CA2665851A1 - Spiro benzazepines as vasopressin antagonists - Google Patents
Spiro benzazepines as vasopressin antagonists Download PDFInfo
- Publication number
- CA2665851A1 CA2665851A1 CA002665851A CA2665851A CA2665851A1 CA 2665851 A1 CA2665851 A1 CA 2665851A1 CA 002665851 A CA002665851 A CA 002665851A CA 2665851 A CA2665851 A CA 2665851A CA 2665851 A1 CA2665851 A1 CA 2665851A1
- Authority
- CA
- Canada
- Prior art keywords
- benzazepine
- phenyl
- carbonyl
- dihydro
- oxospiro
- 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
- -1 Spiro benzazepines Chemical class 0.000 title claims description 155
- 229940116211 Vasopressin antagonist Drugs 0.000 title description 5
- 239000003038 vasopressin antagonist Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 193
- 238000000034 method Methods 0.000 claims abstract description 51
- 206010019280 Heart failures Diseases 0.000 claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 102000004136 Vasopressin Receptors Human genes 0.000 claims abstract description 17
- 108090000643 Vasopressin Receptors Proteins 0.000 claims abstract description 17
- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 16
- 201000006370 kidney failure Diseases 0.000 claims abstract description 16
- 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 15
- 206010020772 Hypertension Diseases 0.000 claims abstract description 15
- 206010021036 Hyponatraemia Diseases 0.000 claims abstract description 14
- 239000002536 vasopressin receptor antagonist Substances 0.000 claims abstract description 14
- 230000000694 effects Effects 0.000 claims abstract description 13
- 208000006011 Stroke Diseases 0.000 claims abstract description 9
- 206010048962 Brain oedema Diseases 0.000 claims abstract description 8
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 8
- 208000006752 brain edema Diseases 0.000 claims abstract description 8
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 8
- 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 8
- 206010003225 Arteriospasm coronary Diseases 0.000 claims abstract description 7
- 201000006474 Brain Ischemia Diseases 0.000 claims abstract description 7
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 7
- 208000003890 Coronary Vasospasm Diseases 0.000 claims abstract description 7
- 206010016807 Fluid retention Diseases 0.000 claims abstract description 7
- 206010047163 Vasospasm Diseases 0.000 claims abstract description 7
- 206010008118 cerebral infarction Diseases 0.000 claims abstract description 7
- 201000011634 coronary artery vasospasm Diseases 0.000 claims abstract description 7
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 140
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 112
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims description 42
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims description 35
- 229960003726 vasopressin Drugs 0.000 claims description 35
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims description 34
- 108010004977 Vasopressins Proteins 0.000 claims description 34
- 102000002852 Vasopressins Human genes 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000003003 spiro group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 125000004494 ethyl ester group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- FLGYZVSYNLBJDV-UHFFFAOYSA-N 2-spiro[1-benzazepine-4,3'-pyrrolidine]-1'-ylacetic acid Chemical compound C1N(CC(=O)O)CCC21C=C1C=CC=CC1=NC=C2 FLGYZVSYNLBJDV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000016571 aggressive behavior Effects 0.000 claims description 7
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- 208000027601 Inner ear disease Diseases 0.000 claims description 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 230000002792 vascular Effects 0.000 abstract description 3
