NO331818B1 - Spirosykliske sykloheksanderivater, fremgangsmater for fremstilling derav, anvendelse derav samt medikament inneholdende minst en slik forbindelse. - Google Patents
Spirosykliske sykloheksanderivater, fremgangsmater for fremstilling derav, anvendelse derav samt medikament inneholdende minst en slik forbindelse. Download PDFInfo
- Publication number
- NO331818B1 NO331818B1 NO20052761A NO20052761A NO331818B1 NO 331818 B1 NO331818 B1 NO 331818B1 NO 20052761 A NO20052761 A NO 20052761A NO 20052761 A NO20052761 A NO 20052761A NO 331818 B1 NO331818 B1 NO 331818B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- dimethylamino
- phenylpentamethylene
- unsubstituted
- mono
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000003814 drug Substances 0.000 title claims abstract description 26
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title claims abstract description 22
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- 125000000217 alkyl group Chemical group 0.000 claims description 45
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- 125000003118 aryl group Chemical group 0.000 claims description 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 32
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
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- 229940098779 methanesulfonic acid Drugs 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
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- 125000005418 aryl aryl group Chemical group 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 claims description 3
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- DGXLYHAWEBCTRU-UHFFFAOYSA-N Fluorocitric acid Chemical compound OC(=O)CC(O)(C(O)=O)C(F)C(O)=O DGXLYHAWEBCTRU-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 3
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- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 3
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- 235000015816 nutrient absorption Nutrition 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
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- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002152667 DE10252667A1 (de) | 2002-11-11 | 2002-11-11 | Spirocyclische Cyclohexan-Derivate |
| PCT/EP2003/012305 WO2004043967A1 (fr) | 2002-11-11 | 2003-11-05 | Derives de cyclohexane spirocycliques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20052761D0 NO20052761D0 (no) | 2005-06-07 |
| NO20052761L NO20052761L (no) | 2005-06-07 |
| NO331818B1 true NO331818B1 (no) | 2012-04-10 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20052761A NO331818B1 (no) | 2002-11-11 | 2005-06-07 | Spirosykliske sykloheksanderivater, fremgangsmater for fremstilling derav, anvendelse derav samt medikament inneholdende minst en slik forbindelse. |
| NO20093060A NO331776B1 (no) | 2002-11-11 | 2009-09-24 | Spirosykliske sykloheksanderivater, fremgangsmater for fremstilling derav, anvendelse derav samt medikamenter inneholdende derivatene. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20093060A NO331776B1 (no) | 2002-11-11 | 2009-09-24 | Spirosykliske sykloheksanderivater, fremgangsmater for fremstilling derav, anvendelse derav samt medikamenter inneholdende derivatene. |
Country Status (28)
| Country | Link |
|---|---|
| US (6) | US7547707B2 (fr) |
| EP (4) | EP1560835B1 (fr) |
| JP (4) | JP4728645B2 (fr) |
| KR (2) | KR101075817B1 (fr) |
| CN (2) | CN100577664C (fr) |
| AR (2) | AR041932A1 (fr) |
| AT (1) | ATE441650T1 (fr) |
| AU (2) | AU2003296563B2 (fr) |
| BR (2) | BRPI0315296B8 (fr) |
| CA (1) | CA2505555C (fr) |
| CO (1) | CO5580765A2 (fr) |
| CY (2) | CY1110558T1 (fr) |
| DE (2) | DE10252667A1 (fr) |
| DK (2) | DK1560835T3 (fr) |
| EC (1) | ECSP055786A (fr) |
| ES (4) | ES2587013T3 (fr) |
| HK (3) | HK1080478A1 (fr) |
| IL (2) | IL168473A (fr) |
| MX (1) | MXPA05004959A (fr) |
| NO (2) | NO331818B1 (fr) |
| NZ (1) | NZ540575A (fr) |
| PE (1) | PE20040830A1 (fr) |
| PL (2) | PL215227B1 (fr) |
| PT (2) | PT2062898E (fr) |
| RU (1) | RU2354656C2 (fr) |
