JP2007517857A - 治療に有用な化合物 - Google Patents
治療に有用な化合物 Download PDFInfo
- Publication number
- JP2007517857A JP2007517857A JP2006548476A JP2006548476A JP2007517857A JP 2007517857 A JP2007517857 A JP 2007517857A JP 2006548476 A JP2006548476 A JP 2006548476A JP 2006548476 A JP2006548476 A JP 2006548476A JP 2007517857 A JP2007517857 A JP 2007517857A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- dihydro
- chloro
- benzo
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 167
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 39
- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 201000009273 Endometriosis Diseases 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 8
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- 208000001362 Fetal Growth Retardation Diseases 0.000 claims abstract description 8
- 206010070531 Foetal growth restriction Diseases 0.000 claims abstract description 8
- 206010019280 Heart failures Diseases 0.000 claims abstract description 8
- 206010020772 Hypertension Diseases 0.000 claims abstract description 8
- 206010061218 Inflammation Diseases 0.000 claims abstract description 8
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- 208000005107 Premature Birth Diseases 0.000 claims abstract description 8
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- 208000012322 Raynaud phenomenon Diseases 0.000 claims abstract description 8
- 206010047700 Vomiting Diseases 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
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- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
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- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 4
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- OCIOIOFHZYPZMC-UHFFFAOYSA-N 1-[4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]butan-1-one Chemical compound C1CN(C(=O)CCC)CCC1C1=NN=C2N1C1=CC=C(Cl)C=C1CN(C)C2 OCIOIOFHZYPZMC-UHFFFAOYSA-N 0.000 claims description 3
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- NBNGJKUNWJBONP-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(3-fluorophenyl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1=CC=CC(F)=C1 NBNGJKUNWJBONP-UHFFFAOYSA-N 0.000 claims description 3
- KGIPOTCNKIWDSY-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2CCC(CC2)C=2N3C4=CC=C(Cl)C=C4CN(C)CC3=NN=2)=C1 KGIPOTCNKIWDSY-UHFFFAOYSA-N 0.000 claims description 3
- IQCZYHLCFHWYEP-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1=CC=C(F)C=C1 IQCZYHLCFHWYEP-UHFFFAOYSA-N 0.000 claims description 3
- KGKBDXALAUYHBL-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-cyclopropylmethanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1CC1 KGKBDXALAUYHBL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002840 nitric oxide donor Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- DAZVNXGSTMSXNP-UHFFFAOYSA-N 1-[4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-2-(2-methylphenyl)ethanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)CC1=CC=CC=C1C DAZVNXGSTMSXNP-UHFFFAOYSA-N 0.000 claims description 2
- GWELJOVUHDEZOG-UHFFFAOYSA-N 1-[4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-2-cyclopropylethanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)CC1CC1 GWELJOVUHDEZOG-UHFFFAOYSA-N 0.000 claims description 2
- DMEKQAADBPOJEO-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1-methylcyclohexyl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1(C)CCCCC1 DMEKQAADBPOJEO-UHFFFAOYSA-N 0.000 claims description 2
- LUNAHEGNSDARJA-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1h-indol-2-yl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 LUNAHEGNSDARJA-UHFFFAOYSA-N 0.000 claims description 2
- HMOVLAJSVILELK-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1h-indol-3-yl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C1CCN(C(=O)C=2C3=CC=CC=C3NC=2)CC1 HMOVLAJSVILELK-UHFFFAOYSA-N 0.000 claims description 2
- QZGGATRCENWZPA-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(1h-indol-6-yl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C1CCN(C(=O)C=2C=C3NC=CC3=CC=2)CC1 QZGGATRCENWZPA-UHFFFAOYSA-N 0.000 claims description 2