- 206010008132 Cerebral thrombosis Diseases 0.000 abstract 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 102000005962 receptors Human genes 0.000 description 19
- 108020003175 receptors Proteins 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
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- 150000001412 amines Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- NSNIKRZHVXKHOQ-UHFFFAOYSA-N ethyl 4-[3-(1,3-dioxoisoindol-2-yl)propyl]-1-(4-methylphenyl)sulfonyl-5-oxo-2,3-dihydro-1-benzazepine-4-carboxylate Chemical compound C12=CC=CC=C2C(=O)C(C(=O)OCC)(CCCN2C(C3=CC=CC=C3C2=O)=O)CCN1S(=O)(=O)C1=CC=C(C)C=C1 NSNIKRZHVXKHOQ-UHFFFAOYSA-N 0.000 description 9
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- 229920006395 saturated elastomer Polymers 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 229910052740 iodine Inorganic materials 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
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- 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 description 5
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- GYHCTFXIZSNGJT-UHFFFAOYSA-N tolvaptan Chemical compound CC1=CC=CC=C1C(=O)NC(C=C1C)=CC=C1C(=O)N1C2=CC=C(Cl)C=C2C(O)CCC1 GYHCTFXIZSNGJT-UHFFFAOYSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
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- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
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- Cardiology (AREA)
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- Urology & Nephrology (AREA)
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- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82667106P | 2006-09-22 | 2006-09-22 | |
| US60/826,671 | 2006-09-22 | ||
| PCT/US2007/078926 WO2008036759A1 (en) | 2006-09-22 | 2007-09-19 | Spiro benzazepines as vasopressin antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2665851A1 true CA2665851A1 (en) | 2008-03-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002665851A Abandoned CA2665851A1 (en) | 2006-09-22 | 2007-09-19 | Spiro benzazepines as vasopressin antagonists |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7825111B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2076517A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2010504352A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101541807A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2007299822A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2665851A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008036759A1 (cg-RX-API-DMAC7.html) |
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| CA2462903C (en) * | 2001-10-12 | 2011-09-20 | Serenix Pharmaceuticals, Llc | Beta-lactamyl vasopressin v1a antagonists |
| EP1868434A4 (en) | 2005-03-22 | 2011-10-26 | Azevan Pharmaceuticals Inc | BETA-LACTAMYL ALKANIC ACIDS FOR THE TREATMENT OF PREMIERSTRUELLEN FAULTS |
| AR066834A1 (es) * | 2007-06-06 | 2009-09-16 | Janssen Pharmaceutica Nv | Espirobenzoazepanos como antagonistas de vasopresina, composiciones farmaceuticas que los contienen, proceso de preparacion y usos para el tratamiento de afecciones cardiacas, renales y del sistema nervioso central. |
| CA2804001C (en) | 2010-07-01 | 2021-02-09 | Azevan Pharmaceuticals, Inc. | Methods for treating post traumatic stress disorder |
| JP5968466B2 (ja) | 2012-12-26 | 2016-08-10 | 株式会社三和化学研究所 | 新規ベンゾアゼピン誘導体及びその医薬用途 |
| TW201600522A (zh) * | 2014-02-20 | 2016-01-01 | 赫孚孟拉羅股份公司 | 螺－唑酮 |
| DK3122743T3 (da) | 2014-03-28 | 2023-02-20 | Azevan Pharmaceuticals Inc | Sammensætninger og fremgangsmåder til behandling af neurodegenerative sygdomme |
| ES2951874T3 (es) * | 2017-09-05 | 2023-10-25 | Neumora Therapeutics Inc | Antagonistas del receptor de vasopresina y productos y métodos relacionados con los mismos |
