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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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
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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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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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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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- 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)
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- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
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- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- 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 |
Family
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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 (enExample) |
| EP (1) | EP2076517A1 (enExample) |
| JP (1) | JP2010504352A (enExample) |
| CN (1) | CN101541807A (enExample) |
| AU (1) | AU2007299822A1 (enExample) |
| CA (1) | CA2665851A1 (enExample) |
| WO (1) | WO2008036759A1 (enExample) |
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| CN1606554B (zh) * | 2001-10-12 | 2013-03-20 | 阿泽范药品公司 | β-内酰胺后叶加压素V1a拮抗剂 |
| AU2006227199A1 (en) | 2005-03-22 | 2006-09-28 | Azevan Pharmaceuticals, Inc. | Beta-lactamylalkanoic acids for treating premenstrual disorders |
| 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. |
| EP2587919B1 (en) | 2010-07-01 | 2017-12-13 | Azevan Pharmaceuticals, Inc. | Methods for treating post traumatic stress disorder |
| KR101983880B1 (ko) * | 2012-12-26 | 2019-05-29 | 가부시키가이샤산와카가쿠켄큐쇼 | 신규 벤조아제핀 유도체 및 그 의약 용도 |
| TW201600522A (zh) * | 2014-02-20 | 2016-01-01 | 赫孚孟拉羅股份公司 | 螺－唑酮 |
| EP3122743B1 (en) | 2014-03-28 | 2022-11-09 | Azevan Pharmaceuticals, Inc. | Compositions and methods for treating neurodegenerative diseases |
| CA3072766A1 (en) * | 2017-09-05 | 2019-03-14 | Blackthorn Therapeutics, Inc. | 2,6-diazaspiro[3.3]hepatan-2-yl derivatives and pharmaceutical compostions thereof useful as vasopressin receptor antagonists |
| IL273228B2 (en) | 2017-09-15 | 2025-04-01 | Azevan Pharmaceuticals Inc | Preparations and methods for treating brain injury |
| 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 |
| WO1991005549A1 (en) * | 1989-10-20 | 1991-05-02 | Otsuka Pharmaceutical Co., Ltd. | Benzoheterocyclic compounds |
| 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 |
| 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 |
| 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 |
| CA2143117A1 (en) | 1992-10-07 | 1994-04-14 | Ben E. Evans | 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 |
| JP4916639B2 (ja) | 2000-07-05 | 2012-04-18 | オーソーマクニール ファーマシューティカル， インコーポレイテッド | バソプレシン拮抗質としての非ペプチド系置換スピロベンゾアゼピン |
| CA2432825A1 (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 |
| DK1633719T3 (da) * | 2003-06-17 | 2010-01-04 | Janssen Pharmaceutica Nv | Substituerede spirobenzazepiner |
| HRP20051005A2 (en) * | 2003-06-17 | 2006-09-30 | Janssen Pharmaceutica N.V. | Process for the preparation of nonpeptide substituted spirobenzoazepine derivatives |
| CA2637838A1 (en) | 2006-01-20 | 2007-07-26 | Janssen Pharmaceutica N.V. | Novel solid forms of (4r)-1-¬4-(2-chloro-5-fluorobenzoyl)amino-3-methoxybenzoyl|-1,2,3,5-tetrahydro-spiro¬4h-1-benzazepine-4,1'-¬2|cyclopentene|-3'-carboxylic acid |
-
2007
- 2007-09-19 EP EP07842807A patent/EP2076517A1/en not_active Withdrawn
- 2007-09-19 CN CNA2007800432304A patent/CN101541807A/zh active Pending
- 2007-09-19 AU AU2007299822A patent/AU2007299822A1/en not_active Abandoned
- 2007-09-19 CA CA002665851A patent/CA2665851A1/en not_active Abandoned
- 2007-09-19 JP JP2009529371A patent/JP2010504352A/ja active Pending
- 2007-09-19 US US11/857,954 patent/US7825111B2/en not_active Expired - Fee Related
- 2007-09-19 WO PCT/US2007/078926 patent/WO2008036759A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US7825111B2 (en) | 2010-11-02 |
| WO2008036759A1 (en) | 2008-03-27 |
| US20080076754A1 (en) | 2008-03-27 |
| CN101541807A (zh) | 2009-09-23 |
| JP2010504352A (ja) | 2010-02-12 |
| EP2076517A1 (en) | 2009-07-08 |
| AU2007299822A1 (en) | 2008-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140919 |