09 US US06/310,336 patent/US4401822A/en not_active Expired - Lifetime
-
1983
- 1983-02-04 YU YU254/83A patent/YU41278B/xx unknown
-
1984
- 1984-02-16 HK HK121/84A patent/HK12184A/xx not_active IP Right Cessation
-
1986
- 1986-09-09 SE SE8603773A patent/SE460968B/sv not_active IP Right Cessation
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