| JP2020534274A (ja) | 2017-09-15 | 2020-11-26 | アゼヴァン ファーマシューティカルズ，インコーポレイテッド | 脳損傷を治療するための組成物及び方法 |
| US20200337590A1 (en) | 2018-01-16 | 2020-10-29 | Bayer Aktiengesellschaft | Assistance in the treatment of cardiac insufficiency |
| CN109608411A (zh) * | 2018-12-17 | 2019-04-12 | 上海合全药物研发有限公司 | 一种叔丁基-1-氧亚基-6-氧杂-9-氮杂螺[4.5]癸烷-9-甲酸基酯的制法 |
| TW202220958A (zh) * | 2020-08-07 | 2022-06-01 | 美商卡司馬療法公司 | Ｔｒｐｍｌ調節劑 |
| CN112939864B (zh) * | 2021-01-29 | 2022-05-06 | 中国医科大学 | 螺[苯并[c]氮杂-1,1’-环己基]-3-酮类化合物 |
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| US4617302A (en) | 1984-10-15 | 1986-10-14 | Eli Lilly And Company | Inotropic agents |
| DE69026708T2 (de) | 1989-10-20 | 1997-04-03 | Otsuka Pharma Co Ltd | Benzoheterozyklische verbindungen |
| US5258510A (en) | 1989-10-20 | 1993-11-02 | Otsuka Pharma Co Ltd | Benzoheterocyclic compounds |
| JP2905909B2 (ja) * | 1991-04-19 | 1999-06-14 | 大塚製薬株式会社 | バソプレシン拮抗剤 |
| US5985869A (en) | 1989-10-20 | 1999-11-16 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| US5663431A (en) | 1992-01-30 | 1997-09-02 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2708605A1 (fr) * | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| US5849780A (en) | 1992-01-30 | 1998-12-15 | Sanofi | 1-benzenesulfonyl-1-1,3-dihydroindol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2686878B1 (fr) * | 1992-01-30 | 1995-06-30 | Sanofi Elf | Derives du n-sulfonyl oxo-2 indole, leur preparation, les compositions pharmaceutiques en contenant. |
| US5686624A (en) | 1992-01-30 | 1997-11-11 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| AU5292393A (en) | 1992-10-07 | 1994-04-26 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
| US5512563A (en) | 1993-07-29 | 1996-04-30 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| US5464788A (en) | 1994-03-24 | 1995-11-07 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
| US5753648A (en) | 1995-01-17 | 1998-05-19 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| AUPP150098A0 (en) | 1998-01-27 | 1998-02-19 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide derivatives |
| AU7178001A (en) * | 2000-07-05 | 2002-01-14 | Ortho Mcneil Pharm Inc | Nonpeptide substituted spirobenzoazepines as vasopressin antagonists |
| WO2002047679A2 (en) * | 2000-12-15 | 2002-06-20 | Emory University | Nonpeptide agonists and antagonists of vasopressin receptors |
| US7011898B2 (en) * | 2003-03-21 | 2006-03-14 | Air Products And Chemicals, Inc. | Method of joining ITM materials using a partially or fully-transient liquid phase |
| CN100467454C (zh) | 2003-06-17 | 2009-03-11 | 詹森药业有限公司 | 取代的螺苯并氮杂 |
| US20040259857A1 (en) | 2003-06-17 | 2004-12-23 | Xiaohu Deng | Process for the preparation of nonpeptide substituted spirobenzoazepine derivatives |
| JP2009523806A (ja) | 2006-01-20 | 2009-06-25 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | （４ｒ）−１−［４−（２−クロロ−５−フルオロベンゾイル）アミノ−３−メトキシベンゾイル］−１，２，３，５−テトラヒドロ−スピロ［４ｈ−１−ベンズアゼピン−４，１’−［２］シクロペンテン］−３’−カルボン酸の新規固体形態物 |
-
2007
- 2007-09-19 JP JP2009529371A patent/JP2010504352A/ja active Pending
- 2007-09-19 CA CA002665851A patent/CA2665851A1/en not_active Abandoned
- 2007-09-19 WO PCT/US2007/078926 patent/WO2008036759A1/en not_active Ceased
- 2007-09-19 US US11/857,954 patent/US7825111B2/en not_active Expired - Fee Related
- 2007-09-19 AU AU2007299822A patent/AU2007299822A1/en not_active Abandoned
- 2007-09-19 EP EP07842807A patent/EP2076517A1/en not_active Withdrawn
- 2007-09-19 CN CNA2007800432304A patent/CN101541807A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7825111B2 (en) | 2010-11-02 |
| CN101541807A (zh) | 2009-09-23 |
| EP2076517A1 (en) | 2009-07-08 |
| AU2007299822A1 (en) | 2008-03-27 |
| WO2008036759A1 (en) | 2008-03-27 |
| US20080076754A1 (en) | 2008-03-27 |
| JP2010504352A (ja) | 2010-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140919 |