HRP20110626T1 - Derivati benzotiazepina i njihova uporaba kao modulatora ampa i nmda receptora - Google Patents
Derivati benzotiazepina i njihova uporaba kao modulatora ampa i nmda receptora Download PDFInfo
- Publication number
- HRP20110626T1 HRP20110626T1 HR20110626T HRP20110626T HRP20110626T1 HR P20110626 T1 HRP20110626 T1 HR P20110626T1 HR 20110626 T HR20110626 T HR 20110626T HR P20110626 T HRP20110626 T HR P20110626T HR P20110626 T1 HRP20110626 T1 HR P20110626T1
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- Prior art keywords
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- compound
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- 102000003678 AMPA Receptors Human genes 0.000 title claims 2
- 108090000078 AMPA Receptors Proteins 0.000 title claims 2
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 title 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 title 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 title 1
- 150000007657 benzothiazepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 17
- 125000005843 halogen group Chemical group 0.000 claims abstract 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000003277 amino group Chemical group 0.000 claims abstract 5
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- -1 N-methylaminocarbonyl group Chemical group 0.000 claims 5
- 230000029936 alkylation Effects 0.000 claims 5
- 238000005804 alkylation reaction Methods 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 229940100198 alkylating agent Drugs 0.000 claims 4
- 239000002168 alkylating agent Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 2
- 239000004327 boric acid Substances 0.000 claims 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- BZMMRNKDONDVIB-UHFFFAOYSA-N (1-ethoxycyclopropyl)oxy-trimethylsilane Chemical compound CCOC1(O[Si](C)(C)C)CC1 BZMMRNKDONDVIB-UHFFFAOYSA-N 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims 1
- RTBXJPBWBIMMQZ-UHFFFAOYSA-N 3-[(1,1-dioxo-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepin-8-yl)oxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(OC=2C=C3S(=O)(=O)NCCNC3=CC=2)=C1 RTBXJPBWBIMMQZ-UHFFFAOYSA-N 0.000 claims 1
- DQGDFFMFRHJVHJ-UHFFFAOYSA-N 3-[(1,1-dioxo-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepin-8-yl)oxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=C3S(=O)(=O)NCCNC3=CC=2)=C1 DQGDFFMFRHJVHJ-UHFFFAOYSA-N 0.000 claims 1
- ONLLJIGRRWECRE-UHFFFAOYSA-N 4-[(1,1-dioxo-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepin-8-yl)oxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(NCCNS2(=O)=O)C2=C1 ONLLJIGRRWECRE-UHFFFAOYSA-N 0.000 claims 1
- JKOKNPWVNITDHQ-UHFFFAOYSA-N 4-[(1,1-dioxo-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepin-8-yl)oxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(NCCNS2(=O)=O)C2=C1 JKOKNPWVNITDHQ-UHFFFAOYSA-N 0.000 claims 1
- WNYVYGICYQDPFZ-UHFFFAOYSA-N 4-[(5-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,5-benzothiadiazepin-8-yl)oxy]phenol Chemical compound C=1C=C2N(C)CCNS(=O)(=O)C2=CC=1OC1=CC=C(O)C=C1 WNYVYGICYQDPFZ-UHFFFAOYSA-N 0.000 claims 1
- WMTZBQNPKULSHB-UHFFFAOYSA-N 8-phenoxy-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepine 1,1-dioxide Chemical compound C1=C2S(=O)(=O)NCCNC2=CC=C1OC1=CC=CC=C1 WMTZBQNPKULSHB-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000006264 Korsakoff syndrome Diseases 0.000 claims 1