- LEGRMMSSDMQWQP-UHFFFAOYSA-N [4-(8-chloro-5-methyl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)piperidin-1-yl]-(2-hydroxy-5-methylphenyl)methanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C)CC2=NN=C1C(CC1)CCN1C(=O)C1=CC(C)=CC=C1O LEGRMMSSDMQWQP-UHFFFAOYSA-N 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- -1 methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy Chemical group 0.000 description 32
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- 235000002906 tartaric acid Nutrition 0.000 description 1
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- LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 description 1
- JLIKTOWFNQDEME-UHFFFAOYSA-N tert-butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(=O)NN)CC1 JLIKTOWFNQDEME-UHFFFAOYSA-N 0.000 description 1
- AEZFANXHWGQBKU-UHFFFAOYSA-N tert-butyl 4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NN=C(CCl)O1 AEZFANXHWGQBKU-UHFFFAOYSA-N 0.000 description 1
- YGNDVJKXCYLPEG-UHFFFAOYSA-N tert-butyl 4-[5-[(2-amino-5-chlorophenyl)methoxymethyl]-1,3,4-oxadiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(O1)=NN=C1COCC1=CC(Cl)=CC=C1N YGNDVJKXCYLPEG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 description 1
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- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 229940074410 trehalose Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ICJGKYTXBRDUMV-UHFFFAOYSA-N trichloro(6-trichlorosilylhexyl)silane Chemical compound Cl[Si](Cl)(Cl)CCCCCC[Si](Cl)(Cl)Cl ICJGKYTXBRDUMV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 239000003871 white petrolatum Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 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
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- 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
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- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0400700.1A GB0400700D0 (en) | 2004-01-13 | 2004-01-13 | Compounds useful in therapy |
| US54486604P | 2004-02-13 | 2004-02-13 | |
| PCT/IB2005/000263 WO2005068466A1 (en) | 2004-01-13 | 2005-01-05 | Compounds useful in therapy |
Publications (2)
| Publication Number | Publication Date |
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| JP2007517857A true JP2007517857A (ja) | 2007-07-05 |
| JP2007517857A5 JP2007517857A5 (enExample) | 2008-02-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006548476A Withdrawn JP2007517857A (ja) | 2004-01-13 | 2005-01-05 | 治療に有用な化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20070167430A1 (enExample) |
| EP (1) | EP1706409A1 (enExample) |
| JP (1) | JP2007517857A (enExample) |
| BR (1) | BRPI0506848A (enExample) |
| CA (1) | CA2554382A1 (enExample) |
| GB (1) | GB0400700D0 (enExample) |
| WO (1) | WO2005068466A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013523853A (ja) * | 2010-04-13 | 2013-06-17 | エフ.ホフマン−ラ ロシュ アーゲー | バソプレシンアンタゴニストとしてのアリール−/ヘテロアリール−シクロヘキセニル−テトラアザベンゾ[e]アズレン |
| JP2013523675A (ja) * | 2010-03-31 | 2013-06-17 | エフ.ホフマン−ラ ロシュ アーゲー | アリール−シクロヘキシル−テトラアザベンゾ[e]アズレン |
| JP2013525396A (ja) * | 2010-04-26 | 2013-06-20 | エフ.ホフマン−ラ ロシュ アーゲー | ヘテロビアリール−シクロヘキシル−テトラアザベンゾ[e]アズレン |
| JP2014527993A (ja) * | 2011-09-26 | 2014-10-23 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | V1aアンタゴニストとしてのオキシ−シクロヘキシル−4H,6H−5−オキサ−2,3,10b−トリアザ−ベンゾ[e]アズレン類 |
| JP2014531462A (ja) * | 2011-10-05 | 2014-11-27 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | V1aアンタゴニストとしてのシクロヘキシル−4H,6H−5−オキサ−2,3,10b−トリアザ−ベンゾ[e]アズレン |
| JP2016539168A (ja) * | 2013-12-05 | 2016-12-15 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | trans−8−クロロ−5−メチル−1−[4−(ピリジン−2−イルオキシ)−シクロヘキシル]−5,6−ジヒドロ−4H−2,3,5,10b−テトラアザ−ベンゾ[e]アズレン及びその結晶形態の合成 |
| KR20200100111A (ko) * | 2017-12-15 | 2020-08-25 | 리히터 게데온 닐트. | 바소프레신 v1a 수용체 길항제로서 트리아졸로벤즈아제핀 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2616937A1 (en) | 2005-07-29 | 2007-02-08 | F. Hoffman-La Roche Ag | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
| JP5313875B2 (ja) | 2006-04-12 | 2013-10-09 | バーテックス ファーマシューティカルズ インコーポレイテッド | 増殖性疾患の処置のためのタンパク質キナーゼplk1の阻害剤として有用な4,5−ジヒドロ−[1,2,4]トリアゾロ[4,3−f]プテリジン |