| SI (2) | SI2062898T1 (fr) |
| WO (1) | WO2004043967A1 (fr) |
| ZA (1) | ZA200504725B (fr) |
Families Citing this family (99)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| DE10252667A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| PL1842533T3 (pl) * | 2003-08-06 | 2013-08-30 | Gruenenthal Gmbh | Postać aplikacyjna zabezpieczona przed nadużyciem |
| DE102004020220A1 (de) * | 2004-04-22 | 2005-11-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| DE10361596A1 (de) * | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE10360793A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10360792A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102004032103A1 (de) * | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102004039382A1 (de) * | 2004-08-13 | 2006-02-23 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| WO2007062175A2 (fr) * | 2005-11-21 | 2007-05-31 | Amgen Inc. | Antagonistes cxcr3 |
| DE102006019597A1 (de) | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102006033114A1 (de) | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| DE102006046745A1 (de) * | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| DE102007009319A1 (de) * | 2007-02-22 | 2008-08-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007011485A1 (de) | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| BRPI0906467C1 (pt) | 2008-01-25 | 2021-05-25 | Gruenenthal Gmbh | forma de dosagem farmacêutica com formato exterior modificado resistente à ruptura e com liberação controlada |
| WO2009118174A1 (fr) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Cyclohexyldiamines substituées |
| HUE026184T2 (en) | 2008-03-27 | 2016-05-30 | Gruenenthal Gmbh | (Hetero-) aryl-cyclohexane derivatives |
| CN102046591B (zh) | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
| JP5542119B2 (ja) * | 2008-03-27 | 2014-07-09 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | スピロ（５．５）ウンデカン誘導体 |
| CN102046633B (zh) * | 2008-03-27 | 2015-03-25 | 格吕伦塔尔有限公司 | 取代的螺环状环己烷衍生物 |
| BR122013017393A2 (pt) | 2008-03-27 | 2019-10-15 | Grünenthal GmbH | Compostos derivados substituídos de 4-aminociclohexano, medicamentos contendo pelo menos um composto e uso dos referidos compostos |
| KR101690094B1 (ko) | 2008-05-09 | 2016-12-27 | 그뤼넨탈 게엠베하 | 분무 응결 단계의 사용하에 중간 분말 제형 및 최종 고체 제형을 제조하는 방법 |
| WO2011009604A1 (fr) * | 2009-07-22 | 2011-01-27 | Grünenthal GmbH | Forme galénique inviolable stabilisée à loxydation |
| PE20121067A1 (es) | 2009-07-22 | 2012-09-05 | Gruenenthal Chemie | Forma de dosificacion de liberacion controlada extruida por fusion en caliente |
| KR102074089B1 (ko) * | 2009-12-04 | 2020-02-05 | 선오비온 파마슈티컬스 인코포레이티드 | 다환형 화합물 및 이의 사용 방법 |
| TWI582092B (zh) * | 2010-07-28 | 2017-05-11 | 歌林達股份有限公司 | 順式－四氫－螺旋（環己烷－１,１’－吡啶［３,４－b］吲哚）－４－胺－衍生物 |
| WO2012016703A2 (fr) * | 2010-08-04 | 2012-02-09 | Grünenthal GmbH | Forme galénique pharmaceutique comprenant 6'-fluoro-(n-méthyl- or n,n-diméthyl-)-4-phényl-4',9'-dihydro-3'h-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine |
| BR112013002696A2 (pt) * | 2010-08-04 | 2016-05-31 | Gruenenthal Gmbh | forma de dosagem farmacêutica compreendendo 6'-fluor-(n-metil- ou n,n-dimetil-)4-fenil-4',9'-diidro-3'h-espiro[cicloexano-1,-1'-pirano[3,4-b]indol]-4 amina 13'' |
| KR101828768B1 (ko) * | 2010-08-04 | 2018-02-13 | 그뤼넨탈 게엠베하 | ６’플루오로（Ｎ메틸 또는 Ｎ，Ｎ디메틸）４페닐４’，９’디하이드로３’Ｈ스피로［사이클로헥산１，１’피라노［３，４，ｂ］인돌］４아민을 포함하는 약제학적 투여형 |
| HUE039328T2 (hu) * | 2010-08-04 | 2018-12-28 | Gruenenthal Gmbh | 6'-Fluor-(N-metil- vagy N,N-dimetil-)-4-fenil-4',9'-dihidro-3'H-spiro[ciklohexán-1,1'pirano[3,4,B]indol]-4-amin összetételû gyógyszerészeti adagolási forma a neuropátiás fájdalom kezelésére |
| WO2012028319A1 (fr) | 2010-09-02 | 2012-03-08 | Grünenthal GmbH | Forme pharmaceutique inviolable comportant un sel inorganique |
| CN103179956A (zh) | 2010-09-02 | 2013-06-26 | 格吕伦塔尔有限公司 | 包含阴离子聚合物的抗破碎剂型 |
| CA2808541C (fr) | 2010-09-02 | 2019-01-08 | Gruenenthal Gmbh | Forme pharmaceutique inviolable comportant un polymere anionique |
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