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- NGXPOGBRTZWTBL-UHFFFAOYSA-N [3-[(1,1-dioxo-2,3,4,5-tetrahydro-1$l^{6},2,5-benzothiadiazepin-8-yl)oxy]phenyl]methanol Chemical compound OCC1=CC=CC(OC=2C=C3S(=O)(=O)NCCNC3=CC=2)=C1 NGXPOGBRTZWTBL-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 230000003001 depressive effect Effects 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 210000001652 frontal lobe Anatomy 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- KDGKTJGPFXIBEB-UHFFFAOYSA-N n-hydroxyformamide Chemical group ONC=O KDGKTJGPFXIBEB-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- 230000002739 subcortical effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0901300A FR2943342B1 (fr) | 2009-03-20 | 2009-03-20 | Nouveaux derives de benzothiadiazepines,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110626T1 true HRP20110626T1 (hr) | 2011-10-31 |
Family
ID=40863576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110626T HRP20110626T1 (hr) | 2009-03-20 | 2011-08-31 | Derivati benzotiazepina i njihova uporaba kao modulatora ampa i nmda receptora |
Country Status (44)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2642586T3 (es) * | 2009-07-27 | 2017-11-16 | Gilead Sciences, Inc. | Compuestos heterocíclicos condensados como moduladores de canales iónicos |
| EP2588197B1 (en) | 2010-07-02 | 2014-11-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| US9150591B2 (en) | 2010-08-10 | 2015-10-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| ES2687027T3 (es) | 2010-11-04 | 2018-10-23 | Albireo Ab | Inhibidores de ibat para el tratamiento de enfermedades hepáticas |
| KR20140033377A (ko) | 2011-05-10 | 2014-03-18 | 길리애드 사이언시즈, 인코포레이티드 | 나트륨 채널 조절제로서의 융합된 헤테로시클릭 화합물 |
| UY34171A (es) | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
| AU2015224425B2 (en) * | 2011-07-01 | 2017-02-09 | Gilead Sciences, Inc. | Fused benzoxazepinones as ion channel modulators |
| NO3175985T3 (sr) | 2011-07-01 | 2018-04-28 | ||
| WO2013118845A1 (ja) | 2012-02-08 | 2013-08-15 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| CN118852054A (zh) | 2019-02-06 | 2024-10-29 | 阿尔比里奥公司 | 苯并硫杂二氮杂环庚三烯化合物及其用作胆汁酸调节剂的用途 |
| CR20220160A (es) | 2019-09-16 | 2022-06-16 | Takeda Pharmaceuticals Co | Derivados de piridazin-3(2h)-ona fusionados con azol |
| IL293379B2 (en) | 2019-12-04 | 2026-04-01 | Albireo Ab | Benzothia(dia)azepine compounds and their use as bile acid modulators |
| CN111620838A (zh) * | 2020-05-16 | 2020-09-04 | 西安都创医药科技有限公司 | 一种氯代苯并硫氮杂卓化合物的制备方法及其制备的产品及其应用 |
| CN111548325A (zh) * | 2020-05-16 | 2020-08-18 | 西安都创医药科技有限公司 | 一种卤代苯并硫氮杂卓化合物的制备方法及其制备的产品及其应用 |
| CN111518055A (zh) * | 2020-05-16 | 2020-08-11 | 西安都创医药科技有限公司 | 一种苯并硫氮杂卓氧化物的制备方法及其制备的产品及其应用 |
| CN111574475B (zh) * | 2020-06-03 | 2022-09-20 | 西安都创医药科技有限公司 | 卤代苯并硫杂卓氧化物的制备方法及其制备的产品及其应用 |
| CA3196488A1 (en) | 2020-11-12 | 2022-05-19 | Albireo Ab | Odevixibat for treating progressive familial intrahepatic cholestasis (pfic) |
| BR112023010799A2 (pt) | 2020-12-04 | 2023-10-03 | Albireo Ab | Compostos de benzotia(di)azepina e seus usos como moduladores de ácidos biliares |
| CN115368363B (zh) * | 2021-05-17 | 2024-02-20 | 中山大学 | 一种手性或消旋的嘧啶并二氮杂环庚酮类化合物及其制备方法和应用 |