| EP2102207B1 (en) * | 2006-12-07 | 2010-06-02 | F.Hoffmann-La Roche Ag | Spiro-piperidine derivatives as via receptor antagonists |
| ES2351949T3 (es) * | 2006-12-29 | 2011-02-14 | F. Hoffmann-La Roche Ag | Derivados de azaspiro. |
| EP2356123B1 (en) | 2008-11-13 | 2012-10-03 | F.Hoffmann-La Roche Ag | Spiro-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulenes |
| JP5384659B2 (ja) | 2008-11-18 | 2014-01-08 | エフ.ホフマン−ラ ロシュ アーゲー | ジヒドロテトラアザベンゾアズレンのアルキルシクロヘキシルエーテル |
| AU2013202813B2 (en) * | 2008-11-28 | 2014-10-23 | F. Hoffmann-La Roche Ag | Arylcyclohexylethers of dihydrotetraazabenzoazulenes for use as vasopressin via receptor antagonists |
| RU2507205C2 (ru) * | 2008-11-28 | 2014-02-20 | Ф. Хоффманн-Ля Рош Аг | Арилциклогексилэфиры дигидротетраазабензоазуленов для применения в качестве антагонистов рецептора вазопрессина v1a |
| NZ599356A (en) | 2009-09-25 | 2013-08-30 | Vertex Pharma | Methods for preparing pyrimidine derivatives useful as protein kinase inhibitors |
| KR20120096474A (ko) | 2009-09-25 | 2012-08-30 | 버텍스 파마슈티칼스 인코포레이티드 | 단백질 키나제 억제제로서 유용한 피리미딘 유도체의 제조 방법 |
| US8492376B2 (en) * | 2010-04-21 | 2013-07-23 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8513238B2 (en) * | 2010-05-10 | 2013-08-20 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[E]azulenes |
| JOP20190245A1 (ar) | 2017-04-20 | 2019-10-15 | Novartis Ag | أنظمة توصيل إطلاق مستدام تتضمن روابط بلا أثر لنقطة الربط |
| TW201938171A (zh) | 2017-12-15 | 2019-10-01 | 匈牙利商羅特格登公司 | 作為血管升壓素V1a受體拮抗劑之三環化合物 |
| CN114644635B (zh) * | 2020-12-21 | 2023-02-03 | 上海济煜医药科技有限公司 | 三氮唑类三并环衍生物及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481360A (en) * | 1983-08-26 | 1984-11-06 | The Upjohn Company | 4H-1,2,4-Triazol-3-yl compounds |
| WO2001058880A1 (en) * | 2000-02-08 | 2001-08-16 | Yamanouchi Pharmaceutical Co., Ltd. | Novel triazole derivatives |
| PL359340A1 (en) * | 2000-05-19 | 2004-08-23 | Triazole derivatives |
-
2004
- 2004-01-13 GB GBGB0400700.1A patent/GB0400700D0/en not_active Ceased
-
2005
- 2005-01-05 WO PCT/IB2005/000263 patent/WO2005068466A1/en not_active Ceased
- 2005-01-05 BR BRPI0506848-7A patent/BRPI0506848A/pt not_active IP Right Cessation
- 2005-01-05 JP JP2006548476A patent/JP2007517857A/ja not_active Withdrawn
- 2005-01-05 CA CA002554382A patent/CA2554382A1/en not_active Abandoned
- 2005-01-05 US US10/588,878 patent/US20070167430A1/en not_active Abandoned
- 2005-01-05 EP EP05702410A patent/EP1706409A1/en not_active Withdrawn
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013523675A (ja) * | 2010-03-31 | 2013-06-17 | エフ.ホフマン−ラ ロシュ アーゲー | アリール−シクロヘキシル−テトラアザベンゾ[e]アズレン |
| JP2013523853A (ja) * | 2010-04-13 | 2013-06-17 | エフ.ホフマン−ラ ロシュ アーゲー | バソプレシンアンタゴニストとしてのアリール−/ヘテロアリール−シクロヘキセニル−テトラアザベンゾ[e]アズレン |
| JP2013525396A (ja) * | 2010-04-26 | 2013-06-20 | エフ.ホフマン−ラ ロシュ アーゲー | ヘテロビアリール−シクロヘキシル−テトラアザベンゾ[e]アズレン |
| JP2014527993A (ja) * | 2011-09-26 | 2014-10-23 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | V1aアンタゴニストとしてのオキシ−シクロヘキシル−4H,6H−5−オキサ−2,3,10b−トリアザ−ベンゾ[e]アズレン類 |
| JP2014531462A (ja) * | 2011-10-05 | 2014-11-27 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | V1aアンタゴニストとしてのシクロヘキシル−4H,6H−5−オキサ−2,3,10b−トリアザ−ベンゾ[e]アズレン |
| JP2016539168A (ja) * | 2013-12-05 | 2016-12-15 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | trans−8−クロロ−5−メチル−1−[4−(ピリジン−2−イルオキシ)−シクロヘキシル]−5,6−ジヒドロ−4H−2,3,5,10b−テトラアザ−ベンゾ[e]アズレン及びその結晶形態の合成 |
| KR20200100111A (ko) * | 2017-12-15 | 2020-08-25 | 리히터 게데온 닐트. | 바소프레신 v1a 수용체 길항제로서 트리아졸로벤즈아제핀 |
| JP2021506821A (ja) * | 2017-12-15 | 2021-02-22 | リヒター ゲデオン ニュイルヴァーノシャン ミューコェデー レースヴェーニュタールシャシャーグRichter Gedeon Nyrt. | バソプレシンV1a受容体拮抗薬としてのトリアゾロベンズアゼピン |
| JP7428647B2 (ja) | 2017-12-15 | 2024-02-06 | リヒター ゲデオン ニュイルヴァーノシャン ミューコェデー レースヴェーニュタールシャシャーグ | バソプレシンV1a受容体拮抗薬としてのトリアゾロベンズアゼピン |
| KR102719165B1 (ko) | 2017-12-15 | 2024-10-17 | 리히터 게데온 닐트. | 바소프레신 v1a 수용체 길항제로서 트리아졸로벤즈아제핀 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2554382A1 (en) | 2005-07-28 |
| US20070167430A1 (en) | 2007-07-19 |
| EP1706409A1 (en) | 2006-10-04 |
| GB0400700D0 (en) | 2004-02-18 |
| BRPI0506848A (pt) | 2007-06-12 |
| WO2005068466A1 (en) | 2005-07-28 |
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