| TW202313579A (zh) | 2021-06-03 | 2023-04-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
| WO2024240249A1 (zh) * | 2023-05-25 | 2024-11-28 | 正大天晴药业集团股份有限公司 | 一种苯并噻二氮卓化合物及其用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0636124A1 (fr) * | 1992-04-15 | 1995-02-01 | Aventis Pharma S.A. | Derives d'acide 3,4-dihydro-2h-1,2,4-benzothiadiazine 1,1-dioxyde-3-carboxylique, leur preparation et les medicaments les contenant |
| WO1999041246A1 (en) * | 1998-02-11 | 1999-08-19 | Du Pont Pharmaceuticals Company | Novel cyclic sulfonamide derivatives as metalloproteinase inhibitors |
| CN1293665A (zh) | 1998-02-18 | 2001-05-02 | 神经研究公司 | 新化合物及其用作阳性ampa受体调节剂 |
| US6156746A (en) * | 1998-08-25 | 2000-12-05 | Bristol-Myers Squibb Company | 1,2,5-benzothiadiazepine-1,1-dioxides with n-2 imidazolylalkyl substituents |
| GB0209467D0 (en) * | 2002-04-25 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| DE10300973A1 (de) * | 2003-01-14 | 2004-07-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Carbonsäuren und deren Ester, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| FR2877338B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2879201B1 (fr) * | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2009
- 2009-03-20 FR FR0901300A patent/FR2943342B1/fr not_active Expired - Fee Related
-
2010
- 2010-03-02 JO JO201077A patent/JO2780B1/en active
- 2010-03-03 AU AU2010200815A patent/AU2010200815B2/en not_active Ceased
- 2010-03-04 UY UY0001032475A patent/UY32475A/es unknown
- 2010-03-11 TW TW099107121A patent/TWI388326B/zh not_active IP Right Cessation
- 2010-03-17 SA SA110310217A patent/SA110310217B1/ar unknown
- 2010-03-17 CA CA2696705A patent/CA2696705C/fr not_active Expired - Fee Related
- 2010-03-17 ZA ZA2010/01905A patent/ZA201001905B/en unknown
- 2010-03-18 PT PT10290141T patent/PT2246339E/pt unknown
- 2010-03-18 NZ NZ595082A patent/NZ595082A/en not_active IP Right Cessation
- 2010-03-18 PL PL10290141T patent/PL2246339T3/pl unknown
- 2010-03-18 KR KR1020117024772A patent/KR101431504B1/ko not_active Expired - Fee Related
- 2010-03-18 SI SI201030006T patent/SI2246339T1/sl unknown
- 2010-03-18 RS RS20110385A patent/RS51919B/sr unknown
- 2010-03-18 EA EA201101334A patent/EA020259B1/ru not_active IP Right Cessation
- 2010-03-18 MY MYPI2011004188A patent/MY154001A/en unknown
- 2010-03-18 PE PE2011001589A patent/PE20120113A1/es not_active Application Discontinuation
- 2010-03-18 MX MX2011009638A patent/MX2011009638A/es active IP Right Grant
- 2010-03-18 MA MA34178A patent/MA33131B1/fr unknown
- 2010-03-18 DK DK10290141.0T patent/DK2246339T3/da active
- 2010-03-18 GE GEAP201012414A patent/GEP20135862B/en unknown
- 2010-03-18 CN CN201080012931.3A patent/CN102361860B/zh not_active Expired - Fee Related
- 2010-03-18 JP JP2012500288A patent/JP5437473B2/ja not_active Expired - Fee Related
- 2010-03-18 EP EP10290141A patent/EP2246339B1/fr active Active
- 2010-03-18 ES ES10290141T patent/ES2368691T3/es active Active
- 2010-03-18 WO PCT/FR2010/000227 patent/WO2010106249A1/fr not_active Ceased
- 2010-03-18 SG SG2011064367A patent/SG174274A1/en unknown
- 2010-03-18 BR BRPI1009200A patent/BRPI1009200A2/pt not_active IP Right Cessation
- 2010-03-18 AT AT10290141T patent/ATE513822T1/de active
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